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Nov 8, 2023 · 19m · top-founders

How This Founder Plans to use AI to help Remote Sales Team Managers Run Better Teams

Matt Schenker · 9m spoken Nathan Latka · 7m spoken
0:00 / 0:00

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Host Nathan Latka interviews Mattermore co-founder Matt Schenker about building an AI co-pilot designed to reduce stress and improve managerial effectiveness for remote SaaS sales teams. The conversation explores Mattermore's behavioral science foundations, technical architecture, customer discovery process, and bootstrapping strategies ahead of its upcoming MVP launch.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 44.8% of the talking time here. How this is scored →

Nathan as informed peer 4.4 Guest teaching 4.0 Guest disagreement 3.0 Nathan pushing back 5.4
05100:0010:000:00–4:22 · Nathan as informed peer 4/10 Episode Preview and Background on Mattermore Nathan challenges the necessity of an AI solution for sales management by offering his own lightweight 3-person sales process as a counterexample. Matt educates Nathan on sales stress research and the behavioral psychology gaps in manager-rep asynchronous communication.4:22–7:35 · Nathan as informed peer 4/10 Probing for Beta Customers and Practical Use Cases Nathan presses Matt to bypass marketing buzzwords and name a concrete customer use case or active client. Matt protects client confidentiality and admits the product is early in beta and pre-revenue.7:37–10:11 · Nathan as informed peer 2/10 Customer Discovery, Post-Call Reports, and LLM Rubrics Matt explains his customer discovery sprints and walks through the technical pipeline connecting call transcripts from Gong or Otter into Claude using academic behavioral rubrics. Nathan listens without challenging the methodology.10:11–13:33 · Nathan as informed peer 6/10 Debating Technical Differentiation Versus Traditional Coaching Nathan interrupts to challenge Matt on the true technical moat of the product, bluntly suggesting Matt should just be a human coach rather than an AI SaaS platform. Matt rejects the premise, detailing how software solves visibility and continuous data tracking that manual coaching cannot.13:33–16:25 · Nathan as informed peer 6/10 MVP Launch Timelines and Bootstrapping Strategies Nathan frankly states he is lost on the product value and questions why an MVP would take 6-9 months, pushing Matt on when he will actually charge customers. Matt clarifies the distinction between an immediate 2-week internal pilot and a broader public launch while explaining how consulting funds his personal runway.0:00–4:22 · Guest teaching 5/10 Episode Preview and Background on Mattermore Nathan challenges the necessity of an AI solution for sales management by offering his own lightweight 3-person sales process as a counterexample. Matt educates Nathan on sales stress research and the behavioral psychology gaps in manager-rep asynchronous communication.4:22–7:35 · Guest teaching 1/10 Probing for Beta Customers and Practical Use Cases Nathan presses Matt to bypass marketing buzzwords and name a concrete customer use case or active client. Matt protects client confidentiality and admits the product is early in beta and pre-revenue.7:37–10:11 · Guest teaching 6/10 Customer Discovery, Post-Call Reports, and LLM Rubrics Matt explains his customer discovery sprints and walks through the technical pipeline connecting call transcripts from Gong or Otter into Claude using academic behavioral rubrics. Nathan listens without challenging the methodology.10:11–13:33 · Guest teaching 5/10 Debating Technical Differentiation Versus Traditional Coaching Nathan interrupts to challenge Matt on the true technical moat of the product, bluntly suggesting Matt should just be a human coach rather than an AI SaaS platform. Matt rejects the premise, detailing how software solves visibility and continuous data tracking that manual coaching cannot.13:33–16:25 · Guest teaching 3/10 MVP Launch Timelines and Bootstrapping Strategies Nathan frankly states he is lost on the product value and questions why an MVP would take 6-9 months, pushing Matt on when he will actually charge customers. Matt clarifies the distinction between an immediate 2-week internal pilot and a broader public launch while explaining how consulting funds his personal runway.0:00–4:22 · Guest disagreement 2/10 Episode Preview and