As a leading platform of conversational AI agents, Sierra helps businesses “elevate [their] customer experience.” And this dedication to providing swift, reliable, and empathetic help extends to the company’s own workforce. 

“I think of our employees as my customers,” said Natasha Clare, Sierra’s Head of Operations. “We want everyone that joins Sierra to feel like they had a high touch onboarding experience.” While this was easy enough when Natasha joined the recently formed company in May 2023, Sierra grew tenfold within a year and expects continued, fast-paced hiring in the months ahead. 

Natasha and Business Ops team member Nittai Malchin handle onboarding, compliance, benefits, payroll, and countless other People tasks for Sierra’s workforce. They want to maintain a high level of employee support as Sierra aims to hit its ambitious growth goals. There is no room for slow and clunky processes across a patchwork of different software systems.

Sierra joined Rippling PEO and united HR functions across payroll, onboarding, compliance, and benefits administration alongside device and expense management support. 

Now, Sierra’s administrators can hire, manage, and pay its growing workforce efficiently. And employees get a comprehensive HR experience that sets them up for success.

We couldn’t function without Rippling.

Bret Taylor 

CEO of Sierra, Chairman of OpenAI, Former CEO of Salesforce

Rippling allows Natasha to deliver on her goal of providing a premium onboarding process for every new team member, even as Sierra quickly scales. “It’s a really streamlined, centralized experience for employees,” Natasha said. “Our employees appreciate having one centralized location for healthcare enrollment, payroll, and employee information. It really is a one-stop shop.” 

She also said employees find Rippling’s Expense Management feature easy to use, since their direct deposit information is already in the system and linked to payroll, which allows the team to get quickly reimbursed for business purchases. 

According to Clay Bavor, Sierra’s co-founder, Rippling’s ease-of-use helps the company promote its culture. “One of our company values is craftsmanship,” he said. “While we think of that through the lens of what our product looks like, it applies to all of our operations, including the tools we use and vendors we partner with. We really care about what we put in front of our teams and we love the look and feel of Rippling.”

Instead of cobbling together different point solutions for different processes, “our entire HR function is run on Rippling,” Natasha said. She uses Rippling for every step of the onboarding process, including distributing and storing tax documents and confidentiality agreements, setting new hires up for payroll, enrolling them in healthcare and 401(k) plans, and running background checks. 

“There’s no other platform that we use that’s central in the same way,” Natasha said. “Rippling is our one HR platform that every single employee uses.”

In addition to unifying HR systems, Sierra takes even further advantage of Rippling’s all-in-one platform by unifying employee processes across IT and finance. This includes using Device Management to provision laptops during onboarding and Expense Management to process employee reimbursements.  

"We've been growing fast and Rippling's had no issues keeping pace. It gives every new hire peace of mind so we can focus on supporting our customers,” said Clay.

The upshot of having so many systems under the same roof? Automated workflows that yield massive time-savings for Sierra’s HR team. 

Natasha appreciates that Rippling serves as a repository for all employee data, which eliminates the need for any manual payroll calculations. And while she used to manually register remote employees for state taxes, Rippling PEO now handles it without her lifting a finger. 

“I’m in Rippling every day,” she said. “It’s nice to have a dashboard checklist of things I need to accomplish as an admin. Rippling helps keep me on track.”

And Nittai (on Sierra’s Business Ops team) finds Rippling to be a welcome upgrade from Gusto, which he used in prior roles at other companies but had to supplement with other systems (like Kandji for device management and a separate payroll provider for international contractors) to manage and pay his workforce. “We felt the overhead of having separate systems. You’re basically duplicating the same amount of work,” he said. “I’m a fan of being able to centralize.”

Rippling provides the two-person ops team “time savings and efficiency,” Natasha said. “I think it’s a really convenient platform.”

Our entire HR function is run on Rippling… There’s no other platform we use that’s central in the same way.

Natasha Clare

Head of Operations at Sierra

• Time saved: With Rippling, Sierra can quickly run payroll, process expense reimbursements, and let new hires breeze through onboarding with minimal manual work. 
• Consolidated systems: Rippling is Sierra’s one system for every HR function, device management, and expense reimbursement. 
• Ready to scale: Rippling helped Sierra’s headcount soar from six to 60 in a year and has the company ready to continue down its hyper growth path.