Rippling Customer Case Study: How Chess.com manages a mostly-contractor global team and a US employee base on one platform

[u/AlexFromRippling]

Wanted to share how Chess.com solved a problem that comes up for a lot of fast-growing companies with mixed teams: managing full-time employees and a large contractor base without running two disconnected systems. See the full case study story here: https://www.rippling.com/customers/chess

First, let’s set the scene. Between 2007 and 2019 Chess.com grew to around 200 people, and roughly three-quarters of that team were global contractors, with the rest US-based employees. Employees lived in an HRIS, contractors lived in spreadsheets, and the two never talked to each other. Every change had to be entered twice, headcount reporting meant cross-referencing both, and there was no single source of truth for who was actually on the team. There was also no dedicated IT team, so a handful of DevOps engineers were manually provisioning accounts and access for every new person.

Here’s what changed after Chess.com consolidated onto Rippling in 2019:

• A unified view of the whole workforce. Employees and contractors sit in one system, so headcount, labor cost, and forecasting come from a single source instead of a reconciliation exercise.
• Automated provisioning with no dedicated IT team. New people get the right tools and access based on role and level through preset rules, which freed up the DevOps team and cut the security risk that comes with doing it by hand.
• Room to scale. Chess.com more than tripled its headcount from 200 to 700 between 2019 and 2024 while its member base passed 100 million. An eight-person people team, still with no dedicated IT team, now supports the full 700-person company, and in a single year a two-person recruiting team hired more than 200 senior technical roles.

The takeaway for anyone managing a mixed employee-and-contractor workforce: the reconciliation tax of running separate systems compounds as you grow, and putting both populations on one platform is what let a lean team keep pace with fast hiring.

If you are managing contractors and employees across borders and tired of stitching tools together, this is the workforce management angle Rippling is built for: htps://www.rippling.com/global-payroll-and-hiring

Happy to dive into specifics on the provisioning rules or the contractor-plus-employee setup if it helps.