How Chegg saves hundreds of hours a year on employee leave management

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Sparrow x Chegg


The edtech company trusts Sparrow to manage employee leave from start to finish.


Chegg is a leading student-first connected learning platform. Their mission is to help every student achieve their best—through high school, college, and beyond.

To do that, Chegg gives students tools and resources designed to help them absorb course materials quickly, retain information more effectively, learn in-demand career skills, excel in their classes, and save money on required materials.

On top of helping to improve educational outcomes for students, Chegg champions a variety of social causes through their research and advocacy arm, Chegg.org. That includes running student scholarship programs and partnering with leading nonprofit organizations to fight against food insecurity and fund research on the latest issues affecting modern students.

Chegg’s life-changing learning platform and positive corporate impact wouldn’t be possible without its nearly 1,700 devoted, talented employees based around the globe.

Chegg stats

Putting employees first with thoughtful, holistic care

Chegg puts students first in their work, and employees first in their workplace. In 2023 alone, Chegg won multiple Comparably Best Workplace awards, for compensation, happiness, work-life balance, perks and benefits, and global culture, among others.

The accolades make sense; Chegg has created a workplace environment that’s as innovative and fun as it is inclusive and collaborative. Chegg’s robust suite of employee benefits are designed to support employees holistically, addressing physical and mental health, as well as quality of life, personal goals, and family needs.

In addition to comprehensive health and medical care, Chegg also offers employees a flexible time off policy, five volunteer days a year, two weeklong company-wide breaks throughout the year, 401(k) matching, a three-month sabbatical after 10 years of employment, tuition reimbursements, a monthly lifestyle stipend, and a home office stipend.

"Managing leave in-house was painstaking. It was taking two and a half full-time employees to complete one leave."

Tracy Clemente Headshot Tracy Clemente
Director of North America Benefits

“Our benefits philosophy isn’t one-size-fits-all,” said Tracy Clemente, Director of North America Benefits at Chegg. “The employee landscape is continually evolving, as is the benefit space.”

When Chegg’s employee population began taking more parental leaves, for example, Clemente wanted to ensure they were looking out for employees at every stage in their family-forming journey. So they added infertility benefits and family-forming services to their benefits package.

“I’ve always approached my benefits role as a caregiver, and I’m constantly looking for new ways to better care for our Chegg employees,” she explained.

That’s why Clemente advocated for a company student loan repayment program. “Chegg’s mission is to support students, and many of our employees are still students, either attending graduate school or business school, or just committed to being lifelong learners,” she said. “So we implemented a loan repayment program to reduce their financial stress.” Chegg has since paid off over $2 million in loan repayments.

"We did the best we could, but we'd still get texts at all hours asking us for help and saying 'I don't understand this.'"

Tracy Clemente Headshot Tracy Clemente
Director of North America Benefits

Chegg is also committed to providing a variety of leave options for employees. “We’ve been evolving our leave policies over the years,” Clemente said. Now, in addition to short-term disability leave and parental leave, the company offers 12 weeks of 100% paid caregiver leave.

“As far as use cases, I’ve seen everything from someone taking care of an ill spouse to moving an aging parent into a facility,” she explained. “Three months of time off may seem small in the big picture, but these are the things that have a huge positive impact on our employees and their families.”

To deliver the best possible employee experience during leave, Chegg reached out to Sparrow for expert guidance.

Chegg map

The challenge: Maintaining a white glove employee experience while managing leave in-house

Chegg has always been committed to giving employees one-on-one assistance during the leave process, but the administrative load was significant.

“It was painstaking,” Clemente said. She and her lean team handled everything in-house, from managing paperwork and ensuring compliance to calculating payroll. “It was me, one other person, and a single incumbent in payroll shouldering all the work,” she explained. “So it was basically taking two and a half full-time employees to complete one leave.”

On top of the administrative work, Clemente and her team also had the added responsibility of walking employees through the leave process. “I held one-on-one meetings with each employee taking leave to explain how the state benefits worked, and I’d be drawing diagrams on whiteboards in conference rooms just to help them make sense of it all,” she said.

Despite her dedication, Clemente said the employee experience suffered. “We did the best we could, and there were many times when we’d get texts at all hours asking for help or clarity,” she explained. “But we still had a lot of people saying, ‘I don’t understand this.’”

"Whenever I vet a vendor, I'm looking for a true partnership, and that's exactly what we got from Sparrow. It was a no brainer to work with them."

