above: First Selectwoman Jen Tooker, at Town Hall in downtown Westport, has a lot to smile about these days.
Photographs by Katharine Calderwood
Looking for some hope in American politics? You’ve come to the right interview. Westport Selectwoman Jen Tooker shares her thoughts on public service, what leading this town has taught her, and what she envisions for the state of Connecticut.
Let’s launch right in with the big news: You’re running for state governor! When and why did you decide to run?
I have been thinking about it for a while. Part of the decision making was certainly talking with my family. This line of work is absolutely a family business. I have a 24-year-old son, a 21-year-old daughter and a 16-year-old daughter. They needed to be all in. I’m blessed to have been in local elected office for almost fourteen years now. The kids know what campaigning looks like; they know what having a mother in an elected office looks and feels like. But certainly this is on a much greater scale and greater stage. This is my second career. My first career was in financial services and I was pulled into public service. It’s a calling to serve my community, and now I want to make a positive difference on the state level. Connecticut is in an affordability crisis. We have one of the highest tax burdens in the nation and the highest utility costs in the continental U.S., and these things need to change. Connecticut needs to become a place where people can come live, work and afford to retire. A piece of that puzzle is becoming a business-friendly state. You and I have talked about my longtime support for the business community here in Westport. A critical component of making sure that Connecticut’s long-term economy is stable and thriving and growing is to ensure that we are a place where people can start and grow a business.
Did the larger political climate play a role in your decision?
Yes. Connecticut is going to need a governor who has open communication with Washington. Every morning I might be waking up to something I agree with and something I don’t agree with. But it’s going to be incredibly important for the governor of the state of Connecticut to ensure that when there are policies that will be good for the people, we’re able to implement those here.
“Since I first met Jen ten years ago while contemplating a run for office, she has been a constant mentor. Her straightforwardness and honesty have provided invaluable guidance and insight. Over the years, I’ve witnessed her quietly and selflessly support countless women—and men—in their professional and personal endeavors. Jen is always willing to meet with anyone who reaches out, offering her advice and support without seeking recognition or praise. She helps simply because she genuinely cares about empowering women and strengthening the community.”
Andrea Moore
Second Selectwoman
“Since Jen Tooker took the reins as our First Selectwoman in Westport, she has supported and furthered local commerce with her forward-thinking and personal perspective on the importance of women in business.”
Jamie Camche
Founder, JL Rocks
How has your training helped you to reach across the aisle as a Republican in a Democratic town and get things done?
Every board and commission in Westport is Democrat-controlled. As I talk to people—and I talk to lots and lots of people, whether they be residents or business owners—most people are ready for somebody who’s going to focus on what unites us, not what divides us. They want a leader who’s going to bring people together, create consensus, and focus on issues that we can agree on. With twenty-five years in financial services, I certainly know and understand how to get a deal done and how to compromise. We should celebrate leaders who know how to do that instead of making them out to be villains.
You’ve been involved in organizations that may be considered more Democratic-leaning, like Sustainable Westport and Earthplace. Where do you fall on issues like climate and conservation?
Being the leader of a coastal town where storms have gotten more frequent and more severe, it is clear to me that we need to focus on sustainability, and certainly focus on ensuring our infrastructure is resilient. We’ve been working on a number of things with regard to stream management and flood mitigation. Every time we propose an upgrade to infrastructure, it includes a sustainability component. That’s been a focus of this community, and it will continue to be a focus on a larger stage. We run emergency management mock operations on a regular basis because of the increase of severe weather that we’re experiencing as a state, so, you know, we acknowledge it.
Jen refers to Operations Director Tom Kiely as her “right hand man“.
As we are both moms, it’s hard not to focus on the state of the planet. What are your kids up to these days?
Jack is 24. He’s living and working in the city, so he’s largely off the payroll. He’s happy, and we’re lucky to have him back on this coast after college in California. Riley’s my middle, and she is a junior at SMU in Dallas and is very much enjoying her life there. Nicole, my youngest, is 16. She’s a junior at Hopkins in New Haven.
