How ezCater's CTO uses empathy to break down creative barriers
Despite a career centered around data and technology, Erin DeCesare’s top priority is people. This mindset is paying off big time.
Starting out in a data engineering company after college, DeCesare became the go-to person for keeping communication open between her tech team and other departments. From this experience, she learned how to connect with every type of employee, which improved collaboration.
“I was always straddling the line of talking to the business and talking to the tech team,” she says. “And that turned into the superpower of being able to really understand the business needs and making technology approachable, and then creating a more valuable portfolio and having the teams feel understood.”
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DeCesare transitioned to Vistaprint in 2010, and describes her eight-year tenure there as transformative. These years solidified her view that a business runs better when its people feel connected and valued. Along with advancing her knowledge of tech, she honed her skills as a manager of people. Part of her training as she moved into senior leadership was learning the importance of showing up with intention and energy, and she realized just how much her emotional presence matters.
“Had I not had that experience, I could see myself going down a dangerous path that was more about command and control, just trying to drive direction into teams,” DeCesare says. “Instead, [this] really shaped my [view that] my job is to help them feel creative, and give them enough strategic prompting that they can solve the problems.”
DeCesare’s well-rounded experience led to her most recent role as chief technology officer at food-for-work platform ezCater, where she’s been since 2019. The company connects businesses with caterers and restaurants that deliver employee-selected meals to the workplace or events. She has continued to bring different departments together for collaboration, and is well known for her method of one-word check-ins with her team members, who are spread out across multiple states. She strives to ensure everyone is confident with their current project — and takes the time to work through any needs if they aren’t.
The result is a supportive workplace where people feel comfortable sharing how they feel and what they need to be successful. This leads to deep trust and better solutions, DeCesare says.
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She recently spoke with EBN about the power of one-word answers, how to introduce AI and why cross-functional collaboration is the key to creative breakthroughs.
In project meetings, you ask your team members to share one word that describes how they are feeling. What does this achieve?
If we’re talking about a project over Zoom and we’re sensing we’re kind of stuck, or people are frustrated, we go around the room and say one word and that makes it very approachable. It’s like a light dose of emotion. Typically, all it takes is having done one of these creative prompting sessions with a group for them to feel what I’ll call “creative safety” with one another. There’s something really important about the specific approach of the one word, so you’re not asking them to expose their deep emotions.
When the words are there, you can do the secondary prompting, such as, would anyone like to share more about what is at the root of that response? Or based on what we heard, what might be the best next way to approach this conversation?
It will often be words like “overwhelmed,” or “confused,” and these are words that are really disarming. And these words come out, and then you realize, oh, the reason why this person is feeling so heated is because they’re worried they’re now accountable for the solution. And with this word of, “I’m overwhelmed,” you say, “Oh my goodness, I had no idea that’s where this was coming from.” It naturally brings the temperature down, and suddenly, when you pick back up on the conversation, people are much more open and more accommodating and willing to compromise.
Erin DeCesare, CTO at ezCater
How did ezCater introduce AI to its workforce in a way that made it appreciated instead of feared?
We brought in a senior manager to help with our AI transformation, and he would meet with different functions and first [ask], “What are the things that take up time in your day? Where are the things that are not particularly adding a whole lot of value, but you just have to get through it?” There’s something magical when the first experience someone’s having with AI is, “This made my job so much easier — I was able to pull together [a task] in a matter of minutes, versus hours.” It’s just so much more inviting. We’re not fully there yet, but I would say we’ve created this culture of people being really hungry for hearing more about how AI can make them better, so it really was important that we started the way we did.
Then, as we thought about bringing AI into our product, customer service has always been a big part of our value [proposition], so that certainly triggered [the question of] are we going to get rid of humans as part of this process? No, in fact the term human-in-the-loop [the addition of human input and expertise into machine learning and AI] is so critical, because if we just trusted AI on its own, those occasional hallucinations are really dangerous. It was about getting people to appreciate that humans are still an incredibly important part of this process, but AI is just helping us automate and scale in a way that’s making us competitive with customers.
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What are the advantages of bringing together departments from across the organization to work on technology and other projects?
We have been doing a lot more experimentation with cross-functional groups, because that’s a failure pattern I’ve seen throughout my own career, and talking to peers — that engineering can often become very siloed. When you throw in members from marketing or customer service or operations, there’s a different mindset that comes with those people, so having them be part of our creative prompting sessions on how we want to approach a problem, having the cross-functional set of people at the table, naturally brings that into the conversation.
Having those additional voices has been a huge shift. We’ve been practicing different techniques now for about two years, and that was really where the nature of the conversation catapulted into a creative space, in a way I don’t know that we could have gotten there just on our own with engineering.
