A resident for 20 years, Jill and her husband Larry Penn raised their three children in Greenwich, where she built a strong record of community involvement and leadership. She served on the Board of Selectmen, helping guide the town through COVID, and on the Board of Estimate and Taxation, where she was unanimously elected Chair—the first Democrat to hold that seat in town history. During her tenure, she helped keep property taxes low while maintaining strong services and planning for the future.