Andrew Brown sold his first startup to Google - and felt empty. He spent three years searching for an enterprise SaaS business he would never want to sell. He found it in SaaS partnerships with platform companies desperate to add payroll but unable to build it themselves.
In this episode, Andrew reveals how Check built an enterprise SaaS model targeting just a few hundred platform partners, raised $119M, and turned the SVB bank collapse into the proudest day in company history. You will learn why enterprise SaaS with a small TAM can still be massive, how investor introductions created trust, and why two years of stealth gave Check a 2-3 year head start.
Check is a payroll infrastructure startup that embeds payroll directly into other software platforms, powering over 3 million employees across all 50 US states.
🔑 Key Lessons
- 🏢 Enterprise SaaS partnerships with small TAMs unlock massive markets: Check targets only a few hundred platform partners, but each serves hundreds of thousands of businesses and millions of employees.
- 🧠 Stealth mode protects differentiated enterprise SaaS from competitors: Andrew kept Check in stealth for two years, gaining a 2-3 year head start before competitors saw the embedded fintech opportunity.
- 💰 Aligned pricing turns enterprise SaaS into compounding revenue: Check charges per employee and per company, so revenue grows automatically as partners grow their customer base.
- 📉 Crises reveal the true strength of platform partnerships: When SVB collapsed on a Friday payday, Check fronted funds and paid every employee within 24 hours.
- 🎯 Customer pain beats top-down analysis for enterprise SaaS ideas: Check was born from Homebase telling Andrew that payroll was too complex to build in-house.
Chapters
- Introduction
- Andrew's favorite quote - William Gibson on the future
- What Check does - embedded payroll for platforms
- Size of the business - 100+ people, $119M raised
- Before Check - selling Oyster to Google
- The void after selling - why Andrew wanted a generational business
- Finding the idea through Homebase's payroll pain
- Building in stealth for two years
- Getting commitment from Homebase without a contract
- What it took to sign the first 4-5 partners
- Selling into a small TAM of a few hundred partners
- Sales cycle length and onboarding process
- Per-employee pricing aligned with partner growth
- Three years to $1M ARR and the COVID impact
- Raising $119M while still in stealth
- Challenges - divorce, decade of grind, SVB collapse
- Lightning round
Resources
