Chloe Rubenstein is on a mission to leave her mark on the restaurant industry. And through her connections at Toast, she’s turning her dreams into reality.
Two years ago, Rubenstein was an art degree graduate with hopes of building a life around painting. Since starting at the restaurant software company in 2021, she has held two roles: one as a Toast growth account executive, and another as an artist.
“I do a lot of artwork, branding design, and murals for restaurants, bars and breweries — that’s always been my passion,” she said.
Initially, Rubenstein was worried that walking a tightrope between her day-to-day role and her side hustle would prove to be too difficult to balance. Lucky for her, she works with passion enthusiasts. Toasters are empowered to partner with their managers to incorporate outside interests into their schedules, without compromising their professional success at Toast.
“Doing these creative projects has been nothing but welcomed and supported within the Toast community,” Rubenstein said. “When I do something exciting outside of work, leadership wants to hear about it. Toast took a chance on me, and now I’ve been here for two years.”
Now, Rubenstein can see her murals all over her favorite Boston joints, physical reminders that Toast supports employees taking time for pursuits out of work. Through benefits like unlimited PTO, wellness stipends, and mental health support, cups are never half-empty at Toast — they runneth over.
Creating Community Through Food
“One of my favorite projects at Toast so far has been a community cookbook where everyone submitted a favorite family recipe,” said Alex Campanella, senior strategic growth manager. Toast then published a real cookbook for each employee to take home. “I keep it on my shelf to this day with all my other cookbooks,” Campanella said. “It’s cool to see our team’s diversity and the different types of food from different backgrounds and origins.”
Alex Campanella’s passion requires a trek across international borders — and zooming down mountains.
“My fiance’s brother and I run ski trips, so once a year, we take a weeklong trip to Banff, Canada, and bring a bunch of people with us,” he said. “Having the ability to take that time off is essential to feeling like my best self.”
Campanella is also getting married this year, and his honeymoon will take place in New Zealand. Campanella never doubted that his time off would be not only approved, but also encouraged by his manager.
“Having flexibility and support from my leadership team to go live these important moments of my life is such a massive asset,” he said.
Having the flexibility and support from my leadership team to go live these important moments of my life is such a massive asset.”
Toasters are also encouraged to get out and give back in their own neighborhoods. An example of this is the Local Committee Chair program through Toast.org. Toast.org is the company’s philanthropic branch, and it enlists employees to organize volunteer events in their communities. This not only creates an opportunity for remote and hybrid Toasters to meet one another, but it also gives employees the chance to give back to causes that mean the most to them.
Rahul Jain, a principal talent acquisition partner based out of Toast’s Bangalore office, is a Local Committee Chair. “I feel so much more connected with Toast and my local community, and that’s where I achieve a sense of fulfillment,” Jain said.
Just as Toast invests in its employees, employees like Jain, Rubenstein and Campanella invest in the Toast community. Through Toast employee resource groups, Toast.org and the Internal Doughbility program, employees are able to give back and customize their experience — just like the customers who rely on their platform.
“The beautiful thing about Toast is that once you’re through the door, you can choose how you want to shape your career,” Rubenstein said. “Toast makes sure that you can go where your energy flows.”
Community engagement, encouraged
In two years, Chloe Rubenstein has established herself as a Swiss army knife at Toast.
Beyond her roles of growth account executive and painter, she is also one of the presidents of Multigrain — Toast’s LGBTQIA+ employee resource group — and a member of the Council of Advocates For Equity, or The CAFE, for short.
“I think one of the most amazing things about working at a company like Toast is that my team knows only doing my regular sales job is not going to keep me driven,” Rubenstein said. “I need community engagement.”
As part of her mission to make a difference, Rubenstein has utilized resources like a learning and development stipend to attend Out & Equal, a four-day conference dedicated to inclusion and equity, in Las Vegas. She thought it might be a big ask, so she prepared a speech highlighting how she wanted to learn about creating safe spaces, but her manager approved her attendance immediately.
“That information has been invaluable,” Rubenstein said. “Putting our groups at the forefront of what people think of when they picture Toast drives me to be as active and engaged as possible within each of the communities we serve.”
The CAFE
Launched in 2022, The CAFE brings together employees from across the business to champion our Diversity, Equity, and Inclusion strategy and leverage their combined perspectives and partnerships to enrich the Toast experience for all. “It’s great that we have a DEI leadership team, but we can’t be inclusive if we’re not hearing from the people we’re sending the elevator back down to,” Rubenstein said.
Other victories for Multigrain? Hosting in-person meetups, launching a companywide lunchtime drag bingo over the holidays, and bringing Toasters around the globe together through monthly virtual happy hours.
Giving back, globally
Just as restaurants rely on Toast’s software to improve operations and guests’ experiences, Toast relies on the communities it serves. That’s why the team makes a point to give back through Toast.org.
“At Toast.org, the mission is to solve food issues and help communities across the globe,” said Jain.
Toasters have many opportunities throughout the year to give back to causes that mean the most to them. The Toast.org team hosts two major volunteer events a year: “A Toast to the Earth,” dedicated to caring for the environment, and “Season of Giving,” focused on fighting food insecurity. Additionally, for every hour Toasters log in our volunteer platform, they’re gifted a monetary donation to direct towards an organization of their choice.
I feel so much more connected with Toast and my local community, and that’s where I achieve a sense of fulfillment.”
“For me personally, when Toast decided to help a few underprivileged local government schools and children during Diwali, it was a huge accomplishment,” Jain said. “I remember getting involved to donate study desks to five classrooms in a government school where children would previously sit on the floor to study. We also sponsored lunch to more than 1,000 children during the eve of Diwali, and held a volunteering session at our Bangalore office where Toasters joined hands to fill 200 backpacks and lunch bags for children in the local public school.”
Making a difference isn’t something that Toast decides to do when convenient — it’s an integral part of the company’s culture.
Like dough, careers rise
Alex Campanella’s career at Toast began in 2019 after accepting a role as territory account executive. He’s now held three roles since — and none of them have been in sales.
“Even when I had just joined the team with a brand new manager, the first part of the conversation we had was around discussing where I wanted to go and what my career trajectory looked like from my perspective,” he said. “That’s all thanks to our Internal Doughbility program.”
While a fun play on words, to employees like Campanella, having an established internal program dedicated to career mobility is also so much more than that. It’s a testament that company leaders are invested in their employees as people, with fluctuating ambitions and a desire to continuously sharpen skill sets.
“I’ve always been encouraged to ask myself, ‘What am I interested in?’” he said. “I’ve been able to rely on my managers to put me in situations that give me experience for the roles I want to pursue.”
I’ve always been encouraged to ask myself, ‘What am I interested in?’”
Managers at Toast are not only willing to be advocates for their direct reports, but they have even been known to engage in role-playing exercises to help them nail the interview for their next opportunity.
“It creates a real sense of trust and authenticity that Toast doesn’t just want what’s right for the company, but for each individual contributor,” Campanella said.