Did all of your kids go to Hopkins?
No, Jack went all the way through Staples. Riley did her freshman year at Staples and decided she wanted a smaller environment, and so she graduated from Hopkins.
How do your kids view you as a leader?
Wow. You’ll have to ask them! What I can tell you is they’re fiercely proud of me. I think they view me as a good listener and somebody who likes to solve problems. They view me as empathetic. They see that I care deeply. I care about people, and I care deeply about this community and state. They know I’m not afraid to make tough decisions, to get in the mix.
What does your husband Mo do?
He works for the Hartford. As of January, he’s the newly appointed president.
Congrats to him as well! Are either of you originally from Connecticut?
Yes, he grew up in Simsbury. His family has been here for many generations. I was born in Chicago, but I grew up in Dallas.
“Jen Tooker has been much more than a friend; she has been a tireless advocate and ally, not only to me but to entrepreneurs throughout Westport. Under her leadership, downtown Westport has flourished, and in the aftermath of COVID-19, local restaurants have rebounded more successfully than in many neighboring areas. This success is a direct reflection of Jen’s ability to listen, collaborate and take thoughtful, decisive action.”
“Now more than ever, Connecticut needs strong, innovative leadership. We need someone who understands the challenges facing small businesses, families and communities across the state—someone who can make tough decisions while remaining accountable to the people. Jen Tooker exemplifies that kind of leadership. I can think of no one more capable of guiding our state than Jen Tooker.”
Bill Taibe
Owner, Kawa Ni,
Colorado and Connecticut,
Norwalk Art Space Cafe
Have you gained insight from the in-laws on how things used to be in Connecticut?
They talk a lot about the Connecticut of before, when there was no income tax, and it was affordable and quality of life was super high. That’s what I hope to bring back.
I feel like your approach is characterized by warmth and kindness. Do you agree with that, and how do you think we can spread that?
That’s really the question of, gosh, the greater part of the last decade. I would agree with the characterization, and that’s because I genuinely really like people. I believe in the goodness of people. I also believe that the tone is set at the top. When you’re in a leadership position, how you treat people, how you work with people, how you listen to people—it matters. So another reason why I continue to pursue a path in this line of work: Our kids are watching.
Are there local or state leaders who have inspired you?
I’ll tell you who really I’ll credit: my father. He passed a little over three years ago. He was able to see me elected into this job. He lived with us for the last 18 months of his life. He was a man who also loved people and believed in the goodness of humankind. He was a diehard extrovert, like me. Any spare moment he had, he volunteered. He was coaching my soccer team or sitting on the school board or driving a carpool. A lot of people say this line of work is politics. Actually, this line of work is public service. The more we can remind people of that—people who are trying to get into this line of work as well as community members—the better. My job is to serve. I learned that from my dad. He wasn’t an elected leader, but he served his community in any way he could for decades.
I understand public service but I don’t necessarily understand politics.
Right? I have 28,000 bosses in this job. I mean, there’s the campaign and the stump speeches, and debates and promises you make, and all that. But then you wake up the next morning and you’ve won, and then it’s governing, and governing is public service. That’s what we’re here to do. There are many ways to do that. I’ve chosen the elected official way, but my dad chose a different way, as many people do.
I know you’ve mentioned Jim Marpe as a mentor. Has he been an inspiration?
One hundred percent. He continues to be a mentor to me.
What have you learned from him?
You don’t have to spend much time with Jim to realize that he cares deeply. I believe that’s an important piece of choosing to do this line of work—you need to care about the people you’re serving and the community you’re leading. Jim still has a great way of building coalitions around issues, around people, around ideas. He’s very thoughtful, very deliberate, and he cares. As a result, he can build coalitions in a masterful way.
Do you think caring so much can make the job harder? Does it take a tough skin?
