Prioritizing practical solutions over politics and bringing people together to solve tough problems are the hallmarks of First Selectwoman Jen Tooker’s leadership. In government, and as a successful business executive with almost 25 years of management experience in the international property/casualty reinsurance industry, Jen has employed these skills over and over to get challenging things done.

 For the last decade, as First Selectwoman and Second Selectwoman prior to that, Jen has been instrumental in Westport’s rise as one of the most desirable and well-run municipalities in the nation. Jen has been responsible for significant upgrades to the Town’s infrastructure and amenities, building an ever more vibrant business community, increasing access and quality of town services for residents, advancing Westport’s public safety, and ensuring that Westport continues to be the best place to live, work, play, and learn in the region – a place where everyone is welcome and feels like they belong.

Over the years, Jen has also served on Westport’s Board of Finance, Conservation Commission, and Board of Education, gaining on-the-ground know-how in all key aspects of local government. As Second Selectwoman, Jennifer worked on a number of important initiatives to promote the positive development of our children such as Westport Together, which focuses on the social and emotional health and well-being of our community. This alliance between the Town and Westport Public Schools revitalized and rebranded its longstanding partnership to engage more of our community partners, strengthen programming and enhance coordination among other non-profit community agencies.

Drawing on her business experience, Jen has created an environment where entrepreneurs can successfully launch and grow their businesses. Most recently, Jen worked with Westport residents to launch StartUp Westport. Westport is home to many tech founders and funders so the goal was to grow the local ecosystem of entrepreneurship and innovation in technology and related fields. This public/private partnership hosts events that deliver content and opportunities to network, as well as a Mentorship Program and Special Interest Groups (SIGs). The response has been overwhelmingly positive, and Westport is well on its way to becoming the startup tech and innovation hub of CT.

Back in 2018, when the local economy was struggling, Jen launched Westport Means Business - a series of events that bring local business owners and entrepreneurs together to establish connections, exchange ideas and promote Westport as the best place to start and grow a successful business. In response to the COVID-19 crisis, then First Selectman Jim Marpe appointed Jen as Chair of the ReOpen Westport Advisory Team in May 2020. This team was tasked with helping Westport businesses open and operate safely and with confidence during the global pandemic.

Jen also served on the Board of Directors for the Women’s Business Development Council, which provides entrepreneurial training, financial education and professional development to current and aspiring female small business owners across Connecticut.

In addition to her work with the local business community, Jen is passionate about helping every child access a quality education, and she has devoted countless volunteer hours to this critical mission. Jen has served on the boards of organizations committed to securing a high quality and affordable education for children in all communities across Connecticut, including the State Education Resource Center and Bishop Frank Caggiano’s Education Commission for the Diocese of Bridgeport. Most recently, she served as a Board Member of the Adam J. Lewis Academy in Bridgeport.

Raised in a close-knit, middle-class family that prioritized education, Jen was able to realize her own dream of attending the University of Notre Dame. After earning her degree in Economics and International Studies, she went on to spend more than a decade living and working abroad. This experience broadened her perspective and reaffirmed her belief that the freedoms and opportunities we enjoy as Americans are unmatched anywhere in the world.

Since moving to Westport, Jen has been a dedicated community volunteer. She has donated her time and talents to a number of local organizations including the Westport-Weston Family YMCA Board of Trustees, the Westport Sunrise Rotary Club, the Sunrise Rotary 21st Century Foundation Board, the Bedford Family Social Responsibility Fund Committee, and as a coach for the Westport Soccer Association. All her kids are better soccer players than she is, so she has hung up her cleats for now!

Family is so important to Jen. She and her husband Mo Tooker have three children; Jack (23), Riley (21) and Nicole (16). A commitment to building a better future for Westport for her family and yours is Jen’s North Star.