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How Khan Academy simplified leave—even as it got more complex

How Khan Academy offers user-friendly leave management for employees and People Ops—despite having more leaves, across more states, with ever more complexities.

Nikki Henderson
Nikki Henderson
How Khan Academy simplified leave—even as it got more complex

Challenge: Employees taking more complex leaves across dozens of new states outgrew Khan Academy’s manual leave management process consisting of spreadsheets and an external consultant.

Solution: Dedicated leave of absence software with a user-friendly interface that could handle dynamic leave modeling, paperwork submission, payroll calculations, and reporting—across dozens of US states.


  • People Ops saves time by eliminating complex state leave laws research and scaling time spent per leave.
  • Payroll team eliminates manual work with Cocoon’s payroll calculations, summaries, and supplement pay breakdowns.
  • Leave-takers feel confident in the paperwork they’re submitting and their overall leave plan.
  • Improved team function and company perception of People Ops as a polished and organized team.

Keep reading for the whole story ↓

Simplify leave management, even as you scale

Simplify leave management, even as you scale

Khan Academy spent 40+ hours per leave of absence, which became unmanageable as they scaled—they found a better leave management system with Cocoon. Talk to our team to see how you can too.

Meet Crystal Kung @ Khan Academy

Khan Academy is a 501(c)(3) nonprofit educational platform offering personalized learning resources for all ages in order to provide a free, world‑class education for anyone, anywhere. In a similar vein, Khan Academy’s People Operations team strives to provide an excellent employee experience for their employees all across the US. This is where Crystal Kung, Head of Total Rewards, comes in. She’s worked across the tech sector and was intrigued by Khan Academy's purpose and impact as a nonprofit ed-tech organization. And as you might expect, Khan Academy employees are quite tech savvy, which influences the tools they use and company culture—things that were put to the test during the global pandemic. This prompted Crystal to search for a new leave management system to give employees a better leave experience, no matter where they were.

Enacting a competitive leave policy… suddenly across dozens of new states

“Before the pandemic,” Crystal explains, “leaves were easier to manage due to them mostly being basic parental and medical leaves based in California. We could manage them in a Google Sheet, working with an external leave consultant to help People Ops and Finance with leave administration.” Each basic leave took about 40 hours of work to manually model the leave, work through a plan with leave takers and managers, and follow through on paperwork from start to finish. But this system started to break down during the pandemic. 

“Suddenly everybody started moving across the country, including states where we didn’t operate yet, we saw a mini baby boom, and there were more medical and caregiver leaves that came with complexities we hadn’t yet encountered.” It also didn’t help that some people had moved from states with generous paid leave laws to states that did not. With the increased demand for leaves, this left Crystal, her team, and their external leave consultant struggling to keep up with each leave and subsequent requests, while also keeping track of constantly changing state laws. “I wanted to find a solution that worked for People Ops while delivering a great employee experience that made sense for Khan Academy’s size and operations.”

What Khan Academy looked for in a leave management system

“I knew we couldn’t afford a dedicated headcount to just leaves… but I also wanted a personalized service that could handle the most common types of leave, offering hands-on help for employees’ paperwork,” Crystal says. “It was also important that the system offered dynamic reporting and leave modeling for the People team and employees to understand what was going on for each leave.” Other important factors were training for managers and HR admins, easy manual census uploads or  integration with their HRIS, an understanding of Khan Academy’s industry, and being minority-owned as “a nice bonus.” Naturally this made Cocoon a top contender.

“Cocoon ultimately won me over because of its support style, the user-friendly UI, and general ease of use. The fact that they can help leave takers fill out government forms that are confusing for (even me as an HR pro who has led a few leave of absence programs!) was huge."

“Cocoon ultimately won me over because of its support style, the user-friendly UI, and general ease of use. The fact that they can help leave takers fill out government forms that are confusing for (even me as an HR pro who has led a few leave of absence programs!) was huge. I even vetted the backgrounds of the customer support team to make sure they had real experience on this topic—and they do.” 

Cocoon is a win-win-win for People Ops, Payroll, managers, and leave takers

Upon implementing Cocoon, it was a huge relief for the People Ops and Payroll team, saving them hours of manual tasks and high-pressure work managing the forms and pay calculations for each unique case. “We don’t have to do last minute, and frankly difficult, research for each leave in each state just in case a new obscure leave law comes out under our radar,” Crystal says, relieved. “Plus, the Payroll team loves the payroll summaries, supplement pay breakdowns, and how Cocoon is able to factor in state, disability, and supplemental pay.” 

Crystal also says Cocoon has saved the People team time and money. “As more people go on leave, it’s like a snowball effect of savings because redundant administrative work is automated. Plus when you think about some of the stressful and mundane tasks Cocoon eliminates, you know that it boosts team energy and how they feel about their day-to-day work.”

For leave takers, they loved that Cocoon handled complex paperwork, and that they could dynamically model their leaves privately before sharing with their manager and People Ops. “Now, employees can show up to a conversation with their manager with a plan and understanding how their leave will work more or less, and managers get help and suggestions to prepare their team and report for the leave. It’s a lot less pressure and fear for everybody.” 

How Cocoon bolsters Khan Academy company culture

Overall, Crystal says that Cocoon has helped refine the image of People Ops coming out of the pandemic as a more organized and polished team. “One of our company values is ‘working responsibly and sustainably’ and Cocoon definitely supports that value.  Another one is ‘bringing out the joy’ which you can feel with Cocoon’s UI. You know, someone might be going through a really difficult time on their leave, and you can tell that Cocoon puts effort into giving them the best experience possible whether it’s through features or the graphic design to bring out the joy. So it’s a joyful process to use it.”

“Being in HR navigating through the pandemic and societal changes in the past three years has been very hard,” Crystal admits, “but there’s help out there! And we’re glad we found it with Cocoon.”

It's time to enter the next generation of employee leave