VP, Media & Content

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 600+ fully remote people in 60+ countries working hard to serve the global chess community. We are here to support 200M+ 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

We are hiring a VP, Media & Content to serve as the operational and strategic leader across our Content and Media organization. This role is about running a media operation at scale with excellence: making sure productions ship on time, teams are unblocked, creators are supported, and every piece of content that touches our community reflects the quality our brand demands. You will oversee the full media and content pipeline - video production, social media, editorial storytelling, and broadcast - while serving as the connective tissue between content, partnerships, and events to ensure our deals and activations are holistic and community-first.

This leader will report directly to our Chief Chess Officer and work alongside senior leaders across Partnerships, Business Development, Events, and International teams. You’ll directly manage the Content and International Content teams while providing high-level operational oversight that keeps the broader media flywheel turning. The ideal candidate is someone who is passionate about content, operationally minded, and brings deep relationships with leaders across top tier sports, tech, and media companies.

What you'll do

Content & Media Operations (Primary)

• Lead, develop, and scale a multi-layered leadership team - including Directors and VPs - creating the conditions for them to thrive, make decisions autonomously, and grow into the next generation of leaders at the company.
• Set the organizational structure and team design for the Media function, making deliberate decisions about how the team is built, layered, and resourced to support a multi-year content strategy - not just today's roadmap.
• You Own the day-to-day of a multifaceted, talented, and international team. When something slips, you’re the one who catches it before it becomes a problem.
• Lead day-to-day operations of the Content and Media teams, ensuring productions run on schedule, resources are allocated effectively, and output quality is consistently high across all platforms (YouTube, Twitch, TikTok, social, and editorial).
• Own the content calendar, production pipelines, and cross-functional workflows that keep a high-volume, multi-platform media operation running smoothly.
• Drive accountability. Set goals, track KPIs, clear blockers, hold people to commitments. This isn’t a “set the vision and delegate” role, you’re in the details day in and day out.
• Drive operational accountability across the team—set clear goals, track KPIs, remove blockers, and ensure leaders and individual contributors deliver on commitments.
• Care obsessively about what our community experiences. Review content, flag quality issues, and cultivate a culture where everyone takes ownership of the brand’s voice and standard.

• Serve as the strategic bridge between content and commercial partnerships - ensuring that sponsorship deals, brand integrations, and activations are packaged holistically with content IP, creator relationships, event tie-ins, and community value at their core.
• Collaborate closely with our Business Development and Partnerships leads (who handle deal execution) to make sure commercial opportunities are enriched with content that is authentic and impactful.
• Think like a media executive who understands that the best partnerships combine IP, creators, events, product integrations, and community - and who won’t let a deal close unless it has that holistic potential.

• Own the Media P&L: manage budgets, headcount, and resource allocation with the rigor and accountability expected of a senior executive running a scaled content organization.
• Directly manage team leads and senior managers across Content and International; provide operational oversight and strategic direction for adjacent functions including Social, Broadcast, and Editorial.
• Build scalable processes, reporting structures, and team rhythms that allow this organization to operate at a high level whether the CCO is in the room or not.

Preferred Skills

• 10+ years of experience in content, media, or digital entertainment with progressive leadership responsibility, including P&L ownership of large, multi-functional teams.
• Demonstrated experience as a leader of leaders - you have managed Directors, VPs, and senior individual contributors, and have a track record of developing executive-level talent, not just managing it.
• Proven track record of delivering content and IP at scale - you’ve built or run a content engine at a platform, media company, or brand (think Twitch, YouTube, Snapchat, a major sports league, or a high-growth digital-native brand).
• Experience shaping organizational strategy: you've made or meaningfully influenced decisions about team structure, hiring philosophy, and long-term capability building at the department or division level.
• Deep operational excellence: you run things on time, on budget, and at a quality bar that sets the standard. You are not primarily a creative or strategist - you are the person who makes the machine hum.
• Experience packaging business deals that combine content, talent, and media assets into holistic commercial partnerships. You understand the intersection of editorial integrity and commercial value.
• An industry network that opens doors. You know creators, platform executives, brand marketers, and media buyers - and they take your call.

Nice-To-Have Skills

• Background in events, live production, or esports - understanding how to activate brands and content through in-person and broadcast experiences.
• Experience in business development or commercial partnerships, particularly in media, gaming, or sports.
• Familiarity with chess, gaming communities, or passion-driven digital audiences.
• Experience operating inside a founder-led, fast-moving organization where Slack is the lifeblood and the pace is relentless

Who You Are

• You are not a “pure exec.” We have the team - what we need is a leader who rolls up their sleeves, reviews content, flags issues, and is in the details daily. You care so much about what our community experiences that you want to touch everything, knowing you can’t.
• You know when to lead through your team and when to step in directly - and you've built organizations that don't depend on you being in every conversation to function at a high level.
• You are hungry. You want to own editorial and storytelling not just for our company, but for the chess world. You see the opportunity to shape how an entire sport is consumed globally.
• You thrive in high-volume communication environments and can manage the pace of a Slack-heavy, globally distributed organization without losing focus.
• You understand platform-specific content strategy - short-form vs. long-form, memes vs. editorial, youth culture vs. legacy media - and you know that young blood and fresh ideas are essential to staying relevant.
• You can work alongside a deeply involved founder/CCO who loves content and will always be engaged in this area. That doesn’t make you less hands-on or less accountable - it makes you better.
• You love chess - or are ready to fall in love with it.

About the Opportunity

• This is a full-time opportunity
• We are 100% remote (work from anywhere!)
• This role is open to candidates who can work in USA/CAN/EMEA

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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