Vice President Chess Instructor Jobs (NOW HIRING)

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 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
We are hiring an SVP, Commercial Strategy to lead and unify Chess.com's B2B revenue-driving efforts across product, content, advertising, and partnerships. This is a senior, company-shaping role responsible for connecting how we monetize what we build with how we engage our global audience.
This is not a traditional sales role, nor is it a traditional content management or "run big live events" role. It is the strategic and creative engine behind how Chess.com turns its entire ecosystem into meaningful, scalable revenue.
Chess.com sits at the intersection of an amazing product, incredible content, and an extremely engaged community at a massive global scale. We have a subscription business serving tens of millions of users, a rapidly growing advertising business, and a powerful content engine that serves the global chess community, both on our own site and apps, as well as on Youtube and every major social media vertical. We have the most active competitive chess ecosystem in the world, and our chess broadcasts, both of our own IP as well as coverage of the larger professional events ecosystem, are the most viewed in the world.
Each of these surfaces has commercial value. Your opportunity is to connect them.
The best candidates see the untapped commercial potential of Chess.com holistically. You understand how to take product features, audience engagement, content reach, and live moments and turn them into integrated partnerships that create value for both users and brands.
You will directly report to the Chief Chess Officer and work alongside leadership across Product, Growth, Monetization, Ads, Sponsorships, Partnerships and Content. You will also support and partner with key leaders in Business Development and Events, ensuring alignment across all commercial initiatives.
This role is for a leader who can think creatively, operate strategically, and close meaningful deals. You bring structure to opportunity and turn ideas into revenue.
Who You Are
You think in systems, not silos. You see how product, content, ads, and community connect, and you instinctively look for ways to turn that into meaningful commercial value.
You are commercially creative. You don't just sell existing inventory. You design partnerships that didn't exist before and make them feel obvious in hindsight.
You are comfortable operating at both a strategic and executional level. You can shape a vision for how Chess.com grows revenue and also get deals across the line.
You understand that user trust is everything. The best partnerships improve the experience. The wrong ones damage it. You know the difference and act accordingly.
You are energized by scale and complexity. Chess.com has one of the most engaged audiences in the world, and you see the opportunity to build something special around it.
You love chess or are ready to fall in love with it.
What you'll do
Commercial Strategy & Integration
Support the commercial strategy across Chess.com's full ecosystem, identifying and developing integrated commercial opportunities that span multiple surfaces and feel native to the Chess.com experience. This includes product, subscription offerings, advertising inventory, sponsorships and brand partners, (external) content platforms, and events and community. You connect these into a cohesive revenue strategy.
Work closely with Product and Monetization teams to identify features and user experiences with more commercial potential. You help shape how partnerships can enhance, not degrade, the user experience.
Partner Business Development with Ads and Growth teams to align direct sales, inventory strategy, sponsorships and audience targeting with broader commercial initiatives. You ensure that large deals are supported by scalable execution.
Define how Chess.com packages its audience, content, and product into compelling propositions for global brands. You are not selling impressions. You are selling access, engagement, and creative integration at scale.
Business Development & Partnerships
Enable high-value business development efforts across the company by bringing commercial strategy, product integration expertise, and senior brand relationships to the table. You support a team that builds and closes partnerships with major global brands across categories such as finance, technology, media, and consumer goods.
Support the structuring and negotiation of large, integrated deals that span multiple verticals. These may include product integrations, branded content, advertising campaigns, event activations, and talent collaborations.
Help provide visibility into deal flow, forecasting, and revenue performance and support the existing sales/sponsorships pipeline, connecting the dots across the entire organization for a holistic strategy that makes sure we are attracting the right partners, for the right prices, providing the best value to our community.
Collaborate with Communications and Content teams to ensure commercial activations strengthen the Chess.com brand and resonate with the community.
Build long-term relationships with senior decision makers across brand marketing, media buying, and partnership teams. You are a trusted partner, not just a vendor.
Content, Events & Community Alignment
Work across Chess.com's content ecosystem to ensure commercial opportunities are integrated thoughtfully into YouTube, social media, editorial, and creator collaborations.
Oversee the intersection of partnerships and competitive programming. Events, broadcasts, and live moments are important commercial levers, and you ensure they are used strategically within broader deals.
Support a selective portfolio of in-person events as part of integrated partnerships. You understand how live experiences can amplify brand relationships, without needing to design event formats or operate event logistics directly.
Collaborate with community and social teams to ensure branded activations feel authentic and additive to the user experience.
P&L and Team Leadership
Own the commercial performance across all content, community, and events, connecting the thriving ecosystem of partnerships and sponsors with the traditional streams of Chess.com's subscription business and advertising revenue. You set targets, support pipeline health, and drive accountability across teams.
Provide strong support for the current leaders of Business Development, and Events, and work cross-functionally with Monetization, Product, Ads, and Content leadership. This is a leader-of-leaders role where you set strategy and create alignment, while empowering strong operators to execute.
Build scalable processes, reporting structures, and team rhythms that allow the commercial organization to operate with clarity and consistency.
Preferred Skills

• 10+ years of experience in commercial strategy, business development, partnerships, advertising, or digital media with progressive leadership responsibility.
• Demonstrated experience closing large, complex deals with global brands. You have structured partnerships that combine multiple channels and deliver meaningful revenue.
• Experience working at the intersection of product, content, and monetization. You understand how digital platforms generate value and how to translate that into commercial opportunity.
• Strong understanding of digital advertising, including direct sales, inventory strategy, and campaign execution.
• Experience developing creative, product-integrated partnerships that enhance user experience rather than disrupt it.
• Proven ability to operate cross-functionally across product, marketing, content, and sales teams in a fast-moving environment.
• Track record of building and leading high-performing teams, including managing senior leaders and driving accountability.
• Deep relationships across brand marketing, media, and partnership ecosystems.

Nice-to-Have Skills

• Background in gaming, esports, or passion-driven communities where audience engagement is central to the product.
• Experience working with creators, influencers, or talent partnerships as part of commercial strategy.
• Familiarity with live events and broadcast environments as part of integrated brand activations.
• Experience operating in a founder-led, fast-moving organization.

About the Opportunity

• This is a full-time opportunity
• We are 100% remote
• This role is open to candidates who can work in USA/CAN/EMEA due to team alignment and business needs

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