Why Now Is the Best Time to Join the Member Experience Team at Stride!

Navigating the world of insurance and taxes as a self-employed worker is tricky and convoluted, whether you’re new to freelancing or a longtime business owner. This is where Stride’s Member Experience team, known around the office as MX, shines: we help self-employed people make tough decisions surrounding their health and finances so they can focus on doing what they do best.

Right now, we’re hiring a new cohort of Member Experience Associates. As Stride’s resident product experts, you’ll consult members on their benefits, act as the first responder to any problems, and translate customer insights into product improvements. Beyond that, you’ll form meaningful connections and be a trusted guide among Stride’s members.  

We sat down with the rest of the team to find out what it’s like to be an MXer—check out the interview to get an inside look!

What sort of background are you looking for in candidates?

Jordan, Member Experience Manager: We’re looking for people who are intrinsically motivated to help others make big, tricky decisions. Simplifying complex issues for our members is a huge part of the job, so we love seeing that candidates have experience learning and teaching complicated concepts. We pride ourselves on being transparent, empathetic, and knowledgeable, so top notch communication skills are a must! One of our company values is being a power owner–we’re always impressed by candidates who demonstrate initiative and ownership.

How does someone thrive on the Member Experience team?

Nikki, Member Experience Manager: If you’re passionate about helping our members, consider yourself a team player, and are eager to learn the ins and outs of our products, you will thrive on MX. Deciding which health insurance plan to choose or preparing to file taxes as an independent contractor can be really daunting. It’s our job to understand each member’s unique needs and boil down these complicated topics so they can make the best decision. Open Enrollment and Tax season are our busiest times of the year and our product offerings are constantly evolving so you should be excited by new challenges and be ready to tackle them as a team!

Why is now a great time to join Member Experience at Stride?

Sam, Member Experience Associate: MX is a fast-paced, collaborative team that does impactful work felt across the entire company. First and foremost, you’ll become a product expert, advising our members on everything from insurance to Stride Tax. You’ll gain invaluable exposure working on cross-company initiatives with various Stride teams and pick up some neat skills along the way. The landscape at Stride is constantly changing; each day presents new challenges and avenues for growth. Right now is an especially great time to join the MX team because Stride is partnering with exciting companies within the tech community and evolving our product offering. You’ll have a unique opportunity to shape the Stride customer experience as we continue to grow. More importantly, you’ll laugh a lot, learn about different cultures, eat tasty food, and maybe play on our company volleyball team! Are you in or are you in?

What makes you all excited to come to work everyday?

Tade, Member Experience Manager: We all have our own reasons for loving our jobs, but there are a few reasons that resonate with all of us. Firstly, the people we serve are hardworking, passionate, creative, and impressive people, and a lot of them don't have great resources for answering benefits-related questions about topics like health insurance or taxes. Guiding them through those questions so they can get back to doing what they do best is truly a rewarding experience. Secondly, there are also incredible growth opportunities within our team. We are constantly working cross-functionally with the rest of the Stride team on projects that touch marketing, data analytics, and product development, just to name a few. No day is ever the same, because opportunities to try new things are always coming our way. Finally, Stride is really, really good at hiring amazing talent. I am constantly blown away by how universally intelligent and caring our teammates are, both on the MX team and across the company. MXers in particular are empathetic, strong, goofy, weird, and relentlessly hardworking people. They make me want to produce the very best work that I can, and their support has absolutely elevated my work to the next level.

What does the future of Member Experience look like?


Regina, VP Customer Operations: The future of MX is so bright you gotta wear shades!

More than one-third (36%) of U.S. workers are in the gig economy. As this number continues to grow, so do the opportunities here at Stride! Our mission is to help people who work for themselves be more productive and successful. The MX team works directly with members to guide them through important decisions and complex topics that are critical to success—namely, health insurance and taxes. The future of MX at Stride includes expanding our product portfolio to meet the vast needs of the gig economy. We want our members to view us as a partner throughout their self-employed journey, not just during Open Enrollment or tax season.

Ready to work alongside deeply passionate teammates, solving the toughest problems self-employed people face while making time to roast each other in group chats? Make the best decision ever and join the Member Experience team!