For me, caring is a motivator to keep going. Certainly you need a thick skin in this line of work, but I don’t think it means that I will care less. Because when you care, you have empathy, gratitude, respect, compassion—critical attributes of a leader.
There’s such economic disparity in the state. How will you tackle that?
We need to reduce the cost of living, and what I mean by that is we absolutely need to reduce the tax burden. We need to have opportunity for people to work and earn a good living in our state. We need this business-friendly component and the component of reducing cost of state government, which would then alleviate the high tax burden. Then we need to focus on reinvigorating our cities. I have a plan to attract tech and innovation, cybersecurity and AI companies to our cities, like we’ve done with Startup Westport here. That model is not exactly replicable and scalable, but components of it are.
“Jen’s unwavering commitment to a solution-oriented approach, combined with her passionate belief in making a difference, truly sets her apart. She listens, she helps, and she has the energy to make it happen.”
Lori Cochran-Dougall
Executive Director,
Westport Farmers’ Market
“I’ve had the privilege of getting to know Jen Tooker over the past few years since she became First Selectwoman. Jen has been a steadfast and passionate advocate for women-owned and locally owned businesses in Westport. I look forward to learning more about her vision to improve the lives of Connecticut residents if she is elected governor.”
Kitt Shapiro
Owner, WEST
What have you learned from leading Westport?
We are a very blue town, and being a Republican chief elected official has taught me a lot about, like I said, working across the aisle, making sure that we focus on initiatives where we can gain consensus. Also, being the leader in such a severe minority party, I get challenged a lot on my views and positions. I’m a lot smarter for it. There’s that old adage that single-party rule is not great. You start to surround yourself only with people who think like you. Every organization—and there’s data to prove it—is better with diversity of thought around the table.
When you are facing pushback, how do you remain calm and composed?
If I’m getting a lot of pushback, I try to understand what’s driving it. If you get to the core of why people are pushing back, that’s three-quarters of the story. Many times your path forward becomes clear once you understand the opposing view. So how do I stay calm, cool and collected? I love that challenge. I think that’s kind of really life, right? In the face of adversity, you take a moment, you pause, you reflect and think, where’s the path out? I do stay calm and cool, as long as things don’t get personal. That’s where it does go wrong in this line of work. Nothing good comes from that. We’re seeing more and more of it, even at the local level.
What accomplishment from your time as selectwoman are you most proud of?
Two things. I’m really proud that we’re finally going to put a shovel in the ground on a brand new Long Lots Elementary School. It’s due to the hard work of many people, including a 100% volunteer building committee; to live in a town where that can happen—we are so lucky. The other is more of an operational answer. We deliver incredible value for the taxpayer dollar. Westport has one of the lowest mill rates in Fairfield County. The assets we maintain with those dollars—Compo Beach, Longshore, the Library. I mean, my gosh, we deliver real value for money.
What do you hope to accomplish in the remainder of your term?
We’re midstream on a lot of projects—downtown upgrades, the Longshore Park improvement plan. I also hope to put in place a path to convert some of our town-owned buildings to affordable housing.
You have a longstanding tradition of power walking and talking with Second Selectwoman Andrea Moore to Compo Beach on weekends. Will that continue?
Yep! She’s just a wonderful human. I am so lucky to call her a friend and a colleague, and, honestly, if I could do all of my meetings on the run, I would!
Other Westport traditions?
I love Compo Beach in all seasons. When I round that corner on Compo Road South and see Ned Dimes Marina there and Compo Beach in the distance, everything comes down a notch for me. Everything. I also love to paddleboard on the Saugatuck River and Mill Pond.
Anything to add?
Westport’s in great shape. This place is rockin’. Just imagine if we can take a few components of such a successful municipality here and transfer it to the state level. Just imagine the impact that would have.
Portraits: Andrea Moore by Andrea Carson; Jamie Camche by Kyle Norton; Bill Taibe by Garvin Burke; Lori Cochran-Dougall by Eileen Clark Sawyerw; Kitt Shapiro by Jerri Graham