After financial circumstances derailed her plans for higher education, Dexter turned her struggle into a passion for helping others navigate a non-traditional career path.

Dexter, you’re a Member Experience Associate here at Stride—tell us a bit about what you do.

As a Member Experience Associate, I help guide people through the crazy world of health insurance and self-employed taxes. There isn’t a ton of accessible education on these topics, which can be a serious barrier to healthcare or to the pursuit of financial independence. Whether it’s over the phone or via email, I can help with everything from picking the right plan, to filling out the application, to calculating taxable income!

I’ve also had the amazing opportunity to work alongside our mobile engineering team to improve our mobile app experience and ensure that our members’ voices are always heard!

Where are you from originally?

I’m from Golden, Colorado, but I’ve wanted to live in San Francisco since I was ten years old. Needless to say, it's a dream come true to be here now!

What were you doing before you joined Stride?

Before joining Stride I’d worked as a cashier, a hostess, a barista, a nanny, and an enumerator (someone who goes door-to-door in neighborhoods to gather data) for the U.S. Census!

Why did you choose to work at Stride?

Even though I really wanted to, I wasn’t able to go to college due to financial circumstances. I worked multiple minimum wage jobs while trying to find my footing without a degree, but I was laid off when the pandemic hit. 

When I got the chance to interview with Stride, I knew it would be the opportunity of a lifetime. Everyone who interviewed me was kind, genuine, and knowledgeable, and no one held my education against me. I never fathomed I’d have the luxury of working for a company that aligned with my values, but now I have tons of friends and mentors who are just as passionate about making an impact as I am.

What’s the most rewarding part about working at Stride?

I’m incredibly humbled to be in a position to support others who have also been laid off or who are trying to find their footing outside of the traditional employment system. I know what that’s like, and I want to touch other people’s lives in the same way that Stride touched mine.

What’s your favorite memory at Stride (so far)?

I won’t drop any names… but someone at Stride has a killer Little Mermaid impersonation. Volleyball at Dolores Park is a very close second though!

What are some of your hobbies and interests?

I love visiting art museums, watching movies with friends, and exploring the San Francisco culinary scene (my favorite find so far is the kalbijjim croissant)!

What opportunities are you most excited for within the next year at Stride? 

Open Enrollment is right around the corner! It’s the only time of year when most people can enroll in a new plan or switch to a different one, and I’m excited to help tons of people get health insurance for next year!

What’s your current dream vacation?

I love traveling solo; after being cooped up by Covid, I’m dying to backpack across Vietnam, Cambodia, and Thailand!

What’s on your Spotify playlist these days? 

I think my top artists right now are Remi Wolf, ARIZONA, Grimes, and BIGBANG. Oh, and Sam Smith, of course.

Want to work with Dexter to help everyone get their own affordable benefits? We’re hiring!