Senior Employment and Benefits Counsel

Our Legal team is a strategic partner at the heart of the business—focused on enabling growth, innovation, and operational excellence while also responsibly managing and mitigating risk. We work cross-functionally with all teams across the organization including Trust & Safety, Finance, Marketing, Sales, People, and Operations to build a trusted, compliant, and scalable marketplace. Whether it's shaping product design, negotiating key transactions, or supporting new initiatives  and growth, our mission is to make it easier for the business to move forward—confidently and responsibly. We pride ourselves on being pragmatic, solution-oriented, and business-minded. Around here, Legal isn’t a roadblock—it’s the Road to Yes.

As a Senior Employment and Benefits Counsel, you’ll play a key role in navigating complex labor and employment matters while helping to protect and scale a dynamic two-sided marketplace. You’ll collaborate closely across the Legal and People teams and partner with cross-functional stakeholders to advise on a wide range of issues related to employment law and benefits. Thumbtack attorneys are trusted advisors and problem-solvers, working on fast-moving, high-impact matters every day. Success in this role means building strong relationships across the business and delivering timely, pragmatic guidance that both identifies and mitigates risk—enabling the company to move quickly and confidently.

• Advise on employee relations matters, including terminations, performance management, investigations, accommodations, and other workplace issues
• Lead and support employment-related initiatives, such as policy development, process improvements, and training programs
• Lead and support employment related litigation matters
• Draft, review, and refine employment related documents, including agreements, policies, and internal communications
• Partner on privacy and cybersecurity initiatives impacting employees and workplace operations
• Advise on employee benefits related matters, including equity incentive programs
• Collaborate cross-functionally to educate teams on legal considerations related to employment and benefits matters, driving aligned and informed decision-making

• J.D. from an accredited law school and an active license to practice law in the U.S.
• 5-7 years of legal experience in a top tier law firm and/or publicly traded company, advising clients on employment and benefits related matters, including employment related litigation
• Strong analytical, strategic thinking, and communication skills—both written and verbal
• Sound judgment with the ability to balance legal risks against business goals
• Self-starter who thrives in a collaborative, fast-paced environment

• For candidates living in San Francisco / Bay Area, San Jose, New York City, or Seattle metros, the expected salary range for the role is currently $212,500 - $280,000
• For candidates living in Austin, TX or Washington DC metros or in California, Massachusetts, New Jersey, or Washington states, the expected salary range for the role is currently $187,000 - $240,000 
• For candidates living in all other US locations, the expected salary range for this role is currently $178,500 - $230,000

Actual offered salaries will vary and will be based on various factors, such as calibrated job level, qualifications, skills, competencies, and proficiency for the role.

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