[Remote] Head of Legal & Compliance

Note: The job is a remote job and is open to candidates in USA. Check is a fintech company dedicated to improving payroll processes. The Head of Legal & Compliance will lead the legal function, manage regulatory relationships, and support corporate matters as the company scales its operations.

Responsibilities

• 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

Skills

• 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
• Familiarity with AI tools and curiosity about how they can improve legal workflows
• Experience and appetite for managing and coaching a small team

Benefits

• Offers Equity
• Offers Bonus
• Target variable incentive compensation equal to 10-15% of total cash compensation.
• 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.
• 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
• $100 monthly stipend for home internet and mobile phone expenses
• 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
• Regular happy hours, game nights, and other in-person events

Company Overview