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 insurance 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?

Rose-Ann, Member Experience Advisor: We’re looking for people who demonstrate clear communication and empathy—it’s important to understand how to communicate effectively and empathetically with members, many of whom may be going through the process of finding themselves health insurance for the first time! We’re also looking for experience learning and teaching complicated concepts—explaining the process of applying for plans and the details of each plan can be confusing. We also love people who demonstrate initiative and ownership—we pursue projects that improve the customer experience, from improving the accuracy of customer data to coordinating in-person events to recording webinars to educate our members.

How does someone thrive on the Member Experience team?

Nikki, Member Experience Lead: If you’re passionate about helping our members and being a team player, you’ll thrive on MX. Deciding which health insurance plan to choose for the year or preparing to file taxes as an independent contractor for the first time can be really daunting, but MXers are great at boiling down really complicated topics and empathizing with each member’s unique needs to help them through these big decisions. Open Enrollment and Tax season are MX’s busiest times of year. Back-to-back calls and long days are common, but we come in ready for new challenges so the days always go by really quickly with a resilient and supportive team!

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

Patrick, Member Experience Advisor: MX is a tight-knit team that carries big cross-functional impact across the company. We're lucky to have just landed an amazing VP of Customer Operations, Regina Pitstick. She worked her way through college, has a passion for developing talent, and has an appreciation for non-traditional backgrounds. Between her and your direct manager, you'll have the support needed to align your day-to-day contributions to the team with your personal trajectory. Need help figuring out where that's headed? This is an opportunity to work with every functional group at Stride. We'll help you hone in on your skills, passion, and goals to ensure mutual success. Get in touch with me if you want to talk more!

What makes Member Experience at Stride different than Member Experience at any other company?

Stoddard, Member Experience Advisor: I’m going to make a bold claim and say that our team is more collaborative, fun, and supportive, and has better leadership than any other Member Experience team out there. Stride MXers have the opportunity to grow rapidly from an entry-level position. Practically every MX team member becomes a cross-company player within their first year. We pass stories, data, and ideas from our members to every other team at Stride. Second, we are licensed insurance brokers that help people make complicated and important decisions around investing in their well-being. Member Experience may use Bitmojis and GIFs more than any other team, but we are trusted as experts who help people who work for themselves make faster, smarter decisions. Finally, we are growing and adding responsibilities to our team! If you are looking for an entry-level role that will give you a prime starting point to expand your career in health technology, Stride’s MX team is the PERFECT place to start.

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. First, the people we serve are hardworking, passionate, creative, and impressive, and a lot of them don't have great resources for answering insurance and tax questions. Guiding them through those questions so they can get back to doing what they do best is truly a rewarding experience. 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!

About 35 percent of the US workforce and 16 percent of the entire population is a part of the gig economy, with continued growth expected. As the gig economy 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 our members to guide them through important decisions and complex topics that are critical to their success—health insurance and taxes. The future of MX at Stride will include expansion to meet the vast needs of the self-employed population. In addition, we will focus on improving operational efficiencies while retaining the high quality of service that our members are accustomed to. We want our members to view us as a partner throughout their self-employment 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!