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Gibson Gives Back: Jen Whitaker Fights Homelessness One Step at a Time

Jen Whitaker

For Jen Whitaker, a global real estate advisor on Cape Cod, helping people find their dream homes comes naturally. All the while, Jen is conscious of the glaring housing crisis that current and hopeful Cape Cod residents face as home prices continue to rise. When she learned of the Homeless Prevention Council’s (HPC) mission to keep people in their homes and their communities, Jen knew she had to get involved. This year, she serves as Co-Chair of the Walk for Home, one of HPC’s largest annual fundraisers. Read on to discover how Jen is tackling the Cape Cod housing crisis, one step at a time. 

Tell us a bit about the Homeless Prevention Council and the Walk For Home! What initially inspired you to get involved with this organization? How long have you been involved? 

The Homeless Prevention Council was established in 1991 to combat and prevent homelessness on the Lower Cape. Its goal is to focus on prevention efforts that help residents stay in their existing housing, as access to affordable housing continues to be a major challenge. The council provides personalized case management solutions to promote stability for all who live in the community.  This will be the 5th annual Walk for Home and all proceeds will go towards the prevention of homelessness.

As a Nauset Rotary member, I had several opportunities to participate in community activities HPC was sponsoring over the years. In 2020, I was asked to join HPC’s board. I began participating in the Walk for Home, and was asked to be the chair for 2023 with Christina Caron and Amanda De Oliveira.

Do you have any fun memories from the walks over the years? What are some of the challenges you’ve faced?

My favorite part of the walks in the past is watching the younger generation get involved. Kids from the Provincetown school system always arrive with signs and enthusiasm — they are amazing!  

Another personal highlight was assisting the organization with the search for a new building. With more families in need, HPC was taking on more clients, which in turn required more staff and more office space. As a board member, it was a natural fit for me to represent the organization in the search. I am thrilled to announce that they have sold their building and will be moving into their new building at the end of March. 

In terms of challenges,  getting people to take time out of their busy schedules to attend a walk can be a bit of a hurdle. Many will give money, which is ultimately our goal, but the feeling of community gets missed if you don’t attend. Those who do come in person are always rewarded by the sense of camaraderie. 

As an agent focused on philanthropic giving, how do you stay engaged throughout the year?  

I stay engaged by attending board meetings and showing up for events, along with donating a small portion of every real estate transaction to HPC. I try to inspire those around me: my goal is to see all agents on the Cape give or participate in some way to the housing crisis we are experiencing.

Do you have any recommendations for those considering taking a deeper dive into philanthropy?  

Join an organization! You don’t have to be a board member or a president of a club, just get in there and participate. It’s not always about the money — your time is just as valuable. 

The 2023 Walk for Home will take place on Saturday, June 10 at 10:00am in Provincetown and Chatham. To learn more about the Homeless Prevention Council, the Walk for Home, and how you can help, visit

Jen Whitaker can be reached at 508.237.8038 or, or by visiting our Orleans office at 6 Route 6A, Orleans, MA. 



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