How Root Insurance ditched Workday and 4 other vendors to end third-party dependencies

The Challenge

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. 

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.

The Solution

While Root evaluated Workday alternatives like UKG, Root felt the comparison to Rippling wasn't even close.

One platform to replace five vendors

Root went all in on Rippling: Core HRIS, Payroll, Benefits, Learning Management System, Recruiting, and Custom Reporting.

The implementation team made it work

Sara had been through multiple HRIS implementations over her career, so she knew what good looked like. Even with that experience, she credits Rippling's implementation team for the successful launch.

“100%, the implementation team is why we had a successful launch. The responsiveness, the timeliness, and A+ customer service just made all the difference," Sara explained.

When Root brought complex challenges, Rippling found solutions

Root hit some snags during implementation. The Fidelity stock integration required a manual workaround involving a report with over 300 columns. A benefits upload glitch swapped two employees' information because the system was using first names instead of unique identifiers.

But Rippling fixed the issues the same day. "That honestly blew my mind," Sara said.

Sara spoke confidently about Olivia, the implementation lead. "She was clearly incredibly intelligent and very knowledgeable about the product," Sara said. "If she didn't have an answer on the spot, she made sure to find it soon after."

The Impact

Switching to Rippling changed how Root's departments work. Teams that were dependent on IT and external vendors suddenly had direct control. Even the skeptics became believers.

Finance can finally build their own reports

For Root's Finance team, being able to build custom reports without middlemen was game-changing.

Sara walked them through Rippling's reporting capabilities. "I was showing them the platform, and they were like, ‘Wow, I can build custom formulas, I can do so much,’” Sara said. "They went from asking ‘Is this gonna be good enough?’ To saying ‘It's actually gonna be better’."

Before Rippling, any report change required going through Root's IT team, who contacted Syssero, who handled the back-end Workday work, who eventually returned the report. "I don't even know if I've seen them respond as fast as a day, but sometimes it takes days," Sara said.

Now, Finance just goes in and builds what they need.

Turned skeptics into believers

The team had real concerns. They needed training to happen in sequence — employees had to complete Training A before accessing Training B. 

"We didn't realize that our operations team, which is 70% of our company, needs training to be in order," Sara explained. "At the time, Rippling couldn't do that."

What changed? Rippling delivered. "We got access to the sequencing feature, and the team was elated that Rippling actually did what we wanted," Sara said. Conversations with them have been so much easier since then.

Enterprise power without the gatekeepers

The theme across departments is consistent: Rippling offers enterprise-level capabilities without forcing you to go through gatekeepers or wait for third-party vendors.

Root teams used to Workday had gotten used to a specific workflow. “If they need a report changed or a new report, they have to go to us, then we go to Syssero, who does the back-end Workday work, then they send it back," Sara said. "That could take days."