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Ocra Origins: Leo Connelly, Technical Program Manager

Ocra’s young leaders parlayed their love of event parking operations into building SaaS solutions that create win-win outcomes for operators & their technology partners.

Here’s the story of founding member Leo Connelly, Technical Program Manager, taco connoisseur, & Boston sports super-fan.

My parking story starts in 2019, right after I graduated college.

I was crashing on a friend’s couch in Boyle Heights while attempting to get my foot in the door in tech. I wanted to be a UX designer and reached out to my friend Ethan (our CEO) to get advice on how to break into that world. 

At the time, Ethan was running a parking operation called ParkPlace. I offered to do pro bono UX work for that business. However, he didn’t need UX designers; he needed parking attendants.

Being on the team was more important to me than my role on the team, so I decided to be the best parking attendant I could be. Ethan invited me to come back, and soon I was spending every weekend parking cars for events at the LA Coliseum or Exposition Park! 

The more time I spent working the team, the more I realized the urgent need for software that helps operators manage the complexities of their business.

In our case, we were seeing a ton of success using customer demand channels like SpotHero and ParkWhiz, but it was becoming increasingly difficult to manage so many different platforms.

Nate, our COO, and I collaborated with Ethan to ideate what solutions we needed to build for ourselves in order to grow at scale as operators.

The very first feature we built was called “One-Click Rate Adjustment” – for short, “OCRA”, which is now the name of our company (the rebrand of which I led with Sarah, our VP of Growth). It allowed us to change rates across all seller channels at once, saving us a lot of time logging in to multiple seller consoles to change rates manually.

When COVID hit and events shut down, we either had to pivot or give up – and giving up wasn’t an option! I had a strong feeling that our ideas and the software we wanted to build for ourselves were solid and could be useful for other parking operators, so we started there. 

I pushed us to take the Lean Startup approach. This involved starting to build relationships for user research and product market fit and listening to industry experts. We learned about the operators’ issues and connected our own experiences with what we heard.

Eventually I became the owner of all design for the original product, including developing growth hacking features and building the first iteration of the Rate Parity tool from scratch. I established a true disciplined UX process that our team still uses today. It’s what allows us to crawl-walk-run and deliver high-quality solutions quickly that we can then iterate on.

While I liked designing, our development team grew in 2021, and I saw new opportunities to drive growth for Ocra. I had studied computer science and decided that I wanted to become a software engineer.

I was able to successfully integrate and learned how to build technically solid front-end architecture. I drew from my experience having worked as an operator and attendant to build B2B parking software, following the UX process that I instilled.

Today, I’m the company’s first Technical Program Manager, which is an exciting role for me because it’s a combo of all of my strengths: creating scalable, useful processes; solving highly technical problems; and connecting all facets of the business, and all of my team members, so we can do our best work.

My approach to work at Ocra involves putting the company first and bringing humor, excitement, and energy so everyone reaches their max potential.

I believe we perform better together, when everyone is bringing their unique skills and vision to the table, and that solving problems is fun when we’re supporting one another and truly listening to our customer.

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