Corrupted Engineering from weak CTO leadership - Engineering Chess.com Employee Review

1.0
14 Feb 2025
Recommend
CEO approval
Business outlook

Pros

You can play chess while at work...

Cons

Although the leadership was reluctant to admit it, Chess.com was preparing for a public IPO. The company struggled to meet IPO requirements, leading to intense micromanagement of the entire engineering department. The situation was dire—made worse by the fact that power was concentrated in the hands of a single individual: the Chess.com CTO, who exercised control over the entire company. Poor communication, a confusing culture, and a toxic environment of backstabbing. There were a dozen of YES man always trying to make the CTO happy. To me, the company was more about ChessCTO.com.

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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