Deputy General Counsel

About the Role

As the Deputy General Counsel, Legal Operations & 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-enabled legal function.
In this role, you’ll partner closely with the General Counsel and 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 excited about leveraging AI to improve how legal work gets done. 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 enjoys helping legal teams evolve through thoughtful adoption of new technologies.

What You’ll Do

• Help set the strategy for the Legal Department and all matters under its purview.
• Partner with the General Counsel and 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.
• Help identify opportunities to leverage AI to improve legal research, drafting, knowledge management, and operational efficiency.
• 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.
• 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, and other high-stakes matters.
• 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 curiosity about AI and enthusiasm for incorporating AI tools into legal workflows. Experience evaluating or adopting AI-enabled workflows is a plus.
• Experience working on class action litigation and consumer protection issues.
• Experience supporting B2B and B2C platform, 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.)