Head of Legal & Compliance

About this role

## About Check

Payroll is broken. Come fix it alongside a team that’s as passionate as you are!

At Check, you'll use creative problem-solving, critical thinking, and grit to impact every business we build. We ignore conventional role boundaries in favor of the unique strengths and values each builder brings to our team, and our mission. We simplify the complex, make a real impact, and create a better future for businesses of every size.

## About the role

The Head of Legal & Compliance at Check is a growth and execution role supporting the company as we scale to hundreds of millions of dollars in annual revenue over the next several years. This is not a 0→1 build. We have strong foundations: our regulatory posture, contract structures, and legal operations are largely established — you’ll come in to run them at the ever-increasing pace of our business, with thoughtfulness and resourcefulness. You'll spearhead regulatory issues and agency relationships, support corporate and board matters, and handle the steady volume of day-to-day legal questions that come with the territory of a fast-growing fintech startup. You'll also be the legal authority in our commercial deals, walking partners and their counsel through our agreements, simplifying the complex, and working with our GTM teams to get deals done.

We have ambitious goals for our business, and you will help ensure we execute on our vision with sound judgment. At its core, this role is not about eliminating risk, it’s about navigating it. We're looking for someone who articulates tradeoffs clearly, helps the business formulate a high-conviction strategy, and designs an execution plan for us to move forward safely.

This role sits on the Leadership Team and reports directly to the CEO. You'll manage a small legal and compliance team, including our our BSA/AML compliance officer, as well as outside counsel relationships.

## In this role, you will:

• **Run Check's legal function** - you’ll build and lead a small,...