Revenue Builders · 10 Sep 2026 · From the week of 7 September
Recruiting the Right People and Selling Real Differentiation with Brad Scott, VP of Worldwide Sales at Glean
These are notes on the conversation, checked against its transcript. The episode itself has the full discussion.
In brief
Brad Scott, VP of Worldwide Sales at Glean, discusses building sales organizations at Snowflake, Veza and Glean, which he says are three very different growth stages. He covers how he interviews for curiosity, hardship, self-awareness and deal judgment, and how interview process discipline affects hiring. He also explains how AI-native products differ from AI-bolted ones, how Glean runs its blueprint and proof-of-value process, and how he sees AI changing sales headcount and work. His central argument is that the caliber of people is the biggest separator between great and average sales organizations, and that teams should stay anchored in fundamentals while messaging changes every 90 days.
For founders
- Leave time at the end of interviews for candidates to ask questions, since weak candidates ask one or two and stop, which Brad says is disqualifying for him.
- Ask candidates about hardship and overcoming adversity, because Brad says people who have not faced tough things will find startup or non-incumbent sales roles very hard.
- Gate proofs of value behind checkpoints: Brad says Glean maps the customer's workflow and gets the economic buyer bought in before plugging in any data, after early-stage experiences of months of wasted engineering time.
- Explain AI-native versus AI-bolted differences with specifics tied to the buyer's role, because Brad says buyers hear the same buzzwords from every vendor.
- Treat the caliber of people as the main lever: Brad says a great product with great people makes a great sales organization, and he ranks people above messaging and market timing.
For revenue leaders
- Ask candidates to walk through a deal they won and a deal they lost, and probe why and how, to get at their thought process.
- Ask candidates what their former bosses will say they struggle with, and tell them you will call those bosses, as host John McMahon says he does.
- Use the back channel for prior-experience checks, since Brad says salespeople are good at selling themselves and the back channel is sometimes the only channel.
- Have reps automate prospect lists, LinkedIn outreach and customer value decks, since Brad says the best reps on his team have done this to free time for learning and customer work.
- Give rejected candidates direct, compassionate feedback on the specific gap, since Brad says leaving them to linger hurts reputation and referrals.
What was said 24, most useful first
Leave space at the end of an interview for the candidate to ask questions, because weak candidates ask one or two and then say they are good. Listen
Brad says candidates who truly want to understand why this company and opportunity matter keep asking questions, and those who stop early will not pass his screen. He treats the quality of their questions as evidence of the curiosity they will need in discovery with customers.
“I like to leave space at the end of every conversation for the person on the other end to ask me questions.”
Candidates who have overcome hardship in life, career or athletics are better bets for startup and non-incumbent sales roles. Listen
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.”
Ask a candidate what their former bosses would say they struggle with, and tell them you will call those bosses. Listen
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?”
AI-bolted products are older products with an AI module attached, while AI-native products are built with AI as a core part of the product from the start. Listen
Brad says every company now claims to be an AI company, usually because some module uses an LLM. He says buyers hear the same story and buzzwords, so sellers need a deeper education on what is a truly unique differentiator and why it matters to that specific buyer.
“it's an adjunct product or something that hangs off of it is much different than a product that was built intentionally from the ground up with AI as a Core part of it”
Systems of record are hard to replace with AI, because they are wired into many departments and underpin revenue, so AI will not simply vibe-code them away. Listen
Brad says pulling the inner workings out of products that underpin Fortune 500 revenue is incredibly painful, so he expects replacement to take much longer than the disruption thesis suggests. A host added that companies typically bought at least five packages to attach to Salesforce and wrote their own code in each department, and Brad agreed that ripping it out would kill the patient.
“everyone can't vibe code their own salesforce and those systems of record are going to be pretty sticky.”
The best reps on Brad's team have automated daily and weekly work such as prospect lists, LinkedIn outreach and customer value decks, freeing time to learn and get in front of customers. Listen
Brad says the freed time lets top reps learn from the best people, study their process and spend time in customers' offices. He says AI makes the best reps much more productive, while average reps can level up by removing manual work like QBR decks and research.
