Senior Legal Counsel

About Us

Chess.com is one of the largest gaming sites in the world and the #1 platform for playing, learning, and enjoying chess.

We are a team of 650+ fully remote people in 60+ countries working hard to serve the global chess community. We are here to support 250M+ chess players worldwide with the best possible product, content, and tools to serve the community!

We are a tech company. A gaming company. A content company. And we do it all with passion and commitment to the game. Above all we prize our mission-driven, flat, life-celebrating, no-corporate culture, and we look forward to meeting you and learning more about what you can bring to the team.

About You

As Senior Legal Counsel, you will be the most senior legal leader inside Chess.com, reporting directly to the CFO. This is a newly created role born from the company's continued growth and increasing complexity across areas like intellectual property, global compliance, employment law, data privacy, commercial partnerships, and potential future capital markets activity. You will own and build our internal legal function, serve as the strategic legal advisor to the executive team and board, and establish the frameworks that allow Chess.com to move fast while managing risk thoughtfully.

You are someone who has spent years developing deep legal expertise, ideally in technology, gaming, or digital media, and you are ready to bring that experience to a company where you will have real ownership and impact. You recognize that every business decision carries some degree of risk. Your strength lies in clarifying those variables, assessing the potential outcomes, and guiding leadership toward the most strategic path forward. You are comfortable operating across jurisdictions, translating complex legal concepts for non-lawyers, and working in a flat, remote-first culture where trust and direct communication matter more than hierarchy.

This role is ideal for someone who wants to build something meaningful. You will not be inheriting a fully built-out legal department. Instead, you will have the opportunity to shape legal strategy and partner closely with leadership to support the next chapter of Chess.com's growth, including building the infrastructure and discipline of a public-ready company.

What you'll do

• Lead the legal function: Serve as the primary legal advisor to the CEO, CFO, and broader executive team on strategic and operational legal matters across all Chess.com business units.
• Shape legal strategy: Develop and implement a legal strategy that supports the company's growth objectives, including commercial expansion, international operations, and building public-readiness across the organization.
• Manage commercial transactions: Draft, review, and negotiate a broad range of commercial agreements, including partnership deals, licensing agreements, endorsement contracts, vendor agreements, and content licensing arrangements.
• Oversee corporate governance: Support board governance, manage entity structure across the group, and continuously strengthen the company's governance, reporting, and compliance infrastructure as the business scales. Coordinate with outside counsel on corporate transactions, equity matters, and other corporate legal needs.
• Drive compliance and risk management: Ensure compliance with applicable laws and regulations across all jurisdictions where Chess.com operates, including data privacy (GDPR, CCPA, COPPA), digital safety, consumer protection, and employment law.
• Protect intellectual property: Oversee the company's IP portfolio, including trademarks, copyrights, and domain strategy. Manage enforcement actions and coordinate with external IP counsel as needed.
• Support data privacy and trust: Provide legal guidance on data privacy matters, partner with the security and product teams on privacy-by-design, and serve as a resource for data protection compliance across the group.
• Manage external counsel: Oversee relationships with outside law firms, manage legal spend, and ensure outside counsel is being used strategically and efficiently.
• Support employment and people matters: Partner with the People team to provide guidance on employment law, workforce compliance, and other people-related legal matters across the company's global footprint.
• Handle litigation and disputes: Manage litigation, regulatory investigations, and dispute resolution with the support of external counsel. Serve as the internal coordinator for legal proceedings.
• Leverage AI tools: Effectively leverage AI tools for legal strategy, tactics, and efficiency across the legal function.
• Partner cross-functionally: Work closely with teams across the company, including Finance, People, Product, Engineering, Content, Trust & Safety, and Partnerships, to provide practical, timely legal guidance.

Skills & Qualifications

• JD from an accredited law school and active bar membership in good standing
• 10+ years of legal experience, with a mix of law firm and in-house roles. Experience at a senior level in-house is strongly preferred.
• Broad commercial and corporate legal experience, including contract negotiation, corporate governance, M&A, and regulatory compliance
• Strong expertise in technology, digital media, or gaming law, with practical knowledge of IP, data privacy, and e-commerce regulations
• Deep familiarity with data protection frameworks, including GDPR, CCPA, and COPPA
• Experience managing outside counsel relationships and legal budgets
• Track record of operating as a trusted advisor to C-suite executives and board members
• Excellent judgment with the ability to balance legal risk against business opportunity in a fast-paced environment
• Clear, direct communication style with the ability to translate complex legal concepts for non-legal audiences 
• Comfort working in a fully remote, globally distributed team across multiple time zones
• High degree of autonomy, ownership, and accountability

Preferred Skills

• Background in the gaming, sports, entertainment, or digital content industrie
• Experience building or scaling an in-house legal function from early stages
• Familiarity with international employment law across multiple jurisdictions
• Knowledge of AI law and emerging regulations around artificial intelligence
• Experience with SEC reporting frameworks, public company governance, or capital markets transactions
• Understanding of the chess world, competitive gaming, or online communities
• Fluency in Spanish or another widely spoken language is a plus

About the Opportunity

• This is a full-time opportunity
• We are 100% remote, always have been, always will be!
• This role is open to candidates who can work in the United States for timezone alignment purposes.

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You can learn more about us here:

• https://www.chess.com/article/view/how-chess-com-virtual-team-works-together
• https://www.chess.com/about