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Five Burning Questions: Elisa Hebert, VP Engineering Operations at Boston Tech Startup, Fairwinds

Elisa Hebert is an executive leader with 20 years experience driving business and tech teams. As we hear in this interview, Elisa values a constructive and supportive leadership style and has experience building teams at businesses where she also supported 2 successful exits.

Hebert confronts problems head on and brings a fearless but empathetic approach to difficult situations; having the ability to separate the business from the personal and is a champion leader.

Fairwinds is a Boston-based Kubernetes focused software and services company, helping their customers adopt cloud-native infrastructure and thrive.

I hope you enjoy this interview as much as I did!

You have to move to a desert island, what’s the one thing you bring?

Assuming I have access to food and water, and some way to build a shelter (I’m pretty handy), the one thing I’d bring is my wife. (Also making an assumption that someone is caring for my kids back at home…)

After finding somewhere safe to sleep and having access to the basics like water and food, the thing that’s missing in terms of basic human needs is companionship.

So I’d bring my favorite companion - my wife.

If you didn’t work in tech, what would you be doing?

I find the people who work in tech - specifically emerging or front-edge tech - to be really interesting. They have a curiosity that I find compelling. If I wasn’t working in tech, I’d still be drawn to that curiosity - where people were interested in always making things better, to find creative solutions, always looking for ways to evolve and innovate.

I find the machine of a business fascinating - that doesn’t have to be specifically in tech. I’m interested in the ways leadership plays out in the running of a business, and the leadership qualities I’m drawn to - I think they’re kind of the same qualities of humanity that I find appealing. One of the biggest ones is respect for other people, respect for their time, respect for their talent, respect for their culture. And that plays out in some interesting ways, especially in bigger companies.

You weathered one pandemic; how has your strategy changed for future unknowns?

I actually gave a talk on the concepts of antifragility and emotional elasticity. I did NOT come to this concept naturally; I was the kid who didn't want to go to middle school, I wanted to stay in elementary school because I was comfortable there. And then I didn't want to go to college. I didn't want to go to summer camp and then I didn't want to come home from summer camp. I liked knowing what was going to happen. I like rigor. I like order. That's sort of my base state.

Over the last decade - I’m in my 40s now - I’ve been learning to be more flexible. Becoming a parent certainly has influenced this. My older daughter is going to be 11 soon, and in that time I’ve been learning to be more flexible and listen to the moment rather than trying to plan several steps ahead.

I think it’s important to look to the future - to look for possibilities and challenges. Do some thought exercises about what I might do in certain situations. But spending a lot of time planning those things might be wasted time, because the likely outcome isn’t one you’ve figured out (I still do really like to do deep planning, so this one is a work in progress for me). Kicking around some possible outcomes and thinking about how you would feel about things is good for emotional maturity.

Why do you think Boston is such an incubator for tech start-ups?

I'm in Denver now, but I grew up in Rhode Island and I went to school in Providence. While I was at RISD, I took some classes at MIT, so I was in and around Boston quite a bit.

The stereotypical New Englander is impatient and moves quickly. I think that actually can be both an asset and a challenge - some of it I unlearned when I moved to Denver, which is culturally a slower pace.

I think impatience can drive innovation - it can drive efficiency and speed, looking for the better solution. A lot of start-ups are in that space. What's broken and how do we fix it? And here's a solution, why is it imperfect? How do we make a better solution? How do we improve this solution? There’s also a little bit of grittiness in the Boston archetype. I think that overlays too - people are ready to get their hands dirty to find solutions that are exceptional.

There's a lot of higher education in the Boston area, New England in general. You have Harvard, Brown, Yale. You have MIT, Berkeley. Schools where the best minds in their field go. So you have this concentration of intellectual excellence.

There’s the dark side to that concentration and network - it can become homogenous and an echo chamber when you’re talking about access to funding for start-ups. If you didn’t go to an elite university, if you don’t have that pedigree, or - frankly - if you don’t fit the white-male-ivy-educated archetype of who typically gets funding… how do you get a seat at the table? Never mind a seat at the table, how do you even get into the room?

There’s some great organizations challenging these norms - but more funders need to really challenge themselves in this regard. How many Black female founders are you backing?

You are forced to go on Shark Tank for an invention that is not your current start-up, what do you pitch?

I’m not the idea person - I’m the guy behind the guy. That’s my sweet spot. So it’s highly unlikely I’m front and center for any pitch, especially on TV!

My strength is taking that idea and making it real - operationalizing it, resourcing it with incredible talent, and driving a business that can grow and thrive. I enable businesses that are exceptional places to work, provide awesome opportunities for people, a good margin for the business, and excellent service or products to the customer. I think that’s a win-win. When you can reach that trifecta of: good for the company, it's good for the team, and it's good for the customer.

I want to be a part of making that machine go! I want to drive that machine. I want to be constantly asking, “Why do we do it this way?” You should always be asking that question. We should be constantly interrogating ourselves about if this is the right way to do it - and if it's not, we change it.

OK, so back to the question. What would I want to pitch on Shark Tank? Have you heard of Dapper Boi?


It’s a mature start-up in the apparel space, making gender-neutral and size-inclusive clothes. Their jeans are the first pair of pants I've ever owned that really feel right on me - they honor both the way my female body is shaped and my more masculine style. THE POCKETS! I'm wearing them right now, actually.

They're raising on a SAFE now (listen up, investors!) I've been supporting the CEO a little bit with their pitch deck - they're an amazing company that makes super high-quality apparel. If there's one product I would have been in the room for the beginning of, it's their jeans. I really can't say enough how perfect they are.

Come mingle with the startup community!

We hope you enjoyed this interview with this innovator! We’ll have more coming your way soon. In the meantime, don’t miss out on your opportunity to network with the startup community. Grab your free ticket for Startup Boston Week 2022 today!


Choji is alive and well. He's a Konaha-nin, a jonin who's taking S and A ranked missions for the village. He has a beautiful wife from the Hidden Cloud and an equally beautiful daughter named Xho-cho who is an Akimichi prodigy.


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Tommylee Jones
Tommylee Jones
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