Senior Manager, Player Experience

Chess.com

3d • Remote

About The Position

This role exists to make our products serve real people, not just experiment metrics. You are the company's clearest window into the actual human experience of using Chess.com, and your job is to keep that experience honest, felt, and acted upon across the whole organization. You'll work closely with senior leadership, including the CEO and CGO, and it's on you to figure out how to reach into product, design, data, research, and community to drive change. The breadth is the point. You'll stand up and lead the function, managing a small, hands-on team directly and extending your reach far wider through the people you influence, not just the ones who report to you.

Requirements

• A track record of changing products through deep user understanding. Whether over many years or a few high-impact ones, you've done user research, product discovery, or design work that actually changed what got built. We care more about judgment and hunger than years on a resume.
• A bias for watching over assuming. You'd rather sit with one real user for an hour than debate in a conference room, and you know how to keep an interview low-pressure so people behave like they normally would.
• AI-native. You already use AI daily to analyze research, find patterns, and prototype. Working artifacts are how you think, not an afterthought.
• First-principles thinker with real empathy. You want to understand why before jumping to solutions, and you can get a stranger to open up about what they're genuinely feeling without leading them there.
• High-velocity, work-out-loud communicator. You operate primarily in writing across many time zones, and you can move from a detailed friction point in one thread to an exec-level takeaway in the next without becoming a bottleneck.
• Comfortable with both qualitative and quantitative signal. You can read a funnel to know where to look, then go find out why. You don't need to be a data scientist, but you respect the numbers and build on them.
• A builder of influence across the whole company. You create alignment by making the player's experience impossible to ignore, and you find your own ways into the functions where you can drive the most change.
• You've managed or closely mentored a small team, or you're ready to step into it. You lead by setting the bar with your own work, not just directing others.
• You love chess and care deeply about our mission, and about players at every level, from a confused first- timer to a serious improver to a die-hard community member. If you're light on Chess.com specifically, you make up for it by diving in hard before you ever walk in the door: using the app thoroughly, forming sharp opinions, and interviewing your own network.

Responsibilities

• Get inside the experience of real players. Spend real time watching actual players, and people who aren't players yet, use our products. Not the hypothetical user in a planning doc, the real person sitting there delighted or lost. You do this work yourself, and just as importantly you get other leaders and teams doing it too, because nothing replaces seeing it with your own eyes.
• Close the loop, don't just generate insight. Find the friction, get it to the people who own the surface, and then go back and watch real players hit the improved flow to confirm it actually got better. You're accountable for the outcome, not just the writeup. A complete loop, observe to fix to re-observe to share, becomes the template the rest of the org can copy.
• Make sure every kind of player has a seat at the table. Cover the full journey, from chess aware and chess curious to chess player, chess improver, and chess community member, so we don't sharpen the experience for one group while quietly breaking it for another. Keep a living roster of real, memorable players across that journey that product and marketing teams can picture, point to, and literally talk to when they need a gut check.
• Turn signal into action across the company. Synthesize what you see into concrete, undeniable findings and get them in front of the right owners. Pull from every channel, support tickets, app reviews, forums, and social, and connect the dots into themes the company can act on, sharing what's net-new rather than what's already known.
• Spread the mindset. This is not a solo function. Get leaders, PMs, and anyone who shapes the product to watch real players themselves, because a person who has personally seen a player get stuck makes different decisions forever after. You are the evangelist for player empathy company-wide.
• Own the experience. You're the company's advocate for the real player. You won't ship the fixes yourself, you partner with the PMs and engineers who do, but you bring findings that are concrete and impossible to ignore and stay on it until the product is genuinely better. How you reach into each team to make that happen is yours to shape.
• Lead and grow the function. Stand it up and manage a small team directly, turning strategy into clear objectives. This stays a hands-on role, you'll do the research yourself as much as you lead it, not manage from above. Set the bar through your own work, and raise the people around you, your direct team and the wider group you shape through influence.
• Use AI to move fast. Record and analyze interviews with AI, surface patterns across hundreds of sessions, and build rough prototypes that make a problem, or a fix, tangible. You bring working artifacts into the conversation, not just decks.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed