Deputy General Counsel

About the Role

As the Deputy General Counsel, you will step into a uniquely strategic leadership lane with a clear succession path to General Counsel. You will work shoulder-to-shoulder with our current General Counsel, receiving intentional mentorship and exposure across the full spectrum of enterprise-level legal strategy. This role is designed to set you up for success as you transition into the General Counsel position after a defined and supportive onboarding period.

You will be the key force in shaping the next evolution of our legal function. Leading a high-performing legal team, you will navigate complex legal landscapes spanning internet and e-commerce regulation, consumer protection, employment, privacy, intellectual property, commercial transactions, and global compliance. Your remit will extend beyond legal stewardship; you will influence business strategy, partner cross-functionally at all levels, and ultimately hold a critical seat at the executive table.

For a forward-thinking legal leader, this is an opportunity to learn the intricacies of the business from the inside out, build trusted relationships with senior leadership, and eventually step into the General Counsel role with both confidence and clarity.

What Youll Do

• Set the strategy for the Legal Department and all matters under its purview
• Partner with the GC and CEO to advise on legal strategy
• Run the day-to-day operations of the Legal Department, managing a high functioning, driven team
• Respond promptly and effectively to legal issues and requests from internal functions.
• Advise various teams with respect to laws and regulations applicable to the companys business and platform and assist teams in evaluating legal risks.
• Oversee the most significant legal matters while delegating and providing support to the team for all other legal work
• Provide advice with respect to privacy and intellectual property matters.
• Oversee outside counsel in connection with litigation and disputes involving the company.
• Provide advice to the human resources department with respect to employment law matters.
• Assist the company in drafting and negotiating commercial agreements.
• Assist in training employees on legal issues and company policies.

Desired Outcomes

First 30 Days: Foundation & Immersion

• Establish a foundational understanding of our business model, product ecosystem, regulatory posture, and global operating footprint.
• Build rapport with the General Counsel, CEO, and key executive stakeholders.
• Assess the structure, workflows, and capabilities of the legal team.
• Begin reviewing top ongoing matters: litigation, regulatory matters, proactive legal initiatives, privacy frameworks.

First 60 Days: Operational Leadership & Strategic Alignment

• Take ownership of select legal workstreams with increasing autonomy.
• Partner with the General Counsel to refine Legals strategic priorities for the upcoming year.
• Begin implementing proactive legal initiatives in alignment with the Legal OKRs.

First 90 Days: Department Stewardship & Enterprise Integration

• Lead day-to-day operations of the legal department, ensuring responsiveness, quality, business alignment and mentorship of the Legal team.
• Establish yourself as a primary legal advisor to key cross-functional teams.
• Oversee material litigation, regulatory matters, or commercial negotiations.
• Socialize a vision for Legal that reinforces operational excellence and proactive risk management.

By 120 Days: Succession Readiness & Executive Integration

• Demonstrate readiness to assume expanded responsibilities from the General Counsel.
• Take full leadership responsibility for team management and strategic planning.
• Serve as a key contributor to executive discussions, bringing strong judgment and clear business-oriented legal guidance.
• Finalize a transition roadmap for assuming the General Counsel position within the agreed-upon timeframe.
  

What Were Looking For

• 12+ years of relevant legal experience with ability to work both independently and with a team, including a minimum of 10 years in-house experience.
• Experience working on class action litigation and consumer protection issues.
• Proven experience communicating complex and nuanced legal issues using common sense language that is both approachable and easy to digest.
• Excellent written and verbal language skills are required.
• A strong desire to mentor a performance-driven legal team, enabling them to continue their high-level work
• Strategic and outside-the-box thinking with regard to legal matters and approaches
• A desire to change the status quo in the DIY/Self-Help space
• B2B and B2C platform experience
• Strong experience or desire to utilize AI to drive team results
• Significant experience providing counsel to e-commerce companies with products or services offered to consumers.
• Experience counseling companies with international operations is preferred.
• Strong interpersonal skills, business judgment, strategic thinking and work ethic and must be dynamic and team oriented.
• Ability to work efficiently with cross-functional teams and manage numerous complex projects simultaneously under tight deadline pressure.
• Experience working on domestic and international regulatory matters
• Familiarity with U.S. and international privacy laws and regulations is a plus.
• A track record of taking the law seriously but not yourself.

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.