5 Great Startups to Work for in Boston

By BrainStation June 10, 2019

As we’ve discussed, Boston has quickly become one of the country’s hottest tech hubs, and the only thing holding Beantown back from maintaining that breakneck growth is a shortage of local tech talent.

So, there is an abundance of jobs in Boston, but which companies should job-seekers target? We rounded up five of the best startups to work for in Boston.


Even in Boston’s overheated tech ecosystem, it’s tough to match the growth rate of the restaurant point of sale and management system Toast. Founded in 2011, the company’s recent announcement that it raised $250 million in new venture capital – bringing its valuation to $2.7 billion, nearly double where it stood just last July – was just the latest piece of good news from a company that now employs about 1,500 people, half of whom work at the company’s Fenway headquarters.

Toast was also featured on the Deloitte 2017 Technology Fast 500 listing, the Forbes 2017 Cloud 100, and the Forbes Fintech 50 for 2019. Employees rave about the company’s positive culture, fast pace, and abundant opportunities for advancement. If you’re interested in one of the dozens of open jobs the company has open in Boston, Toast leadership recommends showing your personality in your interview.

“While we have a set of core values that guide our evaluation process, we strongly encourage candidates to bring their full selves to the interview table,” said Natalie Audelo, Employer Brand Manager. “We want their unique skills, qualities, and passions to shine through. We look for candidates who have a compelling story and come to the table with great energy and no ego.”


Touted as the world’s first and only conversational marketing platform, this Back Bay-based tech company is gaining a reputation for treating its employees right. In fact, Drift was deemed to have the eighth-happiest employees in the United States among small and mid-sized companies in a Comparably poll, while the startup also placed 15th in their ranking of the companies that best-compensate their employees.

With 180 local employees, Drift’s benefits and perks include beer on tap, a well-stocked kitchen, free daily meals and happy hours, and after three years of working for Drift, all employees are eligible for a month-long sabbatical. One employee describes the vibe at the office as “high-energy.”

Investors have been enthusiastic too. Since being founded in 2014, Drift has raised $107 million in funding, including most recently a $60 million round in April 2018 led by Sequoia Capital.


An end-to-end cybersecurity solution built to empower defenders, Cybereason has 110 employees at its headquarters in the hub of Copley Square. Founded in 2012 by Israeli intelligence cybersecurity experts, Cybereason is another company to turn heads nationally for taking care of its workforce. The company placed ninth in the U.S. in Comparably’s roundup of which companies offer the best compensation, 16th in the ranking of which companies have the happiest employees, and 23rd for the best perks and benefits.

And those perks really are extensive, including flexible spending account, wellness programs, company equity, an unlimited vacation policy, paid volunteer time, commuter benefits, beer on tap, a stocked kitchen, happy hours, and fitness subsidies.


If you’re interested in a Boston-based company with an increasingly global presence, look no further than Flywire. The fintech company, which helps universities, hospitals, and businesses process payments in foreign currencies, was named by Forbes to its October 2018 list of the next $1 billion startups after bringing in estimated 2018 revenue of $75 million, a figure CEO Mike Massaro says is growing nearly 50 percent per year.

The company was also featured on the 2019 Forbes Fintech 50, and last year, saw 130 percent and 65 percent growth in payment volumes in Asia-Pac and EMEA respectively, while also growing its client base by 80 percent and 50 percent in the respective regions. Still, 100 of the company’s 350 employees are based in Boston. In July 2018 Flywire raised $100 million in Series D from Temasek, Bain Capital Ventures, and F-Prime Capital, bringing its total funding to $145 million.

So Flywire – which was founded in 2009 – is clearly on an upward trajectory, but what’s it like working there? Extensive perks and benefits offered to employees include generous parental leave, a remote work program, a flexible work schedule, an onsite gym, life insurance, a stocked kitchen, a game room, happy hours, and professional development support.


With more than $320 million in venture funding and a $1-billion-plus valuation, ezCater – billed as the only nationwide marketplace for business catering – is another major Boston success story. More than 400 of the company’s 590 employees are based in Boston, and after a recent $150 million Series D funding round, the company plans to hire another 300 employees in 2019 and is also set to move to a new headquarters on Water Street.

“This is more fuel in the tank to keep the rocket pointed straight up and fast,” Co-Founder and Chief Executive Stefania Mallett said of the recent funding.

The company takes pride in its culture, “sane working hours” and deep flexibility around work/life balance. Other benefits include stock options, as much vacation as you want, 401K, subsidized transit passes, and even cupcakes.

Sound good? A Senior Manager at the company recommends hopeful employees bring a positive, can-do attitude to their interviews.“In addition to their technical expertise, good candidates will demonstrate traits in line with our company values, from being ‘insanely helpful’ to ‘aiming higher’ and ‘owning it,’” said Senior Engineering Manager Phil Morris. “We strive to be a better team and company with every person we hire.”