Sawyer Hollenshead is a senior designer & frontend developer at Nava PBC, building government services that are effective and accessible to all. I’m interested in researching, prototyping, designing, and building practical, purpose-driven digital services.

Here’s what I’ve been working on

State of Vermont: Integrated Eligibility & Enrollment Program

Modernizing and simplifying the process of applying to fragmented safety net programs.

The vision for Vermont’s Agency of Human Services’ Integrated Eligibility & Enrollment Program is to ensure that Vermonters can easily gain and maintain access to the benefits that they’re eligible for, like Medicaid and food assistance. Sounds straightforward, but integrating these programs is a massive undertaking. In almost every state, the benefits application experience is fragmented. Applicants have different applications for each program, different numbers to call, and different offices to visit. Staff have siloed systems and manual, repetitive processes. Nava’s partnership with Vermont on this initiative has so far included two phases…

Phase 1 was a “document uploader,” focused on helping Vermonters submit documentation that proves their eligibility. By the end of Phase 1, the document uploader was fully integrated with the State’s on-premise document management system and was available to 100% of Vermont’s benefits programs. A much higher percentage of Vermonters are now submitting documents on the same day as the request, and applicants are receiving eligibility determinations and their benefits many days (and sometimes weeks) sooner.

Phase 2 of this work is now underway, and the goal for this phase is to build an MVP of an integrated online application that will ultimately provide a single application experience to Vermonters applying for any human services program. This work is building on a lot of our team’s experience working on’s application experience.

Unravelling complex policies and improving an eligibility application for millions of Americans seeking health coverage.

Since the launch of, over 23 million people have enrolled in health insurance, and America reached its lowest uninsured rate ever. At a high level, the application determines whether a person’s family is eligible for an insurance plan and whether they’re eligible for any cost savings to make their insurance more affordable. In addition, the application determines whether a person is eligible for Medicaid or the Children’s Health Insurance Program (CHIP), programs that provide free or low-cost health coverage to millions of Americans.

It’s important that the process for applying and enrolling in health coverage is simple and accessible for everyone. To support that vision, I was part of the design team that tackled the challenge of determining how to redesign and structure the complex eligibility application experience on

Centers for Medicare & Medicaid Services (CMS) Design System

Oftentimes multiple contractors are responsible for different parts of complex initiatives, like, and each team has its own processes and codebases. Without a shared, living source of truth for UI standards, this results in fragmented and visually inconsistent user experiences. As part of the team, I led the design and technical implementation of the CMS Design System, a set of open-source design and frontend development resources for creating Section 508 compliant, responsive, and consistent websites – based on the U.S. Web Design System.

Reading Highlights

Using a serverless approach, natural language processing, and email to export and remember takeaways from everything I read.

After stewing in frustration for quite awhile about the current state of digital reading platforms, I decided to do what any sane programmer would do: Devise an overly complex solution for a seemingly simple problem. The prompt: How might I gather all my highlights from Kindle and put them into a personal online archive, where I can share, browse, and reflect on everything I’ve read? The result: