Head of Legal & Compliance

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.

• Drive commercial contracting - you'll guide our commercial negotiations and MSA reviews, helping our GTM teams build judgment on tradeoffs and ROI; you’ll be in the weeds where the deal requires it and reduce administrative friction where the team can move without you.
• Own Check’s regulatory relationships - you and your team will run point on licensing, audits, and related matters that carry real implications for Check and our ecosystem; you’ll partner with the BSA/AML compliance officer and the broader team on Check's compliance obligations as a money transmitter.
• Serve as strategic thought leader - you’ll be a key strategic voice in our business decisions, identifying the risks that matter most, mapping out how they impact our path, and recommending a clear solution that keeps us moving forward.
• Support the corporate and board cadence - you’ll lead or contribute to board presentations, financing and valuation diligence, cap table administration, and day-to-day governance.
• Partner across the org - you’ll serve on the Security Leadership council to build and maintain our privacy and data policies, partner with the Head of People on sensitive employment matters, and handle IP and other emerging needs as they arise.

Requirements

• Juris Doctorate and active bar membership, with strong academic and professional credentials. NY or CA bar preferred.
• 6+ years of related professional legal experience - a combination of private practice and in-house counsel experience is a plus.

Qualifications

• Exceptional raw caliber - you’re highly intelligent and a fast learner, with outstanding written and verbal communication skills to help simplify complex topics for any audience.
• Sound, decisive judgment - you can quickly form and defend a clear point of view on risk and how to navigate it, even when you don’t have all the information.
• Strength in commercial contracting and negotiation - you’ve owned a recurring MSA before, with mastery over the variables and fluency reviewing terms with partners.
• Curiosity - you may not come from a fintech or payroll background, but you’re great at diving deep into new subject matter and quickly building expertise, be it our industry, AI regulation, data protection, or anything that comes next.
• Resourcefulness - you’ve successfully operated with limited resources in the past, in a fast-paced, commercially and technically complex environment.