“they have automated their like daily and weekly processes. So their prospecting list, their LinkedIn outreach, their, you know, creation of customer value decks, etc, like all of that happens.”
Glean's blueprint stage maps a customer's real workflows, with the economic buyer bought in, before any proof of value starts and data is connected. Listen
Brad says the second stage of Glean's sales process is the blueprint process, where the team sits with business units such as sales, engineering and legal to map how work gets done today. They then ask whether transforming that process has value and ties to the outcomes the customer wants, and only after the economic buyer is on board do they plug in data sources and systems for a proof of value.
“we call the blueprint process, we actually come into your office, we sit down with you”
Early-stage companies get burned by proofs of value that absorb engineering and product time for months without a result, so Glean now uses checkpoints before starting one. Listen
Brad says that early on, when companies are begging for people to talk to them, they run into proofs of value that drag on. Four months later they have spent sales, engineering and product time and have nothing, and the deal sits on the forecast for quarters, which is why Glean now sets checkpoints.
“And then it's four months later, you've sunk all of your time, all of your engineers time”
Transformative AI programs succeed when the CEO drives them, and they stall when they become technical evaluations handed to a CIO. Listen
Brad says very few transformative AI programs happen without CEO involvement, and he judges the shape of a deal by the C-level sponsorship. Relaying what David from Bain said on stage at Glean's conference, he says that when a CEO's initiative to change business outcomes is handed to a CIO and becomes a technical look under the hood, it becomes a coin flip and takes much longer to implement.
“very few transformative AI programs happen within companies now if the CEO isn't involved”
Brad cites almost a billion dollars of ROI over three years from a General Motors system that speeds up car design, built by Glean's team on site. Listen
He says Glean's team went out and worked with General Motors to build a system that brings many data sources and disparate teams together to design vehicles faster. He uses the figure to argue that earning time and buy-in from a customer is what makes it possible to build solutions that transform the business.
“Their ROI on that is almost a billion dollars over three years.”
Glean places forward deployed engineers after SEs and AI outcomes managers have taken a customer to a set state, and chooses where to spend them by whether the industry is new and the outcome can be repeated. Listen
Brad says Glean's FDEs come in on the tail end and go the last mile to customize the technology, while many companies use FDEs to prop up a technology gap. He says the decision on where to place these scarce people asks whether the industry is new to Glean and whether the outcome designed with the customer can be made repeatable.
“is it an industry we haven't been in before and is that industry and if that outcome that we go design with that customer then repeatable”
John McMahon's four questions for value messaging are what problems you solve, how you solve them, how you do it better than anyone else, and where you have done it before. Listen
He says these core principles stay the same while the answers change faster than at any point in the last 20 years. He argues that companies able to capture those changes and get them to sellers with the least friction will do well, and that sales, product and marketing need a shared vision for this to work.
“what problems do we solve? How specifically do you solve them? How do you solve them differently or better than anybody else? And where have you done it before?”
The caliber of people in a sales organization is the biggest separator between great and average sales teams, ahead of product, messaging and market timing. Listen
Brad says he sees the quality of people early when he walks into a sales organization, across AEs, sales leaders, SEs, product teams and company leadership. He says that with a great product, recruiting great talent lets you create a great sales organization, and he calls this the biggest differentiator.
“I think very early you can tell and you're struck by the quality and caliber of the people you're surrounded with.”
Listen to the episode Sales team, hiring & comp Link to this
Brad hires for people who are intellectually curious about their teammates, how the company runs, the product, and their customers. Listen
He says great hires push the product team to build better products and dig into a customer's business and how the technology could transform it. He links this to recruiting because a candidate who cannot show curiosity during the sales process will not show it in customer discovery.
“they're intellectually curious about their teammates, the way the organization runs, pushing the product team to build better products, and then incredibly curious about their customers”
Probe a candidate's deal history by asking about a deal they won, a deal they lost, and why and how each happened. Listen
Brad uses these questions to get into how the candidate structured and prosecuted opportunities with other customers. He pushes for full detail to reach their thought process.
“tell me about a deal you've won, tell me about a deal you've lost. Why, How?”
First-line managers have to sell themselves as well as the company, because reps are joining the manager. Listen
Kaplan says a rep who does not think their manager is going anywhere, and has not been sold on the manager, will not join, because they would be putting a ceiling on themselves. He says the dynamic changes at CRO level, where you can rely more on questioning and selling the opportunity. Brad agreed and added that once trust is earned you can flip back to digging in, but you should not flip so far that you stop digging in.
“if I'm a rep, I'm coming to work for the manager.”
Listen to the episode Sales team, hiring & comp Link to this
In a competitive hiring market, interviewers risk falling over themselves and not digging in, which causes them to miss things. Listen
Brad says the most competitive talent market ever makes interviewers eager to please candidates, so they miss things and fail to dig in where needed. He says the balance between selling and questioning is hard to hold right now.
“I think that's the danger right now is it is such a competitive environment that people are falling all over themselves”
Back-channel references are sometimes the only reliable channel, because salespeople are good at selling themselves. Listen
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.”
At Glean, all recruiting calls are recorded, managers synthesize notes into Greenhouse, and panel interviews are recorded so the final reviewer can check the detail. Listen
Brad says the final sign-off reviewer gets the synthesized notes with links back to the recordings, so they can dig deeper into what was said and how the candidate presented. He says Glean drinks its own champagne, using a tool that automatically ingests that data.
“All the calls are recorded. All the managers then take and synthesize those notes and put them into the tool we use called Greenhouse.”
The right hiring profile changes with company stage, so a candidate who would not have fit at $25M in revenue may fit well later. Listen
Brad says Glean has hired people in the last six months who would not have been a fit three years ago, when it was at $25M in revenue and lacked the resources to train or support them. He says those hires are now going to survive and flourish at Glean because the company has more resources.
“Three years ago here when we were at 25 million in revenue, it didn't have the resources.”
Give rejected candidates direct, compassionate feedback on why it is not a mutual fit, rather than leaving them to linger. Listen
Brad says the worst thing is to leave candidates to wonder why, and he names specific reasons such as position, segment, geography or experience gaps, and what the company does not have in place to support them. He offers to make introductions or to talk again in a year, and says this helps the company's reputation and referrals.
“the most generous thing that you can do is to give direct, compassionate feedback that says, hey, look, this is potentially not a mutual fit.”
SaaS companies that are not true systems of record will be disintermediated, and some will linger as zombie companies for 10 to 15 years. Listen
He says companies that sit across an organization as the blood and guts, rather than as systems of record, will likely have a longer and harder road and will be disintermediated by new companies. He points to Sabre, which he says still exists as a shell of its former self, as an example of how long that decline can take.
“there's going to be this long tail of these other companies”
Brad predicts enterprise software companies will employ more salespeople in five years, with flatter organizations and AEs managing teams of agents. Listen
He says Glean and most of his peers have more SDRs now, not fewer, and that as AI gets cheaper more work gets done, which he links to Jevons paradox. He says the common thought pattern at Glean's Work AI Institute is that organizations will be flatter, with AEs managing agents that do the legwork and drudgery.
“I actually think it's going to be more. I think it's going to be more people.”
Listen to the episode Sales team, hiring & comp Link to this
As inboxes fill with AI-generated outreach, in-person touches like handwritten notes and office drop-offs now differentiate salespeople with customers. Listen
Brad says his inbox is full of low-quality AI slop, and that customers respond to what he calls the IRL stuff, including in-person visits, handwritten notes and drop-offs. He argues that relying on teams of bots and agents is not how buyers want to buy right now.
“The in real life, in person, in your office, handwritten notes, drop offs, all of those sort of like, what's old is new again.”