On The Revenue Leadership Podcast, Jonathan Moss said an ROI pitch failed, but giving two to three budgeted revenue FTEs to Experity's data team got GTM data prioritised.
Norton says he carved this role out above anything else and didn't mind that it sat outside sales, because he just needed the work done. He has seen the same pattern elsewhere and thinks trading revenue headcount for dedicated data or AI capacity is probably replicable. He explains that data teams treat the revenue leader as one stakeholder among many, alongside product and the CFO.
“The first role that I put into the new headcount plan was an applied AI leader for sales.”
Listen to the episode Episode Hiring & team building Link to this
Moss's pitch was that acquisition, expansion and retention fund everything, including the data team, so GTM data is the easiest ROI. It produced only a little momentum. In planning, the revenue org instead gave two to three budgeted FTEs to the data team, which hired net-new people focused only on the GTM domain.
“we're actually going to allocate, you know, two, three FTEs of the overall revenue organization to this because it's so important”
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Enablement had already shrunk from 32 to 16 when roughly 450 people were in customer-facing roles. In her ride-alongs she found all 16 remaining people working on the same thing. She reallocated the headcount mostly to RevOps, hired AI content creators and a builder from JP Morgan Chase, and rebuilt enablement to 10-12 people with more technical, systems-thinking profiles. She reports significantly higher productivity.
“Not one person was working on something unique versus everybody else.”
Listen to the episode Episode Hiring & team building Link to this
Kyle Norton says leaders should stack-rank their organization and identify people whose departure would not hurt, then use those roles to fund an applied AI hire. He says Owner.com has three or four people in applied AI and many open roles, and that one person is enough to start. A host from bootstrapped STA adds that the first such investment is the most important and makes the next ones obvious.
“Go and do the stack rank of your organization and figure out who are the people that if they walked out the door today, you'd be like, oh, okay, we'll be fine.”
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On [Un]Churned, Pradeep Raman said Microsoft deliberately staffs at N-1, one fewer person than a job requires, and has done so by design across his 27 years there.
He said bragging about multiplying headcount, like valuations, can become detached from the actual business. It can also mask weak product-market fit by willing growth into existence through hiring. When a new leader asked to be pushed harder, he set that goal of the highest-performing team with the fewest people.
“can you be the highest performing team with the least amount of people?”
Listen to the episode Episode Hiring & team building Link to this
She said that even when revenue isn't a problem, overhiring blurs job definitions, makes people step on each other's toes, and leaves more new people who don't know what they're doing than experienced ones. She finds lean growth more intellectually interesting because it forces hard prioritisation, automation and use of data. She admitted she has to consciously push herself on this, and that there were points at Stripe where more people probably would have meant faster revenue growth.
“You actually just slow the entire machine down with coordination cost.”
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He frames the scaling question as putting the right people in the right place to make great products and attracting top talent to a small team. G&A fills in as needed. Lawyers, for example, scale with the number of contracts, not with raw revenue. He describes the product as running on its own, so his hiring addresses product scaling (infrastructure, abuse reduction, enterprise) rather than revenue scaling.
“AI has made it easier to run a very high revenue company with fewer people resources. So we don't need to scale people linearly with revenue. Fortunately, we've avoided doing that entirely.”
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Pradeep says that across his 27 years at Microsoft, there has always been more work than hours or resources. He calls this by design and says it is how the company has been successful. He describes the approach as: if a job takes N people, the company likes to have N-1 and still get the job done. He notes that the shortfall has a snowball effect that catches up over time, and says the current pace of AI progress makes everyone's workload heavier.
“if it takes N people to do a job, we, we like to have n -, 1 and still want the job to get done.”
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He says from his previous jobs the best work and the fastest output came from small teams, while large projects with many engineers and stakeholders became muddy, with everyone having opinions and communication overhead. He argues that to build well you need fewer people who are the right people and focused on the right things, and he treats the limited bandwidth this creates as a feature rather than a bug.
“I always felt that the best work we ever did was with the small team.”
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On Grit, Jack Zhang said Airwallex hired big-bank veterans on pedigree, rewrote much of the system after following their advice, and took years to fire people it should have fired in weeks.
Frederik uses the ICE criteria of intelligence, character, coachability and experience to score candidates in interviews. He usually takes people strong on intelligence, character and coachability over those with more experience, because those people grow quickly, while experience is a matter of days, weeks or months. He still wants a minimum level of relevant experience.
“I usually take people that are very high intelligence character and then coachability as well over the over the experience because those people are going to grow quickly.”
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She contrasts builders with managers and says this distinction is interesting now, because even in a big company it is now kind of like being at a startup.
“this builder versus manager is also really interesting like there have been a lot of very successful operators who have come in and they have been exceptional at optimizing things that are already in place”
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She says candidates are assessed on how they would approach new ways of doing things, rather than how they were successful in previous roles, because past success no longer carries the same premium. She describes a split between leaders who want to hand off the work and those who see the AI shift as an energising learning challenge.
“we're testing more for the learning velocity, how they're thinking about approaching like new ways of doing it”
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She says investors and recruiters are recalibrating the profile for executives at a $50 million business, where a consistent record of growth from $30 million to $300 million no longer guarantees a hire. The focus has moved to intellectual curiosity and comfort with building as well as optimising, and she says this applies to any executive role.
“And I would say like, 70 % of that is out the window.”
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He said Airwallex hired many people from big banks, and the founders had to rewrite much of the system afterward because first-principles thinking matters more than experience. He made the point while discussing recruiting mistakes.
“first principle thinking is a lot more important than the experience”
Listen to the episode Episode Hiring & team building Link to this
Jack said the hires from big banks told the founders their approach was wrong and proposed building the product in a different direction. The founders doubted themselves because the hires had more experience. The company had to rewrite much of the system afterward.
“We should have done that in weeks, not years.”
Listen to the episode Episode Hiring & team building Link to this
He said the people he has taken risks on, who were not the strongest on paper or from the flashiest companies, have tended to work out better. He guessed that some people follow a job for the clout, or joined successful companies only after the success had happened. Mirzadegan offered the hypothesis that people with fancy logos have less to prove than someone for whom the role feels existential, and Kleczynski agreed.
“I found the people that have the greatest backgrounds on LinkedIn often performed the worst.”
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Mark Roberge said it is intuitive to hire for prior experience, and that most CEOs and inexperienced sales hiring leaders do so. He said it does not hurt to have experience but that focusing only on it leads to bottom-half performers in the industry. He argued that DNA, meaning traits such as work ethic, is a bigger driver of success.
“those people that put the most weight on years of experience selling to my buyer and my product type, fails.”
Listen to the episode Episode Hiring & team building Link to this
Mark Roberge says founders often look for specialists when hiring a first sales leader, marketer or product leader. He argues that a company still pivoting does not yet know its product, messaging, market or marketing, so a specialist can feel like a square peg in a round hole.
“when we hire athletes who are smart, who execute, who want to learn fast, who want to work hard, we set ourselves up more optimally for finding the right answer.”
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On The Dave Gerhardt Show, Dasha described an 'anti-sell', telling candidates why they shouldn't join, such as that people who want a clear swim lane won't fit a Series A startup.
Dasha lays out the reasons to join and the reasons a candidate probably wouldn't want to. Her example: someone who dislikes ambiguity and wants a clear swim lane won't fit a Series A startup. If a candidate balks, both sides have avoided a bad fit. If they are excited to wear many hats, it is a good fit.
“We call that the anti sell. And it works so what you're like, look. Here are all the reasons you should join. And here are all the reasons you probably don't wanna join.”
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Mandia says that as a self-funded company, Mandiant told new hires they would be billed out about 80% of the time and that the company could then hire two more engineers. He says they attracted people by saying they would work twice as hard but be twice as good. He says there was no lifestyle selling.
“We literally attracted people by saying, you're going to work twice as hard, but you'll be twice as good.”
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Chris Vik said that when recruiting for a small company from Copenhagen, he labelled up front the two questions candidates would likely have. First, why would you join a small company the world has never heard of. Second, why would you be excited about a company that does quality assurance and test automation. He said labelling them matters because those objections will hit you later in the recruitment process.
“it's really important to label it because you know that those two objections will hit you down in the recruitment process”
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He said Circle's mission is a major transformation that could contribute to global economic prosperity, but that it is hard because the world does not believe in it and because it requires changing laws and managing constant macro shocks. He said the breadth of the subject, covering law, regulation, technology, economics and cryptography, is also difficult. He said he tells candidates it will be the hardest job they have had when he is directly involved in hiring them.
“I always tell people this is gonna be the hardest job because the world doesn't believe in it and like that's uncomfortable for people.”
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Ranked by how many independent voices make each point and how specific their evidence is. Co-hosts of a show count as one voice, and a point needs at least two shows to appear here.
said Joubin Mirzadegan (Grit), Jeanne DeWitt Grosser (Grit), Anastasios Angelopoulos (Grit), Pradeep Raman ([Un]Churned), Karri Saarinen (Grit)
He said bragging about multiplying headcount, like valuations, can become detached from the actual business. It can also mask weak product-market fit by willing growth into existence through hiring. When a new leader asked to be pushed harder, he set that goal of the highest-performing team with the fewest people.
“can you be the highest performing team with the least amount of people?”
Listen to the episode Episode Hiring & team building Link to this
She said that even when revenue isn't a problem, overhiring blurs job definitions, makes people step on each other's toes, and leaves more new people who don't know what they're doing than experienced ones. She finds lean growth more intellectually interesting because it forces hard prioritisation, automation and use of data. She admitted she has to consciously push herself on this, and that there were points at Stripe where more people probably would have meant faster revenue growth.
“You actually just slow the entire machine down with coordination cost.”
Listen to the episode Episode Hiring & team building Link to this
He frames the scaling question as putting the right people in the right place to make great products and attracting top talent to a small team. G&A fills in as needed. Lawyers, for example, scale with the number of contracts, not with raw revenue. He describes the product as running on its own, so his hiring addresses product scaling (infrastructure, abuse reduction, enterprise) rather than revenue scaling.
“AI has made it easier to run a very high revenue company with fewer people resources. So we don't need to scale people linearly with revenue. Fortunately, we've avoided doing that entirely.”
Listen to the episode Episode Hiring & team building Link to this
Pradeep says that across his 27 years at Microsoft, there has always been more work than hours or resources. He calls this by design and says it is how the company has been successful. He describes the approach as: if a job takes N people, the company likes to have N-1 and still get the job done. He notes that the shortfall has a snowball effect that catches up over time, and says the current pace of AI progress makes everyone's workload heavier.
“if it takes N people to do a job, we, we like to have n -, 1 and still want the job to get done.”
