Founder-Led Sales Stories with Pete Kazanjy - Startup Sales Expertise From Founders Who've Done It

Peter Kazanjy
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Join Pete Kazanjy, author of Founding Sales, in conversation with a who's who of founders who have successfully completed their founder-led sales journeys. Founder-Led Sales Stories is where founders who have successfully completed their founder led selling journey (recently!) share their stories with those who are still in the middle of it! The better to help learn from their successes and avoid their mistakes.

Episodes

  1. Nooks: From Virtual Classroom to $70M AI Pipeline Machine with Rohan Suri

    3D AGO

    Nooks: From Virtual Classroom to $70M AI Pipeline Machine with Rohan Suri

    Join Pete in conversation with Rohan Suri, Co-Founder of Nooks, the AI pipeline generation platform that helps sales teams dial faster, coach better, and build targeted prospect lists. Pete and Rohan dive into how Nooks pivoted from a Stanford student project to sales tech powerhouse by "following the heat" of customer usage. You'll hear about their game-changing trial-based sales motion that doubled as product feedback loop, and how they transformed a $50/month product into deals worth up to $500K. Rohan shares the "aha moment" when Modern Health begged to keep their product running during procurement, their LinkedIn content strategy that created outsized awareness, and why they insist on hiring two AEs at a time (spoiler: one didn't work out!). Nooks' founder-led approach helped them secure $70M from Kleiner Perkins, Lochy Groom, and Tola Capital, build a team of 30 sellers, and expand from a simple virtual sales floor to a full-stack AI pipeline platform with coaching and prospecting tools More on Nooks here: https://www.nooks.ai/ Sales motion details: AI pipeline generation platform, B2B companies with inside sales teams, SDR/BDR leaders as buyers, $5K-$500K deal range (avg ~$50K), 30-day trial-led sales cycle with real-time call blitz demonstrations.

    1h 11m
  2. UserEvidence: MarTech Category Creation and Mountain Town Sales Teams with Evan Huck of UserEvidence

    SEP 22

    UserEvidence: MarTech Category Creation and Mountain Town Sales Teams with Evan Huck of UserEvidence

    Join Pete in conversation with Evan Huck, Co-Founder and CEO of UserEvidence, the customer evidence platform helping B2B tech companies prove their value with compelling customer stories. Pete and Evan dive into Evan's "community thought leadership" approach that landed their first big logos, his "perfect discrimination" pricing strategy (charging exactly what each customer could bear), and how he built a killer sales team from ski instructors and raft guides in Jackson Hole. Evan shares the brutal reality of creating a new MarTech category, why he outsourced cold email despite being an expert himself, and his deliberate "NRR curve design" strategy that made fundraising possible (hint: two-year deals with built-in expansion). Evan's successful founder-led sales efforts powered UserEvidence to $7M ARR with a team of 15 sales professionals, successfully raising $21m while selling to marketing leaders at companies like Salesforce, HPE, and Siemens. More on UserEvidence here: https://www.userevidence.com/ Sales motion details: Customer evidence platform, B2B tech companies with 150+ employees, product marketers and customer marketers as buyers, $30-60K average selling price with expansion to $80-100K at enterprise level, multi-touch sales cycle requiring 3-4 interactions over time.

    1h 7m
  3. From Boba Shop Brainstorming to $1M ARR with Zero Sales Experience - How Sai and Atul Built an AI Roleplay Empire

    SEP 15

    From Boba Shop Brainstorming to $1M ARR with Zero Sales Experience - How Sai and Atul Built an AI Roleplay Empire

    Join Pete in conversation with Sai Guduguntla and Atul Raghunathan, Co-Founders of Hyperbound, makers of AI role-play software that's revolutionizing how large sales teams train and onboard. Sai and Atul share their wild journey from AI engineers with zero sales experience to closing 40 enterprise customers in just 11 months. They accidentally built their product to train themselves first, then realized every sales org needed the same solution! The guys dive into how they leveraged LinkedIn virality to book solid for three straight weeks (including Saturdays!), their clever "build a custom bot on the spot" demo technique that closes deals, and why they waited until $1M ARR before making their first sales hire. Their unique path through Y Combinator (where they applied with 17 different ideas!), pivoting multiple times, and sending 25,000 LinkedIn messages for customer research proves that technical founders can crush enterprise sales when they think systematically. More on Hyperbound here: https://hyperbound.ai/ Sales motion details: AI role-play software for sales training, 500+ employee B2B companies with 50+ sellers, sales enablement and revenue leadership buyers, $40K average deal size with contracts reaching six figures, 1-2 month sales cycle.

