Cocoon
Designing an In-Product Compliant Pregnancy Disability Leave Tracker
San Francisco, CA
Lead Product Designer: Me
Lead Engineer
Legal
Operations
March - June 2024
Challenge
Employees needed a way to manage extended disability leave related to pregnancy, which had different requirements and processes than standard leave types. The system needed to handle multiple scenarios:
Cases where employees had already exhausted disability leave but had remaining entitlements
Situations where employees had exhausted both disability leave and entitlements
Cases where no extended disability time was needed
My Contributions
Results
Process
Research & Analysis:
My initial goal was to understand the inner workings of our products and its gaps, as well as the legal implications behind pregnancy leave. I conducted comprehensive interviews with:
Operations team handling manual Americans with Disabilities Act (ADA) leaves
Product Manager overseeing leave processes
Legal team for compliance requirements
Key Findings:
The stakeholder interviews uncovered existing system had gaps in handling compliance, Serious Health Condition (SHC) forms, and flexible approvals for extended leaves.
Solutioning
Crazy 8:
With these in mind, I facilitated a design studio where we each came up with 8 sketches in 8 minutes to keep ideas flowing. Lots of unique solutions were brought up by our cross-functional partners.
Milestones
Upon discussing company and product priority, the team and I created a few milestones.
First milestone: Allowing users to extend pre/post birth disability with existing entitlement.
Second Milestone: Enabling intermittent leave (non continuous leave).
Third Milestone: Enabling Employers to Approve/Deny leave extensions without entitlements.
Working with the legal and my engineering team, I designed an initial milestone (M1) solution of adding a toggle for ADA leave, representing the conditional leave as a shaded indicator.
I also created a leave accommodation request form considering the JSON-forms backend our engineers intended to use to implement it.
Finally in addition to the M1 designs, I drafted proposals as to how the approval/denial mechanism would work on the engineering side.
Final Designs
Feedback and Iterations:
After some design review, it was decided that rather than a toggle, engineers would work on improving the backend system to be able to calculate the sections of leave that would need approval. Thus, I expanded the leave time to have more clear copy and distinctions between the different leave types and coverages.
Conclusion
I was really happy to be given the opportunity to work as a product designer on our startup team. It was definitely a challenge to balance my engineering commitments while also taking on the role of designer - time management was key.
This was my first time really getting into the weeds of what we did at Cocoon - learning the landscape took way longer than I had originally budgeted for. I was proactive in asking questions and made sure I had a solid understanding of everything before proceeding. It was a lesson learned to always give some wiggle-room for projected timelines.
Design is really the bridge between our product, our users and our engineering team. I learned to make design decisions while taking into account the trade offs from so many perspectives: business, engineering, and user experience.