Listen to the episode Episode Hiring & team building Link to this
He says from his previous jobs the best work and the fastest output came from small teams, while large projects with many engineers and stakeholders became muddy, with everyone having opinions and communication overhead. He argues that to build well you need fewer people who are the right people and focused on the right things, and he treats the limited bandwidth this creates as a feature rather than a bug.
“I always felt that the best work we ever did was with the small team.”
Listen to the episode Episode Hiring & team building Link to this
said Asad Zaman (Topline), Parag Agarwal (Grit)
He says companies are hiring many SDRs, BDRs and SMB AEs, along with an aggressive number of technical sellers. He argues that even if every company became 50% more efficient per head, growth in the market would keep headcount rising. He cites a company with 300 employees aiming for $2 billion in revenue this year as an example of that growth.
“I don't see any situation where companies are not hiring BDRs, SDRs. I don't see it.”
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He says it seems counterintuitive, but if there are many valuable things to build and customers need them, more engineers are better until you saturate the opportunity space. He attributes today's extreme growth rates in some companies to multiplying three factors: how fast and well you can hire, how quickly you can channel that capacity into valuable things, and how fast customers adopt them. He has never once concluded he needs fewer people because everyone is more productive.
“I have never once sat down and been like, oh, Everyone's going to be so much more productive. So maybe I need fewer people.”
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Asad says that compared with companies from previous eras, AI companies are leaner at each stage. He says they are moving through stages at a pace never seen before, which creates strong demand, citing Anthropic growing about 10x a year on revenue. He says the number of employees those companies need over a year is staggering.
“If you look at companies per stage and stage and compare them to companies from previous eras, they are leaner per stage.”
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Lean advocates prize efficiency and coordination costs, while aggressive hirers face hypergrowth markets where the opportunity outruns capacity.
said Frederik Maris (Revenue Builders), Katie Bullard (Topline), Jack Zhang (Grit), Marcin Kleczynski (Grit)
Frederik uses the ICE criteria of intelligence, character, coachability and experience to score candidates in interviews. He usually takes people strong on intelligence, character and coachability over those with more experience, because those people grow quickly, while experience is a matter of days, weeks or months. He still wants a minimum level of relevant experience.
“I usually take people that are very high intelligence character and then coachability as well over the over the experience because those people are going to grow quickly.”
Listen to the episode Episode Hiring & team building Link to this
She contrasts builders with managers and says this distinction is interesting now, because even in a big company it is now kind of like being at a startup.
“this builder versus manager is also really interesting like there have been a lot of very successful operators who have come in and they have been exceptional at optimizing things that are already in place”
Listen to the episode Episode Hiring & team building Link to this
She says candidates are assessed on how they would approach new ways of doing things, rather than how they were successful in previous roles, because past success no longer carries the same premium. She describes a split between leaders who want to hand off the work and those who see the AI shift as an energising learning challenge.
“we're testing more for the learning velocity, how they're thinking about approaching like new ways of doing it”
Listen to the episode Episode Hiring & team building Link to this
She says investors and recruiters are recalibrating the profile for executives at a $50 million business, where a consistent record of growth from $30 million to $300 million no longer guarantees a hire. The focus has moved to intellectual curiosity and comfort with building as well as optimising, and she says this applies to any executive role.
“And I would say like, 70 % of that is out the window.”
Listen to the episode Episode Hiring & team building Link to this
He said Airwallex hired many people from big banks, and the founders had to rewrite much of the system afterward because first-principles thinking matters more than experience. He made the point while discussing recruiting mistakes.
“first principle thinking is a lot more important than the experience”
Listen to the episode Episode Hiring & team building Link to this
Jack said the hires from big banks told the founders their approach was wrong and proposed building the product in a different direction. The founders doubted themselves because the hires had more experience. The company had to rewrite much of the system afterward.
“We should have done that in weeks, not years.”
Listen to the episode Episode Hiring & team building Link to this
He said the people he has taken risks on, who were not the strongest on paper or from the flashiest companies, have tended to work out better. He guessed that some people follow a job for the clout, or joined successful companies only after the success had happened. Mirzadegan offered the hypothesis that people with fancy logos have less to prove than someone for whom the role feels existential, and Kleczynski agreed.
“I found the people that have the greatest backgrounds on LinkedIn often performed the worst.”
Listen to the episode Episode Hiring & team building Link to this
Mark Roberge said it is intuitive to hire for prior experience, and that most CEOs and inexperienced sales hiring leaders do so. He said it does not hurt to have experience but that focusing only on it leads to bottom-half performers in the industry. He argued that DNA, meaning traits such as work ethic, is a bigger driver of success.
“those people that put the most weight on years of experience selling to my buyer and my product type, fails.”
Listen to the episode Episode Hiring & team building Link to this
Mark Roberge says founders often look for specialists when hiring a first sales leader, marketer or product leader. He argues that a company still pivoting does not yet know its product, messaging, market or marketing, so a specialist can feel like a square peg in a round hole.
“when we hire athletes who are smart, who execute, who want to learn fast, who want to work hard, we set ourselves up more optimally for finding the right answer.”
Listen to the episode Episode Hiring & team building Link to this
said Lauren Hughes (The Revenue Leadership Podcast), Asad Zaman (Topline), Mark Roberge (The Science of Scaling)
The team compared ramp for hires from competitors or prior PEO roles with hires from SaaS or other businesses. Lauren Hughes said prior PEO hires ramped faster 'for the most part', and that people from adjacent businesses like rental car sales 'sometimes' work well. She thinks the profiling also helped ramp time.
“people who've worked in sales at like rental car companies sometimes work really well.”
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Asad Zaman says enterprise sales is a different craft once a company has a brand and infrastructure behind it. He says a mid-market person can be hired into an enterprise role, or an enterprise person into a strategic role, but there is little flexibility beyond that. Companies that have scaled very fast, he says, often find candidates won't even take their calls.
“The thing about mid-market and enterprises, you kind of need people that have certain like relevant experience.”
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He says many founders overweight industry experience at the expense of proven enterprise sales experience. He describes a veteran with 10 to 20 years in the industry who is only a 50% performer, and says the enterprise seller from SaaS will win.
“I would much rather teach someone how restaurants work than to try to teach them how to do really good enterprise selling.”
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Ron Gabrisko calls hiring from his network the cheat code, because he knows what he is getting. He also says hiring people already in the industry helps, since they already know the market and the product.
“The cheat code is I'm hiring for my network so I know what I'm getting.”
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Ron Gabrisko says that hiring people from big data and from the same space removed a learning curve, so they did not hire people with no real experience. He says that by three to six months in, you have a good idea of who is putting in effort. He expects that people with effort who come from the space will eventually be successful, and most of those hires were pretty successful going into year two.
“So we hired people that came from big data and came from this space.”
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The sceptics of pedigree are rebuilding products or functions from scratch during the AI shift, while the defenders hire into established motions like enterprise sales where the craft itself transfers.
said Jonathan Moss (The Revenue Leadership Podcast), Sam Jacobs (Topline), Eleanora White ([Un]Churned), Jared Collins ([Un]Churned)
Moss says the need varies from about 10 to 40 hours a week. Contracting it frees full-time headcount for generalist, AI-capable builders.
“And if we need specialties we can contract that for the amount of time that we need it because we also don't need it all the time.”
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His criteria are a foundation in revenue architecture and how recurring-revenue businesses work, generalist GTM and operations understanding (with domain-specific agents such as a marketing ops agent filling gaps), curiosity, systems thinking and agency. He says people who use AI only as search are probably not a fit. He sometimes hires from engineering or other functions and teaches revenue architecture.
“The second thing is we look for more generalists than specialists.”
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Sam Jacobs says he sees specialization within a function collapsing. He argues this does not diminish the need for the function but creates an opportunity for people who are more fluent in cross-functional tools to be effective.
“I see the collapse of specialization within a particular function. That doesn't diminish the need for the function, but does create an opportunity for those that are more fluent in all of these cross-functional tools to be effective.”
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Sam says his own team wants to be general marketers and feels the leverage from AI lets them work across functions within marketing. He expects the marketing team to still exist but the roles within it to become more cross-functional, because the intelligence of how to run each discipline will sit within AI rather than in discrete functional specialists.
“the role of the people within the team will be more cross-functional because the additional intelligence of how to do that function will be embedded within AI as opposed to a discrete functional discipline.”
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She said she does not think the company will get away from the generalist CSM, while strategic accounts will still need specialists. She argued the specialist information will come through the agents the team designs, which lets CSMs work at scale and still deliver.
“I don't think we're going to get away from that”
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Collins said he expects CSMs to be dangerous on a lot of topics, enough to know when to bring in a specialist. Dell can draw on large teams of experts and on its view of similar customer profiles. He said the principle is that everybody owns the customer relationship, and the CSM's job includes bringing the right people in at the right times.
“I kind of expect my CSMs to be generalist in the sense they need to be kind of dangerous about knowing a lot about a lot of things”
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said Gaurav Agarwal (Topline), Cassie Vaughn ([Un]Churned)
He said generalists will not take over, but specialists with more than two or three spikes will absorb those spikes. He used the example of a growth person who also understands data, sales ops, sales and success. He said which spike eats which is yet to be determined.
“the one with the best taste and the drive to work and learn and improve, eats up adjacent departments.”
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She said the job description she is using for future CSM hiring is someone with deep domain expertise who can speak to customers' objectives in a real way. She recommended specialising in an industry, a function or a use case deeply to its core. She said a self-starter who keeps up with AI and tools matters more than someone who simply runs a playbook, since the playbook work is what AI will do.
“stop being a generalist and specialize in something like learn an industry, learn a function, learn a use case deeply to its core”
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Generalist advocates expect AI agents to supply specialist know-how, while specialist advocates sell into verticals or functions where customers demand deep domain fluency from the person in front of them.
What one named guest described doing or seeing. Each is a single account, not a point several operators agree on.
“are you a pain expert or you a great marketer? Because if you're a pain expert, I can never move you to something else? If you're a great marketer, I can put you anywhere.”
“But if you say what your favorite experience and it's about ownership that's a huge green light for”
“You kind of have these filters that you add on to the interview process at the end, bar raisers or whatever you want to call them, where they're just mostly selecting for culture and intensity and so on.”
“So Now I'm paying $100 an hour instead of 50, you know, for these people. So my margin is really bad on my contractors.”
“I like to leave space at the end of every conversation for the person on the other end to ask me questions.”
“By Thursday afternoon, he was deploying to production crazy meaning on our commercial web app.”
