About the Role

Pearl is looking for an AI-focused General Counsel to lead legal strategy for a global business that has served millions of customers and is building AI-powered products for professional services. As the company’s lead legal advisor, you’ll work directly with the CEO, executive team, and Board of Directors on decisions that span corporate strategy, product innovation, consumer trust, and global operations.

You’ll own Pearl’s legal strategy and guide the company across a broad range of matters, including AI development and usage, products and platforms, intellectual property, privacy and data protection, consumer protection, corporate governance, financing and strategic transactions, employment, AI and regulation, litigation and disputes, and global compliance. We’re looking for someone with strong legal and commercial judgment who helps leaders weigh trade-offs and finds creative, practical solutions to complex challenges.

The General Counsel will also lead and develop a highly-functioning, strong & lean Legal team that is industry-leading in its in-house AI adoption. That means further developing the people and practices behind strong AI tooling and legal advice, implementing additional ways to bring AI into the function, and stepping in personally on the matters that matter most. This role is for a leader who can set direction at the executive level and engage directly when a matter calls for their judgment.

What You’ll Do

Lead legal strategy and executive counsel

• Set the Legal function’s priorities in line with Pearl’s business strategy, product plans, and most significant risks.
• Help leaders distinguish legal requirements from business choices and decide when to proceed, mitigate, or change course.
• Anticipate emerging issues and bring Legal and the Exec team into important decisions early.

Guide governance, transactions, and enterprise risk

• Oversee corporate governance, Board support, equity matters, corporate policies, and global entity management.
• Lead legal strategy for financing, M&A, strategic partnerships, diligence, and other significant corporate initiatives.
• Partner with Finance and leadership on the legal aspects of investor communications and significant corporate disclosures.
• Own the approach to major litigation, class actions, disputes, investigations, and regulatory inquiries.
• Partner proactively with PR and Marketing to advance Pearl’s mission, communicate the value of its products and services, and highlight its broader impact on consumers, independent professionals, and the markets it serves.
• Direct outside counsel on critical matters, with clear expectations for strategy, quality, and cost.

Support responsible product innovation and growth

• Partner with Product, Engineering, and business leaders on AI-enabled products and customer experiences.
• Guide legal decisions involving consumer protection, marketing, subscriptions, privacy, data use, intellectual property, and evolving AI regulation.
• Oversee major commercial negotiations and establish practical standards for routine agreements.
• Partner with People and business leaders on significant employment matters, internal policies, and compliance issues.
• Support the legal needs of Pearl’s international operations, working with local experts where appropriate.
• Enable teams to confidently comply with the variety of regulations impacting the e-commerce industry: privacy, security, consumer protection, algorithmic pricing, evolving global AI statutes, and others.

Lead a lean Legal organization

• Further mentor and develop legal leaders and create clear ownership, effective delegation, and strong accountability across the team.
• Set the department’s operating model, staffing priorities, budget, and outside counsel strategy.
• Champion industry-leading use of AI across Legal to help the team work more effectively and serve the business efficiently.

What We’re Looking For

• 10+ years of in-house legal leadership experience in technology, B2B/B2C or 2-sided internet marketplaces, platform e-commerce, or similarly complex business.
• Experience as a General Counsel or senior legal leader in a highly regulated industry with meaningful responsibility for legal strategy, executive advice, and Board matters.
• Demonstrated AI fluency and the ability to lead its adoption across Legal.
• Business-minded legal judgment and a track record of finding practical paths through complex issues so teams can move quickly.
• Strong corporate generalist judgment, with depth in governance, consumer protection, and complex litigation or regulatory matters.
• Experience leading legal work on significant financing, M&A, or other strategic transactions.
• Experience advising on technology products, privacy and data use, and legal issues affecting customer-facing businesses.
• The ability to lead a team, develop senior legal talent, and decide when to delegate and when to engage directly.
• Clear, concise written and verbal communication, including the ability to advise executives and align stakeholders in an often-asynchronous environment.
• A J.D. and active membership in good standing with a U.S. state bar.
• A humble leader who takes enabling organizations, but not themselves, seriously.

Remote From these States: California, Florida, Georgia, Idaho, Illinois, Massachusetts, Michigan, New Jersey, New York, North Carolina, Ohio, Oregon, Pennsylvania, Texas, Virginia, Washington, and Wisconsin.

Pay Transparency: Pearl will provide pay transparency information upon application to those in qualifying jurisdictions. (Employment is with JustAnswer LLC, a Pearl company.)