Cindy Phan

Helping millions of Medicare beneficiaries find and enroll in Medicare coverage.


Choosing a health care plan can be one of the most stressful thing for people, especially for individuals 65 and older or with certain medical conditions that require increased health and prescription drug needs.

What if we could take off as much of the burden as possible, simplifying things to get at the core of what you need to know to make a decision?

In June of 2018, I started building a team tasked with replacing a suite of legacy tools that support the Medicare beneficiary coverage experience. The goal: to not only modernize these tools from a user experience, design, and technical perspective, but push the boundaries for how we could help beneficiaries navigate this complex and stressful space.

CompanyAd Hoc, LLC


ClientCenter for Medicare and Medicaid Services

My RoleSenior Program Manager


Overview of the Project

Our goal put simply: replace a legacy tool built more than a decade ago with a tool that would make it easier for Medicare beneficiaries, or those who help them, to find and enroll in a Medicare plan that best meets their health and financial needs. To accomplish this, we needed to transform this big vision into a product that could be built to serve people. Though our goal could be written down in one sentence, the path to get there was not so simple. Using Agile development, product thinking, and strategic trade-offs, we worked with our government customers to answer the core questions that would guide our work:

  1. What does success look like?
  2. Who is our user?
  3. What are their pain points?
  4. How do we prioritize all the features we can build to ensure that we have a strong foundation that we can improve upon in the future?
  5. How do we ensure that we are continuously gathering feedback from those who will use the tool so we can improve over time?
  6. How do we ensure that the tool is performant, stable, and reliable?

It was a big job, and we only had 4 people on the team on day 1 and a year until we had to launch. As the leader of this team and this work, there were four main pillars I focused on building to ensure that we had the right team capable of delivering on our goals.

Medicare Drug Selection

Pillar 1

Build for and with the user.At the core of everything was the user. It was important to instill a human-centered approach in all aspects of our work - whether it design, product, or engineering. The legacy site looked and functioned like it was built in the 90’s. Over the years, beneficiaries, advocacy organizations, and support organizations had spent years providing feedback to CMS about their pain points and improvements they’d like to see. Our first task was to collate all that feedback and gather real-time feedback so we could build a full understanding of all the needs of our various users types and personas and what we could build and improve for them. This was then translated into user stories and solutions brainstormed. We then did exhaustive user testing to validate whether our solutions tracked with user expectations and needs, iterating where needed. /p>

Medicare Pharmacy Selection

Pillar 2

Build a strong and supportive team while giving people the opportunity to grow and thrive.In order to meet our deliverables on a compressed timeline, it was important to be strategic about the roles on the team and who would fill them. On day 1, there was only 4 people on the team. My job was to:

  1. Identify the needs of the project
  2. Identify the roles needed to fill those needs
  3. Create a team structure that would ensure delivery while remaining flexible
  4. Interview individuals to join the team, assessing their technical skills and program fit.
  5. Making an offer
  6. Onboard team members and ensure their professional growth

Through this process, I developed a team structure of 28 individuals across Product, Design, and Engineering. This team would be split into 5 functional areas - UX, Data API, Beneficiary API, Front-end, and DevOps.

Once people joined the team, it was important to make clear their work and how it fed into the larger vision of the product, but also to invest time into understanding the professional goals each person had. As a manager, my goal is to be an advocate for people’s skill and career development - being aware of how they’d like to grow and opportunities to let them do that, and promoting them if they are doing their jobs and excelling. I am a strong believer that someone should be able to trust their manager to be aware of their work, their goals, and work with them to chart a path forward. In my almost 4 years running this team, I have supported the growth of 19 individuals across Product, Design, Research, and Engineering to become Senior Practitioners or Team Leads, continuing to chart paths forward with them.

Pillar 3

We all work better together if we work cross-functionally. In building this team, it was important that we were not only cross-functional but that we understood that each team was a customer of each other, that we each had our own perspective and needs that needed to be met by each other. Whenever a large initiative started, whether it was very policy focused, technically focused, or design focused, we kicked off the initiative together. It was important for us all to have a shared understanding of the work that was about to start, the work that was already in flight, and the work that was about to be launched. This ensured that:

  1. Everyone understood the work and how it feeds into our larger goals.
  2. There was team alignment and consensus on the path forward.
  3. Critical input or feedback on approach or constraints could be solicited early on and regularly.