Kyle Norton says leaders should stack-rank their organization and identify people whose departure would not hurt, then use those roles to fund an applied AI hire. He says Owner.com has three or four people in applied AI and many open roles, and that one person is enough to start. A host from bootstrapped STA adds that the first such investment is the most important and makes the next ones obvious.
“Go and do the stack rank of your organization and figure out who are the people that if they walked out the door today, you'd be like, oh, okay, we'll be fine.”
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Enablement had already shrunk from 32 to 16 when roughly 450 people were in customer-facing roles. In her ride-alongs she found all 16 remaining people working on the same thing. She reallocated the headcount mostly to RevOps, hired AI content creators and a builder from JP Morgan Chase, and rebuilt enablement to 10-12 people with more technical, systems-thinking profiles. She reports significantly higher productivity.
“Not one person was working on something unique versus everybody else.”
Listen to the episode Episode Hiring & team building Link to this
Moss's pitch was that acquisition, expansion and retention fund everything, including the data team, so GTM data is the easiest ROI. It produced only a little momentum. In planning, the revenue org instead gave two to three budgeted FTEs to the data team, which hired net-new people focused only on the GTM domain.
“we're actually going to allocate, you know, two, three FTEs of the overall revenue organization to this because it's so important”
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Norton says he carved this role out above anything else and didn't mind that it sat outside sales, because he just needed the work done. He has seen the same pattern elsewhere and thinks trading revenue headcount for dedicated data or AI capacity is probably replicable. He explains that data teams treat the revenue leader as one stakeholder among many, alongside product and the CFO.
“The first role that I put into the new headcount plan was an applied AI leader for sales.”
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Yash said he was taking 30 to 35 calls a week during early enterprise inbound while also cleaning data and building systems. Varun suggested he see how far Clay's screening and scoring systems could go before hiring more of the team. Yash said that in hindsight he should have intentionally said no to more calls to fully use the automation.
“why don't you see how far you can push the systems, the screening, the scoring with clay before we actually go out and try and hire more of the team?”
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She has 10-plus functions in go-to-market. She intends to classify each one: never needs more people than today, needs to add only a few a year, or scales non-linearly with revenue. Then the team would ask whether anything could change the shape of the curve for the functions that must scale. This was a planned exercise at the time of the interview, not one already completed.
“what is the theoretical end state of your function?”
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Freya says the nurture role can be an added responsibility for an existing marketer, and a one-person team can use AI to help build the workflows. A dedicated hire could also take on legacy CRM data and cross-sell and upsell, since she says many enterprise clients only focus on net-new accounts and most CRMs hold stagnant data.
“I don't think it has to be an additional hire.”
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He said he has never had a reference go badly, so he assumes references will be positive by design. Instead he asks the reference what he needs to look out for in the first 90 days, and says the truth usually starts to come out in that answer. He says he uses the answer to help the person even when the hiring decision has already been made.
“I'm getting to know this individual in the first 90 days, what do I need to look out for?”
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Kaplan says he asks every reference the same question after saying they like the candidate, and that it worked well in a recent hire at Force Management. He says references who want their friend to succeed give honest answers about areas where the person struggles.
“I always ask the same question. Hey, we like XYZ person also. We like them a lot. What is the one thing that you think I'll be able to help them with the most?”
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Brad says candidates can seem great after a couple of conversations, so the team treats understanding a candidate's prior experience through back-channel references as one of the most important parts of the process. He notes that in this environment, one degree of separation is usually enough to reach a candidate's former managers.
“Sometimes the back channel is the only channel.”
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Bob Kocis said he usually asks candidates during the interview process whether he can call one of their customers. He said top sellers who have built great references will offer several names, while many candidates have none because they have not built those relationships.
“Hey, can I call one of your customers?”
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Bove asks candidates who their best executive relationship or favorite champion is, why, and how they turned that person into a champion. She also asks who she could call as a reference and insists it must be a customer, not a co-worker. She says RDs and directors can ask these questions in interviews.
“who's your best executive relationship or who's your favorite champion and why tell me how you built them into a champion?”
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Frederik says an unstructured hour can end with only a feeling about whether he liked a candidate. He now prepares a sequence of questions that qualifies, during the interview, the attributes he is looking for. The result is a clear reason to like the candidate and a clear view of the risks.
“at the end of the interview instead of saying I like this person you know exactly why you like that person and what the risks are”
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Kaplan says Force Management created a success profile for a major recent hire, and candidates and interview conversations were both measured against it. He says the profile is table stakes and that hiring decisions should be evidence-based rather than made on general impressions.
“for me the success profile is to center of the universe It's that you know The competencies and success behaviors Of what success looks like evidence? Of what Success looks like in the role”
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He described a large software company whose VPs and directors listed traits on three whiteboards in a hiring workshop, with each person naming different attributes. He said none of the traits were wrong, but the group lacked a common language to evaluate candidates. Keenan agreed and went a layer further, asking whether anyone had analysed what the job actually requires.
“None of these are necessarily the wrong thing to look for. But none of you have said the same thing. You don't have a common language.”
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John McMahon uses this question to see how a candidate perceives their own performance and how they read his reactions to their answers and questions. He notes that salespeople ask themselves the same thing in front of customers. He says he is not looking for a right or wrong answer, but for how the candidate frames the situation.
“How do you think you're doing in this interview?”
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John says he recently told a candidate he knows the three bosses they listed from their last three jobs and will call them, then asked what those bosses would say the candidate struggles with. He also asked what he as their potential leader would need to do to help them elevate. He says authentic answers show who people really are. Brad responded that this tests self-awareness and willingness to be vulnerable.
“But when I call them, what are they going to tell me that you struggle with?”
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Ganesan said describing yourself through friends' eyes externalizes the question and reveals self-awareness. He then runs references to see whether they match. In his view, founders who know their weaknesses can manage them; the ones blind to their weaknesses usually have trouble.
“I'm trying to see if the references match someone's self-awareness... It's the people who are blind to the weaknesses that usually have challenges.”
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Dasha lays out the reasons to join and the reasons a candidate probably wouldn't want to. Her example: someone who dislikes ambiguity and wants a clear swim lane won't fit a Series A startup. If a candidate balks, both sides have avoided a bad fit. If they are excited to wear many hats, it is a good fit.
“We call that the anti sell. And it works so what you're like, look. Here are all the reasons you should join. And here are all the reasons you probably don't wanna join.”
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Chris Vik said that when recruiting for a small company from Copenhagen, he labelled up front the two questions candidates would likely have. First, why would you join a small company the world has never heard of. Second, why would you be excited about a company that does quality assurance and test automation. He said labelling them matters because those objections will hit you later in the recruitment process.
“it's really important to label it because you know that those two objections will hit you down in the recruitment process”
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Jason said he tells candidates they will be tempted to say what he wants to hear, because they are selling themselves. He asks them to consider whether the company will need to have a disappointing conversation about expectations in 90 days. He said this surfaces whether the job is right for them before the company is stuck with a mismatch.
“But think through 90 days from now. Are we going to have a conversation because we're disappointed because you can't deliver on the expectations of the role”
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Moss says the need varies from about 10 to 40 hours a week. Contracting it frees full-time headcount for generalist, AI-capable builders.
“And if we need specialties we can contract that for the amount of time that we need it because we also don't need it all the time.”
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She says contractors bill heavily because they are paid hourly, and they cost her about $100 an hour versus $50 for employees. California rules mean she cannot set their schedules or make them part of the core business. Clients want full-time, trained employees on their company laptops, and contractors bill her for internal one-on-ones and team huddles.
“So Now I'm paying $100 an hour instead of 50, you know, for these people. So my margin is really bad on my contractors.”
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Her AI-native clients usually have one mid-level ops person who is ready to become more strategic but is quickly overwhelmed. Jen says she is not trying to outsource RevOps. She supplies specialists, speed to decision and special projects so clients can spike and come down on resourcing. Structure built for 50 SDRs is outgrown when the team becomes 75 and then 200.
“I'm not trying to outsource revops. I'm trying to give your team specialists. I'm trying to give your team speed to decision.”
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Zhang says the hard part of hypergrowth hiring is not finding candidates, since many people want to work at AI companies, but keeping the bar high. Modelled on Revolut and Amazon, Decagon added a final-stage filter that selects mostly for culture and intensity, introduced roughly as it geared up to go from 50 to 500. Zhang and Ashwin personally met every hire until about 300 people. Long-tenured employees seen as good representatives of the culture now run these interviews. A majority pass, and Zhang says that if the last step cuts most people, something is probably wrong.
“You kind of have these filters that you add on to the interview process at the end, bar raisers or whatever you want to call them, where they're just mostly selecting for culture and intensity and so on.”
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Asked what share of candidates fail Decagon's bar-raiser step, Zhang did not know the exact number but said it is definitely a minority. His reasoning is that because it is the last step, a high cut rate there signals a problem.
“If you're cutting the majority of people, the last step to the process, that's probably something wrong.”
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Parallel started in stealth, so there was no inbound interest. For almost a year before hiring, he met many people and asked each a standard question about the best three people they had worked with, then met some of those. The founding team was him plus six others, and he deliberately made half of them people he had not known before. He says much of Parallel's later hiring has come through this multi-hop network channel.
“what are the best three people you've ever worked with? And I would go meet some of them over time.”
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Andy said mid-level people are often in Slack with the hiring manager and can pass along a profile directly. He gave the example of backdooring to mid-level RevOps people while interviewing at Carta, who helped him understand the company. He also gave an example of a revenue leader at a large company being connected to a mid-level person at an AI company.
“No, you can backdoor to anybody at the company and be able to get in as well too.”
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Kyle said Owner has relied on him posting on LinkedIn rather than on recruiters, and that this saved hundreds and hundreds of thousands of dollars. He also said the posts bring founders asking for advice, which he treats as an easy form of advisory work.
“It's all been like Kyle writes a LinkedIn post and then 1,600 people apply and then we just wade through it. And that was awesome. Like we saved hundreds and hundreds of thousands of dollars because of it.”
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Austin said the window for addressing a concerning issue is very short, because the longer it goes unaddressed, the more likely it is to recur when the manager is absent. He said he looks for managers to hear the concern, avoid making excuses, and take swift action. He called making excuses bad management.
“So I think within a 24 maybe in some cases 48 hour period that manager has to come up with a point of view on like what are we doing about this”
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Austin argued that a C-level performer lowers the energy of everyone around them and affects the company's future potential. He said one bad event is remembered more than ten good ones, so the cost of a weak performer is outsized. He said he does not see this as being transactional, and that failing to correct it is a mistake.
“the C player is driving everyone's energy down and is impacting everyone's future potential”
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Jack said the hires from big banks told the founders their approach was wrong and proposed building the product in a different direction. The founders doubted themselves because the hires had more experience. The company had to rewrite much of the system afterward.
