Meet the Women Behind Faces of Change: Erin DeCesare, CTO, ezCater

Last year, Insight Partners launched the Faces of Change Executive Leadership Academy with a cohort of six inspiring women from our portfolio of ScaleUp software companies. The program provides these executives with resources, connections and coaching to support their development and the advancement of female and minority employees.

To celebrate Women's History Month, we interviewed each of the women who were selected to be a part of the program. In the interview below, learn more about one of the members, Erin DeCesare, Chief Technology Officer at ezCater. 

What advice would you give yourself 10 years ago?  

10 years ago was when I had my son and the time that my leadership scope was expanding. I made the difficult decision to take a step back in my career in order to have enough flexibility in my personal life, which caused me an enormous amount of stress. If I could go back and give myself advice, I would have told myself that your career is a marathon, not a sprint. Don't worry so much and embrace the moment. 

How did you get to where you are? What was your career path? 

I started my career as an engineer, but quickly realized that I enjoyed working with our business stakeholders. Unlike many of my peers, I enjoyed being a bridge between tech and business teams. This allowed me to take on a leadership role in the program management space. I then transitioned to Vistaprint where I managed a team of 300 global engineers before pivoting into a data analytics leadership role. Most recently, I was recruited to become the CTO at ezCater and I'm excited to be back at a high growth company with so much energy.

What’s been the most unexpected part of your career?  

When my leadership was expanding at Vistaprint, the company decided to expand geographically. I had a team in Barcelona but was tasked with building a team from scratch in Prague. While it was a challenging experience, it helped me understand how to effectively create communication channels and a culture that allowed people to feel connected even though they were in different timezones. To make a global expansion program successful, I believe you need to make the commitment to travel because there's no substitute for being in the office and listening to people on the ground. 

Have you had a mentor? Share a story of how they impacted your growth. 

I had the fortune of having an amazing executive coach. It was helpful to have an objective third party observe how I was showing up with my team and identify my blind spots. Something that had been a key part of my success to that point was my ability to solve problems regardless of the constraints or issues going on at the company. Instead of continuing to always make it work, my executive coach pushed me to become more comfortable pushing back on on business constraints and focus on solving the root problem. 

What’s your superpower that’s made you successful in a ScaleUp?  

I would say my superpower is pragmatism. When companies begin to scale, they can begin to overinvest in technology, processes, or team, which costs both the company and individuals. By taking a pragmatic approach, I try to understand the right size of investment on any of these dimensions and what's the minimum thing that's needed to get us to the next level.