The Value of Staying True to the Inspiration Behind the Innovation

The early days of CarGurus will likely look familiar to anyone in the startup world: A one room “office,” simple but functional IKEA furniture (that we built ourselves) laid out wherever it would fit, and a makeshift enclosure serving as a conference room. 

I was hired as a senior engineer, the seventh employee brought into the company since it was founded, and one of the first “technical hires.” I was eager for an opportunity to feel empowered in my work—and (along with a few pieces of furniture) the startup world put that together for me.

The small company I joined 13 years ago looks totally different today. My journey through the phases of personal growth from engineer to CTO and the business’ growth from startup to public company exposed me to challenges that many small upstarts face. But being with the same organization from its early startup days and beyond the IPO—a trajectory that, in some sense, paralleled my own evolution—has taught me far more about what it means to build a team with a healthy approach to growth. 

When looking back at what made us successful early on, the critical characteristics that defined us were being nimble, hungry, and focused. On the whole, we have stayed true to these terms even though their definitions have changed and grown along with our team. Nonetheless, as organizations grow, they can also preserve these qualities by 1) encouraging a team’s sense of ownership and pride through empowerment, 2) keeping teams nimble by being mindful of the process overhead that is introduced as they grow, and 3) structuring teams in a way that minimizes interdependencies to concentrate decision-making and maximize agency. 

Tech leaders looking to build a team with a healthy approach to growth should trust their teams to do what’s right, provided that everyone is aligned on the overall company goals and mission.

Empowerment Draws Entrepreneurial Talent

When I joined CarGurus, my experience had been grounded on the frustrating process-oriented culture that plagues large companies. While there was a reason for the process, I wanted to work where I felt more directly involved in the company’s various operational challenges that would allow me to wear many different hats. While I might not have called it that at the time, it was very much an entrepreneurial mindset. And in the early days of the company, people with that mindset were in high demand; jacks-and-jills-of-all-trades who were not afraid to take ownership and work on multiple things at a time. 

Although CarGurus is no longer a startup, I still highly value employees with the same entrepreneurial mindset that inspired me to join the company and made our initial set of team members successful. It is no secret that the more people one has to coordinate with–whether communication, consensus-building, or dividing responsibilities–the more difficult it is to reach decisions and act on them in an expedited manner. 

Employees with an entrepreneurial mindset working in an environment where they are empowered to make decisions and work relatively independently are able to sidestep many of those obstacles and move fast. In order to attract that kind of talent, however, leaders need to be intentional about ensuring the same kind of empowerment that comes from working at a small startup remains as that startup evolves into a larger company. Keeping these employees motivated and engaged requires making sure they can remain productive with minimal overhead and take advantage of opportunities for career development, team building and personal achievement. 

One big lever leaders can use to preserve the entrepreneurial culture in their teams as their company grows is to support the career growth of their initial talent through a managerial track. Not only does this career growth help promote cultural consistency across growing teams, it also has the benefit of keeping key employees challenged and motivated through career growth. People advancing into senior roles, like engineering team lead, need to spend more time during their work day mentoring and growing fellow employees who are on their own career paths—a big departure from my previous experience centered around developing and improving software. 

As Cargurus scaled through the 2010s, my focus moved away from being about solving technical problems tied to technology to solving more growth, culture and operational problems tied to employees. Not only did I find this personally challenging, I also found it deeply rewarding. My sense of ownership was not limited to pride in the product we had built over years, it now extended to the personal and professional bonds I created with my teams. I now encourage the company’s leadership and our talent managers to embrace a similar approach. 

When talking about empowering talent to get the job done, it is important to briefly touch upon organizational structures and how these evolve as companies grow. I have seen organizations that are structured in such a way that decisions and corresponding work need to involve numerous teams. While it is always important to ensure decisions are approached from a holistic standpoint, once a decision is made on what needs to be done, teams should be structured in a way that minimizes the coordination and dependencies they have with other teams. 

Teams should be created in a way that empowers them to get the job done on their own. Not only does this improve a team’s ability to execute quickly, it also contributes to each team member’s sense of ownership of their work. Teams operating under this model are more likely to think in broader terms, not just what they need to do from an execution standpoint to fulfill their piece of the puzzle.

Change Only What Needs to Change

Change is nothing new in the tech and business world. Just because a company gets bigger doesn’t mean it needs to reinvent itself. Often, as companies scale, there’s a temptation to implement new processes and restructure departments simply because of the perception that other companies of this size do things this way. However, entrepreneurs who fall victim to the temptation risk getting away from what made the company successful in the first place. 

When it’s clear that change is needed or unavoidable (as is the case during the current global pandemic), I recommend taking a measured approach. One of the biggest cultural shifts at CarGurus during my time was the creation of our product team. It was very necessary and advantageous to the larger business, but it meant that the engineers who were used to playing a principal role in product strategy would have to share that responsibility with their product team counterparts. In the interest of making gradual and measured organizational changes, we chose to build the product team slowly by transitioning a single, trusted employee into the product role, working out kinks in process and delivery, and creating a template for expectations and role functions. Only then did the company start to scale the product team to fit the evolving needs of the business as it scaled, too. 

For many (myself included) startup days can be an exciting time with open-ended and dynamic projects that change the fabric of society in big or small ways. As the CTO of a public company, I make it a point to encourage my staff to create new things and bring new ideas to work every day. While I am now able to support and grow our team in a way that simply wasn’t possible during the company’s startup days, the same excitement I felt when I joined the company over a decade ago powers our culture today. 

While every company is different, I encourage founders and startup leaders to stay in touch with the values and energy that enticed them to take a leap of faith into the startup world—and prioritize scaling their companies with people that share the same values.

Kyle Lomeli

Kyle Lomeli the CTO and a founding engineer of CarGurus.

  • Originally published November 17, 2020, updated May 5, 2023