“We should have done that in weeks, not years.”
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said Kyle Norton (The Revenue Leadership Podcast, Topline), Jonathan Moss (The Revenue Leadership Podcast), Lauren Hughes (The Revenue Leadership Podcast)
Norton says he carved this role out above anything else and didn't mind that it sat outside sales, because he just needed the work done. He has seen the same pattern elsewhere and thinks trading revenue headcount for dedicated data or AI capacity is probably replicable. He explains that data teams treat the revenue leader as one stakeholder among many, alongside product and the CFO.
“The first role that I put into the new headcount plan was an applied AI leader for sales.”
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Moss's pitch was that acquisition, expansion and retention fund everything, including the data team, so GTM data is the easiest ROI. It produced only a little momentum. In planning, the revenue org instead gave two to three budgeted FTEs to the data team, which hired net-new people focused only on the GTM domain.
“we're actually going to allocate, you know, two, three FTEs of the overall revenue organization to this because it's so important”
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Enablement had already shrunk from 32 to 16 when roughly 450 people were in customer-facing roles. In her ride-alongs she found all 16 remaining people working on the same thing. She reallocated the headcount mostly to RevOps, hired AI content creators and a builder from JP Morgan Chase, and rebuilt enablement to 10-12 people with more technical, systems-thinking profiles. She reports significantly higher productivity.
“Not one person was working on something unique versus everybody else.”
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Kyle Norton says leaders should stack-rank their organization and identify people whose departure would not hurt, then use those roles to fund an applied AI hire. He says Owner.com has three or four people in applied AI and many open roles, and that one person is enough to start. A host from bootstrapped STA adds that the first such investment is the most important and makes the next ones obvious.
“Go and do the stack rank of your organization and figure out who are the people that if they walked out the door today, you'd be like, oh, okay, we'll be fine.”
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said Joubin Mirzadegan (Grit), Jeanne DeWitt Grosser (Grit), Anastasios Angelopoulos (Grit), Pradeep Raman ([Un]Churned), Karri Saarinen (Grit)
He said bragging about multiplying headcount, like valuations, can become detached from the actual business. It can also mask weak product-market fit by willing growth into existence through hiring. When a new leader asked to be pushed harder, he set that goal of the highest-performing team with the fewest people.
“can you be the highest performing team with the least amount of people?”
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She said that even when revenue isn't a problem, overhiring blurs job definitions, makes people step on each other's toes, and leaves more new people who don't know what they're doing than experienced ones. She finds lean growth more intellectually interesting because it forces hard prioritisation, automation and use of data. She admitted she has to consciously push herself on this, and that there were points at Stripe where more people probably would have meant faster revenue growth.
“You actually just slow the entire machine down with coordination cost.”
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He frames the scaling question as putting the right people in the right place to make great products and attracting top talent to a small team. G&A fills in as needed. Lawyers, for example, scale with the number of contracts, not with raw revenue. He describes the product as running on its own, so his hiring addresses product scaling (infrastructure, abuse reduction, enterprise) rather than revenue scaling.
“AI has made it easier to run a very high revenue company with fewer people resources. So we don't need to scale people linearly with revenue. Fortunately, we've avoided doing that entirely.”
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Pradeep says that across his 27 years at Microsoft, there has always been more work than hours or resources. He calls this by design and says it is how the company has been successful. He describes the approach as: if a job takes N people, the company likes to have N-1 and still get the job done. He notes that the shortfall has a snowball effect that catches up over time, and says the current pace of AI progress makes everyone's workload heavier.
“if it takes N people to do a job, we, we like to have n -, 1 and still want the job to get done.”
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He says from his previous jobs the best work and the fastest output came from small teams, while large projects with many engineers and stakeholders became muddy, with everyone having opinions and communication overhead. He argues that to build well you need fewer people who are the right people and focused on the right things, and he treats the limited bandwidth this creates as a feature rather than a bug.
“I always felt that the best work we ever did was with the small team.”
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said Frederik Maris (Revenue Builders), Katie Bullard (Topline), Jack Zhang (Grit), Marcin Kleczynski (Grit)
Frederik uses the ICE criteria of intelligence, character, coachability and experience to score candidates in interviews. He usually takes people strong on intelligence, character and coachability over those with more experience, because those people grow quickly, while experience is a matter of days, weeks or months. He still wants a minimum level of relevant experience.
“I usually take people that are very high intelligence character and then coachability as well over the over the experience because those people are going to grow quickly.”
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She contrasts builders with managers and says this distinction is interesting now, because even in a big company it is now kind of like being at a startup.
“this builder versus manager is also really interesting like there have been a lot of very successful operators who have come in and they have been exceptional at optimizing things that are already in place”
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She says candidates are assessed on how they would approach new ways of doing things, rather than how they were successful in previous roles, because past success no longer carries the same premium. She describes a split between leaders who want to hand off the work and those who see the AI shift as an energising learning challenge.
“we're testing more for the learning velocity, how they're thinking about approaching like new ways of doing it”
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She says investors and recruiters are recalibrating the profile for executives at a $50 million business, where a consistent record of growth from $30 million to $300 million no longer guarantees a hire. The focus has moved to intellectual curiosity and comfort with building as well as optimising, and she says this applies to any executive role.
“And I would say like, 70 % of that is out the window.”
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He said Airwallex hired many people from big banks, and the founders had to rewrite much of the system afterward because first-principles thinking matters more than experience. He made the point while discussing recruiting mistakes.
“first principle thinking is a lot more important than the experience”
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Jack said the hires from big banks told the founders their approach was wrong and proposed building the product in a different direction. The founders doubted themselves because the hires had more experience. The company had to rewrite much of the system afterward.
“We should have done that in weeks, not years.”
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He said the people he has taken risks on, who were not the strongest on paper or from the flashiest companies, have tended to work out better. He guessed that some people follow a job for the clout, or joined successful companies only after the success had happened. Mirzadegan offered the hypothesis that people with fancy logos have less to prove than someone for whom the role feels existential, and Kleczynski agreed.
“I found the people that have the greatest backgrounds on LinkedIn often performed the worst.”
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Mark Roberge said it is intuitive to hire for prior experience, and that most CEOs and inexperienced sales hiring leaders do so. He said it does not hurt to have experience but that focusing only on it leads to bottom-half performers in the industry. He argued that DNA, meaning traits such as work ethic, is a bigger driver of success.
“those people that put the most weight on years of experience selling to my buyer and my product type, fails.”
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Mark Roberge says founders often look for specialists when hiring a first sales leader, marketer or product leader. He argues that a company still pivoting does not yet know its product, messaging, market or marketing, so a specialist can feel like a square peg in a round hole.
“when we hire athletes who are smart, who execute, who want to learn fast, who want to work hard, we set ourselves up more optimally for finding the right answer.”
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said Dasha (The Dave Gerhardt Show), Kevin Mandia (Grit), Chris Vik (Revenue Builders), Jeremy Allaire (Grit)
Dasha lays out the reasons to join and the reasons a candidate probably wouldn't want to. Her example: someone who dislikes ambiguity and wants a clear swim lane won't fit a Series A startup. If a candidate balks, both sides have avoided a bad fit. If they are excited to wear many hats, it is a good fit.
“We call that the anti sell. And it works so what you're like, look. Here are all the reasons you should join. And here are all the reasons you probably don't wanna join.”
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Mandia says that as a self-funded company, Mandiant told new hires they would be billed out about 80% of the time and that the company could then hire two more engineers. He says they attracted people by saying they would work twice as hard but be twice as good. He says there was no lifestyle selling.
“We literally attracted people by saying, you're going to work twice as hard, but you'll be twice as good.”
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Chris Vik said that when recruiting for a small company from Copenhagen, he labelled up front the two questions candidates would likely have. First, why would you join a small company the world has never heard of. Second, why would you be excited about a company that does quality assurance and test automation. He said labelling them matters because those objections will hit you later in the recruitment process.
“it's really important to label it because you know that those two objections will hit you down in the recruitment process”
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He said Circle's mission is a major transformation that could contribute to global economic prosperity, but that it is hard because the world does not believe in it and because it requires changing laws and managing constant macro shocks. He said the breadth of the subject, covering law, regulation, technology, economics and cryptography, is also difficult. He said he tells candidates it will be the hardest job they have had when he is directly involved in hiring them.
“I always tell people this is gonna be the hardest job because the world doesn't believe in it and like that's uncomfortable for people.”
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said Jesse Zhang (Grit), Michelle Bove (Revenue Builders), Lindsay Shookus (Revenue Builders), Kevin Mandia (Grit)
He says deciding where to spend time is a constant effort of self-reflection but not especially hard. What is hard is evaluating early hires when you may have no clue what you are doing yourself, because you then have to judge whether someone will be world-class at it. He says this gets easier once a team starts forming.
“I think the hard part is like forming the initial bench of like just like teammates that can do a lot of things that you would be doing and do it better than you.”
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Bove says her goal as an RD is to hire people who are better at sales as a rep than she is, and that she builds a tree of strong people by promoting from within. At Zscaler she took over a team of reps who had sold far more software than she had, and she says RDs must humble themselves rather than feel intimidated.
“your goal is to hire people that are better at sales as a sales rep than you”
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Lindsay Shookus said Lorne Michaels told his team to hire people who can take their job and let them be so good that you are scared they might take over. She recalled being threatened by one candidate around age 26 while leaving her role, but later saw the two women she hired for her department now run it. She said Lorne was good at not micromanaging strong people, such as a set designer.
“hire people who can take your job. Like, let them be so great that you're scared they might take over for you.”
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Mandia says leaders for sales, marketing and engineering are needed early. He warns that hiring functional experts too early, such as legal counsel or a CFO, can build an org that grows out of proportion, and gives the example of having 30 attorneys. He says he hires people who are better than him to run their functions.
“you got to be careful, but when it comes to the things like sales, marketing, engineering, those leaders, you need pretty early.”
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said Katy Bone ([Un]Churned), Frederik Maris (Revenue Builders), Chris Vik (Revenue Builders)
Katy said she had never done an EBR and sent the prep even after a friend told her it was not needed. She said she did it because it was something she would do if she worked at Gainsight. She later learned from the recruiter that the panel thought they had missed a real EBR because of that email.
“So before that interview, I sent out an EBR prep to everyone.”
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Frederik says that in the first 20 minutes he has an open conversation, asking how the candidate prepares for a meeting, how they run it and what they do in it. He then asks why they have not done that in this meeting, and asks them to rate their progress against the goals they set. He says this shows whether they can correct course and pushes them out of a standard demo routine.
