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Special Project

Special Project
From the 16th Annual Shorty Awards

Making Open Enrollment Approachable with Stride

Finalist in Insurance


How do you make something complex and scary like healthcare accessible?

Whether you’ve just turned 26 and you’re getting kicked off your parents’ insurance plan for the first time, or you’re embarking on a new journey of self-employment, the hurdle of finding your own health insurance is a daunting one. The market is full of terms that are hard to understand (what even is a beneficiary?) and acronyms you may have never heard of (OEP, PPO, POS, FSA…).

Stride strives to help independent workers make the most out of their independence. If you’re a freelancer, entrepreneur, or carving your own path, Stride gives you the support you need at every step of your journey.

In honor of this year’s Open Enrollment season, we set out to make health insurance accessible, understandable,  relatable… and maybe even a little bit fun, with three key goals:

  1. AWARENESS. Generate buzz (and excitement!) around Stride’s ability to help independent workers with complex decisions. Lead them to follow Stride on Social Platforms.
  2. EDUCATION. Communicate who Stride is and how Stride should be your go-to resource for finding a new health insurance plan during Open Enrollment.  
  3. ACTION. Encourage sign-ups during Open Enrollment.

Strategy and Execution


For something like health insurance, you don’t want to put your literal life in the hands of just anyone. 69% of online consumers are more likely to trust a friend, family member or influencer recommendation over information coming directly from a brand (via MatterNow). This is best accomplished on social media, where users look for more authentic recommendations. So while the big players in the field hit google and CCTV hard with major ad spends, we focused all of our social media efforts on a campaign centered where Millenial and Gen Z gig workers are speaking to each other: Instagram and TikTok.

We built a robust word-of-mouth network via long-term influencer partnerships. We wanted people to hear from their peers, so we focused entirely on partnering with influencers who understood the unique struggles of being independent workers. Our partnership included Uber drivers, artists, nurses, musicians, and more.

We partnered with 14 total influencers who produced 29 total pieces of content in the span of 2 months, reaching a combined audience of over 1 million independent gig workers, small business owners, freelancers, and more.



Our brief to influencer partners was simple: Be authentic, be you.

Stride exists to empower independent workers and allow them to make the most of their independence. Our content needed to reflect that by allowing each influencer’s unique challenges, humor, and sensibilities to shine. The more niche and personal, the better. So we let our influencers do what they do best and speak from the heart.

This wound up including so many fun personal moments, such as…



We elevated each influencer’s content beyond just their audience by surfacing their posts into our paid media strategy, resharing them organically, and spreading the messaging out across the funnel through more in-depth targeting, generating a combined 43k clicks to Stride's website and over 210k engagements.



We set out to inspire AWARENESS, create EDUCATION, and generate ACTION via social media. In the end, our results speak for themselves.

We were able to engage across age demographics but saw the highest engagement with the young independent workers in the Gen Z and Millenial brackets.

And with 42k clicks to the website driven through the allowlisted influencer content, we know we were able to encourage action with our core demographic to take advantage of this important time period.



Entrant Company / Organization Name

Acadia, Stride


Entry Credits