scorecardresearch Skip to main content

Craig Powell looks to build his third successful software firm in Boston

The Wyc and Robin Show at BC CEOs Club; Campbell visits the Chamber; Another big role for Glynn

Craig Powell, chief executive of AutoReturn.Chris Morris

Craig Powell is hoping that his “dogsled style” of leadership, as he calls it, can help him build his third successful software firm in Boston.

He says he tries to provide his teams with the resources they need along with autonomy to make their own choices, while ensuring they’re pulling in the same direction as quickly as possible. Powell’s latest Iditarod? Running AutoReturn, a software firm that he just moved from San Francisco to a new headquarters on Summer Street in Boston.

Powell started his tech career at the age of 22, not long after he graduated from Brown University, by launching ConnectEDU in 2002. Then, in 2013, Powell left ConnectEDU and subsequently joined a company that became Motus, which calculates corporate reimbursement levels for costs such as car mileage and working from home. That software firm grew from $7 million in annual revenue under his leadership to more than $200 million by the time he left the chief executive’s job in early 2022, seeking another new challenge.

That challenge turned out to be AutoReturn, where he became chief executive a year ago. Its primary software helps cities manage their towing calls. Of its 75-plus municipal clients, none are in Massachusetts yet, but Powell hopes to change that. In November, the company acquired Joyride, an e-commerce marketplace for impounded vehicles. Next up: releasing software to manage street parking. Because of all the changes, the company is in the midst of a rebranding, with a new name expected next month.


Private equity firm Nexa Equity, AutoReturn’s owner, recruited Powell to lead the firm. There was no question in Powell’s mind that AutoReturn would be based in Boston instead of San Francisco, where it began nearly 20 years ago but was operating without a physical office starting early in the pandemic. The tax situation in Massachusetts isn’t great, Powell said, but the taxes are higher in California. More importantly, Powell has a big local network after two decades in Boston’s tech scene. He’s already brought several former colleagues on board, including former Motus coworker Rick Blaisdell, now AutoReturn’s chief technology officer.


“It’s a great tech market,” Powell said of Greater Boston. “You’ve got great schools. You’ve got a great talent pool. [And] I know the Boston tech scene very well. In terms of sourcing talent, it’s easier to do it on home turf.”

Powell hopes to double his workforce over the next year. Today, about 60 people work for AutoReturn, most of them added during the past year in the Boston area. From Powell’s perspective, it’s time to get out of the way and let them run.

Robin Hayes, chief executive officer and president of JetBlue Airways Corp., smiles during a discussion at the U.S. Chamber of Commerce aviation summit in Washington, D.C. on March 2, 2017. Boston Celtics managing partner Wyc Grousbeck gave JetBlue Airways chief executive Robin Hayes a friendly grilling during a Q and A session at the Boston Harbor Hotel hosted last week by the Boston College Chief Executives Club. Andrew Harrer/Bloomberg

Laughing matters with JetBlue chief

Maybe they should have called it the Wyc and Robin show.

Boston Celtics managing partner Wyc Grousbeck gave JetBlue Airways chief executive Robin Hayes a friendly grilling during a Q. and A. session at the Boston Harbor Hotel hosted last week by the Boston College Chief Executives Club. For Hayes, the quips kept coming.

There were serious responses, too. Hayes, a UK native, stood behind his decision to fight the US government in court over JetBlue’s plans to acquire Spirit Airlines, saying the four biggest carriers still hold too much power and adding Spirit would make JetBlue a stronger competitor. He talked about how the industry is moving toward more environmentally sustainable fuel options, such as hydrogen (probably 15 to 20 years away, still) and electric batteries (probably best for smaller planes, such as the ones used by Cape Air). He said JetBlue has made great strides in building up its workforce after industry-wide labor shortages during the past two years.


But the comedy began almost from the start, when he took a jab at New York, JetBlue’s home city, by thanking the attendees for sticking around after lunch was over.

