Head of Legal & Compliance

Responsibilities

• Run Check's legal function: build and lead a small, high-velocity team, coach toward autonomy and cross-functional partnership, leverage outside counsel efficiently
• Drive commercial contracting: guide commercial negotiations and MSA reviews, help GTM teams build judgment on tradeoffs and ROI, reduce administrative friction
• Own Check’s regulatory relationships: run point on licensing, audits, and related matters; partner with the BSA/AML compliance officer on compliance obligations as a money transmitter
• Serve as strategic thought leader: identify key risks, map impact on business path, recommend clear solutions
• Support corporate and board cadence: lead or contribute to board presentations, financing and valuation diligence, cap table administration, and day-to-day governance
• Partner across the org: serve on Security Leadership council for privacy and data policies, partner with Head of People on sensitive employment matters, handle IP and emerging needs

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 (private practice and in-house counsel experience a plus)
• Exceptional raw caliber: highly intelligent, fast learner, outstanding written and verbal communication skills
• Sound, decisive judgment: quickly form and defend a clear point of view on risk and navigation
• Strength in commercial contracting and negotiation: owned recurring MSA, mastery over variables, fluency reviewing terms
• Curiosity: dive deep into new subject matter and quickly build expertise (industry, AI regulation, data protection, etc.)
• Resourcefulness: successfully operated with limited resources in fast-paced, commercially and technically complex environment

Nice-to-Haves

• Familiarity with AI tools and curiosity about improving legal workflows
• Experience and appetite for managing and coaching a small team

Benefits

• Company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance (effective first day)
• Stock options
• Flexible PTO and sick leave
• Up to 16 weeks fully paid parental leave for all new parents, flexible return-to-work
• 9 annual holidays
• 401k retirement plan
• $100 monthly stipend for home internet and mobile phone expenses