Legal Trust & Risk, Strategy & Operations Lead

🚀 Join the Future of Commerce with Whatnot!

Whatnot is the largest live shopping platform in North America and Europe to buy, sell, and discover the things you love. We’re re-defining e-commerce by blending community, shopping, and entertainment into a community just for you. As a remote co-located team, we’re inspired by innovation and anchored in our values. With hubs in the US, UK, Germany, Ireland, Poland, and Australia, we’re building the future of online marketplaces –together.

From fashion, beauty, and electronics to collectibles like trading cards, comic books, and even live plants, our live auctions have something for everyone.

And we’re just getting started! As one of the fastest growing marketplaces, we’re looking for bold, forward-thinking problem solvers across all functional areas. Check out the latest Whatnot updates on our news and engineering blogs and join us as we enable anyone to turn their passion into a business, and bring people together through commerce.

💻 Role

The Legal team at Whatnot protects the platform, enables the business to move fast, and ensures compliance across a rapidly expanding global marketplace. We’re hiring a data-driven Strategy & Operations Lead to serve as the strategic and operational bridge between Legal and our Trust & Risk organization.

You will own the strategy and operations for legal intake, triage, and escalation workflows to ensure that legal issues are surfaced and resolved quickly; build scalable frameworks to identify risk patterns, trends, and root causes of Trust & Risk Legal matters; partner seamlessly with cross-functional with Trust & Risk, CX, and Policy to communicate and drive continuous improvements to processes and policies to mitigate legal risk while improving user satisfaction.

• Design and own the intake, triage, and routing framework (including decision trees, playbooks, macros, and criteria) for escalations directed to Trust & Risk Legal that reduce escalation volume by improving self-serve capacity and direct resolution by non-Legal teams. Resolve complex escalations with a high degree of autonomy, exercising sound legal-adjacent judgment while knowing when and why to bring in Legal, Policy, and Trust & Risk leadership.

• Identify and collect relevant data to surface trends, determine root causes, flag policy gaps, and evaluate whether existing guidance is effective. Recommend upstream fixes (policy, product, process, training) and partner cross-functionally to ship and implement them.

• Build cross-functional communications and visibility framework that drives prioritization and reduces repeat escalations. Partner with Legal, Trust & Risk, CX, Policy, and other cross-functional partners to clarify ownership, streamline processes, and ensure consistent communication and alignment.

• Own investigation and fact-development workflows for high-risk or novel issues within Trust & Risk Legal including user enforcement actions, regulatory inquiries, subpoenas, and other sensitive matters under attorney direction. Produce clear, defensible case memos with timelines, evidence, key unknowns, and recommended actions.

Team members in this role are required to be within commuting distance of our San Francisco, Los Angeles, or New York hubs.

👋 You

Curious about who thrives at Whatnot? We’ve found that low ego, a growth mindset, and high-impact drive go a long way here.

As our Strategy & Operations Lead for Legal Trust & Risk, you should have 4+ years of experience in Trust & Safety, Risk Operations, Legal Operations, Compliance, or a strategy/business operations role supporting legal or risk functions, plus:

• Strong analytical abilities and problem-solving skills. Demonstrated ability to identify patterns in data, diagnose root causes, and drive process improvement. Experience with SQL and building dashboards is required.

• Exceptional judgment and the ability to distinguish between operational, policy, and legal issues, and to make defensible, well-documented first-line calls with incomplete information.

• Proven ability to manage intake queues, triage workflows, and optimize operational efficiency in high-volume, fast-paced environments.

• Excellent written and oral communication skills with the ability to translate complex legal and risk challenges into clear, concise, action-oriented language for diverse audiences.

• A self-starter who can prioritize in ambiguous situations and balance competing stakeholder needs (legal risk, business velocity, user experience).

• Strong project management skills, including planning, prioritizing, execution, and cross-functional stakeholder alignment.

• A builder’s mindset: eager to create scalable systems (templates, macros, decision trees, training, documentation) rather than relying on ad hoc heroics. Comfortable being the “utility player” who ships the first version of critical infrastructure.

• Comfortable working on a lean team in a fast-paced, ambiguous environment, willing to flex across roles and projects where needed.

• Not required to be an attorney, but experience working with or supporting legal teams is a strong plus. Familiarity with trust & safety enforcement, regulatory compliance, IP, fraud, or privacy is a plus.

🎁 Benefits

• Generous Holiday and Time off Policy

• Health Insurance options including Medical, Dental, Vision

• Work From Home Support

  • Home office setup allowance

  • Monthly allowance for cell phone and internet

• Care benefits

  • Monthly allowance for wellness

  • Annual allowance towards Childcare

  • Lifetime benefit for family planning, such as adoption or fertility expenses

• Retirement; 401k offering for Traditional and Roth accounts in the US (employer match up to 4% of base salary) and Pension plans internationally

• Monthly allowance to dogfood the app

  • All Whatnauts are expected to develop a deep understanding of our product. We're passionate about building the best user experience, and all employees are expected to use Whatnot as both a buyer and a seller as part of their job (our dogfooding budget makes this fun and easy!).

• Parental Leave

  • 16 weeks of paid parental leave + one month gradual return to work *company leave allowances run concurrently with country leave requirements which take precedence.

💛 EOE

Whatnot is proud to be an Equal Opportunity Employer. We value diversity, and we do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, parental status, disability status, or any other status protected by local law. We believe that our work is better and our company culture is improved when we encourage, support, and respect the different skills and experiences represented within our workforce.