CarGurus’ New CTO Is Disrupting an Industry While Growing a World-Class Team

Looking out the panoramic windows of the CarGurus office on the Charles River, employees can pick out several iconic Boston landmarks: the Museum of Science, Fenway Park and the historic Back Bay neighborhood, where the company is set to open a brand-new office in fall 2023, ushering in the next exciting era of explosive growth and unstoppable momentum. 

Since its founding in 2006, CarGurus has quickly become one of Boston’s biggest names in tech, with presence across the United States, Canada, Ireland and the United Kingdom. Tens of millions of users flock to CarGurus’ virtual marketplace every month to experience a simpler, more modern car buying and selling experience. Add the complications of pandemic-related supply chain issues, low inventory and an unusually hot used car market, and CarGurus’ tech solutions are a welcome relief in what can already be a stressful experience.

But according to the company’s new Chief Technology Officer Matt Quinn, the company is just getting started in taking their industry impact to the next level.

“CarGurus has already established itself as the No. 1 virtual automotive marketplace in North America,” Quinn said. “We’re really on the verge of further disruption thanks to some smart acquisitions, new capabilities and the talented, passionate people here.” 

An established tech leader, Quinn has previously led engineering teams at Amazon, Audible and Vistaprint. Stepping into his new role at CarGurus, he said, seemed like a natural next step for his career and aligned nicely with the company’s ambitious plans to scale. 

“I love finding roles at companies that are in hyper-growth mode and are disrupting established industries,” Quinn said. 

To learn more about the leader’s plans for his team, Built In connected with Quinn. He walked us through how his first few months have gone, what’s impressed him most about the engineering team and what he’s excited to accomplish.

What is your background? What attracted you to CarGurus initially?

CTO Matt Quinn: I’ve worked in Boston tech for nearly three decades, across a variety of roles in both startups and global companies. I started my career as a startup software engineer, got a master’s degree in management, then shifted my focus toward leading teams at larger companies. 

I like thinking about challenges and opportunities from different angles, including technology, people and customers. CarGurus brings value to buyers, sellers and dealers in a way that’s immediate and real, which is why this is a satisfying and motivating place to be a leader. You can deliver real value almost instantaneously. 

What’s been most exciting about your new role so far?

Without a doubt, the most rewarding part of the job thus far has been meeting all the incredible people here and learning about their integrity, empathy and passion for what we’re doing. That’s been very fulfilling, if a bit challenging in a virtual environment. But we’re slowly returning to the office and working toward a hybrid model. That will give people continued flexibility while fueling a lot of the community and collaboration CarGurus was built on, and that’s core to our business. 

What has surprised you about the company since you’ve joined?

The first thing that really struck me about CarGurus is our cultural focus on diversity, equity, inclusion and belonging, which is incredibly important to me. I’ve sought out companies that share those values, and I was thrilled to see it and experience it at CarGurus. The company is determined to create a workplace where everyone can thrive and has equitable opportunities to grow, contribute and develop. This value shines through every day, in person or remote, and in big and small ways. Whether it’s the team sharing different perspectives on Slack, to thinking through decisions that have the potential to impact different groups, leaders always strive to navigate those moments as a team to ensure everyone is heard. 

The second thing I’ve learned is just how complicated and fascinating the car buying and selling industry is. Even if you’re not a car enthusiast, CarGurus is an environment where you’re able to work on heavily scaled systems with high complexity and have a tangible opportunity to transform the traditional buying and selling model through technology. My appreciation for that experience has grown dramatically since starting in January.

Let’s talk more about the scale of the products your team builds. How does the size of CarGurus’ user base impact the engineering team?

We have over 30 million customers visiting our site every month. That alone drives a significant opportunity for the engineering team. Our site is also incredibly refined in terms of how it presents cars to customers, and all of the tools we provide dealers on the back end. Lastly, we’re integrating a lot of assets and subsidiaries. Between those three areas, there’s a lot to work on and a lot of unique challenges to solve. 

The engineering team here has already built amazing systems and products. What I’m most excited about is empowering our existing teams to continue to think and build in new ways. I’m equally excited to elevate that group while bringing in new people and fresh perspectives to the table. 

Speaking of new team members, what do you look for when hiring?

One of our core values is that we are pioneering. I try to find people who have an intense curiosity, bring in new ideas and solutions, challenge the status quo and act as change agents. Along with that, I look for people who have an owner mindset and feel empowered to act on their curiosity, and test new ideas to see if they’re something we should move forward with as a team. And lastly, although perhaps most importantly, I look for people who are collaborative and kind. Ego can be destructive, so I ask my team to check their egos at the door. I look for people who are constructive in every conversation, no matter how difficult. 

What’s your leadership style?

I care deeply about technology, engineering, code and architecture, but I care an equal amount about people and my team. I strive to empower people on my team, while at the same time offering feedback and guidance to help them grow. I also recognize that feedback needs to be bi-directional, and so I welcome it to help me grow. That, in turn, helps my team grow and enables us all to work together toward our shared goals. In service to that mentality, I try to ask good questions and listen deeply to my teams, and seek a greater understanding of people’s challenges and opportunities.

Giving and receiving feedback can be somewhat uncomfortable at times, so I encourage people to lean into difficult conversations. When done right, these discussions really lead to constructive solutions. 

As you said, feedback can be tricky to give and take. How do you keep these conversations meaningful?

There are two things we do to promote useful feedback. The first is that we talk about wins and misses at the same time, which balances the conversation. The second thing is, when we talk about misses, we always keep it constructive. We try to find improvements that we can make in order to make the team stronger and avoid that miss the next time. That changes the conversation from one of criticality into one that focuses on learning and positive discussion.

Encouraging feedback opens the door for dialogue. That builds an environment where folks can bring forth ideas and perspectives and can challenge the way we’re doing things today. We’re trying to inculcate that mindset into our culture, so in every discussion I have throughout the organization, it’s all related heavily to feedback and encouragement.

What advice do you have for tech talent, especially in this hot job market?

In the current market, it’s very tempting to focus on climbing the ladder, getting the next big title and getting promoted. But I think it’s important to remember that getting that next title doesn’t always equate to growth. 

If you strive to continue learning in every role and put yourself in a position where you’re feeling challenged, you will feel positive pressure to increase and enhance your own individual performance. Promotions and new titles will follow as a result of that growth. 

What advice do you have for other leaders who are stepping into a new company?

I think it’s important to talk to as many people as you can while you’re exploring a company or ramping up once you’re there. I learned a tremendous amount about CarGurus even before I started and I’ve continued connecting with as many people as possible since I’ve been here. I think that the listening aspect of joining a company helps you understand and respect the past, as well as the culture that exists today. That will allow you to build the relationships you’ll need to shape the future successfully. 

You can’t just walk into a company with a radically new point of view and foist it on the team. You have to balance your perspectives with what already exists, and appreciate all of the great work these teams have already done.