“so why why haven't you done that in this meeting”
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Chris Vik said his team treated hiring as an audition and asked leaders to check whether candidates prepared, took notes, sent a summary, knew the value proposition and understood the market. He argued that if candidates did not qualify whether the opportunity was worth their time, there was no basis to trust that they would qualify once hired.
“how someone does anything tells you how they do everything”
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Jonathan said that candidates who research the product will cover 10 to 15 features or benefits in a five-minute pitch, which he takes as evidence of work ethic. Using a hurdle such as at least 10 features or benefits as an example, he said this makes the judgement binary for the manager. Candidates pitch three times and must improve each time, which he treats as evidence of coachability.
“let's say the hurdle is you gotta have at least 10 features or benefits that you touch on during that five minute pitch.”
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said Christopher O'Donnell (The Science of Scaling), Marc Ferrentino (Topline), Aviv Canaani (The Revenue Leadership Podcast), Arvind Jain (Grit)
He says there are many skeptics and you have to find people who are genuinely, deeply curious. This applies across the company, not only to engineering; everyone at Day AI uses Claude Code for most of their work. He says this holds whatever your business is, not just because Day AI sells an AI product.
“The people who think that stuff is unbelievably cool and are already playing with it nights and weekends and then figure it out from there.”
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Marc says his developer interviews used to be a written test with no AI, but they realised that did not measure how productive candidates would be, so seeing how people use AI is now part of the interview. He says the same logic applies to marketers: he wants the 10x marketer, and a marketer who knows how to use AI is a 100x marketer, which is the person he wants on the team.
“we're all looking for the 10x developer, but the 10x developer who knows how to use AI is a 100x developer. And so it's the same thing with the marketer.”
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Aviv says some team members, such as the director of RevOps and the head of creative, came in with other backgrounds but love AI tools. He says AI adoption is a personality trait, and that people who are not open to it may not be the right fit. He says the team is not all AI-first but that enough people should be comfortable with it.
“No one comes with like 10 years of experience like in AI.”
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Jain says Glean changed its interview process to check whether candidates are inquisitive and AI-forward. He says the company does not expect anyone to be an AI expert. Glean still looks for hard work, talent and teamwork in every hire.
“the goal for AI fluency is not that are you an AI expert? Are we not expecting anyone to be that?”
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said Jonathan Moss (The Revenue Leadership Podcast), Sam Jacobs (Topline), Eleanora White ([Un]Churned), Jared Collins ([Un]Churned)
Moss says the need varies from about 10 to 40 hours a week. Contracting it frees full-time headcount for generalist, AI-capable builders.
“And if we need specialties we can contract that for the amount of time that we need it because we also don't need it all the time.”
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His criteria are a foundation in revenue architecture and how recurring-revenue businesses work, generalist GTM and operations understanding (with domain-specific agents such as a marketing ops agent filling gaps), curiosity, systems thinking and agency. He says people who use AI only as search are probably not a fit. He sometimes hires from engineering or other functions and teaches revenue architecture.
“The second thing is we look for more generalists than specialists.”
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Sam Jacobs says he sees specialization within a function collapsing. He argues this does not diminish the need for the function but creates an opportunity for people who are more fluent in cross-functional tools to be effective.
“I see the collapse of specialization within a particular function. That doesn't diminish the need for the function, but does create an opportunity for those that are more fluent in all of these cross-functional tools to be effective.”
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Sam says his own team wants to be general marketers and feels the leverage from AI lets them work across functions within marketing. He expects the marketing team to still exist but the roles within it to become more cross-functional, because the intelligence of how to run each discipline will sit within AI rather than in discrete functional specialists.
“the role of the people within the team will be more cross-functional because the additional intelligence of how to do that function will be embedded within AI as opposed to a discrete functional discipline.”
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She said she does not think the company will get away from the generalist CSM, while strategic accounts will still need specialists. She argued the specialist information will come through the agents the team designs, which lets CSMs work at scale and still deliver.
“I don't think we're going to get away from that”
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Collins said he expects CSMs to be dangerous on a lot of topics, enough to know when to bring in a specialist. Dell can draw on large teams of experts and on its view of similar customer profiles. He said the principle is that everybody owns the customer relationship, and the CSM's job includes bringing the right people in at the right times.
“I kind of expect my CSMs to be generalist in the sense they need to be kind of dangerous about knowing a lot about a lot of things”
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said Venky Ganesan (The Twenty Minute VC), John McMahon (Revenue Builders)
Ganesan said describing yourself through friends' eyes externalizes the question and reveals self-awareness. He then runs references to see whether they match. In his view, founders who know their weaknesses can manage them; the ones blind to their weaknesses usually have trouble.
“I'm trying to see if the references match someone's self-awareness... It's the people who are blind to the weaknesses that usually have challenges.”
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John says he recently told a candidate he knows the three bosses they listed from their last three jobs and will call them, then asked what those bosses would say the candidate struggles with. He also asked what he as their potential leader would need to do to help them elevate. He says authentic answers show who people really are. Brad responded that this tests self-awareness and willingness to be vulnerable.
“But when I call them, what are they going to tell me that you struggle with?”
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John McMahon uses this question to see how a candidate perceives their own performance and how they read his reactions to their answers and questions. He notes that salespeople ask themselves the same thing in front of customers. He says he is not looking for a right or wrong answer, but for how the candidate frames the situation.
“How do you think you're doing in this interview?”
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She said the question is not specific to startups but tests whether a candidate can think 'could we have done something different?' She finds people more open as individuals when they answer it.
“I like to ask, you know, what's their biggest career mistake so far and what would they do to change?”
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said Asad Zaman (Topline), Frederik Maris (Revenue Builders), John Kaplan (Revenue Builders)
He described a large software company whose VPs and directors listed traits on three whiteboards in a hiring workshop, with each person naming different attributes. He said none of the traits were wrong, but the group lacked a common language to evaluate candidates. Keenan agreed and went a layer further, asking whether anyone had analysed what the job actually requires.
“None of these are necessarily the wrong thing to look for. But none of you have said the same thing. You don't have a common language.”
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Frederik says an unstructured hour can end with only a feeling about whether he liked a candidate. He now prepares a sequence of questions that qualifies, during the interview, the attributes he is looking for. The result is a clear reason to like the candidate and a clear view of the risks.
“at the end of the interview instead of saying I like this person you know exactly why you like that person and what the risks are”
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Kaplan says Force Management created a success profile for a major recent hire, and candidates and interview conversations were both measured against it. He says the profile is table stakes and that hiring decisions should be evidence-based rather than made on general impressions.
“for me the success profile is to center of the universe It's that you know The competencies and success behaviors Of what success looks like evidence? Of what Success looks like in the role”
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Mark Roberge said to identify the top 10 reps, find what they share, and use that as the hypotheses for an interview scorecard. For each attribute, write three sentences defining it, plus a paragraph showing what a high, medium and low score sounds like. Every six months after a hire, check whether the hire performed and whether the scorecard predicted it, then iterate.
“And every six months after we make a hire, we assess. Do they do well or not? And did the scorecard catch it?”
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said Lauren Hughes (The Revenue Leadership Podcast), Asad Zaman (Topline), Mark Roberge (The Science of Scaling)
The team compared ramp for hires from competitors or prior PEO roles with hires from SaaS or other businesses. Lauren Hughes said prior PEO hires ramped faster 'for the most part', and that people from adjacent businesses like rental car sales 'sometimes' work well. She thinks the profiling also helped ramp time.
“people who've worked in sales at like rental car companies sometimes work really well.”
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Asad Zaman says enterprise sales is a different craft once a company has a brand and infrastructure behind it. He says a mid-market person can be hired into an enterprise role, or an enterprise person into a strategic role, but there is little flexibility beyond that. Companies that have scaled very fast, he says, often find candidates won't even take their calls.
“The thing about mid-market and enterprises, you kind of need people that have certain like relevant experience.”
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He says many founders overweight industry experience at the expense of proven enterprise sales experience. He describes a veteran with 10 to 20 years in the industry who is only a 50% performer, and says the enterprise seller from SaaS will win.
“I would much rather teach someone how restaurants work than to try to teach them how to do really good enterprise selling.”
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Ron Gabrisko calls hiring from his network the cheat code, because he knows what he is getting. He also says hiring people already in the industry helps, since they already know the market and the product.
“The cheat code is I'm hiring for my network so I know what I'm getting.”
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Ron Gabrisko says that hiring people from big data and from the same space removed a learning curve, so they did not hire people with no real experience. He says that by three to six months in, you have a good idea of who is putting in effort. He expects that people with effort who come from the space will eventually be successful, and most of those hires were pretty successful going into year two.
“So we hired people that came from big data and came from this space.”
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said Alan Chhabra (Revenue Builders), AJ Bruno (Topline), Seong Park (Revenue Builders)
Alan says most AI companies are engineering-heavy, so a partner leader without technical grounding will be seen as the stepchild. He says he used to believe technical skills could be taught to smart people, but no longer does, and he does not require two engineering degrees, only real technical fluency. He says relevant backgrounds include understanding piping, cooling and water.
“if you are a candidate that doesn't understand technology in this landscape”
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He says this is not a one-to-one match to any single profession. He says QuotaPath has always hired from curiosity, as startups typically do, and it now screens for curiosity about how candidates can handle technical tools.
“okay, you know SQL, but you don't have to write in SQL ever.”
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Seong says Cursor has had success moving product managers into go-to-market roles, because they come from a credible technical base and can be coached on account management and soft skills. He also says pre-sales people make an easy move into the customer success function. He adds that management consultants with an AI-native mindset are also good fits.
“Looking at pre-sales people, right? Because again, that is a very easy evolution.”
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said John Kaplan (Revenue Builders), Marcin Kleczynski (Grit)
Kaplan says he asks every reference the same question after saying they like the candidate, and that it worked well in a recent hire at Force Management. He says references who want their friend to succeed give honest answers about areas where the person struggles.
“I always ask the same question. Hey, we like XYZ person also. We like them a lot. What is the one thing that you think I'll be able to help them with the most?”
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He said he has never had a reference go badly, so he assumes references will be positive by design. Instead he asks the reference what he needs to look out for in the first 90 days, and says the truth usually starts to come out in that answer. He says he uses the answer to help the person even when the hiring decision has already been made.
“I'm getting to know this individual in the first 90 days, what do I need to look out for?”
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Mark Roberge says the traits they look for in sales leaders are managing conflict, coaching, and being exceptional interviewers. The question asks the referee to rank the candidate on these three, which forces them to name strengths and average or below-average areas rather than give constant praise. You can then match the ranking against your own read of the candidate, for example on coachability.
