Why Circle’s Co-Founder Ran 1,500 Sales Demos Before Hiring a Single Rep | Andy Guttormsen

Most founders can’t wait to get out of the demo. Andy Guttormsen ran more than 1,500 of them himself — and the revenue was never the point. Andy was the seventh employee at Teachable, where he helped scale the company from roughly $10K in monthly revenue to a quarter-billion-dollar exit. In 2020 he co-founded Circle, now home to 15M+ members and creators like Jay Shetty, Mel Robbins, and Ali Abdal — a profitable, venture-backed company he grew by personally running eight to ten demos a day for 18 months before ever hiring a sales team. In this conversation with LeanScale co-founder Anthony Enrico, Andy breaks down why founder-led sales became Circle’s unfair advantage, why you hire the sales leader before the reps, the real difference between an audience and a community, and why Circle renamed its RevOps team the “internal AI” team — the most valuable seat in the company. WHAT YOU’LL LEARN Why Andy ran 1,500 demos for product feedback and brand — not first-customer revenue How founder-led sales built its own top-of-funnel flywheel on social Why you hire the sales leader before the reps — and how doing it backwards backfires The “unfair advantage” hire: bringing on people who have lived your customer’s problem The real difference between an audience and a community — and why community is the moat Why a big following doesn’t convert into a community without a real offer and real rituals How Circle drives roughly 30% of new customers through its own customer community Why Circle renamed RevOps the “internal AI” team — and what changed on their plate How accurate data turns meetings into decisions instead of data-integrity debates The GTM tools Circle can’t live without — and the AI category they can’t make work CHAPTERS 00:00 — Cold open + intro 02:10 — 1,500 demos: why the goal was feedback and brand, not revenue 04:45 — Staying close to your first 100 customers 06:43 — The closet, the full calendar, and knowing when to hand off 08:36 — Hiring a coach who became VP of Sales (the Charlie story) 10:00 — Hire the leader, not the reps — why founder win rates mislead 11:52 — The unfair-advantage hire: empathy from lived experience 13:26 — Content vs. community in the age of AI 17:30 — A community is just a business — nail the offer 20:34 — A B2B example: how GrowthX builds community 23:10 — Audience vs. community: 600K followers vs. 1,000 members 26:32 — Circle’s 30% referral loop from eating its own dog food 30:21 — The Teachable RevOps regret and when to bring RevOps in 36:36 — Renaming RevOps the “internal AI” team 42:12 — What accurate data unlocks — and the tools they can’t live without ABOUT THE GUEST Andy Guttormsen is the co-founder and Chief Revenue Officer of Circle, the all-in-one platform where creators and brands build their communities, courses, and digital businesses — now home to 15M+ members and creators like Jay Shetty, Mel Robbins, and Ali Abdal. Before Circle, Andy was the seventh employee at Teachable, where as VP of Growth & Marketing he helped scale the company from roughly $10K in monthly revenue to a quarter-billion-dollar exit. He co-founded Circle in 2020 alongside Sid Yadav and Rudy Santino, and personally ran more than 1,500 sales demos in the company’s first 18 months before building out a sales team. Today Circle is a profitable, venture-backed business with 280+ team members. ABOUT THE LEANSCALE PODCAST The LeanScale Podcast is the show for GTM operators building the next generation of revenue infrastructure. Hosted by Anthony Enrico, co-founder of LeanScale, we go deep with the operators, founders, and executives shaping how modern go-to-market teams are designed, scaled, and transformed. ▶ Subscribe for new episodes ▶ Learn more about LeanScale: https://www.leanscale.team ▶ Follow Anthony on LinkedIn ▶ Follow Andy on LinkedIn KEYWORDS / TAGS RevOps, Revenue Operations, GTM, Go-to-Market, GTM Engineering, Founder-Led Sales, Founder-Led Growth, Community-Led Growth, Product-Led Growth, PLG, Self-Serve, Sales-Led Growth, Circle, Circle.so, Teachable, Creator Economy, Community Building, Online Communities, Audience vs Community, AI, AI Transformation, AI Agents, AI Workflows, Relevance AI, Hex, Wispr Flow, Sales Operations, Marketing Operations, Customer Success Operations, Pipeline Forecasting, Capacity Planning, Data Infrastructure, Context Graph, Demand Gen, B2B SaaS, Enterprise SaaS, CRO, COO, VP of Sales, Startup Sales, First Sales Hire, Sales Playbook, LeanScale, LeanScale Podcast, Anthony Enrico, Andy Guttormsen HASHTAGS #RevOps #GTM #GoToMarket #FounderLedSales #CommunityLedGrowth #PLG #CreatorEconomy #AI #AIAgents #Circle #Teachable #SalesLeadership #StartupSales #DemandGen #B2BSaaS #RevenueOperations #AITransformation #LeanScale #LeanScalePodcast