Head of Legal & Compliance

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, high-velocity team, and coach them toward autonomy and deep cross-functional partnership; you’ll leverage outside counsel efficiently, deploying them resourcefully on spiky and unfamiliar areas of work 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 Many backgrounds could fit this role, but ideal candidates will have most or all of the following: 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 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 Bonus: Familiarity with AI tools and curiosity about how they can improve legal workflows Bonus: Experience and appetite for managing and coaching a small team What we offer: For full-time employees, Check offers company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on their first day of work. We also provide stock options, flexible PTO and sick leave, up to 16 weeks of fully paid parental leave for all new parents, flexible return-to-work, 9 annual holidays, a 401k retirement plan, and a $100 monthly stipend for home internet and mobile phone expenses. We accept applications on an ongoing basis with no specified deadline. Travel & Office Policy The Check team is distributed across the US. Roles can be remote, hybrid, or based in one of our offices in New York City or San Francisco. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons a couple of times a year. All Checketeers gather in the spring for a required 3-day company offsite. For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays and there are regular happy hours, game nights, and other in-person events. Remote work at Check requires the ability to perform all responsibilities without distraction or disruption, while maintaining quality, effective communication, and productivity. -- Check is proud to be an Equal Opportunity employer. We do not discriminate based on race, religion, color, national origin, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender, gender identity, gender expression, transgender status, sexual stereotypes, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, provided they are consistent with applicable federal, state, and local laws. Check is committed to providing reasonable accommodations for candidates with disabilities in our recruiting process. Check participates in E-Verify and will provide the federal government with Form I-9 information from all new employees to confirm that they are authorized to work in the U.S. Check does not use E-Verify to pre-screen applicants.