Meet Senior Product Manager Stephen Stradley

Stephen Stradley came to HopSkipDrive with an existing appreciation for social causes and an already well-developed understanding of the impact access to transportation has in people’s lives. His innate interest in using technology to solve problems led him to a position on HopSkipDrive’s product team, where he works to identify issues and create solutions in support of the company’s mission.

Where are you located, how long have you worked for HopSkipDrive, and what exactly do you do for the company?

I’m located in the San Francisco Bay Area, in Oakland, California. I work on HopSkipDrive’s product team, where I focus on the CareDriver app and our ride marketplace. My day-to-day schedule includes working with stakeholders from across our business to identify pain points and areas of need, as well as coordinating with our engineering team on requirements and details to enable development that can help meet the most critical gaps. 

Can you talk a bit about your professional and educational background?

My path to HopSkipDrive has been fairly winding, but I am so happy to be here! I studied politics at Whitman College and after graduating, I knew I wanted to make a social impact quickly. So I joined Teach For America, and I taught geography and government to ninth and tenth graders in Baton Rouge, Louisiana, for a few years. 

After leaving the classroom, I dove headfirst into both education technology and transportation technology while moving from a customer success role to a product-team position. I went back to school at Georgia Tech a few years ago to further bolster my business skills and my understanding of the transportation business. I have also worked on the Walmart last mile delivery team, where I focused primarily on building product systems around driver payment and incentives.

What made you want to work at HopSkipDrive?

I first heard about HopSkipDrive from the Series C TechCrunch article. I knew as soon as I finished the article that I was interested in learning more about HopSkipDrive’s business, and I felt that my prior experience both as a teacher and as a gig platform product manager would enable me to contribute to HopSkipDrive’s mission.

What drew you to work in the product field?

When I first arrived at the ed-tech company following my teaching experience, I knew from my first conversation with the Director of Product there that I wanted to work in that department to help synthesize various stakeholder needs and wants towards a software solution. Shortly after meeting him, I decided to enroll in a product management course, and I also began doing side tasks for the product team to gain experience.

What do you think the main strengths of the product team are at HopSkipDrive?

It’s a department of only five (as I write this), and I greatly appreciate the different strengths that every member of the team brings to the table. The variety in background and approach from each product teammate has enabled me to learn things across the business from each person since I started at HopSkipDrive last fall.

Is there anything about your background that you feel makes you uniquely suited to your current role and/or the company? 

While teaching in Baton Rouge, I also served as the varsity basketball head coach — a position that I didn’t realize also came with the responsibility of driving several students home after practice each day. The experience of those trips directly showed me some of the challenges that our CareDrivers deal with today, like coordinating drop-off with parents and navigating last-minute schedule changes.

Is there anything specific about the company culture that is of particular importance to you?

I greatly appreciate the effort that’s made at HopSkipDrive to allow discussion — and even reasoned argument — between colleagues on a matter at hand, while the respect of the community is still prioritized. I believe that in order for teams at our size to be able to grow as we want to grow, we need to be able to respectfully push one another on our ideas to make them the strongest they can be.

What is your favorite thing about working at HopSkipDrive?

I’m still so impressed with how great of a fit each person is for the position that they work in. On all teams and all levels in the company, it feels like each hire is a good person to work with who is set up for success in their role.

How important do you think HopSkipDrive’s mission is, and why?

HopSkipDrive’s mission to create opportunity for all through mobility is critically important to me. While working with the International Rescue Committee in Atlanta (my hometown) during college as an employment specialist, I recognized how challenging it can be for newly resettled people to even get to the jobs and appointments they need access to across the city.

Taking a step back, I recognized that this wasn’t just a pain felt by those new to the U.S. but also by tens of millions of Americans who are unable to get to the places they need to go and do the things they need to do. 

This inspired me to focus my undergrad politics thesis on the political history of blocking transportation access in the Atlanta area, particularly among minority groups. While this thesis was specific to Atlanta, the access problems seen there are unfortunately prevalent throughout our country. It brings me joy to be a part of this team that is working to extend access to students who may otherwise not have it.

Do you have any causes you are passionate about and/or support through volunteering or charitable efforts? 

I serve on the board of a nonprofit foundation in Atlanta that focuses on student success, mental health and employment success for vulnerable populations throughout Georgia. I’m also involved in a couple of Bay Area YIMBY (Yes In My Backyard) groups that push for building more housing in high-demand areas like San Francisco and Los Angeles.

What are your hobbies and personal interests?

While I try to temper it down, I’m a big sports fan in my spare time. I primarily root for my hometown (Atlanta) teams, but I’ll cheer for the Oakland A’s, too. 

I picked up playing Ultimate Frisbee around age 14, and I haven’t really stopped playing Frisbee since! I’ve played on several different mixed gender co-ed teams since moving to the Bay Area and, like many in Ultimate, took up disc golf during 2020 to still get my Frisbee fix.

What is your favorite thing to do on weekends?

On weekends, I love to explore parts of California that I haven’t seen yet or go for long-ish bike rides in the East Bay. In particular, my partner and I love visiting the beaches in Santa Cruz and the Lake Tahoe area when we are able to get away. 

Recently though, my weekends have largely been consumed by preparing for the 2020-postponed wedding that is scheduled for Memorial Day weekend this year!