Background on Mattermore Nathan challenges the necessity of an AI solution for sales management by offering his own lightweight 3-person sales process as a counterexample. Matt educates Nathan on sales stress research and the behavioral psychology gaps in manager-rep asynchronous communication.4:22–7:35 · Guest disagreement 3/10 Probing for Beta Customers and Practical Use Cases Nathan presses Matt to bypass marketing buzzwords and name a concrete customer use case or active client. Matt protects client confidentiality and admits the product is early in beta and pre-revenue.7:37–10:11 · Guest disagreement 1/10 Customer Discovery, Post-Call Reports, and LLM Rubrics Matt explains his customer discovery sprints and walks through the technical pipeline connecting call transcripts from Gong or Otter into Claude using academic behavioral rubrics. Nathan listens without challenging the methodology.10:11–13:33 · Guest disagreement 6/10 Debating Technical Differentiation Versus Traditional Coaching Nathan interrupts to challenge Matt on the true technical moat of the product, bluntly suggesting Matt should just be a human coach rather than an AI SaaS platform. Matt rejects the premise, detailing how software solves visibility and continuous data tracking that manual coaching cannot.13:33–16:25 · Guest disagreement 3/10 MVP Launch Timelines and Bootstrapping Strategies Nathan frankly states he is lost on the product value and questions why an MVP would take 6-9 months, pushing Matt on when he will actually charge customers. Matt clarifies the distinction between an immediate 2-week internal pilot and a broader public launch while explaining how consulting funds his personal runway.0:00–4:22 · Nathan pushing back 4/10 Episode Preview and Background on Mattermore Nathan challenges the necessity of an AI solution for sales management by offering his own lightweight 3-person sales process as a counterexample. Matt educates Nathan on sales stress research and the behavioral psychology gaps in manager-rep asynchronous communication.4:22–7:35 · Nathan pushing back 6/10 Probing for Beta Customers and Practical Use Cases Nathan presses Matt to bypass marketing buzzwords and name a concrete customer use case or active client. Matt protects client confidentiality and admits the product is early in beta and pre-revenue.7:37–10:11 · Nathan pushing back 2/10 Customer Discovery, Post-Call Reports, and LLM Rubrics Matt explains his customer discovery sprints and walks through the technical pipeline connecting call transcripts from Gong or Otter into Claude using academic behavioral rubrics. Nathan listens without challenging the methodology.10:11–13:33 · Nathan pushing back 8/10 Debating Technical Differentiation Versus Traditional Coaching Nathan interrupts to challenge Matt on the true technical moat of the product, bluntly suggesting Matt should just be a human coach rather than an AI SaaS platform. Matt rejects the premise, detailing how software solves visibility and continuous data tracking that manual coaching cannot.13:33–16:25 · Nathan pushing back 7/10 MVP Launch Timelines and Bootstrapping Strategies Nathan frankly states he is lost on the product value and questions why an MVP would take 6-9 months, pushing Matt on when he will actually charge customers. Matt clarifies the distinction between an immediate 2-week internal pilot and a broader public launch while explaining how consulting funds his personal runway.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 39% · guest 61%0:00 · Nathan 39% · guest 61%3:00 · Nathan 39.6% · guest 60.4%3:00 · Nathan 39.6% · guest 60.4%6:00 · Nathan 62.6% · guest 37.4%6:00 · Nathan 62.6% · guest 37.4%9:00 · Nathan 29.5% · guest 70.5%9:00 · Nathan 29.5% · guest 70.5%12:00 · Nathan 22.2% · guest 77.8%12:00 · Nathan 22.2% · guest 77.8%15:00 · Nathan 50.1% · guest 49.9%15:00 · Nathan 50.1% · guest 49.9%18:00 · Nathan 100% · guest 0%18:00 · Nathan 100% · guest 0%
Sharpest disagreement ▶ 12:04 Matt rejects the consulting framing

Matt directly rejects Nathan's suggestion that his company should just be a human coaching practice, arguing forcefully that traditional coaching suffers from a fundamental visibility problem.

 Hardest push from Nathan ▶ 11:39 Nathan questions AI software necessity over coaching

Nathan cuts Matt off to challenge why the venture needs AI in the title at all, asking why Matt doesn't simply offer direct remote management consulting.

