Check: Building a SaaS Startup You’re Not Rushing to Sell

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Andrew Brown is the founder and CEO of Check, a payroll infrastructure startup that embeds payroll directly into other software platforms.

In 2015, Andrew sold his B2C startup, Oyster, to Google. But that big win also left a void in his professional life. He decided his next startup would be something he could work on for a decade or more, rather than just aiming for a quick sell-off.

After spending years carefully searching for the right business idea, Andrew finally landed on the concept for Check when a potential partner revealed just how complex it was to build payroll functionality directly into their HR platform.

Andrew spent several years operating in stealth mode, entirely focused on establishing Check's initial product and early partnerships before ever officially launching.

But earning trust was much harder than Andrew expected, with many early prospects questioning why they should trust an early-stage startup with their payroll solution.

It took years of relationship building through warm introductions, thoughtful cold outreach, and diligently preparing for every meeting to finally land pilots with initial partners.

As Andrew described, payroll is an incredibly complex 50-state problem requiring going state-by-state to ensure proper setup before anyone will trust you with money.

Today, Check has grown to a team of over 100 people and raised $119 million so far.

This episode is part of our First Customers series.

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