The Science of Scaling · 1 Oct 2026 · From the week of 28 September
The Future of Outbound Prospecting in the AI Era
These are notes on the conversation, checked against its transcript. The episode itself has the full discussion.
In brief
Dan Lee, co-founder and CEO of Nooks, talks with host Mark River about how Nooks went from a remote collaboration tool to sales software and what AI could mean for outbound prospecting. He covers early choices such as delaying charging and the first hires: a founding CSM, two sales reps at once, and promotions from SDR to AE. He argues sales is hard to automate because buyers' reasoning is not observable and feedback is slow, so human strategy remains central for now. Much of the discussion covers how agents could change territories, sales roles and the bar for sellers.
For founders
- Dan Lee said Nooks should have started charging sooner, which would have shown the team where to focus earlier.
- Dan Lee said Nooks hired its first two sales reps at the same time, on advice it had received, because a single hire takes months to assess and a miss could set the company back almost a year.
- Dan Lee said product sense comes down to ruthless prioritization and customer empathy, since the company can do anything but not everything.
- Dan Lee said that while Nooks focused on sales he spent 60 to 70 percent of his week observing customers.
- Dan Lee said product-led growth did not fit sales software because sales reps lack permission to connect tools and have no discretionary budget.
For revenue leaders
- Dan Lee said Nooks moved its pipeline generation from Outreach to Nooks and doubled the pipeline created over email.
- Dan Lee said Nooks converts 70 percent of trials to paid customers through a white-glove sales process.
- Dan Lee said average quota attainment has been over 130 percent across the last five quarters, with over 90 percent of the team hitting quota on a quarterly basis.
- Dan Lee said Nooks sets sales compensation goals at levels the team is likely to hit, while company growth goals are set aggressively.
- Dan Lee said a CRM records what happened in a deal but not the reasoning behind a sales move, which he sees as a gap that agents would need to fill.
What was said 25, most useful first
Nooks hired its first two sales reps at the same time rather than one at a time Listen
Dan Lee said that when Nooks moved past founder-led sales they hired two reps at the same time, on advice they had received. His reasoning was that a single bad hire takes three to six months to identify, then a couple of months to replace, which could set the company back almost a year.
“if they don't work out, uh, you know, it takes like, you know, three to six months to figure that out”
Listen to the episode Sales team, hiring & comp Link to this
Nooks converts 70% of trials to paid customers Listen
Dan Lee said Nooks runs a trial in most of its sales processes and today converts 70% of trials to paid customers. He described the sales process as white-glove, and said the founding CSM was involved in these pre-sales trials.
“we convert um 70% of like trials to paid customers”
Charging for the product sooner would have shown the team where to focus earlier Listen
Dan Lee said Nooks did not try charging at all for its first couple of years, when it was run as a project rather than a company. He said the team would probably have figured out much sooner where to focus if it had started charging sooner. He called this a great lesson.
“we probably would have figured out much sooner where to focus uh if we had uh uh started charging sooner.”
Product sense is ruthless prioritization, not building more features Listen
Dan Lee said it is easy to build a ton of features, so the hard part is knowing what is important. Nooks lives by a do more with less value, and he described its approach as rigorously evaluating options against each other and setting clear north-star metrics and leading indicators.
“we can do anything but not everything.”
Ask candidates about their favorite and hardest-working experiences to surface ownership Listen
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”
Dan spent 60 to 70% of each week observing customers using the product while Nooks focused on sales Listen
Dan Lee said that when Nooks went all in on sales, he spent 60 to 70 percent of his week observing customers using the product, which he described as the majority of his time. The team did this by spending time on the sales floor with the sales teams using Nooks.
“Um definitely the majority like 60 70%”
Switching pipeline generation from Outreach to Nooks doubled the pipeline created over email Listen
Dan Lee said Nooks moved its sales team's pipeline generation from Outreach, a sequencing campaign tool, to Nooks. He said this doubled the pipeline created over email. Asked why, he said writing good AI-generated emails is very hard and that Nooks invested heavily in the product experience, including the style and strategy of what gets written.
“we actually doubled our pipeline created over emails.”
Listen to the episode Pipeline & demand generation Link to this
Rep territories exist because of human capacity limits, which agents could change Listen
Dan Lee said a rep has a limited territory, such as a patch of about 150 accounts, because they have only so much capacity to keep accounts in context and to send emails and make calls. He said that if agents could understand sales strategy as deeply as a rep, companies could scale by building agents rather than hiring armies of sales reps.
“they only have so much uh capacity in their head to like you know keep all the accounts in context.”
Treat an account like a chess game: map the board, set a strategy, then plan several moves ahead Listen
Dan Lee said selling to an account is a complex human game of chess. First you map the board: the situation, the stakeholders, their problems and priorities, how they influence each other, and who decides versus who only influences. Then you choose a strategy, such as top-down or bottom-up, and plan a few moves ahead, such as whether an email leads to an event, a demo or a white paper.
“where first you need to understand the board.”
Sales lacks a fast feedback loop, unlike coding, because buyers' reasoning is not observable Listen
Dan Lee said models are good at coding because code is fully observable and can be compiled and tested. Sales is the art of influencing a buying decision across several people, and you may not know how a conversation went until months later. He said sales is also adversarial, multiplayer and under-constrained, which is why he thinks it needs human taste and judgment.
“I don't know how that uh you know, how that sales conversation went until 3 months later if they signed the contract or not.”
