A Gambit Not Worth Taking - Anonymous Employee Chess.com Employee Review

1.0
29 Jan 2026
Recommend
CEO approval
Business outlook

Pros

Fully Remote, and if you enjoy chess, there aren't many other options to make a real living in the industry. If you don't feel secondhand embarrassment easily, and enjoy bad rap and pop music, you'll find plenty of opportunities to watch tech industry cliches unfold in real time.

Cons

Make sure to modify the Glassdoor filters to see all the reviews, as many are hidden by default. * You'll see the culture of the company self-described as "family like" and "non-corporate," which anyone with experience knows describes an unprofessional environment. From lack of accountability, juvenile behavior, cliques and poor management, to "leadership" acting like their actions are beyond reproach. * The company does not care about its users apart from their value as targets for SEO and advertising. Dark patterns are common, especially in the billing process. They amplify controversy to disturbing levels to help drive engagement, while acting like the moral arbiters of chess. * The CTO is insecure and lacks technical depth, which manifests in all the predictable ways and has created a cult of personality where sycophants have learned to survive by reflecting the CTO's desired emotional state back at him. * Communication is chaotic. Meetings devolve into people talking over each other, more interested in hearing themselves speak than actually solving anything. * The stack is antiquated and filled with a significant amount of technical debt, with no leadership or vision to move the product to a manageable state. Also the platform is constantly criticized publicly by chess players and the tech community at large (see "The Real 100x Dev" for an example).

Explore other reviews about Chess.com

5.0
15 May 2026
Anonymous employee
Recommend
CEO approval
Business outlook

Pros

- Generally relaxed work culture - Incredible flexibility due to remote work - 99% of people here are good people and fun to work with - Interesting though still niche product - Seeing incredible growth in recent years

Cons

- Below market pay (they are working on this) - Lack of clear strategy at times, feels reactive - Senior leadership hired externally has generally been terrible, with a couple exceptions (need more internal promotions/growth) - Lack of solid retention incentives for top talent (though this is slowly improving, a bit late however)

5.0
8 May 2026
Recommend
CEO approval
Business outlook

Pros

Fantastic culture and work life balance. The company treats you with respect and positivity. Couldn’t be a better work environment.

Cons

Pay is not up to industry standards

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