Davis Square resident and entrepreneur Ben Orenstein is the second newcomer to announce a bid for the Somerville City Council this year. Orenstein, who launched his campaign website last week, will seek a position as councilor at large.
Wilbert Pineda, an undergraduate student at the University of Massachusetts at Boston, announced a bid for councilor at large in January. Orenstein and Pineda each have openings, as two of the council’s four at-large seats will lack incumbents: Councilors Willie Burnley Jr. and Jake Wilson have announced that they will run for mayor of Somerville instead of reelection to the council.
Orenstein moved to Somerville in 2005 after completing his undergraduate degree at the University of Massachusetts at Amherst. From 2011 to 2017, he worked as a software developer and managing director at the consulting firm Thoughtbot. He’s also launched several of his own ventures, including email-prompted journaling service Trailmix and Refactoring Rails, an online course about the Rails Web development framework.
In 2018, Orenstein cofounded Tuple, a pair programming application that allows programmers to collaborate remotely. He transitioned out of his position as chief executive in 2023 and into roles as board member and head of product, according to his LinkedIn.
He is the second self-identified entrepreneur to launch a political campaign this year. A startup founder named Jason Mackey announced for mayor in February.
This year, Orenstein launched the Somerville Beacon, a Substack publication about local politics. “I started the Somerville Beacon because I felt compelled to start going to the City Council meetings,” Orenstein said. “I realized that a lot of people didn’t know what was happening in the meetings.”
Orenstein says that building housing, increasing safety for pedestrians and bikers in Davis Square and attracting new residents to Somerville are central to his campaign.
“Housing is a citywide issue,” he said on his bid for councilor at large instead of representing his Ward 5 – an area represented since 2023 by Naima Sait.
“In 2019, Somerville legally declared a housing emergency,” Orenstein said, referring to the council’s revision of what is now the Condominium/Cooperative Conversion Ordinance. “Rents and purchase prices have only increased since then. If we were in an emergency then, we’re definitely still in the emergency now, but I don’t see people acting like it’s an emergency.”
Orenstein’s approach to housing requires “aggressive upzoning, streamlined permitting and building thousands of new homes fast,” his campaign website says. Somerville has space to build upward, particularly in Davis Square and near MBTA green line stations, he told Cambridge Day.
For Orenstein, zoning for increased development, safety and attracting new residents are connected. The upzoning would leverage Somerville’s transit network to create housing opportunities for old and new residents, and attracting new residents would benefit businesses and increase the city’s capacity to provide services by increasing tax revenue.
He wants to bring the same sense of urgency to pedestrian and bike safety efforts. “I would love to see us link the community path through Davis Square so you can stay on your bike and bike straight through there without interacting with a car or too many pedestrians,” he said.
Orenstein will hold a campaign kickoff event May 13 at the George Dilboy Veterans of Foreign War Post 529 in Davis Square. As his campaign continues, he says that he plans to continue to engage Somervillians by hosting beautification events throughout the city.
This post was updated April 23, 2025, to correct that Ben Orenstein is from Ward 5.
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