Product-led growth did not fit selling to sales teams because reps lack software permissions and budget Listen
Dan Lee contrasted Cursor, where engineers have budget and access to connect their tools, with sales reps who lack permission to connect Salesforce and have no discretionary budget. He said sales managers may also object when reps use many different tools, so the product-led motion made less sense for Nooks.
“whereas sales reps don't have permission to connect Salesforce uh and they don't have discretionary budget”
Average quota attainment has been over 130% across the team, with over 90% hitting quota each quarter Listen
Dan Lee said the average quota attainment across the sales team was around over 130 percent across the last five quarters. When asked what percent hit quota on a quarterly basis, he said over 90 percent. He attributed the team's reputation to that run of results.
“I think our average quota attainment was around like over 130%.”
Listen to the episode Sales team, hiring & comp Link to this
Set sales compensation goals that are likely to be hit, while company growth goals are set aggressively Listen
Dan Lee said Nooks is growing more than three times year over year, and that upside from new products and enterprise growth is hard to predict. For sales goals they have generally picked targets the team is likely to hit, while company goals are set higher so the team pushes to overachieve. He said he wants to avoid a company tripling year over year whose sales team misses its goals.
“we generally tend to like underestimate a little bit.”
Listen to the episode Sales team, hiring & comp Link to this
The first non-R&D hire was a founding customer success manager who also worked on pre-sales trials Listen
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.”
Junior reps learn to sell through weekly manager feedback on call recordings, which made shared calling a good fit for the product Listen
Dan Lee said many of the early sales teams using Nooks were junior reps in their first job out of school. They learned by getting feedback once a week from their manager on recent calls from recordings, rather than sitting on the sales floor. He said this made collaboration a strong fit because reps need a tight feedback loop to share what works.
“the way they're learning is by getting feedback once a week from their manager”
Listen to the episode Sales team, hiring & comp Link to this
Taste in product is customer empathy: putting yourself in the customer's shoes Listen
Dan Lee split product sense into rigorous prioritization and taste. He described taste as empathy, putting yourself in the customer's shoes and understanding deeply what they care about. He said taste matters more in human-in-the-loop AI products because the bottleneck is quality.
“it's kind of empathy putting yourself in the customer's shoes uh understanding deeply what they care about.”
Manual calling work limited reps to two or three conversations an hour Listen
Dan Lee said reps using Nooks loved the collaboration but were only having two or three conversations in an hour because of manual work. That work included building call lists, finding phone numbers, waiting through ringing and voicemail, preparing scripts, taking notes and logging calls to the CRM. Nooks then focused on automating the calling step first.
“they're only having like two or three conversations in an hour.”
AI-drafted outreach cut a rep's batch of 30 personalized emails from four or five hours to about 30 minutes Listen
Dan Lee said Nooks reps described spending four or five hours writing around 30 personalized emails, and could now produce that batch in about 30 minutes. He said prospects were replying that it was the best email they had ever received.
“what used to take me like four, you know, four or five hours to go write”
Listen to the episode Pipeline & demand generation Link to this
AI models are not yet good at persuading people, so sales strategy still needs a human strategist Listen
Dan Lee said the sales strategy piece is not a model capability today because models are not as good at persuading people. He said a strategic salesperson needs to read the situation and define the strategy before agents can do the work, though he expects models to improve.
“models are not as good at persuading people.”
Company-specific sales intelligence is what Dan says a general model like Claude is not built to capture Listen
Dan Lee said Nooks captures sales intelligence specific to each company, including company-specific email data sets and a feedback loop as the sales process changes over time. He said Claude is built for general reasoning across many use cases and is not as deep for sales specifically.
“capturing that sales intelligence that's like specific for each company.”
A large portion of Nooks' sales team are former customers, and that is approaching a majority Listen
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.”
Most of the SMB and mid-market sales team were promoted from SDRs, with a first SDR-to-AE-to-manager promotion recently Listen
Dan Lee said Nooks has a strong motion of promoting SDRs to AEs, and that the majority of its SMB and mid-market team were promoted from SDR roles, with many working toward enterprise. He said the company recently made its first promotion from SDR to AE to sales manager.
“We actually have a a great motion of promoting SDRs also to AEs.”
Listen to the episode Sales team, hiring & comp Link to this
Each customer has a shared Slack channel, and the CSM works toward the customer's own goals Listen
Dan Lee said Nooks keeps a Slack channel with every customer and regularly checks how each is doing against its goals, such as sales productivity targets, and how Nooks can help. He said the CSM is effectively working for the customer, checking things like whether reps are performing well on calls, whether call scripts are good and whether the data is correct.
“So we have a slack channel with every customer.”
Listen to the episode Retention & customer success Link to this
Be paranoid about the value you deliver, and test whether you are a need-to-have rather than a nice-to-have Listen
Dan Lee said that if he could go back to the start he would be paranoid about how much value Nooks delivers to customers, and rigorous about the mechanism for telling a nice-to-have from a need-to-have. When host Mark River noted the false-positive risk because people tell you what you want to hear, Dan recommended The Mom Test.
“I think be paranoid about how much value you're delivering to customers.”
One experienced seller enabled by agents could prospect at a fraction of the usual effort Listen
Host Mark River suggested that a 12-year veteran who sells into healthcare could be enabled by agents to do the prospecting for about 1/100th of the effort, and Dan Lee agreed. Dan said the general bar rises, companies can grow without hiring armies of reps or lower-quality ones, and agents can help with the research, emails and calls.
“that is enabled by this tech such that they're actually doing the prospecting, but it's like 1/100th of the effort.”
Listen to the episode Sales team, hiring & comp Link to this