Collaboratory honors Diana Willis and Sally Jackson with 2026 Women’s Legacy Fund Philanthropy Impact Award
Collaboratory, Southwest Florida’s regional community foundation, has named two Southwest Florida leaders as its 2026 Women’s Legacy Fund Philanthropy Impact Award honorees. Diana Willis and Sally Jackson will be recognized at Collaboratory’s Women’s Legacy Fund luncheon on Thursday, Nov. 5.
The Women’s Legacy Fund Philanthropy Impact Award recognizes and celebrates extraordinary female philanthropists who exemplify the true spirit of giving. This honor is bestowed upon women who are deeply committed to empowering and inspiring others, both through their financial contributions and dedication to mentorship. They lead by example and generously share their expertise, time and resources with love and intention. Their selfless efforts are focused on uplifting the community and making a lasting positive impact on the lives of others. This award honors these women’s tireless dedication to service and profound role in fostering growth, support, and unity.
Since 2002, Willis and her family have contributed more than $2 million to local organizations, including Pace Center for Girls; Habitat for Humanity; Florida Gulf Coast University; SWFL Children’s Charities; Abuse, Counseling and Treatment, Inc.; CCMI Soup Kitchen; the Heights Foundation; Go Red for Women with American Heart Association and numerous children’s charities. Willis holds several board, advisor, committee and volunteer roles across Southwest Florida.
Willis is vice president and co-owner of Jason’s Deli of Southwest Florida, where she has been instrumental in creating strong culture, operational excellence and meaningful community impact for more than two decades. In 2023, Willis and her team opened their first Foxtail Coffee franchise, bringing the community-focused coffee chain to Southwest Florida.
For more than three decades, Jackson has established a repertoire of community service leadership positions. Since 2021, she has served as a trustee, volunteer and board vice chair for Collaboratory and is chair of the Community Impact and Grantmaking Committee. Jackson currently serves on the local board for Pace Center for Girls, Lee, and is a United Way board member. In 2017, she was recognized with the Pride of Florida Award by Senator Lizbeth Benacquisto and was named a Woman of Distinction in Health Care by Cape Coral Republican Women. Jackson is a 2015 Greater Fort Myers Chamber of Commerce APEX Award finalist and a member of Leadership Lee County’s 2004 graduating class.
Prior to her retirement in 2017, Jackson spent 12 years as system director of government and community relations for Lee Health after an extensive career in business, chamber leadership and state government. At Lee Health, Jackson led relations at the state, federal and local levels and was essential in community health improvement across Southwest Florida through government regulation and funding initiatives. Notably, Jackson helped to initiate the first family medicine residency at Lee Health; SalusCare’s residential Bob Janes Behavioral Triage Center; a We Care voluntary medical and dental partnership with local nonprofits; and the startup Lee Community Healthcare Federally Qualified Health Center clinics in Southwest Florida.
Jackson and Willis will be recognized as Women’s Legacy Fund Philanthropy Impact Award honorees on Thursday, Nov. 5. Established in 2008, the Women’s Legacy Fund is built on generosity, gratitude and the unity of women’s leadership as strategic partners in philanthropy. By pooling financial and intellectual resources, members make thoughtful grant choices that uplift the entire community. The Women’s Legacy Fund seeks to amplify the power women possess to strengthen their communities through philanthropic giving; educate women and the community on current issues and philanthropic strategies; and inspire women to be leaders in philanthropy.
To learn more, visit Collaboratory.org/Womens-Legacy-Fund.
About Collaboratory
Collaboratory is Southwest Florida’s regional community foundation and convener, committed to coordinating solutions to the region’s most pressing social challenges by 2040. For more than 50 years, Collaboratory has mobilized philanthropy and stewarded more than $147 million in charitable investments across a five-county region by bringing together nonprofits, education, government and private-sector partners to drive systems-level change. Through grantmaking, scholarship administration, community research, capacity building and cross-sector collaboration, Collaboratory aligns resources, talent and data to ensure donor dollars are strategically invested for measurable, lasting impact and a stronger, more resilient Southwest Florida. To learn more and get involved, call 239-274-5900 or visit www.Collaboratory.org.