“can you rank them from strongest to, for one, two, three for this individual?”
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Mark Roberge said references tend to be overly optimistic and want to be nice, so he asks them to rank a candidate on work ethic, coachability, culture fit and working well in a team, from highest to lowest. He says this shows what the person is exceptional at and what they are only above average at, and lets you check their answers against what you have already understood.
“Can you rank this individual, each of those attributes, from highest to lowest.”
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said Gaurav Agarwal (Topline), Cassie Vaughn ([Un]Churned)
He said generalists will not take over, but specialists with more than two or three spikes will absorb those spikes. He used the example of a growth person who also understands data, sales ops, sales and success. He said which spike eats which is yet to be determined.
“the one with the best taste and the drive to work and learn and improve, eats up adjacent departments.”
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She said the job description she is using for future CSM hiring is someone with deep domain expertise who can speak to customers' objectives in a real way. She recommended specialising in an industry, a function or a use case deeply to its core. She said a self-starter who keeps up with AI and tools matters more than someone who simply runs a playbook, since the playbook work is what AI will do.
“stop being a generalist and specialize in something like learn an industry, learn a function, learn a use case deeply to its core”
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said Asad Zaman (Topline), Parag Agarwal (Grit)
He says companies are hiring many SDRs, BDRs and SMB AEs, along with an aggressive number of technical sellers. He argues that even if every company became 50% more efficient per head, growth in the market would keep headcount rising. He cites a company with 300 employees aiming for $2 billion in revenue this year as an example of that growth.
“I don't see any situation where companies are not hiring BDRs, SDRs. I don't see it.”
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He says it seems counterintuitive, but if there are many valuable things to build and customers need them, more engineers are better until you saturate the opportunity space. He attributes today's extreme growth rates in some companies to multiplying three factors: how fast and well you can hire, how quickly you can channel that capacity into valuable things, and how fast customers adopt them. He has never once concluded he needs fewer people because everyone is more productive.
“I have never once sat down and been like, oh, Everyone's going to be so much more productive. So maybe I need fewer people.”
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Asad says that compared with companies from previous eras, AI companies are leaner at each stage. He says they are moving through stages at a pace never seen before, which creates strong demand, citing Anthropic growing about 10x a year on revenue. He says the number of employees those companies need over a year is staggering.
“If you look at companies per stage and stage and compare them to companies from previous eras, they are leaner per stage.”
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said Jason Forget (Revenue Builders), Asad Zaman (Topline)
Jason cited Richard Branson's quote that it is better to have a hole on your team than an asshole, and said the second rule is fire fast. He said leaders weigh whether someone producing something is better than reinvesting in someone better, given quota coverage. He said leaders should own the mistake, take corrective action, ask what they learned, and ask references that question next time.
“fire fast. If you've clearly made a mistake, address it quickly and move.”
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Austin argued that a C-level performer lowers the energy of everyone around them and affects the company's future potential. He said one bad event is remembered more than ten good ones, so the cost of a weak performer is outsized. He said he does not see this as being transactional, and that failing to correct it is a mistake.
“the C player is driving everyone's energy down and is impacting everyone's future potential”
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She said she would put the pedal to the metal on hiring again, but would be cognizant of who she hires and would not shorten interviews to save time. She said that if a hire is not a good fit, the decision should be made quickly.
“I really think hiring fast but constantly looking at the talent that was hired and making if you need to make that you know decision that's not a good fit do it quickly right”
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said Jesse Zhang (Grit), Carlos Delatorre (Revenue Builders)
Decagon roughly 10x'd its team in a year, from about 50 to about 500 people. Zhang says that at this pace you have to plan ahead, because you cannot reactively hire this many people without things breaking. The first roughly 100 people were not hired much ahead of need.
“Now, of course, we do hire ahead just because you have to. You have to plan out where you are. Because otherwise, you just cannot reactively hire this many people and things are going to break.”
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He gave these timelines as the reason a senior leader needed six or nine months out has to be searched for well in advance. They are his experience-based estimates from scaling MongoDB.
“it could easily take six months to find them ... and another three months to ramp them”
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Carlos said the team looked strong from outside, but he had not hired senior leaders early enough for the growth rate, and by Q4 the team was well behind plan. The team made the number only through heroics, when Carlos said it should have been a celebration at 120 percent of the number.
“we were probably 10 heads behind plan, maybe 12 AEs behind plan.”
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John's example is a business doing 20 this year and 40 next year, heading toward 80. He says it may need five third-line leaders and ten second-line leaders, and that waiting until the start of the year is too late. He says companies that do not do this often think they are saving money, as the CFO will tell them, but productivity drops and attrition rises.
“instead of five to one, now they go six to one, seven to one, eight to one.”
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said Alex Varel (Revenue Builders), Sam Jacobs (Topline)
Alex says he would encourage his daughter to present agents that act as multipliers of herself in an interview, similar to an artist showing a portfolio. He says sellers without hands-on experience augmenting their productivity or supervising agents will be less capable.
“I want her to come and show the agents that are multipliers of herself, extensions of herself”
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Sam Jacobs says that when moving from SaaS into AI, your application should show you know how to use these tools. He gives examples of building your own personal website or a tool such as an ROI calculator for hiring you. He says this can be used in the job application, interviewing or networking process.
“building your own personal website, building some kind of video game like an ROI calculator for hiring you or something”
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Sam Jacobs says he has been helping people find work and has seen candidates for VP of marketing roles send apps and websites they built with Replit, Lovable or Claude. He says candidates need to show they can work with these tools practically, through conversations with hiring managers and CEOs, not only in theory. He also mentions maybe demonstrating agents you built, trained and leveraged, such as with OpenClaw.
“your work product needs to speak for itself”
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Rosenthal said that when she interviewed at OpenAI, she had to build an app with the API in Python as a final project, and that she kept this part of the candidate process until recently. She wanted candidates to experience sending an API call to GPT and getting a completion back, which she said is mind blowing. She said candidates could get help, but she wanted them to explain what was happening and the limits of the API.
“I want my candidates to experience of sending an API call to GPT and getting a completion back because it is, it's just mind blowing.”
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said Sam Jacobs (Topline), Carsten Schütz ([Un]Churned)
The speaker says no one is looking to hire an AI denier into an AI company. They say what hiring managers want is someone who understands the tools' power as well as their limitations. They warn that going too far into what humans still do can create friction for the candidate.
“no one's looking to hire an AI denier, right, into an AI company”
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Sam Jacobs says candidates should use the tools themselves and then talk clearly about their limits, so hiring managers see where the tool stops and humans take over. He notes that nobody yet knows whether Claude will replace Salesforce or just interact with it, so a candidate who draws that distinction confidently is what hiring managers want. He says this matters more than whether the candidate has every answer.
“Here's where they work. Here's where they don't work and here's where their limits are.”
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He says many candidates know how to help a customer but think only in one-to-one situations. He also looks for candidates who understand which work should stay with humans and which AI can handle, beyond simply automating tasks.
“So they don't think of, OK, this works for this one customer, but how does that scale?”
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Rosenthal said the interview process asks candidates what the limitations of the API are and what they think would be a really hard use case right now. She said she wanted candidates to show they understood that generative AI is its own type of AI with its own limits, and not to jump to every possible machine learning exercise such as predictive analytics.
“What are the limitations of our API? What do you think would be a really hard use case right now?”
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said Adrian Rosenkranz (The Revenue Leadership Podcast), Amanda Kahlow (Revenue Builders)
He said the skill of knowing one tool best is changing, and listed three needs: people who judge whether agents do good work, people who manage constantly evolving knowledge bases, and builders who turn business owners' needs into agents. He said these could be one person or several.
“who are the people on the team that are going to be managing the knowledge bases that are constantly evolving and learning that are used in a bunch of different other workflows?”
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Kahlow says her solutions engineer no longer joins customer calls because the superhuman does. His job is now to train it, collect information from every source, and maintain the brain that replaces his old role, which she describes as no longer forward-facing.
“He is actually building the brain that is replacing himself.”
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said Jason Forget (Revenue Builders), Michelle Donnelly (The Revenue Leadership Podcast)
Jason said that in the early days they looked for grit and people who had grown up in family businesses, played college sports, or served in the military. He said early hires do more transactional deals with fewer long cycles. A host added an example of a CRO hire who struggled at a startup because it had no expense reports or laptops.
“We always tended to look for people that, you know, if someone came from a home that had a family business, really liked those people.”
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She said she goes after people who have done brutal sports and are grinders, and that she looks for grinders in this type of company. She said spotting great talent and giving them the chance to win and be seen is central to her role.
“I hire great people. All of my BDRs are athletes.”
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said Mike Carpenter (Topline), Bob Ranaldi (Revenue Builders)
Mike said his operations groups were abnormally large compared with the rest of the organization and with peers at other companies. At CrowdStrike he said he argued with the board constantly about how many analysts he needed. He credited this staffing with the difference in results over his career.
“I had really large ops groups abnormally large compared to the rest of the organizations that existed around me”
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Mike said he recruited an MIT graduate who had been a financial analyst at Goldman Sachs into a sales organization. Her job was to go through all of the team's numbers and every activity to find anomalies. He said the anomalies were what separated making quota from missing it and growing pipeline from failing.
“her job was to rip through all of our numbers and every activity we did and find anomalies.”
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Bob said he sometimes suggests a RevOps person to fill the data gap, so the CRO is not pulled into tasks that someone else could do better. He described the result as the CRO doing their own job very well while other resources strengthen the data side.
“Let's not bring down the real value points in a CRO by trying to take him or her off to do some things that maybe a RevOps person could do or a finance person could do perhaps better.”
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Mark Roberge said he thinks technical founders have gone too far by wanting a sales leader who can build the data and understand data science at an extremely deep level. He said a data-driven culture is critical, and that the sales leader should have a right-hand analytical person to produce and interpret the data.
“they tend to want to hire someone who can actually create all the data and understand the data science at extremely deep level that's not the job of the CRO”
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said Asad Zaman (Topline), Kyle Norton (The Revenue Leadership Podcast)
Asad Zaman says that if AI results depend on the person using it, companies have a bigger incentive to hire the best people. He says this supply of top talent is roughly flat while demand grows, so prices rise.
“So it drives demand for the very best people.”
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The speaker said SaaS go-to-market models were built around B players because they were easy to find and hire. He said the volume of hiring means many will be B players, but leaders should be willing to hunt for rainmakers and then work to make them more productive. He said the SaaS era penalized A-plus performers as territories shrank, and they often left.
“I think having the audacity to say, I'm going to go and look for these rain makers and it's going to be hard to find.”
