Passion for parking? What it's really like to work at SpotHero, one of Chicago's top tech startups

At SpotHero, a Chicago-based startup, they live by a decidedly different motto: “Don’t get stuck in traffic.” It’s a fitting mantra for a company whose tech platform is taking on the old-fashioned parking industry by making it easier for people to find and rent urban parking spots.

Written by Sam Dewey
Published on Sep. 08, 2016
Passion for parking? What it's really like to work at SpotHero, one of Chicago's top tech startups


A bad job can feel an awful lot like a traffic jam. You’re left stagnant, frustrated with a lack of progress and feeling like you’re late for something better. Anyone stuck in a go-nowhere gig knows that feeling all too well.

At SpotHero, a Chicago-based startup, they live by a decidedly different motto: “Don’t get stuck in traffic.” It’s a fitting mantra for a company whose tech platform is taking on the old-fashioned parking industry by making it easier for people to find and rent urban parking spots.

As a company, they’re growing — fast — and have become a top destination for job seekers across the country. Now at a headcount of about 120, the SpotHero team invited us for a behind-the-scenes tour to get a feel for what working for a high-growth, high-potential startup really looks like. We shadowed folks from their sales, operations, and engineering teams, including Co-founder and CTO Larry Kiss, Backend Developers Chhay Tea and Ashley Kasza, Lead Mobile Developer Ellen Shapiro, Head of Sales Tim Maloney, Sales Analyst Michael McCarthy and Senior Account Executive Nicole Wylie. Want to join them and the rest of the SpotHero team?


What is SpotHero? Who are you as a company and what are some of the problems you’re solving?

Ellen: SpotHero is a company dedicated to helping you find a parking space. Whether that's finding a really cheap price at a slack time or a really well-placed spot in a chaotic time, we're trying to take the worry out of parking for both daily drivers and people who only use us occasionally.

Ashley: We’re making operators’ lives easier by finding customers, and making customers’ lives easier by getting them where they want to go. There’s less worry for everyone involved.

Larry: I heard a story about someone who would never go to a play because they don’t like parking. We’re opening up this person’s world to go see plays. And that’s just one example — seeing the way we’re inadvertently creating new worlds for people is awesome.


What tech are you using to build your solution?

Ellen: Across the engineering team, we're focusing on stability. We've grown very quickly, and as with any startup, some choices were made to facilitate that growth that were not always the best long-term decision. We want to make sure we're ready to scale up even more over the next couple of years, and making sure we've got a solid foundation is really important.

Larry: Most people think the biggest angle is the consumer side. We have a mobile team that’s working on iOS and Android apps, and we also have a backend team that’s working closely with the front end to solving issues like scaling. Then, there’s the non-consumer operating side, and all the analytics that go into it.


How fast are you growing?

Ellen: Fast. On the mobile team, we went from only contractors to having a full-time staff of four and counting in the five months since I started. I'm used to it coming from a couple agencies that grew quickly, but it's a tight rope to walk. You have to make sure that you're not just hiring the person who's available right now, but the person who has the most long-term potential to help you out. When you're swamped, that is not an easy choice to make.

Nicole: I’ve been here for two years. When I started, our sales team was five people. It’s grown a lot, and it’s been really amazing and incredible to be a part of the direction of where we’re going — to provide input and help bring on amazing people. We have so much opportunity. It’s also unique because I really enjoy working with all of my colleagues, and I don’t know if everyone can always say that.

Michael: I’ve been here about 10 months. The supply team has tripled since then, and the entire company has doubled.

That's insane.

Michael: It’s been a wild 10 months. I came on as the second data hire. We are building out our data analytics function, because as we grow and become a mature company, the role of data is really going to blow up. We’ve been focused on acquiring inventory, but now that we have a customer base we’re acquiring a robust data set that’s going to bring so much additional value to our partners. That’s what I’m focused on.


10 months in, you have a ton of responsibility on your plate. Did you think you’d be given as much opportunity for growth when you joined?

Michael: Nicole actually was the person who hired me and absolutely promised that I’d be given a ton of opportunity. One of the reasons I left my previous job was to come in and lead the data analytics from within our team. I think I expected to be given responsibilities, but the receptiveness of the team has been more than I ever could have asked for. I feel like people value my input on the things I specialize in, despite my age and my short tenure with the company. I feel valued, which is really important.


Ashley, you’ve been here since January. How do you feel like you’ve grown since then?

Ashley: It’s been a whirlwind. I’ve been introduced to all kinds of new concepts. I feel like my decisions matter more here, like what technologies or approaches I use. There’s direction, which is nice, but I can also make my own decisions and that’s really great.

Chhay: She came from a Java shop, and we’re a Python shop. She had to ramp up all of those different technologies. She’s done an excellent job.