“If this was a New York luncheon, I think half the people would have left already,” Hayes said.

And then came another poke at NYC, after explaining how he came to root for Boston sports teams after living in this city in the late 1980s. JetBlue now has partnerships with the Celtics, Red Sox, and Bruins. “The good thing in Boston is everyone supports the same team, right? ... Not the same in New York,” Hayes said, referring to the multiple sports teams there. “They fight over football. They fight over baseball. They fight over basketball.”

Grousbeck asked what it’s like working with the Massachusetts Port Authority, which runs Logan Airport — where JetBlue has the largest market share.

“We’ve got Ed, Lisa, and other members of their team here,” Hayes said, referring to Massport chief executive Lisa Wieland and aviation director Ed Freni. “I have to be nice to them anyway because they’re the landlord. But actually they’ve earned it. ”

Hayes offered his services to Grousbeck on the court that night; the C’s were playing the 76ers. “Thank you for that,” Grousbeck deadpanned.


And Grousbeck asked Hayes what he planned to do in the next stage of his life, after running JetBlue for the past 15 years. “Let’s say you go another 15 or 20 years,” Grousbeck said.

“Fifteen days,” Hayes corrected Grousbeck, “if I’m lucky.”

Attorney General Andrea Campbell poses for a portrait in the John W. McCormack Building in Boston on Feb. 16, 2023.Erin Clark/Globe Staff

Chamber meets the new AG

New Massachusetts Attorney General Andrea Campbell was familiar to many people in the room when she spoke to the Greater Boston Chamber of Commerce last week at the Fairmont Copley Plaza hotel. Campbell was a Boston city councilor, after all, and a candidate for mayor.

But this was the first time that Campbell was speaking to the chamber as AG, and she had a lot to share. She offered some autobiographical details, including how she became motivated to pursue a career in public service in part because of the death of her twin brother Andre while in the custody of the Department of Correction at age 29.

Campbell then rattled off a lengthy to-do list: work to prevent gambling addiction amid the rise of legal sports betting, promote more investments in the state’s vocational schools and community colleges, form an elder justice unit within her office to crack down on scams, and enforce the state Housing Choice law’s mandate to approve multifamily zones across the MBTA’s service area. Campbell is also continuing a crusade against competitive electric suppliers that she says drive up costs for unsuspecting consumers — a crusade that began under her predecessor, Maura Healey.


And Campbell reminded the business community that the door to her office will always be open.

“We view the perspective of this community significantly as we are promulgating regulations and thinking about how we approach new industries,” Campbell said. “We want to make sure you’re at the table.”

Passengers exit a Blue Line train at the Government Center stop on March 24, 2023. At a recent event, Greater Boston Chamber chief executive Jim Rooney gave a shoutout to Tom Glynn for taking on the challenge of being the new chair of the MBTA board of directors at a time when the T is in crisis mode. David L. Ryan/Globe Staff

Thanks, Tom, for a seemingly-thankless task

While introducing Campbell at the chamber event, Greater Boston Chamber chief executive Jim Rooney gave a shoutout to Tom Glynn for taking on the challenge of being the new chair of the MBTA board of directors at a time when the T is in crisis mode. Governor Maura Healey named Glynn to the board last month, as well as two other new directors: former Lynn mayor Tom McGee and Rockland Trust vice president Eric Goodwine.

Rooney once worked under Glynn at the transit agency, roughly three decades ago, when Glynn was the T’s general manager, and he has made transportation one of his top issues while leading the chamber. Glynn, meanwhile, has been teaching classes at the Harvard Kennedy School — a much quieter pursuit than chairing the T board.

“You just like running into burning buildings, don’t you?” Rooney told Glynn from the stage, probably speaking what was on the minds of many people in the room.

Another thought that might have been on their minds: just as long as it isn’t an Orange Line car.

Jon Chesto can be reached at Follow him @jonchesto.