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In answering what separates a great CRO from a good one, Michelle said collaboration and surrounding yourself with the very best talent matter most, and that the people part of the job will never change. Kyle responded that the best people are worth even more today than in the past and called it a lesson to double down on.
“If anything, the best people are worth even more today than they were in the past”
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said Marc Ferrentino (Topline), Kristi Faltorusso ([Un]Churned)
Marc agrees that you might need three developers instead of six but still need a developer, and applies the same logic to marketing. He says product marketing or performance marketing will not simply be handed off to AI, and that the individual becomes more productive. He frames this as the next step in a long run of productivity technology.
“It's not that you are replacing someone or you don't need to hire someone. It's that you're making, it's really, I mean, most technology has been a productivity tool for pretty much all of our lives.”
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She says she does not see roles going away, but expects their scopes to evolve, so job descriptions will look very different from those posted over the last 15 to 20 years. She says she does not yet know whether execution will match the paper change, because that level of change takes a long time.
“The customer success role will inherently look very different on paper.”
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said Michelle Bove (Revenue Builders), Lindsay Shookus (Revenue Builders)
Bove says a candidate can be flawless over Zoom or on the phone and then different in person, so she brings a third person to lunch to see how the candidate interacts with someone else. She says you can learn in about an hour whether the person can hang out and whether others want to talk to them, including how they treat the waiter and coworkers. She calls it the lunch or beer test.
“Bring a third person to that lunch, see how they interact with somebody else.”
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At SNL, candidates who auditioned were brought back out and the team spent time with them, and everyone who was hired came and spent time socially with the team. Lindsay Shookus said this helped the team see beyond talent and skill set, because many talented people cannot navigate the show's social hierarchy.
“And afterwards we, we would have them come back out and we would all just spend time hanging with them, right?”
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Lindsay Shookus said Lorne Michaels told the team to take interviewees out from behind the desk. She described taking an assistant candidate to breakfast, where she struggled to hold a conversation and concluded the person was not her fit. She agreed with a host's 'rowboat test' framing, saying hiring people they enjoyed being around worked really well.
“Lorne used to say, like, when you interview people, take them out from behind the desk.”
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said Christina Parra ([Un]Churned), Rebecca Nerad ([Un]Churned), Carsten Schütz ([Un]Churned), Eleanora White ([Un]Churned)
Christina Parra has hired CSMs for seven years across significant market changes. She said what stands out in successful CSMs now is curiosity, agency and urgency, plus willingness to learn and try things themselves. Her example is team members who, whenever Notion launches something, immediately work out how to use it in their own workflow. She looks for these qualities in addition to skills and calls them 'the game changer'.
“what stands out about CSMs that are successful now is curiosity, agency, urgency”
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Nerad said she trains her team on outreach, engagement and listening. She still screens for curiosity and EQ when hiring, because coaching has limits if someone doesn't have those skills naturally. Her team is also currently training on AI skills and comfort with AI tools, as is the rest of Advantive.
“despite the fact that I coach empathy, I also need to hire for it because there's only so far you can go if somebody doesn't inherently have some of those skills.”
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He says customer success was still immature in Europe and Germany at the time, so his previous company, later acquired by SAP, did not expect to find experienced candidates. They looked for people who wanted to keep learning and were good at building relationships.
“there are little to no CSMS who have experience in enterprise architecture.”
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She said Supermetrics has historically looked for people with a hunger to learn and understand their customers' business. She said the ability to learn fast and a natural authenticity in wanting to go deeper are what she has seen set CSMs up to succeed as the team grows.
“that ability to learn fast and that natural authenticity for wanting to go deeper and understand”
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said Joubin Mirzadegan (Grit), Jeremy Allaire (Grit)
For a company he incubated at Kleiner Perkins, Mirzadegan judged that leaving a cushy job for a startup was a personal, household decision, so he spoke directly with the candidate's husband. When the husband asked when the supply problem would be fixed, Mirzadegan said he hoped never, because solving it would mean they were no longer chasing the market. He described current competition for talent against AI labs and overfunded startups as 'full hand-to-hand combat'.
“I said, Hey, we have a supply problem, not a demand problem.”
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He said he always offers to meet with a candidate's spouse, and that spouses have taken him up on it more in the early days. In these conversations he talks about what the company is trying to accomplish, its values, why he thinks the spouse could be an amazing person to work with, and the company's philosophy on people and their families. During COVID he had top executive candidates visit his home for recruiting, with testing beforehand.
“the most important thing is the spouse acceptance factor, right? So you really gotta make sure that the spouse”
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said Simon Farthing ([Un]Churned), Margo Martin ([Un]Churned)
Simon said he would always look first to promote from within, since a talented engineer or technical consultant already knows the customers and the product. He said hiring an FDE off the shelf with no knowledge of either would be quite tough for them to succeed, and that the role can be defined around the internal person.
“if you have a talented engineer or a talented technical consultant, they already know customers, they already know the product.”
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She said an outside hire would have to be taught the business, its processes, procedures, players and three separate organizations, which would be much harder than using someone already there. Her CEO had suggested someone from PwC or a management consultancy who could think strategically. She felt it would be better if that person also knew the business, and Jason Goldsmith had PwC training and IBM consulting experience as well as Deltek knowledge.
“taking someone that's already knows our businesses knows knows our processes knows the procedures knows the players”
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said Parag Agarwal (Grit), Aman Narang (Grit)
Parallel started in stealth, so there was no inbound interest. For almost a year before hiring, he met many people and asked each a standard question about the best three people they had worked with, then met some of those. The founding team was him plus six others, and he deliberately made half of them people he had not known before. He says much of Parallel's later hiring has come through this multi-hop network channel.
“what are the best three people you've ever worked with? And I would go meet some of them over time.”
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Aman said the first 10 to 20 people were mostly known to the founders through their network, so the founders did not do enough rigorous interviewing as they hired fast. By late 2014 the company was growing from about 20 to 50 people, and the performance gap between employees was visible. He identified this as a low point for the company's execution.
“maybe it was all people we'd known in our network as we knew they were good.”
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said Brad Scott (Revenue Builders), Michael Gervais (Revenue Builders)
Brad asks early in the conversation who the candidate is, where they came from and what hardships they have faced. He says that without having faced and overcome tough things, a startup or challenger sales job will be very hard for them.
“if you haven't gone through hardship and you haven't faced tough things and you haven't overcome challenges either in your personal life or your professional career or through athletics, then this job is going to be really hard for you.”
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One of the hosts said he asks candidates what the toughest situation of their life was, and that he has had people break down in his office. He said he learned much more about their character from how they came back from that trauma. Lindsay Shookus added, citing Jamie Dimon, that people who have made mistakes and learned from them are the ones you want to hire.
“I asked people what's the toughest situation you ever been in your entire life”
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Gervais says people who have embraced their fragility and worked through trauma are not whipped around by the external world because they are governed by their values. He contrasts them with people who are still thumping their chest and claiming to be alpha, whom he says not to trust. He describes the first group as the people you want in your life, who will have your back and whom you want to partner with.
“those folks that have experienced trauma and worked through it, they're the best teammates.”
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Ange said many candidates tell interviewers what they want to hear, so she asks about challenges in the past six to nine months and how they dealt with them. She said junior candidates often struggle to name adversity, while account executives usually give a solid answer.
“So I like to talk about adversity and what they've gone through, like anything that they've gone through in the past six months, nine months that really challenged them. And how they dealt with it.”
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said Michelle Bove (Revenue Builders), Bob Kocis (Revenue Builders)
Bove asks candidates who their best executive relationship or favorite champion is, why, and how they turned that person into a champion. She also asks who she could call as a reference and insists it must be a customer, not a co-worker. She says RDs and directors can ask these questions in interviews.
“who's your best executive relationship or who's your favorite champion and why tell me how you built them into a champion?”
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Bob Kocis said he usually asks candidates during the interview process whether he can call one of their customers. He said top sellers who have built great references will offer several names, while many candidates have none because they have not built those relationships.
“Hey, can I call one of your customers?”
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said Brad Scott (Revenue Builders), Frederik Maris (Revenue Builders)
Brad says candidates can seem great after a couple of conversations, so the team treats understanding a candidate's prior experience through back-channel references as one of the most important parts of the process. He notes that in this environment, one degree of separation is usually enough to reach a candidate's former managers.
“Sometimes the back channel is the only channel.”
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Frederik says candidates will name references who speak well of them, so he checks with people he knows who know the candidate. He wants an honest picture of the candidate's strengths and weaknesses. He calls this incredibly important given how good salespeople are at interviewing.
“checking with people that you know that know them or somehow you know you trust to really tell you how they are and what the good things are”
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Sydney Sloan ran back-channel calls on Adam Aarons, speaking with his two former CMOs, who spoke about what a good human being he was. She said that made it easier to have good debates once they agreed to work together. Mark Roberge noted that back-channeling is common practice but that the legality should be checked with legal counsel and HR.
“I did back channel calls. I talked to his former two CMOs and they just talked about what a good human being he was.”
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said Bob Ranaldi (Revenue Builders), John Kaplan (Revenue Builders)
Bob said he applies the ICP concept that John talks about in his book to hiring, defining what the business actually needs first. He said new CROs who rush to bring in their own bullpen without understanding the problems end up with people who have to be replaced. McMahon added that the data should show where the issue really is, such as needing a client success leader rather than new sales leaders.
“define really what is the ideal candidate profile and nail the hell out of that before you go rush off and shoehorn in a CRO or a customer success person.”
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John Kaplan said he often sees people bring in a mentality from a previous job without understanding the culture they are joining or how the business was built. He pointed to Snowflake keeping Chris Degnan in the role after a new boss arrived, and said the company worked out what was already in the kitchen before remodeling.
“first figure out what you got, what's in the kitchen. before you just bring something new”
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said Guy Galon ([Un]Churned), Abbas Haider Ali ([Un]Churned)
He says he has no firm opinion on the generalist versus specialist debate. He thinks small companies probably need generalists who master different aspects, while companies in growth mode probably seek specialists because they scale and need more structure. He says people should be flexible enough to know whether their next role, say at a startup or at a scale-up, calls for being a generalist or for focusing their skills on a specific domain.
“I think you need to be flexible enough to know when you need to be generalist.”
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He said go-to-market functions have incrementally specialized, from SDRs and mid-market and enterprise sellers to solutions consultants, CSMs, TAMs and forward deployed engineers. Early-stage companies don't have those specialized roles, so they look for unicorns who cover everything. Because unicorns are hard to find, let alone a herd of them, companies specialize to create the focus needed to find people and scale the function.
