As the head of product design at eHealth, I led design strategy conversations with the C-Suite, partnered with my peers in product and dev, creatively directed all work, and built up a diverse team that addressed both the needs of the business and its customers.

eHealth's design team amounted to two people who were working without a design leader when I stepped into my role. There was no research team, organized marketing design team, UX content capabilities centralized marketing design or prototyping capabilities. So I build the current multidisciplinary team from the ground up. At its height I had 8 direct reports, two of whom were managers with a direct report each.
To pull this team together I made the case for the roles and head count to senior leadership, wrote the job descriptions, review applications, and designed and managed the interview process for each discipline. 
I received the highest marks across 9 managers including my manager, the Chief Digital Officer, for employee engagement and management. While I was with eHealth I was also given a rating of "Exceeds Expectations" in my first annual review and a bonus above the highest level for my role which was 20% of my salary 
With my team in place I was able to quickly demonstrate to leadership at eHealth that they had a world class design team they could trust. I was told when I started that my biggest challenge was to gain the trust of leadership after a series of failures under the prior design leader and their team. Leveraging the growing confidence in my team, I initiated a redesign of eHealth's primary content site and eCommerce flow to improve customer success in finding and purchasing insurance plans, as well as inspire greater customer confidence by modernizing the overall look and feel of the site. 
We were constrained to working with the existing color palette, logo and logo colors and a mandate from leadership to create a serious/sober and credible design. But outside of that we could re-architect the site, restructure the visual design, address issues of accessibility, and add plenty of new features.
I also was the creative director on all work - helping to kick-off every project and regularly guiding and reviewing all work.
Working with my peers across disciplines we created a project that not only improved the look and brand of our two most important sites, but one that allowed us to modernize accessibility in our interfaces and code, and update analytics.
The Approach
The requirements were to visually reinforce that we were experts on Medicare, but were also approachable and friendly. We also wanted to communicate that we were trustworthy and modern. We also needed consistent design standards that also were accessible.
I led the team to design in two directions to gauge where senior leadership at eHealth wanted to take the brand. I initially wanted the brand to not only be authoritative but softer than it was. For the following initial design direction treatment I wanted to get away from the typical pictures of seniors on the beach. I found what I was looking for in this illustration by Ana Hard - a depiction of vibrant activities that implied the senior doing them. 
While senior leadership appreciated the design, they were more inclined to projecting authority, so working we arrived at the following visual direction. This direction  was approved by the C-Suite. We used both Frontify and Figma to manage assets. These are screenshots from Frontify.
My team also executed a full redesign of the eCommerce flow.  
Analytics post launch verified that using our improved feature, medicare insurance customers were now much more able to find plans that included their doctors and drugs on their own online - without calling an agent. This was a huge win for us and something no other insurance agency was able to do online.
Many customer comments about these tools were nearing elation. Being able to do this on their own was huge for our customers.
Outcome
In 2019, under my direction, the design improvements we made were largely responsible for increasing our online (vs. phone) applications by 50%. In 2020 through this redesign, we increased the number of online applications by 50% again.
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