A winding journey to supporting Midwest innovation

My Journey Into Supporting Midwest Startups

I’m a few weeks into my role as Hyde Park Angels’ new Director of Platform, and yet I didn’t plan to be here.

In fact, my start in tech was unintentional—avoided even. My master’s thesis chair convinced me to consider a contract tech writing role at a former student’s startup, Arbor Networks. Although I was tech-focused in my academic research, I was determined to finish my thesis and apply to PhD programs. After declining the interview and going so far as sending a colleague’s résumé in my place, I decided to maintain my social equity with the person standing between me and graduation. I went onsite for the interview, discovered that the startup managed and protected most of the world’s internet traffic, and learned how I could apply my skills to have a meaningful impact on the world. I was hooked.

Three years later, we were acquired. A year after that, I got the itch to do something new, something bigger. While I loved writing user documentation, no one wants to read the docs, and frankly, no one should have to. I didn’t want to be a band-aid for product issues; I wanted to help users proactively. So when a former colleague asked me to come start the tech support team at a mobile travel app startup called Mobiata, I jumped. I said I’d love to provide awesome support but asked him to let me try a different approach. I wanted to analyze and extract data from support interactions to help make the product better—and as a short-term solution, I’d write help content to empower customers to instantly help themselves with those product issues.

He took a risk on me, one that I’m profoundly grateful for. Expedia acquired that company to become its mobile division, and our team of three was the only tech support team in the organization. By closing the product feedback loop, writing top-notch help articles, and providing white-glove service, that three-person team scaled from supporting 2M+ Mobiata users to 22M+ Expedia users in the same year while maintaining 93% user satisfaction. Other companies noticed our unique approach. I started presenting at conferences and hopping on calls with Fortune 500 companies who wanted to learn how we operated—anything to help more organizations increase success by putting customers first.

Working together to scale outstanding service that benefited both the business and customer was invigorating. We were onto something by building scalable, rewarding relationships, but I felt a gap. We continually found ourselves supporting customers who needed help with their travel bookings, because they knew they could get help from the tech support team. Providing good mobile app support was only one part of driving customer satisfaction. I kept thinking, “How can we set up our travel partners to drive customer satisfaction with bookings?” After a few years navigating how to support a marketplace, I took a big risk. I left the Midwest and moved to Boston to help manage Uber’s East Coast rider- and driver-side support.

Unfortunately, my time at Uber didn’t pan out how I expected. A few weeks into my role, they sent me to Providence with a burner phone and a male pseudonym. I decided to pivot quickly. I accepted an offer to build out the Customer Support team at HPA portfolio company, FarmLogs. I hopped on a plane within a few days of accepting the offer and came home to the Midwest to help invent the future of farming. Within months, we developed a top-notch support function, and a year after that, we developed a streamlined customer success function. We learned how to remotely build and scale meaningful relationships with farmers—people whose businesses are supremely relationship-focused. With more than 1 in 3 U.S. farms using FarmLogs, our Customer Experience department of six people achieved 97% YoY customer satisfaction. We were customers-first, and we advocated for them throughout the organization.

As startups go, my time at FarmLogs wasn’t without its challenges. One of our biggest company challenges was trying to recruit experienced talent to the Midwest. Some of the very things that make the Midwest attractive (e.g., family-friendliness) are the things that candidates seemed to get hung up on. We’d hear questions like, “What happens if I outgrow FarmLogs? What else is here?” To people not from the Midwest, a return to Silicon Valley seemed inevitable, and no one wanted to uproot a family in the process. It was for this reason that a year after I joined FarmLogs, I decided to spend my spare time helping to change that narrative. I co-founded a non-profit conference called Intermitten, which exists to highlight and nurture the Midwest as both a hub of and destination for tech talent and thought leadership. It is one of the most rewarding things I’ve done in my career, and I left our 2017 event asking myself “How do I make this my job?”

It was with that in mind that I decided to move on from FarmLogs, take a break from my 10+ year startup grind, and look for the next way to have a meaningful impact on the Midwest ecosystem. In the meantime, I spent time helping startups lay the foundation for delightful and scalable customer experiences that benefit both the business and customers. I wasn’t sure exactly what my next full-time role would look like, but I decided to wait and trust that the right opportunity would present itself, as it always has. I’m so glad I did. When I learned about the Director of Platform role at Hyde Park Angels, I knew that this was exactly what I’d been waiting for.

I couldn’t be more thrilled to be in this role. The opportunity to support and evangelize Midwest startups at the epicenter — the most active investor group in the Midwest — is a dream for me. I look forward to applying my experience driving organization success through mutually-beneficial relationships, evangelizing the Midwest as a top region in the country for startups and investors, and supporting the people who source and support the innovation of our future.

Alida has laid a fantastic foundation for HPA, which I’m so grateful for. I look forward to carrying on her legacy while also adding my own expertise. This is the beauty of collaboration and diversity. We get to combine multiple sets of talent to create something greater than either of us could have done on our own. And this is why I look forward to collaborating with the Hyde Park Angels community of extraordinary people and leveraging our collective expertise and success to help shape the future of the Midwest and the future of investing.

Stay tuned,