Reviews by job title

6 reviews
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).

2.0
8 Jul 2025

Interesting product, challenging teams

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.

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.

3.0
27 Mar 2025

Fun till it isn't

Recommend
CEO approval
Business outlook

Pros

Friendly coworkers, good benefits, annual trip is nice.

Cons

Slow turn around time, management is unsure of what they want and will change course randomly, there's a lack of communication from topdown, sneaky internal politics at play.

5.0
20 Aug 2021
Recommend
CEO approval
Business outlook

Pros

Fun, Lifelong learner, Good communication

Cons

Actually there is no cons lol

5.0
15 Feb 2023
Recommend
CEO approval
Business outlook

Pros

Very engaging and helpful. Great communication and quick response times. Very friendly.

Cons

A little hard at the beginning due to lack of instructions.

Viewing 1 - 3 of 6 Reviews

Glassdoor has 152 Chess.com reviews submitted anonymously by Chess.com employees. Read employee reviews and ratings on Glassdoor to decide if Chess.com is right for you.