The SaaS Podcast

Andrew Guttormsen, Circle

1,500 Demos: How Founder-Led Sales Built Circle

Andrew Guttormsen is the co-founder and Chief Revenue Officer at Circle, a platform for creators to build communities and memberships. Andrew and his co-founders spent five years as early employees at Teachable, where they saw firsthand how creators often struggled to build engaged communities. After Teachable's acquisition, they saw an opportunity to build a community-first solution tailored to content creators. The plan was to grow slowly, maybe even bootstrap. But when the pandemic hit in 2020, demand for online community tools exploded. The founders raised a small $700K seed round and Andrew threw himself into founder-led sales, personally reviewing every waitlist application and doing 8-10 demos a day. Their efforts paid off. Circle hit $1M ARR in just four months after public launch. Andrew did over 1,500 founder-led sales demos in the first 18 months, and that personal touch drove massive word of mouth. But the journey had its painful moments. An influential customer publicly shared a negative experience with Circle, and Andrew described it as a punch in the gut. The team had to confront their shortcomings head-on and improve fast. The founders also landed anchor customers like Pat Flynn, offering advisor equity in exchange for deep product feedback and co-marketing. A single JV webinar with Pat drove 300 new customers. That anchor customer playbook became a repeatable engine for growth. As Circle scaled, Andrew went from doing all the sales himself to hiring a sales coach, then recruiting a VP of Sales who now runs a 20-person team. They also invested heavily in pricing and packaging, adding a $30,000/year branded app tier that boosted net revenue retention. Fast forward to today. Circle has over 10,000 customers, generates $19 million in ARR with a team of about 150 people, and has raised $30 million in funding.