Interesting product, challenging teams - Anonymous employee Chess.com Employee Review

2.0
8 Jul 2025
Anonymous employee
Recommend
CEO approval
Business outlook

Pros

* Depending on your team, projects can be fun, with direct feedback from consumers. * Work on a product enjoyed by millions of users in a fast-growing environment. * Some great people in the company. * Flexibility over where you work (100% remote) * Annual international all-inclusive retreat

Cons

* A number of senior members of staff at the company lack decent people skills, and do not act in the interest of their colleagues. This can lead to some catastrophic issues for people at the company. * The company functions like a “family”. Depending on how you value that, this could be a pro. However, it also leads to a lack of transparency around formal processes. * All overseas staff outside US are contractors: no healthcare, pension, etc. * Slow career progression with not a lot of opportunities to grow. * Fully-remote company with poor resources in their People/HR teams - slow response times, poor communication in the case of issues which need to be addressed. * A lot of employees working very independently, and not a lot of joint up work across teams. * Several periods of layoffs impacting job confidence.

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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