Lead Commercial Counsel

About the Lead Commercial Counsel at Headspace:

At Headspace, we believe legal should be a catalyst, not a constraint. We’re looking for a trusted, approachable Lead Counsel, Commercial to serve as the go-to legal partner for our commercial operations. Reporting directly to our General Counsel, this is a senior individual contributor role who will act as a key legal advisor, leading through influence, clarity, and collaboration. You’ll own and evolve our commercial contracting strategy—partnering cross-functionally on everything from B2B and health plan agreements to vendor workflows, AI enablement, and legal tech innovation. You connect with courage, not caution—offering clear, solution-oriented advice that earns trust and accelerates business decisions. You understand that enabling the business starts with listening well, spotting real risk (not theoretical friction), and creating legal pathways that balance speed, scale, and sound judgment. If you pride yourself on being the person your business partners call first—not just because they have to, but because they want to—you’ll thrive here.

What you will do:

• Serve as the lead attorney and primary POC for all commercial contracting matters at Headspace, including overseeing B2B, Health Plan, Partnership and Procurement contracting
• Support AI and emerging tech contracting strategy, drafting and negotiating commercial agreements that involve the use, development, or licensing of AI technologies—including data rights, IP, and model training restrictions
• Draft, review, and negotiate a wide variety of commercial agreements including MSAs, Health Plan, BAAs, DPAs, vendor, and strategic partnership agreements. Partner with leadership across business units to provide strategic, pragmatic legal counsel. Solve process gaps and maximize deal efficiency
• Oversee Legal Ops, including owning our CLM integrations and legal AI tooling, optimizing contract workflows, templates, and processes to reduce friction and improve efficiency
• Ensure compliance with healthcare, privacy, and other applicable laws and regulations (e.g., HIPAA, CCPA, GDPR)
• Provide creative, solution-oriented legal advice in a fast-paced, high-growth environment
• Be open to expanding your skillset- we are a small team that has the opportunity to cover a wide range of business needs 
• Manage commercial-focused budget, including external legal support and software

What you will bring:

Required Skills:

• Juris Doctor (JD) from an accredited law school
• Admitted to a U.S. state bar
• 8+ years of commercial contracts experience, including significant in-house counsel exposure
• Deep knowledge of relevant laws and regulations in the health tech space
• Strong command of HIPAA, ERISA, PHI/PII handling, and global privacy regimes (GDPR, CCPA), with practical experience advising on health plan agreements, BAAs etc
• Experience working cross-functionally in high growth companies 
• Demonstrated commitment to fostering diverse and inclusive teams
• CLM & Legal Tech experience
• Experience identifying opportunities for process improvement and use of AI tools
• Excellent judgment, risk management and problem-solving capabilities
• Strong drafting, negotiation, and communication skills
• Comfortable navigating ambiguity and managing complex cross-functional initiatives
• Self-starter mindset with the ability to operate independently and collaboratively

Preferred Skills:

• Experience in healthcare, B2B, and/or D2C services preferred

Location:

This is a hybrid role located in our San Francisco office, working 3 days per week from the office. 

Pay & Benefits:

The anticipated new hire base salary range for this full-time position is $176,400-$240,000 + equity + benefits. 

Our salary ranges are based on the job, level, and location, and reflect the lowest to highest geographic markets where we are hiring for this role within the United States. Within this range, individual compensation is determined by a candidate’s location as well as a range of factors including but not limited to: unique relevant experience, job-related skills, and education or training. 
Your recruiter will provide more details on the specific salary range for your location during the hiring process.

At Headspace, base salary is but one component of our Total Rewards package. We’re proud of our robust package inclusive of: base salary, stock awards, comprehensive healthcare coverage, monthly wellness stipend, retirement savings m