About the Role

As the Deputy General Counsel, AI at Pearl, you’ll serve as a strategic legal leader and trusted advisor helping shape the company’s continued growth while building a modern, AI-first legal function.

In this role, you’ll partner closely with senior leaders across the business to manage complex legal issues and support high-impact business initiatives. You’ll lead a high-performing legal team while working across a broad range of legal matters, with particular emphasis on corporate governance, commercial transactions, privacy, consumer protection, litigation, and global compliance.

This is an exceptional opportunity for an experienced in-house legal leader who is energized by innovation and has demonstrated the ability to apply AI meaningfully within a legal organization. We’re looking for a strategic corporate generalist who combines strong legal judgment with business pragmatism, communicates exceptionally well in both synchronous and asynchronous settings, and can help Pearl move beyond experimentation to build and scale AI-enabled legal workflows that materially improve how the team operates.

What You’ll Do

• Help set the strategy for the Legal Department and all matters under its purview.
• Partner with senior leaders to advise on legal strategy, governance, risk management, and key business initiatives.
• Support the day-to-day operations of the Legal Department and lead a high-performing, collaborative legal team.
• Lead the adoption and implementation of AI across the Legal Department, identifying, building, and scaling practical use cases that improve legal research, drafting, knowledge management, decision-making, and operational efficiency.
• Establish responsible governance and operating practices for the Legal Department’s use of AI, including appropriate standards for accuracy, confidentiality, data protection, and human oversight.
• Serve as a trusted business partner who translates complex legal issues into practical, business-focused guidance for leaders across the organization.
• Strengthen legal operations, entity management, governance processes, and team workflows while enabling the Legal Department to scale alongside the business.
• Advise internal teams on the laws and regulations applicable to the company’s business, platform, and growth initiatives, including consumer protection matters and engagement with regulators such as the Federal Trade Commission and state attorneys general.
• Oversee significant legal matters while delegating effectively and supporting the team across the broader legal workload.
• Provide practical guidance across a broad range of corporate, employment, privacy, consumer protection, and regulatory matters.
• Oversee outside counsel in connection with litigation, disputes, regulatory matters, and other high-stakes issues.
• Draft, review, negotiate, and advise on a wide range of commercial agreements and strategic transactions.
• Help train employees on legal issues, company policies, and risk-aware decision-making.
• Partner cross-functionally with leaders across the company in a highly collaborative, often asynchronous working environment.

What We’re Looking For

• 12+ years of relevant legal experience, including 5+ years of in-house experience.
• Deep experience advising leadership teams on strategic legal, governance, risk management, and business matters.
• Experience serving as a broad corporate generalist, with strength in corporate governance, commercial transactions, and corporate matters.
• Demonstrated technical fluency with AI and a track record of implementing AI-enabled tools or workflows within a legal function. You should be an active practitioner who can evaluate use cases, build practical solutions, drive adoption, and help others develop their AI capabilities.
• Meaningful experience with class action litigation, consumer protection matters, and regulatory inquiries or enforcement actions involving the Federal Trade Commission and/or state attorneys general.
• Experience supporting B2B and B2C platforms, e-commerce, consumer, or subscription-based businesses.
• Experience counseling companies with international operations and navigating domestic and international regulatory issues is preferred.
• Privacy, data governance, and cybersecurity experience are strong pluses.
• Excellent written and verbal communication skills, with the ability to influence diverse stakeholders and adapt communication style across executives, business leaders, and legal partners in a highly collaborative, largely asynchronous environment.
• A demonstrated ability to mentor and elevate a high-performing legal team.
• Strong business judgment, creativity, and comfort operating in ambiguity.
• A desire to challenge the status quo in the DIY/self-help space.
• A track record of taking the law seriously, but not yourself.

Why Join Pearl
At Pearl, we’re redefining how people access expert help—combining AI technology and human expertise to solve real problems at scale.
You’ll play a key role in building scalable legal processes, enabling business growth, and helping define what a forward-thinking legal function looks like inside a dynamic technology company.

The Impact You’ll Have
Your work will directly influence how Pearl balances innovation, growth, and risk. You’ll help shape the Legal Department’s strategy, guide business-critical decisions, and build systems and practices that enable the organization to move faster and smarter.
If you're a business-minded legal leader who enjoys solving complex problems, building strong teams, and bringing modern tools and ideas into the legal practice, we'd love to hear from you.

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.)