In 2013, Jennifer left her 22-year career as an executive with Gen Re, during which time she held various leadership and management positions in the US and European reinsurance markets.  Drawing on her business experience, Jennifer has created strong ties to Fairfield County’s business community, particularly in Westport.  She 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, Jennifer turned her focus to education, specifically working to close the achievement gap in our state which is one of the worst in the country. She has spent many hours working on the boards of organizations committed to high quality and affordable education for children in all communities across Connecticut. She served as a member of the Board of Directors of the State Education Resource Center and on 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.    

As Second Selectwoman, Jennifer has worked on a number of important initiatives.  Focused on the social and emotional health and well-being of our community, Jennifer launched Westport Together. The mission of Westport Together is to promote the positive development of our children. 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. 

Jennifer also created and hosts Westport Means Business - a series of events for the local business community. The events bring together local business owners and entrepreneurs to establish connections, exchange ideas and promote Westport as the best town in which to start and grow a successful business. Most recently, in response to the COVID-19 crisis, then First Selectman Jim Marpe appointed Jennifer as Chair of the ReOpen Westport Advisory Team in May 2020.  This team is tasked with helping Westport businesses open and operate safely and with confidence given the challenges created by the global pandemic.   

Since the moment Jennifer moved to Westport, she 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 Jennifer. Her parents have recently moved to Westport. She and her husband, Mo Tooker, have three children; Jack, Riley and Nicole.  

Jennifer received her Bachelor of Arts degree in Economics and International Studies from the University of Notre Dame.