“If you go into earlier stage companies, those specialized roles don't exist.”
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Actions written 10 Oct 2026 from the most useful of 377 recent insights and checked against them.
Doug describes a Princeton professor with a Harvard PhD who published a resume of failures. It lists the PhD programmes he was rejected from, the grants he did not get and the interviews that did not lead to offers. Doug says people need to know that a golden list of achievements does not show the whole path.
“Hij heeft gewoon een failure achter de andere.”
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John McMahon summarised the Lives of Promise study by Karen Arnold, which followed valedictorians for 14 years after graduation. Per his account, valedictorians were typically playing it safe, conforming to expectations and prioritising high grades and test scores over passionate, specialised pursuits. He said real-world success more often comes from deep specialisation and risk-taking than from broad compliance.
“waar ze 81 hoge schoolvaledictorien trakken voor 14 jaar na de gradatie”
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Early at Eli Lilly, Braden went deep on the pain indication of a drug. A leader, Mike Mason, asked whether he was 'a pain expert' or 'a great marketer'. Braden says focusing on the craft let him move across pharma, nonprofit and online and traditional universities, and that he believes he could do the same at a consumer brand like Yeti. The same leader advised taking jobs with 'enough clay to mold something beautiful', meaning a large gap between what is and what could be.
“are you a pain expert or you a great marketer? Because if you're a pain expert, I can never move you to something else? If you're a great marketer, I can put you anywhere.”
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Braden says he has to build 'a hell of a marketing team' that can do justice to the institution, though he has quite a few remote workers. He says one advantage is that he can recruit people out of the corporate world to come to A&M.
“Paying them on a public university salary and get them to contribute at the level that they would at Yeti or Sony or Coca Cola or American Eagle.”
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The speaker said investors long ago learned to negotiate protections for unusual exits, but employees never thought to ask. As these deals spread and people switch companies more often, the speaker said founders need to be able to answer what happens to an employee's equity if the tech and some of the team are bought but the company stays behind.
“what happens to my equity if the company's tech and some members of the team get bought”
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Dev Ittycheria pushed back on claims that 'everything's changed' with AI. He said recruiting, developing and holding people accountable work as they always have. Young founders he advises who have never hired a go-to-market or finance leader face the same questions he faced founding his first company in 1998, such as how to evaluate someone with skills very different from their own.
“I think how you manage people, how you recruit them, how you develop them, how you hold them accountable.”
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Jason Lemkin said that, in his experience, a departing leader could take one person (with some annoyance), asked permission for a second, and faced friction beyond that. He now sees people he regards as highly ethical ignore this. He attributed it partly to pressure to move fast in the AI era. Dev Ittycheria said he had seen people leave and 'carpet bomb' the organisation trying to recruit, which led to stern words.
“I think it's a symptom of change that the rule of two seems to have died.”
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Jason Lemkin pointed to frontier-lab staff rotating between OpenAI, Anthropic and others, carrying knowledge with them. He also cited faster moves and very different compensation among top executives he knows. He said it can bother you, but the culture has changed and has to be accepted.
“I think you just have to expect people will move from competitors.”
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Dasha lays out the reasons to join and the reasons a candidate probably wouldn't want to. Her example: someone who dislikes ambiguity and wants a clear swim lane won't fit a Series A startup. If a candidate balks, both sides have avoided a bad fit. If they are excited to wear many hats, it is a good fit.
“We call that the anti sell. And it works so what you're like, look. Here are all the reasons you should join. And here are all the reasons you probably don't wanna join.”
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Ross says Foundation 'eats its own dog food': it promotes its content, builds software, speaks at events and empowers its team. It gives staff an unlimited book budget as part of its commitment to learning and professional development. He says this draws great people in. The company is fully remote, with staff in Spain, across Canada, the US and beyond.
“We have an unlimited book budget because we are so committed to learning and professional development that people get books just sent to them all the time.”
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Ross says the most important thing in hiring is to be very intentional about upholding the company's values and to show them to interested candidates. He is transparent about how the company works so nothing feels like a trick after the hire. He then gives new hires big problems and lets them thrive.
“the most important thing to hire great people is to be ridiculously intentional of holding up your values of what you care about as a business. And then showing them to the person who's is interested in the role and seeing how they react to it.”
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Asked about sales reps leaving AI labs with $30-40M, Ganesan said truly motivated people stay motivated with money, while those only acting motivated opt out when the money arrives. For A players, he said, money is a way of keeping score and the game is what they love.
“Money doesn't change people. It reveals them.”
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Ganesan said business velocity matters a great deal to VCs, partly because of this effect. A $200M company might give 2% to hire a senior exec, he said, while a company that quickly reaches $2B can give the same person $20M in RSUs, which he put at 0.1%.
“You quickly become a $2 billion company, you don't need to get, you're going to give RSUs and you give the same person $20 million”
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Ganesan said describing yourself through friends' eyes externalizes the question and reveals self-awareness. He then runs references to see whether they match. In his view, founders who know their weaknesses can manage them; the ones blind to their weaknesses usually have trouble.
“I'm trying to see if the references match someone's self-awareness... It's the people who are blind to the weaknesses that usually have challenges.”
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Ganesan asks why these particular people decided they should be the ones to build the company, and how they see each other's strengths and weaknesses. He treats the answers as a 'precog' for how the founders will make decisions and build the rest of the team.
“I think the company you build is a team you build. And so so much of the DNA of a company is set by its founding team.”
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He said bragging about multiplying headcount, like valuations, can become detached from the actual business. It can also mask weak product-market fit by willing growth into existence through hiring. When a new leader asked to be pushed harder, he set that goal of the highest-performing team with the fewest people.
“can you be the highest performing team with the least amount of people?”
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She described a candidate who currently runs a team and would join Vercel as an individual contributor. If she does the job right, with AI applied to it, Vercel would never hire a team under her. Grosser said many people will have to stop valuing themselves by 'empire building' and suggested people 'maybe' will start asking about headcount-to-revenue ratio, which she thinks might be healthier.
“people are gonna start asking, what was your headcount to revenue ratio rather than did you manage a 1,000-person org?”
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She has 10-plus functions in go-to-market. She intends to classify each one: never needs more people than today, needs to add only a few a year, or scales non-linearly with revenue. Then the team would ask whether anything could change the shape of the curve for the functions that must scale. This was a planned exercise at the time of the interview, not one already completed.
“what is the theoretical end state of your function?”
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She said that even when revenue isn't a problem, overhiring blurs job definitions, makes people step on each other's toes, and leaves more new people who don't know what they're doing than experienced ones. She finds lean growth more intellectually interesting because it forces hard prioritisation, automation and use of data. She admitted she has to consciously push herself on this, and that there were points at Stripe where more people probably would have meant faster revenue growth.
“You actually just slow the entire machine down with coordination cost.”
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At Paid, Manny decided he could handle positioning and enablement himself. He now feels he is working all the time because of it. At Outreach, a product marketer was one of his first hires and he says his life was 'glorious'. He describes this as a wrong lesson he took from reflecting on the past.
“I should have done that because I did that at Outreach and my life was glorious.”
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Dan Lee said former Nooks customers are not yet the majority of the sales team but it is getting close. He said it is important when selling to sales teams to have one of the best sales teams, and that customer love makes people excited to sell the product. He said Nooks does not actively recruit customers, and that its CRO was an early customer.
“a large portion of the sales team is former Nooks customers.”
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Dan Lee said ownership is hard to ask about directly because candidates know the expected answer. He asks about their favorite experience, which shows what they look for next, and when they have worked hardest. A favorite experience involving high ownership and building is a strong green light for him, and when the two answers differ he asks them to explain why.
“But if you say what your favorite experience and it's about ownership that's a huge green light for”
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Dan Lee said co-founder Rohan was doing sales while he did customer success, and that Nooks wanted to invest in making customers successful. He added that the CSM was also involved in pre-sales, because Nooks runs a trial in most of its sales processes. Dan said the hire had not been a CSM before but wanted to become one.
“He joined as our founding CSM.”
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Dave says Exit Five is a simple business that produces content, and that the team's ideas cannot be executed without the right people. He says hiring, firing and onboarding have been painful and emotional, and that the current nine-person team is really good, as each iteration of the team should be better.
“most of the problems with the business is mostly who not how problems.”
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He noted that MongoDB is a roughly $20B public company and that people who have been CEO rarely go back to not being one. He inferred that the Meta offer must have been extraordinarily compelling. His point was that whoever has momentum can take whatever talent it wants.
“When you have the momentum, you can make people offers that just allow you to take whatever talent you want.”
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Discussing MongoDB's CEO leaving after less than nine months to run Meta's enterprise division (MongoDB stock fell 20% in a day), he said money matters but so does attention: the products in the headlines that people's families talk about. He said talent feels 'very unstuck' and is flowing to the most important opportunities, unlike past periods when great people stayed stuck.
“One of the benefits of it is that talent feels very unstuck right now.”
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Freya says the nurture role can be an added responsibility for an existing marketer, and a one-person team can use AI to help build the workflows. A dedicated hire could also take on legacy CRM data and cross-sell and upsell, since she says many enterprise clients only focus on net-new accounts and most CRMs hold stagnant data.
“I don't think it has to be an additional hire.”
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Higgsfield has roughly 50 people in California, about 50 remote and over 300 in Kazakhstan. Its core team is people who won international math and physics competitions, and he notes Kazakhstan's 15% personal income tax as a draw. He rejects framing the Kazakhstan base as labor arbitrage, citing talent density, and hopes to create more dollar millionaires in Central Asia than any other company.
“in Silicon Valley, unfortunately, what I'm seeing is that people just jump between jobs every two years.”
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A host compared current equity to per-seat pricing or token usage, paying for tenure rather than outcomes, sometimes because a manager never had the heart to fire someone. They said performance is measured well only in sales, because it is tied to revenue, while functions like engineering and HR rely on qualitative assessments. They hope that as intelligence enters businesses, they can measure performance quantitatively and then structure equity very differently. In what they called an employer's market, they said the alternative is to spin up agents.
“It feels like how we do equity right now is AI tokens. It's usage of a thing like that. It's not the outcome.”
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Around 2013–2014, when AJ Bruno's previous company brought in a new CEO, he argued three early hires deserved more equity. The new CEO didn't know them and resisted, so AJ offered to forfeit founder shares to fund it, which caused conflict at the board meeting. It happened: Lindsay stayed six years, James similarly, and Max left after three years without vesting everything. AJ still works with James and Max. His lesson was that equity can be meaningful if granted 'very focused' and 'with purpose'.
“you can create a world where those shares are really meaningful, but you have to do it very focused and you have to do it very clear with purpose.”
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