Toast Careers

Debra started at Toast in July 2022 as the new Chief Technology Officer. She has been building her career in tech for over 35 years at some notable brands such as Amazon, Wells Fargo, Cisco, and Microsoft.

Hear more from Debra on how she’s looking to take Toast’s tech to the next level.

What do you think differentiates Toast’s technology team and what excites you about the growth opportunity ahead? 

I think great opportunities are forged by strong teams and I am super excited about the amazing global team we have put in place to execute our 3 year technology vision. Toast Technology consists of two core functions, 1) the engineering teams that align to line of business (LOB) product development and 2) the teams focused on foundational technologies like architecture, infrastructure, resiliency, developer productivity, data and  AI. (Think of these as capabilities the LOB engineering teams use to build great products faster with higher quality.) 

In R&D we are accountable for building products that delight our Toast customers, so to make sure we are laser focused on the custom experience we recently rolled out a new organizational construct called a triad. A triad is a cross functional working group made up of Toasters from engineering, product, and UX design. Each triad is uniquely focused on a specific product and customer experience in order to eliminate friction, enhance internal collaboration (especially with teams like Customer Care as we launch features and products), and increase transparency in all that we build for our customers. It's early days, but I am very excited about this new triad model.

Part of our Toast Technology team’s secret sauce is that we have incredible talent across the globe with Toasters in North America, Europe, and Asia. We are also a beautifully diverse team and are committed to an inclusive environment where everyone can feel safe and do their best work. 

There is just so much that excites me about what's ahead. We are at a unique part of our journey where we have gone beyond what I would call a startup mentality; however, we want to keep asking ourselves “how do you keep that fresh perspective? When you're no longer this little company, how do you still act and be agile, and not get bogged down but bring in practices that help us scale?” It’s an innovator's dilemma.

When I think about growing our tech teams, I think it's a balance of promoting from within, recruiting externally, and making sure we're raising the bar on what great looks like because we're definitely in rare air and we really need to be looking around corners. Our opportunities are only going to grow, as we go global and add more enterprise customers and we have to be ready for those technically, from a regulatory lens, reliability, predictability, scale. 

That's why we are setting our sights on a 3 year plan called DELISH:

It is intentional that part of this technology journey includes "always be learning" so that our Toasters have the opportunity to gain new skills and to grow with the company as we continue to mature our technology.

Tell us more about yourself. 

I’m a 35-plus year veteran in senior technology roles! I do spend a lot of time on my work - there's no question about it. It's funny when I do 1:1s with people who want mentorship, and they ask, “how do you create work-life balance as a C-suite executive in these amazing companies?” My response is that for me the “balance” has always come from the satisfaction I get from my work versus other areas where I might spend my time. It's extremely rewarding  to build these companies and grow them. I find joy in it and that's why I do it and continue to do it. 

And I'm very, very lucky. I have a wonderful partner, my wife, Ramona. We've been together for almost 30 years, and she's a brilliant technologist and data scientist, has worked at a lot of great companies, and has been a founder of two companies on her own. We keep the founder mentality alive in our household! It's not uncommon for a whiteboard to come out during dinner at our house or when we're hanging out. We’re also very close to our families and have three amazing dogs that we love a lot. We spend a lot of time focused on them and on the community. Animal safety and well being is really important to us. 

We also enjoy staying active as we were long distance cyclists and bodybuilders when we were a bit younger 😃 . I still practice yoga and we do great hikes with our dogs. 

What drew you to Toast and the restaurant tech industry?

I love our culture, I love what we stand for, and I love what we do for restaurants and the communities we serve – all the things that make us such an empathetic, humble, amazing company are what drew me to Toast. As a kid I spent a lot of time in a restaurant my dad owned, the Tyson Grille in Philadelphia, busing tables and slicing meat and running down to the sub freezer to bring something out for my dad. The stairs of the restaurant even went to the stairs of the kitchen of our house. It was the cornerstone of our neighborhood. 

I have an older brother and two older sisters and when we were kids, we'd sneak down at night with our friends, and eat ice cream or pie while playing the jukebox. The restaurant was across the street from a school, so all the kids would come for lunch. A lot of people thought we were well off because my dad owned this business, but I knew how hard it was for him  to run a restaurant, to make margins and how expensive it was, and what it meant when someone called in sick. My dad always said to me, “promise me when you grow up you will never go into the restaurant business because it's so hard.” And yet here I am, a technical executive that's worked at huge companies who couldn’t resist the opportunity to bring my hospitality mindset back to the restaurant business.