    1h 21m
  4. Once: Cracking the Six-Figure EdTech Enterprise Sale with Matt Pasternack

    SEP 2

    Once: Cracking the Six-Figure EdTech Enterprise Sale with Matt Pasternack

    Join Pete in conversation with Matt Pasternack, Founder of Once, who's built a $2M+ ARR company selling high-ticket reading intervention programs to the nation's largest school districts. Matt reveals how he navigated the high-stakes education sales landscape by creating artificial compelling events through academic research partnerships - an ingenious approach that generated a 10% positive response rate from typically unresponsive district leaders. Pete and Matt dissect why selling to individual principals was abandoned despite impressive open rates, why Once exclusively targets the top 500 districts with six-figure deals, and the fascinating "trust importation" strategy that unlocked enterprise sales when Matt's own EdTech credentials weren't enough. The conversation highlights the stark differences between selling EdTech to IT departments versus academic officers - including how misunderstanding a single term like "authentic reading" can immediately end a sales conversation. Once's high-touch, relationship-driven approach has powered them to mid-six figure deals with a lean three-person sales team, proving that in education, trust and relationships trump traditional sales tactics. More on Once here: https://www.tryonce.com/  Sales motion details: Reading tutoring upskilling service, Top 500 district targets, Chief Academic Officers and principals as buyer personas, mid-five to mid-six figure ASP, 12+ month sales cycle with year-long validation periods.

    1h 28m
  5. Lassie: From Flying to 100 Dental Offices to $100M ARR Through Extreme Product Obsession with Steijn Pelle

    AUG 22

    Lassie: From Flying to 100 Dental Offices to $100M ARR Through Extreme Product Obsession with Steijn Pelle

    Join Pete in conversation with Steijn Pelle, Co-Founder and CEO of Lassie, the AI healthcare admin worker transforming how doctors run their practices. Steijn and Pete dig into Lassie's fascinating journey from Steijn literally working in his dentist's back office to building a company on track for $100M ARR within a year. They cover Lassie's crazy commitment to product quality (they actually flew to 100+ dental offices nationwide to install their software!), their ruthless "say NO to most leads" ICP discipline, and why they waited until hundreds of customers before making their first sales hire. You'll love Steijn's stories about turning one delighted dentist into an organic growth engine, why they run 40-50 hour work trials for sales candidates, and their "Robinhood-style" waitlist approach that keeps them laser-focused on delighting every customer they take. Steijn's consumer growth background at Coinbase and Robinhood shaped Lassie's unique approach to B2B sales – focusing on turning customers into superfans rather than just closing deals. Their "wedge product" strategy targeting the 80-100 monthly hours doctors spend processing insurance payments has positioned them to capture the entire $100-200K in admin OPEX practices currently waste. More on Lassie here: https://www.golassie.com/  Sales motion details: AI admin automation for healthcare practices, independent doctor-owners target persona, five-figure ACVs, short sales cycles with extremely qualified leads, primarily word-of-mouth acquisition.

    1h 33m
  6. Noyo: Building a Two-Sided Benefits API Marketplace Through 7-Figure Enterprise Sales with Shannon Goggin

    AUG 15

    Noyo: Building a Two-Sided Benefits API Marketplace Through 7-Figure Enterprise Sales with Shannon Goggin

    Join Pete in conversation with Shannon Goggin, Co-Founder and CEO of Noyo, the infrastructure company revolutionizing employee benefits data exchange. Shannon shares her journey from "terrified of sales" product manager to closing seven-figure enterprise deals with insurance giants like UnitedHealthcare (which took 6 years from first contact to close!). Pete and Shannon dig into Noyo's brilliant cold-start solution for their two-sided marketplace, how they bootstrapped with a glorified PDF form library, and why "true believers" were more valuable than early customers. Shannon's candid insights on enterprise sales include why they eventually added advisory services, how they negotiated the tricky balance of selling to both HR software companies and insurance carriers, and her biggest regret: "I wish we'd lowered our prices earlier." Noyo's founder-led sales journey has propelled them to more than $50m in funding - most recently a Series B from Norwest Ventures - all while powering benefits data exchange for industry leaders like Rippling and Gusto, and signing enterprise deals worth up to $1M+ ARR with major insurance carriers. More on Noyo here: https://www.noyo.com/ Sales motion details: Benefits API infrastructure, two-sided marketplace connecting HR software with insurance carriers, $35k-$100k ASP for software companies and $150k-$250k for insurance companies (growing to $1M+), 12+ month enterprise sales cycle, product/operations and distribution leader personas.

    1h 25m
  7. Pylon: The "Anti-Sale Sale" and Slack-based selling with Marty Kausas, founder of Pylon

    AUG 11

    Pylon: The "Anti-Sale Sale" and Slack-based selling with Marty Kausas, founder of Pylon

    Join Pete in conversation with Marty Kausas, Co-Founder and CEO of Pylon, the Modern B2B Support platform. Marty and Pete discuss Pylon's unique "Slack-based sale," Marty's early "Anti-sale sale", and Pylon's wild success at "Founder-Led LinkedIn Content" pipeline generation. Marty's successful founder-led sales efforts powered Pylon to north of 100 customers and millions of ARR before hiring additional sales staff. All of which powered the organization to raising more than $20m from amazing investors like Andreessen Horowitz, General Catalyst, and more. More on Pylon here: https://usepylon.com/ Sales motion details: Modern B2B Support Platform, Series A and B B2B software companies, customer success and support leadership, five-figure ASP. Multi-month sales cycle.

    1h 24m
  8. Tonic: Selling Fake Data To Engineering Leaders with Karl Hanson of Tonic

    AUG 4

    Tonic: Selling Fake Data To Engineering Leaders with Karl Hanson of Tonic

    Join Pete in conversation with Karl Hanson, Co-Founder of Tonic, makers of synthetic data solutions for software and AI development! (The "Fake Data Company"! Lol!) Karl and Pete discuss the ins and outs of a "top down" dev-tool founder-led sales motion (very much not product led), and the implications of this. Karl also talks about how he grew to appreciate the "craft" of sales over time, the secret to charging for pilots, how they drove efficiency and compression in their sales motion, and more. Karl's successful founder-led sales journey ultimately lead Tonic to graduate to a scaled sales organization, having raised $45m from blue chip investors like Heavybit, Bloomberg Beta, and Insight Partners. More on Tonic here: https://www.tonic.ai/ Sales motion details: Synthetic data generation tooling, large engineering organizations targets, engineering leadership and security buyer persona, six-figure average selling price, multi-quarter sales cycle.

    1h 36m
  9. Delve: "Sell to your Uncle", and other founder-led sales insights on the way to 500+ customers and millions in ARR with Karun Kaushik of Delve.

    JUL 25

    Delve: "Sell to your Uncle", and other founder-led sales insights on the way to 500+ customers and millions in ARR with Karun Kaushik of Delve.

    Join Pete in conversation with Karun Kaushik, Delve's Co-Founder and CEO. Pete and Karun talk about "Selling to your uncle", first-principles sales motion evolution, systematizing growth hacks and more. Delve's amazing growth from two MIT dropouts to hundreds of customers, millions in ARR, and a $32m Series A has lessons for everyone on their founder-led sales journey. More on Delve here: https://delve.co/ Sales motion details: Automated compliance software, Pre-Seed, Seed, Series A targets, founder buyer persona, $15k average selling price, 30 day sales cycle.

    1h 4m
  10. Warp Payroll: From 0-160 customers and $2m+ in ARR by removing the compliance pain from payroll with Varunram Ganesh of Warp..

    JUL 21

    Warp Payroll: From 0-160 customers and $2m+ in ARR by removing the compliance pain from payroll with Varunram Ganesh of Warp..

    Join Pete in conversation with Varunram "VG" Ganesh, Warp's founding seller, discussing high velocity sales into the startup market. Pete and VG discuss how Twitter can be leveraged for problem validation, "inbound", and a source of outbound targets, with many more topics. Sales motion details: Payroll software, Pre-seed, Seed, Series A targets, founder buyer persona, $5k average selling price, 30 day deal cycle.

    1h 7m
  • 10 Episodes

About

Join Pete Kazanjy, author of Founding Sales, in conversation with a who's who of founders who have successfully completed their founder-led sales journeys. Founder-Led Sales Stories is where founders who have successfully completed their founder led selling journey (recently!) share their stories with those who are still in the middle of it! The better to help learn from their successes and avoid their mistakes.

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