At MTLC, we’re passionate about creating moments where Massachusetts tech leaders can truly connect. When people from different corners of the industry come together to share ideas and experiences, the exchange builds understanding and strengthens the fabric of our tech community. It’s these conversations that keep our ecosystem vibrant and evolving.
As a follow-up to our Tech Leadership Awards earlier this year, MTLC brought together Force Management CEO Patrick Manzo and CarGurus’ Jason Trevisan, MTLC’s 2025 CEO of the Year. They covered everything from driving innovation to fostering leadership at all levels of a company.
Read on to experience the highlights of this conversation between these two dynamic leaders.
The Power of Transparency
Pat: Congratulations on being recognized as the 2024 CEO of the Year by MTLC. What stood out most to me that evening was the unprompted praise from your team. Multiple people independently described feeling energized by your leadership style.
Jason: Thank you for the kind words. It’s very gratifying to hear that our team feels energized and inspired. That’s what it’s all about.
Pat: That connection clearly resonates with your team. Let’s shift to how it extends outward to your customers. How is CarGurus using AI to innovate and support them? How does this build on the company’s founding principles of being data-driven and transparent?
Jason: Data and transparency have always been core to CarGurus. From the beginning, we broke into an automotive market dominated by large incumbents by offering more transparency than anyone else. If you’re a consumer buying a used car, there’s a lot you don’t know. We aimed to change that.
We also used data to make searching for a car more intuitive—more like Google—helping users find the best match for their individual needs. Now, AI is becoming central to how we operate and innovate.
I’ll share a few examples of how this comes to life for our two distinct customer groups: dealers and consumers. As the leading automotive marketplace in the U.S., we leverage our vast data on pricing, consumer search trends, and merchandising to deliver AI-driven predictive insights that dealers can’t get anywhere else. These insights help dealers perform better in their market by providing real-time guidance on optimizing pricing, inventory selection, and merchandising. Through these insights, we’ve earned a position as a daily thought partner to dealers.
For consumers, we use AI to help make the sometimes overwhelming process of car shopping more personalized and approachable. Our “Discover” tool acts as a virtual assistant, helping users identify the right car for their needs through conversational search. Personalized search and sort features further streamline the experience to help shoppers find their best match.
As you said, we started as a company focused on data and transparency. Today, I believe we’re leading in the market by building on that with AI to make the experience more predictive and personalized for both consumers and dealers.
Pat: That’s a significant shift from how the auto industry traditionally operated. Transparency with consumers actually benefits dealers by making their businesses more efficient. How do you ensure these values are consistently reflected across your customer-facing teams?
Jason: Internally, we democratize access to data and encourage data-driven decision-making across all departments to better serve our customers. On the dealer side, it’s about partnership and education. We’ve invested heavily in account management, with teams now spending days at dealerships, helping them maximize their use of the platform and our data-driven, AI-powered products.
On the consumer side, over the years, we’ve come to appreciate the extent to which emotions, not just data, drive shopping decisions. While we provide the largest selection with the most information on each car and dealer, what resonates most with consumers using our site is the emotional experience of feeling supported as well as informed. That’s why many leads come from our “fair deal” listings, not just “good” or “great” deals. Through the transparency and data on our platform, they have the confidence that they’ve found a good fit. This insight guides our consumer site experience.
Ultimately, this creates a win for both sides of the transaction. A confident, well-informed customer leads to a more efficient sale and better conversion rates for a dealer.
AI-Powered Market Leadership
Pat: You’ve mentioned AI several times. From a CEO’s perspective, it’s essential. How are you using it across the enterprise?
Jason: We think of AI in three buckets: Improving existing products, creating entirely new ones, and boosting internal productivity.
AI is central to our ability to drive innovation, create a more personalized experience for dealers and consumers, and boost operational efficiency. It’s helping nearly every team at CarGurus enhance their workflows and free up time to focus on more high-impact, strategic work. For example, in engineering, it supports code creation. Rapid prototyping is another area. What used to take weeks now takes hours—if not minutes—with AI. This allows our engineers to focus less on routine code and more on strategic problem-solving, system architecture, and designing innovative solutions.
