Hudson executive assistant continues journey from education to municipal government


Hudson executive assistant continues journey from education to municipal government
Photo by/Laura Hayes
Thomas Gregory is Hudson’s new Executive Assistant.

By Laura Hayes, Contributing Writer

HUDSON — Thomas Gregory was several years into his teaching career when he decided to reinvent himself and pursue a career in local government. 

Growing up in Shrewsbury, local government and projects were a frequent topic in Gregory’s home. When he got older, he learned about debt exclusion and taxes.

“There’s always sort of been an interest I’ve had in local government,” recalled Gregory, who is now the new Executive Assistant in Hudson.

Prior to his professional pivot, Gregory was teaching Latin and history and coaching basketball and baseball at St. Sebastian’s School, which is a private boy’s Catholic school in Needham.

When he was a teacher, Gregory worked to be a model for his students — being direct in his expectations while being available to both meet their needs and meet them where they were. 

“Teaching really forces you to be a good listener,” Gregory said.

Listening is also a large component of working in government. 

“You never know what comes through the door,” Gregory said.

Seeking change over a decade ago, Gregory immersed himself in local politics. He got involved in political campaigns in Worcester. There, he took an entry-level job in the city’s Housing and Neighborhood Development department.

That was during the 2008 recession and housing crisis. As such, a lot of his work involved using grant funds to help secure vacant buildings for public use. 

“It was a discouraging time, but at the same time, it was something that really helped encourage me to stay in local government because you can see how the work you do every day had a direct impact on people’s lives,” Gregory said.

Gregory, who had received his bachelor’s degree in classics from the College of the Holy Cross, decided to go back to school and earn his master’s in public administration from Clark University.

When the housing crisis began to subside, Gregory took a job in Shrewsbury as the Assistant to the Town Manager. 

It was his first venture into municipal management. 

He later became the Assistant Town Administrator in Walpole before becoming the Town Administrator in the Town of Spencer for just over three years. 

Then, there was an opening in the Town of Hudson after Executive Assistant Tom Moses announced his plans to retire in May of this year.

“Hudson really appealed to me — a well-managed, stable community, full-service community, a lot going on,” Gregory said. 

Gregory is no stranger to Hudson. Prior to his hiring, he and his family frequented restaurants like Rail Trail Flatbread Co. and would wander around downtown. 

By mid-March, Gregory was one of three finalists before being offered the job that month. His first day was June 7, which also marked his first Select Board meeting.

Since then, Gregory has been busy meeting with the town department heads.

“[One] aspect that appeals to me is this team effort,” he said. “The success of the town is shared among all of those employees who are contributing in some way.” 

Gregory has also been working on getting up to speed on town projects, like the downtown rotary project, downtown revitalization and the Downtown Business Improvement District, and the Hudson Cultural Alliance’s purchase of the Armory.

Gregory has recently had a chance to see the renovations at Centennial Beach and walk through the Hudson Farmers’ Market. 

“All that energy, all that excitement, you can tell people here are really invested,” he said. “They’re invested in the businesses. They’re invested in the community. That’s exciting to be part of.”