Larry: And now she’s calling me out on my code reviews!


What sets your team apart from other sales or engineering teams in Chicago?

Tim: We don't consider ourselves to be an outside organization when it comes to our relationship with our partners (parking operators). We believe in transcending the vendor paradigm and becoming an extension of their team. We add bench depth to their marketing, operations, customer service and accounting teams, and they leverage our expertise as they would any in-house resource.

Ashley: I think culturally we’re also pretty different. We all work in the same room and get along. There are periods where we may slack off for a few minutes, and pretty much the whole room gets into that for a nice break. We do a lot of outdoor activities. We play volleyball and Whirlyball — which are both pretty new to me.

Nicole: We hire a very particular person, and while we’re all very unique, we all come together and work very well together. We all have this entrepreneurial spirit, and we all enjoy working together and utilizing each other's strengths. There’s a lot of ego in a lot sales organizations, and I think that’s checked at the door here. We really care about each other. We enjoy grabbing a beer or hanging out at lunch.


What makes someone successful on your team? What qualities do they need to really thrive?

Ashley: You need to be interested in new things. We iterate quickly, and there’s a lot of new technologies all the time, like Jenkins or new plug-ins. Almost every week there’s something new to learn.

Larry: The reason people have been successful here is because of their scrappiness, curiosity and their ability to not, as we like to say, “get stuck in traffic.” It’s one of my favorite values. It makes so much sense. When it was just Mark, Jeremy and I early on, we would hit something we thought was the biggest roadblock known to man — or at least in our heads — but every time we’d either blast through it or find away around it. Now, that gets harder as you get bigger, but we’re trying to make sure we vet for that, because even at a micro-level at the company you still need to be able to do that.


We are a little bit more than halfway through the year. What does your team hope to complete by the end of the year?

Nicole: So much — growing and making very intelligent decisions on where we're going to go next. We just recently launched in Los Angeles, and it’s been incredible.

Ellen: More stability improvements, and then working from that base, taking advantage of some of the newer features of iOS 10 and Android Nougat. We're also looking at what cool stuff we can do with wearable technology and stuff that's built into cars longer-term, and I'm really, really excited about that.

Larry: Right now, it’s about scaling. We’ve proven out the product and scaling to new cities. That requires infrastructure scaling to the West Coast, to the East Coast, Canada and even starting to internationalizing things. We have this big monolithic code base, which is something a lot of companies go through where it makes sense to build everything in the same spot and deploy it. But as you get bigger, if something goes wrong, everything goes down. We don’t want that to happen, so we’re breaking it apart into smaller pieces and to deploy and build independently.


Not only is SpotHero is one of Chicago’s top up-and-coming startups, but you’re also becoming a national brand. What advice do you have for job seekers who want to join the team?

Nicole: You don’t need to be in the parking industry to join the SpotHero team. I don’t think the majority of our team knew what they were getting into. We were fortunate to have some people, but I think being determined and showing what you can bring to the table is more important.

Ellen: My advice for people looking for engineering jobs has long been the same: curiosity is the biggest thing, and humility is a damned close second.

Larry: Apply! But if you want to stand out, show that you can build stuff on your own but also that you don’t have an ego when you’re doing it — and that you're open to collaboration with others. Show that you aren’t a polyglot developer who just wants to pick the flavor of the day — that you like more stable, open-source projects and languages that have been around and are proven.

Ashley: Be honest about what you know. We understand. I didn’t know a lot of technologies coming in, but everyone has been okay with that as I’ve been learning as I go.


Why did you decide to work here?

Nicole: I had a conversation with one of our old co-founders, and I’ve never been so impressed by senior leadership in my life. I met with Mark Lawrence, and his passion, his determination, and his passion for parking — which might sound odd — was inspiring. I wanted to be a part of that vision and growth and opportunity. At the time, there were 20 of us. It was kind of a leap of faith, but I saw such great people that I knew there was something special here.

Ashley: I really looked for finding a boss who would facilitate what I was doing rather than tell me what to do. At SpotHero, if you want to try a new language or tool, that’s totally fine. During the first week, I remember Larry told me, “If I could buy my developers lifetime licenses for any tool they wanted, I would.”

Chhay: I was looking for a new job and had a few offers on the table, but then I met Larry and the team. They were great, smart people who were trying to build a product that was helping people. That got me really excited.


In one word, how would you describe the culture:

Nicole: Unprecedented.

Tim: Unparalleled.

Ellen: It's hyphenated, but win-win. We're always looking for a way to make sure that nobody gets the short end of the stick, be it between customers and parking facilities, or internally when we're trying to improve our systems.

Responses have been edited for length and clarity. Photography by Jay Hagstrom.

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