VP, Media

Chess.com

3d•Remote

About The Position

We are hiring a VP, Media 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.

Requirements

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 Haves

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

Responsibilities

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.