BUSINESS

Business leaders shadow principals at Boston Public Schools

Mary Skipper now owes Jim Rooney a dinner. The two civic leaders — Boston’s schools superintendent and the CEO

Mary Skipper now owes Jim Rooney a dinner.

The two civic leaders — Boston’s schools superintendent and the CEO of the Greater Boston Chamber of Commerce — made a lighthearted bet in advance of the Principal Partners event on Thursday that brought business leaders together to shadow various Boston Public Schools superintendents. Rooney told Skipper: You line up the school principals to participate, and I’ll find the businesspeople. Skipper said she thought she would end up with more principals than chamber members. Rooney bet her a dinner that he would win.

Time to pay up? The final count, per a chamber spokesperson: 93 business leaders were matched with 87 principals across 86 schools. (One of the schools has two principals.) Rooney wound up at his alma mater, Boston Latin School, shadowing BLS principal Jason Gallagher, along with Babson College executive vice president Katherine Craven, another BLS alum.

Jim Rooney, president and CEO of the Greater Boston Chamber of Commerce passes the alma mater statue while touring Boston Latin School, his alma mater.Craig F. Walker/Globe Staff

From left to right: Jason Gallagher, head of school at Boston Latin School, Jim Rooney, president and CEO of the Greater Boston Chamber of Commerce, and Katherine Craven, chief administrative and financial officer at Babson College, talk in the auditorium at Boston Latin School. Rooney and Craven were shadowing Gallagher as part of the Principal Partners program; all three are Boston Latin alum.Craig F. Walker/Globe Staff

Ever since Rooney started in his role as chamber chief executive a decade ago, he’s been trying to better integrate the business community and Boston Public Schools. Some companies, such as Natixis and Vertex Pharmaceuticals, already had specific school partnerships established. But Rooney found it hard to make much traction for a broader chamber effort with previous school superintendents.

Then came Skipper, a well regarded Somerville school administrator who was tapped by Mayor Michelle Wu in 2022 to lead BPS. Skipper and Rooney already knew each other; they actually live on the same street in Dorchester. So they hit it off quite easily. Among the fruits of those discussions: an agreement to help develop a financial literacy curriculum, to be rolled out this fall, and the Principal Partners shadowing event, reviving a concept similar to the “Principal for a Day” program last tried in 2018.

Boston Public Schools superintendent Mary Skipper, right, talks with seventh-grader Iker Monrroy, during his earth/space science class at Boston Latin School.Craig F. Walker/Globe Staff

On Thursday, the business leaders shadowed principals throughout the morning, then came together at Bank of America’s offices on Federal Street to debrief. Rooney, Skipper, and Wu all spoke, as did B of A executive Miceal Chamberlain.

Rooney said the shadowing program will build a stronger connection between the business community and the city’s schools. That in turn can help teachers keep pace with the city’s ever-changing workforce needs, Rooney said, and send a good message to the kids when “big branded Boston companies” are volunteering on their behalf. Plus, some of his members can provide expertise in developing the school system’s new financial literacy program.

“Historically, the school department has been hard to help,” Rooney said. “In the past, they defined ‘partnership’ as ‘write me a check.’ [Businesses] will do that as a matter of goodwill. But I wanted to do something deeper than that.”