Toast Careers

Approximately two-thirds of Toasters have experience in the restaurant industry and Jen is one of them. Blending her hospitality background with her financial and analytical skills, Jen has been thriving at Toast for almost seven years in various roles, such as finance leader, Chief of Staff, and now SVP and GM of International. Hear more about Jen’s career journey and her current Toast adventure below:

What led you to Toast and what keeps you here?

I started my career managing restaurants. I love the high-intensity, fast-paced environment of a restaurant– there’s nothing like going from an empty restaurant to a full one in a matter of minutes! What I loved most about my job though was the analytical side– inventory turns, revenue per seat, capacity planning for staff with less staff than shifts. That led me to go back to school to get my MBA. After finishing my MBA I took a job at a hospitality consulting firm. The assignment was to support a family-owned Italian coffee concept to become more efficient and expand throughout Italy and into London. It also included moving to Italy, which was certainly a plus! I lived and worked in Italy for 1.5 years and wow– it was a great experience– both in terms of my personal and professional life, but ultimately it was time for me to come home. After returning home I held a few purely finance roles, one of which was at a large public company that was simply not fun or engaging, and I happened to stumble on a role at Toast in finance. At the time it felt like kismet– a tech company, an industry I knew and loved, and a role that I had experience in. It only took me a few interviews to realize that Toast was a company I had to work for! 

What are the top three things that brought you to Toast and what keeps you here today?

1. I believed then and I still believe now that the restaurant industry was clearly underserved from a tech perspective and we had a product that could truly help restaurants.
2. I loved the people that I met and love the people that I get to work with. I have a ‘no jerks’ policy– I think life is too short to work with people you don’t respect and who aren’t kind and nice. You don’t need to be best friends, but you have to be human to one another. The people and the team are a huge reason why I love Toast and love to come to work.
3. I’m constantly learning and growing at Toast. I have had more opportunities at Toast to learn and grow than I could have ever asked for. And while I have held lots of roles at Toast there is never a day that I don’t learn something new and that is so so important to me.

What led you to want to take on this next adventure as GM of International?

I am so fortunate here– the GM of International wasn’t even on my radar, besides the fact that I was aware we were going to invest in international. Chris and Elena, Toast’s CEO and CFO,  approached me and asked if I was interested in the opportunity. I didn’t even have to think twice– after living in Italy 10+ years ago, I knew that at some point I would jump at the opportunity to live in another country for work again. It was a truly life changing experience, made me grow as a human and I was eager to experience that again. 

What advice would you give finance professionals looking to become strategic partners? How do you see finance team members growing their business acumen in their roles?

One of the reasons that I was able to transition from a finance role to an operational role was because I understood the dynamics of our business and understood the why behind the numbers. So often finance teams can just focus on the output number/ metric/ financial– while that is important, it's also important to understand the “why” behind the number. Numbers are just tools to help you tell the story. I encourage all finance team members to be able to understand what is really going on with their partners. You should be able to clearly articulate at more than a surface level what the teams are working on and the impact they have on the business. If you understand the work you can then think about what drives the number that will ultimately help you be a better partner to the business. It goes without saying, that I think regardless of the role, building strong relationships is key to success and one of the things that I love most about all the roles I have held at Toast

What excites you about leading and growing our team globally?

So much of my passion and commitment for Toast comes from my early days because in the early days, it wasn’t guaranteed we would have the success that we do now. That creates a level of urgency, responsiveness, and willingness to dig in and do whatever it takes to make something successful. I love that type of work and I love to surround myself with teams that work that way. Building out our international markets is very similar. While we have high brand recognition in the US, we have little brand recognition in our new markets. While that can be daunting and overwhelming, it's also invigorating. To know just how impactful Toast can be for restaurants is really exciting for me. I love to see the teams problem solving and banding together to make things happen–  it's the epitome of a One Team mindset which, as I tell my team, gives me goosebumps. I love it so much! 

What are key characteristics that we look for in founding team members in these new regions?

We look for people that are really motivated to go the extra mile. People who do well working in the “grey”, there is so much we haven’t figured out so we need people who can be innovative and think creatively to problem solve. I think the ability to deal with ambiguity and complexity is really, really important. Lastly, we want teammates who want to be a part of a founding team and bring a level of excitement and commitment! 

How do you partner with teams across the business to help provide an exceptional experience to Toasters in these new markets?

First, I try to listen and learn from my people partners. I am not an expert in the specific needs of the countries we are operating in, so I lean on the People team to tell me what is market or country specific. I also try to ensure the People team knows my business objectives. I do my best to bring the team into the conversation so they know what I am trying to achieve. Similar to the finance teams, when the People team can understand the business results, the better they will be able to support the international teams. I couldn’t do what I do without their support! 

 Jen DiRico is now a member of the Toast alumni community. We greatly appreciate their many contributions to and lasting impact on Toast!