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Cover Letter · for SVP, Commercial Strategy · Chess.com

Mike Daykhin

chess-com-application.daykhin.com · mike@daykhin.com · LinkedIn · Tel Aviv (EMEA)

Dear Hiring Team,

I have never pursued roles in the traditional way. My career has been built through founder, operator, and invited leadership mandates. Chess.com is one of the few opportunities specific enough, personal enough, and commercially large enough to make me seriously consider stepping out of founder mode.

My professional pattern is what I call business synergy: connecting assets that usually sit in separate silos and turning them into one revenue engine. The CV has the proof points — TNT's non-advertising content stack, Solvo's TV-and-radio audiences distributed through telcos, Lifestyle Platform's Magnit Pay at seven million users. What the CV cannot say is why this role is uniquely relevant for me, and why now.

On top of everything else this role asks for, it applies to one of the biggest, most emotionally engaged and underserved communities in the world — chess players. It hits close to home — I'm part of it.

♟ Chess and me

I learned chess at four, trained in chess school from seven to eleven, and reached first adult category. Then I was bullied at school and drifted to wrestling. After a long break, I rediscovered the game through Chess.com in 2013. Twenty-two thousand puzzles and roughly five thousand blitz games later, I am back over the board almost every day in a Tel Aviv street chess community.

I believe chess is one of the most under-monetized great games in the world. The clearest signal is that fewer than ~500 players globally can sustain themselves playing chess full-time. For a game with this huge global reach, cultural depth, and digital engagement, the commercial surface is surprisingly small.

The untapped potential spans multiple surfaces: subscriptions; broadcasts and creator formats; learning products; partnerships; events; merchandise; and sponsorships. There's also a powerful offline loop — street chess, clubs, and schools — where tools like the ChessClock app with reasonable improvements could better bridge Chess.com into players' real-world routines.

In my spare time I'm slowly writing the show bible for a chess-driven scripted-reality format called Chess Clash: Battle of Kings — think Harry Potter's chess meets Squid Game. The goal is to make chess feel exciting for people who still think it's boring and geeky, especially those who don't play the game yet.

An honest note: much of my large-scale operating experience was built in Russia, so a few company names may be less familiar to an international team — the scale, however, was significant. What I bring across borders is a cross-industry pattern library and an AI-native execution mode that lets me prototype partnership concepts in days, not quarters.

One detail that may say more than a formal closing: I stopped paying for a Chess.com subscription because puzzles became addictive enough to eat my workday, and unsubscribing was the only way to deal with it. That is the strongest product review I can give.

I would love to talk.

Mike Daykhin
mike@daykhin.com · linkedin.com/in/mdaykhin
P.S. Everything above — plus an outside-in deep-dive on Chess.com and a live AI agent built on my profile — lives at chess-com-application.daykhin.com.
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