Five years ago, Root Insurance implemented Workday, hoping it would be a powerful enterprise system. It turned into an expensive administrative burden. They were ready to move away from the platform because of high costs, inflexibility, and a fragmented employee experience. What should have been a powerful enterprise system turned into an expensive administrative burden.
Customization created a trap
Root had implemented Workday five years earlier when they needed an enterprise-level HRIS to support their growth. But Workday's extensive customization options came with a catch: if the initial setup wasn't perfect, fixing it later was nearly impossible.
"Workday can be customizable, and there are pros to that," Sara Wong, HRIS Analyst at Root, explained. "However, if it's not set up correctly, it's almost impossible to fix."
This inflexibility turned even routine tasks into ordeals. "It constantly made everything from even day-to-day tasks to running reports extremely painful," Sara said. "Time-consuming, frustrating to navigate, back and forth with external vendors."
Extra staff and expensive third parties
Root dedicated internal headcount just to manage Workday, but even with internal resources, they still had to pay expensive third-party vendors.
"You need a Workday expert on the other side, and that's not necessarily always a Workday employee," Sara explained. "It's these third-party vendors that are certified in Workday."
Root used a vendor, Syssero, to manage the back end and build reports. "The biggest pain point was that we couldn't build our own customizable reports," Sara said. "We had to go to a third party, and they're not cheap."
Customer service was nonexistent
When bugs or permission issues popped up, Root had to route requests through Syssero just to reach Workday.
Customer service was nonexistent with Workday. We'd have to go through Syssero for support, which was time-consuming. It was also tough to get responses in a reasonable time.
Sara Wong
HRIS Analyst at Root Insurance
The breaking point came when Root's contract was up for renewal. They asked Workday to bid on the business again. Workday said no.
"We asked Workday if they wanted to bid for our contract renewal, and they said no," Sara said. "They didn't even care. That was really horrible customer service."
Four disconnected systems created chaos
Beyond Workday’s HRIS, Root was using up to four separate systems:
- ADP for payroll
- Qualtrics for surveys
- KnowBe4 for learning and development
- Workday's recruiting module
"None of those systems talked to each other," Sara said. "As a result, Root had to add new employees and terminations on a whole separate platform, and if you forgot, they were still in there. It's not a good employee experience.”
Employees had to remember different logins for payroll, engagement surveys, and training.

