Sales and account management are evolving, too. AI helps them automate routine tasks and extract customer insights for more impactful interactions.
I’m also proud of how our finance, legal, and talent teams use AI for high-volume activities associated with parts of the forecasting, contract management, and hiring process. AI helps us get smarter with each iteration.
Pat: How do you balance consistency and autonomy with teams in the U.S., Canada, and the UK with so much innovation underway?
Jason: It starts with being aligned around a single, unifying set of leadership principles and strategic objectives. This anchors us across all geographies.
The bulk of our product innovation and testing happens here in the U.S. This ensures we pass along proven offerings and playbooks to our international teams. Since they’re smaller and more agile, they can then move quickly to localize these to their markets. They have an entrepreneurial spirit that enables them to drive results with exceptional speed and focus. Their mindset inspires us all.
Empowering Teams with Accountability
Pat: That sounds like a powerful dynamic. Now let’s talk culture. CarGurus is often recognized as one of Boston’s best places to work and even won MTLC’s Workforce Culture Award in 2024. What makes your culture unique, and how do you maintain it in a hybrid environment?
Jason: Our culture is the sum of our daily actions. It’s how we do everything we do—the big and the little things—every single day.
When I moved from CFO to CEO, I focused on a simple framework: strategy, people, and operations—all centered on ultimately supporting our customers. I expected to spend most of my time on strategy, but reflecting on my last four-plus years in this role, I’ve spent the most time on people.
We focus on attracting the best talent and creating an environment of “empowerment with accountability” that provides people with both freedom and ownership. This allows them to innovate and grow by putting in the work, taking pride in their efforts, and learning from when things don’t go as planned.
Boston-based employees spend 60% of their time in the office. It’s not a rigid schedule of mandatory days; instead, it’s a flexible model driven by the belief that in-person collaboration is critical for building relationships, mentoring, and sparking innovation. This type of connection is essential to our success. We wouldn’t be where we are today without it.
Pat: What makes a great leader at CarGurus?
Jason: There’s no single blueprint. We embrace diverse leadership styles and help individuals play to their strengths.
We focus on communication, coaching, driving change, impact, and collaboration. We want leaders who demonstrate an ownership mindset, humility, and a growth mindset. Feedback and transparency are key.
This can come to life even before someone joins our team. When I interview candidates, I give honest feedback mid-process. Some appreciate it, others don’t. Those who do tend to thrive here because they understand feedback is part of our culture.
Pat: Do you mean leadership in the traditional sense, or more broadly?
Jason: Definitely the latter. Everyone at CarGurus is a leader. We encourage each person to include growth-oriented goals in their annual objectives. And managers are responsible for making growth opportunities clear to their teams. It’s not just about what you achieve but how you do it and how you help others get there, too. We don’t tolerate people who get results but negatively impact our environment.
Pat: Growth means taking risks, which requires comfort with failure. How do you foster that?
Jason: Innovation is essential, and we’ve built structural support for it—hackathons, science fairs, AI-themed days, and more. But we’ve also shifted our mindset. Town halls now include “wins and learnings,” not just wins. We separate the person from the idea. If an initiative fails but was well-executed and thoughtfully reviewed, that’s a success.
We work hard to build psychological safety so people feel comfortable taking risks, learning from them, and sharing those learnings with others.
Pat: That ties back to the growth mindset—continuous improvement over static performance.
Jason: Exactly. If we attract great people and create an environment where they can innovate freely, even if most ideas don’t work, we’ll uncover the best opportunities. Then we shift into performance mode.
We’re a billion-dollar business looking for the next $100–200 million idea. That takes bold thinking and a safe space to experiment.
Pat: CarGurus is a long-time member of MTLC. How does that support your goals for employee development?
Jason: MTLC’s partnership supports our learning and development efforts. Our team participates in their programs, speaks at events, and joins their peer group sessions. For example, our interns attended MTLC’s “Tech Runs Boston” event, and we plan to host an AI-themed event at our Boston HQ.
I always encourage people to network with peers at other Boston tech companies. MTLC fosters that kind of peer learning, which is incredibly valuable for personal and professional growth.