 Biggest teaching moment ▶ 8:24 Matt breaks down automated post-call rubric generation

Matt educates Nathan on how they extract call transcripts via APIs and run them through academic rubrics in Claude to deliver manager feedback that executives rarely provide.

 Nathan holds their own ▶ 10:11 Nathan challenges LLM data moats and engineering reality

Nathan demonstrates software industry expertise by pointing out that foundational model wrappers without massive proprietary data cannot win, pressing Matt on his technical team and secret sauce.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Episode Preview and Background on Mattermore 4524 Nathan challenges the necessity of an AI solution for sales management by offering his own lightweight 3-person sales process as a counterexample. Matt educates Nathan on sales stress research and the behavioral psychology gaps in manager-rep asynchronous communication.
Probing for Beta Customers and Practical Use Cases 4136 Nathan presses Matt to bypass marketing buzzwords and name a concrete customer use case or active client. Matt protects client confidentiality and admits the product is early in beta and pre-revenue.
Customer Discovery, Post-Call Reports, and LLM Rubrics 2612 Matt explains his customer discovery sprints and walks through the technical pipeline connecting call transcripts from Gong or Otter into Claude using academic behavioral rubrics. Nathan listens without challenging the methodology.
Debating Technical Differentiation Versus Traditional Coaching 6568 Nathan interrupts to challenge Matt on the true technical moat of the product, bluntly suggesting Matt should just be a human coach rather than an AI SaaS platform. Matt rejects the premise, detailing how software solves visibility and continuous data tracking that manual coaching cannot.
MVP Launch Timelines and Bootstrapping Strategies 6337 Nathan frankly states he is lost on the product value and questions why an MVP would take 6-9 months, pushing Matt on when he will actually charge customers. Matt clarifies the distinction between an immediate 2-week internal pilot and a broader public launch while explaining how consulting funds his personal runway.

Statements from this episode (8)

Disclosure
Schenker: Mattermore differentiates by targeting remote SaaS sales managers
“And so one differentiator for us is we have a very specific problem for very specific people, remote sales managers who are selling staffs.”
Matt Schenker Nov 8, 2023 ▶ 1:26
Assertion Contradicted
Schenker: Sales reps have highest stress after teachers and nurses
“So other than teachers and nurses, sales consistently report the highest stress levels out of all occupational groups, which makes sense for anybody that's done sales, right?”
Matt Schenker Nov 8, 2023 ▶ 2:40
Assertion Not checkable as stated
Schenker: Manager relationship is top predictor of salesperson stress
“However, that's the number one predictor of how stressed out somebody is, not how responsive their customers are that week, not how many deals they're closing that week. It's the health of their relationship with their manager.”
Matt Schenker Nov 8, 2023 ▶ 3:03
Assertion Not checkable as stated
Mattermore interviewed 400 sales teams during four customer discovery sprints
“So what we did was, we did six-week sprints where we would interview a hundred sales teams, one right after another. We did that for four consecutive batches,”
Matt Schenker Nov 8, 2023 ▶ 8:08
Disclosure
Mattermore gives academic advisors equity to build Claude LLM management rubrics
“And with automated prompts that we've built along with some of our academic advisors, we've given fractional basis points in the company too. They help us build some rubrics and specific prompts that then we just fed into Claude as an LLM.”
Matt Schenker Nov 8, 2023 ▶ 9:04
Assertion Partly supported
Schenker: Sales enablement software tools exploded from 400 in 2014 to thousands
“And 2014, there were like 400 sales enablement tools. Now we're in the matter of thousands of sales enablement fast tools.”
Matt Schenker Nov 8, 2023 ▶ 9:52
Insight
Schenker: Traditional sales coaching lacks visibility into concept implementation
“What we found through years coaching sales managers was even when you have a coach, there's a massive visibility problem, which is if I ask, okay, how did you do this week, Nathan, compared to last week? You can look at your output from your sales team, but we…”
Matt Schenker Nov 8, 2023 ▶ 12:23
Disclosure
Schenker bootstraps personal expenses through sales consulting and coaching
“We've been able to turn to clients within the sales space and say, all right, we're taking in coaching clients, we're taking consulting jobs, we're taking training gigs.”
Matt Schenker Nov 8, 2023 ▶ 16:05
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