BRATTLEBORO—When Kate O’Connor steps away from her role as executive director of the Brattleboro Area Chamber of Commerce on Dec. 31, it will mark the first time since 1969 that a member of her family will not be involved in public service in this area.
“I have been here for seven years, and I think for a person to grow and for a business to grow, you need new blood,” said O’Connor. “Sometimes if you’re the same person being there for a long period of time, it doesn’t do the person any good, and it doesn’t help the organization.”
Greg Lesch, membership and operations director, will step in as interim executive director after O’Connor leaves, with a permanent executive director expected to be appointed in June.
O’Connor has held her position with the Chamber for the past seven years. During part of that period, she also served on the Selectboard for three terms, stepping down as chair in 2018.
During that time, she saw many significant issues and developments.
The town undertook a massive new public safety building program and faced issues related to homelessness and poverty, climate change, and racial equity in town employment practices, notably how to diversify a town staff that was entirely white.
O’Connor described the challenge of Selectboard meetings that usually had just a handful of participants, yet would sometimes be flooded during complex conversations on difficult issues.
“When we had the issue with panhandling, those meetings were packed, and I remember saying this, because I was chair, that no one’s right, but no one’s wrong, you know what I mean?” O’Connor said.
“We have the charter of compassion, so it was really the question of, ‘Here’s what we want our town to be, we want ourselves to be compassionate,’” she said.
Before the pandemic, the question of how Brattleboro and Windham County could expand the region’s tourism base and support local businesses often emerged at Selectboard meetings, and the board approved a marketing grant to the Downtown Brattleboro Association (DBA) to work with the Chamber to develop a new campaign.
That work started in the fall of 2019, but the whole question of tourism marketing became complex when the pandemic forced a wide array of changes on travel and businesses.
‘How can we make things better?’
Earlier in her career, O’Connor served as an aide to former Vermont Gov. Madeline Kunin. She was a long-time aide to former Gov. Howard Dean, continuing to serve him in his 2004 campaign for the Democratic Party presidential nomination, an experience she later chronicled in a book.
O’Connor said that she never saw public service as being about herself, but about the team effort that is always involved in politics.
“I look at what I have been involved in with other people,” she said. “I sort of look at everything I’ve always tried to do in my time was to help the community, because, you know, I did grow up here.”
“When I was on the Selectboard, I always tried to look out for the taxpayer, because we need a place that’s affordable, where people get the services they need. It’s a wonderful community [and] I have always approached things in the bigger sense of ‘How can we make things better?’”
Often seen as a mediator in her roles on the Selectboard and with the Chamber, O’Connor emphasized the nonpartisan nature of town politics and the absence of party affiliations in town governance as positive forces.
Her father, Timothy J. O’Connor Jr., started in Vermont politics as a Democratic House representative in 1969, serving as speaker of the House from 1975 until he left the Legislature in 1981.
He was the town moderator for 24 years, retiring in 2012. He died in 2018 at the age of 81.
O’Connor’s mother, Martha O’Connor, spent four decades in public service, serving on a wide range of local and state boards, often as chairwoman, including the Brattleboro Selectboard and Brattleboro Union High School board, the Vermont State Board of Education, the Vermont School Boards Association, the Vermont State Colleges Board of Trustees, and the Vermont Lottery Commission. She died unexpectedly in 2019.
“I learned [my approach to leadership] from my parents, to be really honest, because they both taught us that you need to be involved and they sort of showed us how to do it,” O’Connor said. “My brother, sister, and I all learned that it’s not really about you, it’s about serving your community.”
“I really do credit our parents for bringing us along the way that they did,” she said.
O’Connor and her siblings suffered two quick losses with the death of their father in 2018 and their mother’s death the following year. She has moved to the family home to clean house.
“All of their stuff is there. It is a 17-room house, and my father was a packrat,” said O’Connor. “They lived there for 54 years, so my stuff is layered on top of all of that, and my immediate plan is to deal with that.”
“My mother was like, ‘We’re not saving stuff,’ and my father saved stuff. He was like a squirrel, because he didn’t want my mom to know he was saving stuff,” O’Connor said. “She would tell us, ‘Get that box out of here’ and he would, but in 17 rooms you have a lot of places to hide [things] — open a drawer, open a closet — my god.”
“My immediate plan is to deal with all of that,” she said.
She is taking time to think about what will come next.
“When I was up in the governor’s office, and here at the Chamber or on the Selectboard, I got to interact with a lot of people,” O’Connor said. “That gives you the opportunity to make a difference, even if it’s just a small little thing that you’re able to do.”
“I would love to be able to continue to do something that allows me to be involved in the community, because that’s what I really like.”