This approach ensured that the team was building toward a cohesive roadmap, even if everyone was working on different parts at different stages. This also allowed for a very crucial aspect that secured our success in building and launching our products - allowing for a flexibility in moving people around if some teams were experiencing a higher workload than others.

Medicare Plan Selection

Pillar 4

Build strong and transparent relationships with our stakeholders.For this project, we had a complex web of stakeholders we needed to navigate - from client executive leadership, insurance companies, to government stakeholders in UX and product. In order to move our work forward, it was important that we built a transparent and collaborative relationship with our stakeholders, to let them know that:

  1. We are all on the same team with the same goal in mind: helping millions of Medicare beneficiaries.
  2. We would always be diligent in our work and honest in our communication.
  3. They could trust that we would deliver our work while being open and honest as blockers or risks arose so we could adjust our plans or expectations as needed.

We brought our stakeholders along for the journey, developing clear processes and lines of communication to let them understand how we work, and adjusting how we worked to better meet their needs. Because of the investment in building a strong relationship upfront, we reached a stage where we could speak candidly about the best path forward and why it was valuable to beneficiaries. This allowed us to deliver effectively and clearly.

Product Development Lifecycle

The Work Process

For the team, it was important to have enough process for people to understand how work would be done, but enough flexibility for folks to adjust how they worked based on their specific team and the stakeholders in their ecosystem. I developed a multi-step product development lifecycle that met the needs of the team and the client.

  1. Kickoff. Orient team and stakeholders to the problem to be solved, including collating any previous user research and data to guide the conversation. Share the general timeline for product discovery, UX solutioning, requirements gathering, development, and launch.
  2. Gather requirements and user data. Work with necessary parties to identify policy and business requirements. Identify problem to be solved and goals of the work.
  3. Brainstorming and solutioning. Given the requirements, problem, and goals, work with cross-functional team to brainstorm ways to tackle the challenge and propose solutions.
  4. Solution validation and approval.Meet with stakeholders and leadership to propose a solution including the pain points and how they are address with the solution, how this helps reach our goals, and ensure alignment. Have a discussion on areas of concern and agree on a path forward. Conduct user testing to validate if the solution is on the right path, or if adjustments need to be made.
  5. Build. Tasks are broken up into user stories with the appropriate acceptance criteria, and distributed amongst the appropriate team. Ensure team alignment on timeline, and make adjustments as work continues.
  6. Launch readiness and Launch. Thorough user testing and quality assurance validation of the work and the entire system in all environments, including checking for bugs, impacts to functionality and performance, and overall quality. If all looks good, release into production, tracking performance and user metrics.
  7. Learn. Have a team retrospective to discuss what worked well and what could be changed for the future. Conduct user testing and gather user metrics to assess the impact new features have on users. Ask ourselves “Did the solution have the expected impact? Where can we continue to improve and iterate”.

what we accomplished

Since CMS launched the redesigned Medicare Plan Finder, the tool has:

  1. Helped more than 2.6 million Medicare beneficiaries enroll in a Medicare plan, about 40% more enrollments than the legacy tool the previous year.
  2. During Medicare’s Open Enrollment, the redesigned Medicare Plan Finder saw an average of 373,000 visitors a day and peaked at 847 API requests per second.
  3. Zero downtime for the redesigned Medicare Plan Finder, meaning the tool ran smoothly and did not impact an individual’s ability to find and enroll in Medicare.

But most importantly, here are some quotes from the beneficiaries who used the redesigned Medicare Plan Finder:

  1. “I really like it because it’s self-explanatory and gives things in detail. You know up front what each plan costs a month, what your deductibles are, and what drugs are covered and what drugs aren’t. That’s really important. It gives you an estimate right up front.”
  2. “Even I, a 73-year-old guy who’s not very computer savvy can figure it out.”
  3. “They care enough to construct something like this.”