SaaS Interviews with CEOs, Startups, Founders

How do you hit $1 million in contracted revenue in three months and achieve 211% net dollar retention in your first year? Amanda Kahlow is the founder and CEO of 1Mind, an AI platform building go-to-market superhumans that replace SDRs, AEs, and sales engineers. You'll learn: - How to sell AI software for $100,000 to $400,000 using flat subscription pricing instead of metered models. - The unit economics of replacing 89 SDRs and 19 sales engineers with a single custom agent. - How they maintain 80 to 90 percent SaaS margins while running heavy LLM operations. - The strategy behind 1Mind's 600 percent year-over-year growth rate. - Why most enterprise customers purchase a second AI agent within 90 days of going live. - How 1Mind uses their own AI agent to source 78 percent of their eight-figure pipeline. - The reality of managing founder dilution and secondary sales after building a $380 million business. - Why AI agents are expanding past chat interfaces and joining live Zoom calls to run product demos. Amanda is a three-time entrepreneur who previously founded and served as CEO of 6sense, scaling the company through multiple funding rounds and a $380 million valuation before stepping down. Watch this episode on YouTube: https://youtu.be/lFX0n3uYTkw Connect with Amanda: https://www.1mind.com/ Connect with Nathan: https://founderpath.com/

Ahikam Kaufman, veteran fintech founder who sold Check to Intuit for nearly $400M, now leads SafeBooks AI. He discusses building an AI platform for CFOs, automating quote-to-cash and finance data validation, pricing against accountant headcount, investing in a proprietary graph database to avoid AI hallucinations, and landing high-value enterprise engagements.

How do you survive shutting down during the pandemic, pivot a heavily funded business model, and rebuild a team of 8 into a $4M ARR AI powerhouse? Miles Beckett is the CEO of Flossy, a verticalized AI receptionist that automates patient booking and engagement for dental practices. After successfully building and exiting two previous startups for tens of millions, Miles raised a $15M Series A for a dental discount plan. When the market shifted, he pivoted the company entirely to voice AI, made hard cuts to the team, and found explosive product-market fit. Today, Flossy is growing 60 to 70 percent month over month. You'll learn: Why vertical AI agents beat general tools like Intercom How to sell $500/month software to PE-backed roll-ups The reality of firing 30 people to save a company's burn rate How a $1 million breakup fee saved a past acquisition deal Why they rejected a theoretical $40 million buyout The math behind adding $100,000 in new ARR each month How they used a $3M seed round to survive 2020 lockdowns The mechanics of multi-location enterprise SaaS deals Miles is a seasoned operator who previously built and sold Equal to Everyday Health for $30M, and Silver Sheet to AMN Healthcare, before diving into the dental tech space. Watch this episode on YouTube: https://www.youtube.com/watch?v=U2RAjHVdHZM Connect with Miles: https://www.flossy.com/ Connect with Nathan: https://founderpath.com/

How do you pivot a banned college ridesharing app into a voice AI company handling 300 million customer service calls? Brian Schiff is the co-founder and CEO of Flip, a verticalized AI voice assistant that automates customer service calls for transportation, retail, and healthcare brands. After realizing their Cornell ridesharing app was a dead end, Brian and his co-founder Sam pivoted into voice AI. Today, Flip automates up to 90 percent of routine support calls for over 250 enterprise companies and recently raised a $20M Series A at a $100M valuation. You'll learn: How to successfully pivot a failing startup model Why verticalized AI beats horizontal platforms How to implement usage-based pricing at $1.50 per call Why "listen mode" is their best sales tactic How to maintain 75 percent gross margins with AI Why they rejected a theoretical $150 million acquisition offer How to select the right industries for expansion Why competitive B2C markets are best for AI tools Brian started his entrepreneurial journey at Cornell's eLab accelerator. He navigated the near-total collapse of transportation revenue during the pandemic to build a highly efficient business growing 3X year over year. Watch this episode on YouTube: https://youtu.be/gtFt5exyCaI Connect with Brian: https://flipcx.com/ Connect with Nathan: https://founderpath.com/

Dan Bladen, founder and CEO of Kadence, rebuilt a hardware startup into a $15M ARR hybrid-work SaaS serving Boeing, Revolut, and Nasdaq. He discusses the pandemic pivot to workplace ops software, resetting a cap table for new investors, seat-based enterprise pricing, rapid net dollar retention, and SpaceOps AI that accelerates move and scenario planning.

Hmayak Tigranyan, founder and CEO of Buildern, built a construction management SaaS to about $2M ARR with ~300 customers after closing a $3M dev shop. He talks about finding an underserved construction niche, scaling almost entirely via high-intent SEO and long-tail content, running an internal content engine, and the shift to hiring sales as ACV rises.

How do you grow an AI phone system to 5,000 customers and roughly $3M ARR in under two years while still aiming for $10M in revenue this year? Jeremy Goillot is the founder and CEO of The Mobile First Company, which launched Allo as its first product. Allo is an AI phone system and dialer for small businesses, now serving around 5,000 customers with average revenue above $160 per month and a goal of reaching $10M in revenue in 2026. This business is interesting because Jeremy did not stop at a self-serve PLG motion. He started there, saw the churn and activation issues, then layered in demos, lead routing, CRM-based qualification, and expansion to raise ACV and improve retention. The result is a high-volume SMB SaaS business built on strong distribution, fast onboarding, and clear activation metrics. You'll learn: Why Jeremy moved from pure PLG to a sales-assisted motion. How Allo increased average revenue from $18 to over $160 per month. The exact activation metric that predicts churn. How the team uses demo routing based on CRM and team size. Why retargeting was one of the cheapest acquisition channels. How Allo won SEO with long-form content and original screenshots. The keyword prioritization system behind their content strategy. Why 50% of new revenue now comes from expansion. How the team thinks about CAC quality instead of lowest CAC. Why Jeremy raised early without waiting for a co-founder. How he kept about 50% ownership after raising around $20M. What it takes to sell into SMBs at high volume with only 17 people. Jeremy previously led growth at Spendesk before starting The Mobile First Company. He launched the company as a solo founder, raised a $5M pre-seed on his own, then built the team around him while keeping significant ownership. His long-term goal is not just one product, but a broader suite of vertical SaaS tools built under separate brands. If you care about SMB SaaS, PLG versus sales-assisted growth, SEO-led distribution, or building a multi-product software company, this episode is a masterclass for SaaS builders. Watch this episode on YouTube: https://youtu.be/PUZMvjyS3xw Connect with Jeremy: https://www.withallo.com/ Connect with Nathan: https://founderpath.com/

Joey Gilkey, founder and CEO of TitanX and former enterprise seller, bought Phone Ready Leads IP and scaled it into a $9.7M ARR business. He discusses buying IP to move faster than building, the proprietary phone-intent signals and AI moat, high-ACV pricing and expansion-driven growth, and how strategic acquisitions accelerated revenue.

Grant Stanis, CEO of TeamSupport and a seasoned growth leader at private equity-backed software firms, breaks down scaling a B2B support SaaS to 1,000+ customers and $10M–$25M ARR. He discusses pricing per seat, turning support conversations into signals for retention and upsells, relying on referrals and webinars over SEO, expansion-driven revenue, and navigating private equity ownership and big-account dynamics.

Gary Guseinov, serial entrepreneur and CEO who rebuilt CyberDefender into RealDefense, grew it back from ~$7M to ~$70M using acquisition-led, debt-funded scaling. He describes buying back his company cheaply, integrating acquisitions into a shared platform, telemetry-driven just-in-time offers, and a pricing ladder that turns $20 entry products into high-LTV cross-sells.