Tracy Clemente Headshot Tracy Clemente
Director of North America Benefits

Chegg employees had to navigate seemingly endless forms and follow-ups while on leave. “I know what it’s like being on leave—you’re tired,” Clemente added. “You may have gotten a form in the mail from the state, but maybe you haven’t checked your mail in a week because you’re taking care of your new baby. There’s a lot to manage.”

As Chegg’s number of employee leaves increased year over year, Clemente decided they needed a more effective leave management solution, one that could minimize backend work and reduce employee stress.

“The employee experience is what changed it for me—I wanted to give our employees more,” she explained.

When evaluating options, Sparrow stood out from the start. “I interviewed other leave vendors early on, but they always left a bad taste in my mouth,” said Clemente. Sparrow was different.

“Whenever I’m vetting a vendor, I’m looking for that true partnership. And that’s exactly what I felt like from the first meeting with Sparrow,” she said. “It was a no-brainer to move forward with them.”

"Filing claims was the biggest pain point for everyone involved, especially our employees, so they love that Sparrow leads that process so they don't have to."

Tracy Clemente Headshot Tracy Clemente
Director of North America Benefits

The solution: Turning leave management over to the experts

Partnering with Sparrow has given Clemente and her team more time and peace of mind. “Once we introduce our employees to Sparrow, we get to be hands off and Sparrow takes over the process,” she explained.

Sparrow Leave Specialists meet with Chegg employees individually to review the leave process, gather information, and answer their questions. After Sparrow Leave Specialists help Chegg employees complete their paperwork, they file for benefits on their behalf, then follow up with state agencies and insurance providers along the way.

“Filing claims was the biggest pain point for everyone involved, especially our employees, so they love that Sparrow leads that process so they don’t have to,” Clemente said. “There are a lot of moving parts with leave management, and Sparrow Leave specialists are experts.”

"There are a lot of moving parts with leave management, and Sparrow Leave specialists are experts."

Tracy Clemente Headshot Tracy Clemente
Director of North America Benefits

Clemente appreciates that Sparrow Specialists are right by Chegg employees’ sides through every step of the process. “It’s like skydiving, where you have to go with a jumpmaster,” she said. “I always tell our employees, ‘Don’t worry. Sparrow is jumping out of the plane with you, arm in arm.’”

Sparrow’s involvement also means Clemente and her team don’t have to spend dozens of hours corresponding with employees or calculating payroll. Sparrow handles everything, including filling out paperwork for Chegg, keeping track of state leave laws, and generating custom payroll reports.

The time savings has been massive. “My analysis showed that Sparrow saves us 20-40 hours per leave,” Clemente said. “Each leave included multiple one on ones with employees, time spent chasing items down, and payroll reconciliation,” she explained.

"It's like skydiving, where you have to go with a jumpmaster," she said. "I always tell our employees, 'Don't worry. Sparrow is jumping out of the plane with you, arm in arm.'"

Tracy Clemente Headshot Tracy Clemente
Director of North America Benefits

However, Clemente and her team are most proud of the way Sparrow has improved their employee experience. “With Sparrow, the employee leave experience is streamlined, and each employee has an advocate in their Leave Specialist,” she said.

“Sparrow feels like an extension of our internal team that provides high-touch, white-glove service, guiding our employees through their leave journey.”

"Sparrow feels like an extension of our internal team that provides high-touch, white-glove service, guiding our employees through their leave journey."

Tracy Clemente Headshot Tracy Clemente
Director of North America Benefits

The result: Freedom to build upon their benefits package

With Sparrow’s support, Chegg’s benefits team has gained back hundreds of hours a year—and they’re putting that time to good use.

“I’ve been able to redirect my focus and budget into creating even more resources for our employees,” said Clemente. “We have amazing policies for a variety of scenarios, but what about the life that happens in between? What happens if a single parent becomes ill? Or someone has to care for an aging parent?”

Clemente and her team are constantly brainstorming new ways to round out their benefits programs and support employees through their entire lifecycle at Chegg, whether they’re fresh out of college or well established in their career.

“We want benefits that are going to grow with our employees during the time they’re with us,” she explained. “And Sparrow has given me the time to build upon those.”



Give your employees the gift of stress-free leave—without sacrificing HR’s time. Sparrow handles every aspect of employee leave administration for you. Explore our offerings or book a demo today.