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...