Lousillia Bailey

Lousillia Bailey

lbailey@chapa.org
(617) 681-5437

Lousillia joined CHAPA in early 2025 as the Executive Assistant to CEO, Rachel Heller. In her role as EA, she will provide calendar management, facilitate internal and external communications, and support preparation for upcoming commitments, playing a strategic role in the organization’s administration. Lousillia is a Dorchester native who has supported executives & c-suites at both nonprofit and corporate organizations. She also brings a strong and passionate commitment to the communities she serves as a woman of color by fostering equality and inclusivity while doing her part to continue to create safe and inclusive environments for everyone she is in contact with. Outside of her role, Lousillia enjoys painting, spending time with loved ones, cheering on her Boston sports teams, and reading.

Jenna Connolly

Jenna Connolly

jconnolly@chapa.org

(617) 631-8679

Jenna joined CHAPA in 2018 as Communications & Events Manager. As Director of Communications & Events, she is responsible for strategizing and implementing CHAPA’s communications and media plan and overseeing the Events & Logistics Manager.

Previously, she served as Resource Development & Communications Manager at Allston Brighton Community Development Corporation. She also completed two terms with AmeriCorps, including a year of building affordable homes in Austin, Texas for Habitat for Humanity.

She holds a Master of Public Administration with a concentration on Gender, Leadership, & Public Policy from UMass Boston and a certificate in PR Strategy from Cornell University. She is passionate about multimedia storytelling and enjoys creative writing and photography in her spare time.

Contact for: press inquiries, logo or ad needs

Maritza Crossen

Maritza Crossen

mcrossen@chapa.org
(617) 804-6558

Maritza Crossen joined CHAPA in 2011. As Director of Strategic Initiatives Maritza oversees the marketing, outreach and education for CHAPA’s 40B homeownership portfolio, working towards CHAPA’s goal of closing the racial homeownership gap. Maritza also assists in CHAPA’s fundraising efforts, securing opportunities to support CHAPA’s mission as well as oversees CHAPA’s Membership Program. She previously served as CHAPA’s Director of Programs, responsible for CHAPA’s 40B Team, the MassAccess Accessible Housing Registry, My Mass Mortgage website the Massachusetts Homeownership Collaborative and CHAPA’s New England HUD Housing Counseling Network. Maritza previously worked for New Ecology, Inc. as an associate green building consultant. She holds a Bachelor of Science in Business Administration from the University of Vermont and a Masters in Urban and Environmental Policy and Planning from Tufts University.

David Gasser

David Gasser

dgasser@chapa.org
(617) 701-7498

David Gasser became CHAPA’s Programs Director in 2021, after joining the agency as a Program Manager in 2019. As Program Manager, he contributed to CHAPA’s Chapter 40B monitoring efforts, particularly managing the resale of affordable homes to first-time homebuyer households. Prior to joining CHAPA, David worked for seven years at the Oak Hill Community Development Corporation, first as a Foreclosure Prevention & Housing Specialist and then as the Director of Homeownership Programs. David is a graduate of Case Western Reserve University and earned a J.D. from Boston College Law School. He is a member of the Massachusetts Bar.

Jennifer Gilbert

Jennifer Gilbert

Since her first post-college job at a Philadelphia homeless shelter, Jennifer Gilbert has worked to make more housing and make housing more accessible. Her 25+ years of experience have lent her the opportunity to “sit” at multiple seats around the housing table: developer, manager, funder, government, planning board member, grant-maker, technologist.

From 2018-2025, she founded and led Housing Navigator Massachusetts, Inc., taking a Tech for Good nonprofit from an idea to a nationally-recognized, free 24/7 affordable housing search tool with 35,000+ users each month. Under her leadership, Navigator debuted statewide and town-by-town Housing Supply Dashboards — a first for transparency about the Massachusetts affordable housing supply – that enable data-driven policy to identify gaps and increase housing production. Housing Navigator MA data is cited regularly in local press, planning meetings,research, and advocacy.

Prior to founding Housing Navigator MA, Jennifer was the initial Executive Director of the Kuehn Charitable Foundation launching its practice-based Kuehn Fellows program (now in its sixth round with 29 alumni Fellows). She further guided over $3 million in investments in affordable housing and historic preservation. Earlier in her career, she spent 15 years as development and strategy consultant with a national practice overseeing complex, mission-driven real estate development projects fostering the creation of 1000+ units of affordable housing, arts spaces, early education centers, and a health clinic in partnership with Vanderbilt University Medical Center.

Jennifer holds an MCP from MIT, a JD from Northeastern University where she was a Skadden Fellow for Public Interest Law, and BA magna cum laude from the University of Pennsylvania. She stays involved in her local community through recent service on the City of Cambridge’s Charter Review Committee (2022-2024) and Alewife Zoning Advisory Group.

Rachel Heller

Rachel Heller

rheller@chapa.org
(617) 701-7491

Rachel Heller became CHAPA’s CEO in 2016, after joining the agency as the Director of Public Policy in 2012. Rachel is responsible for providing strategic leadership and overseeing all activities of the organization. She works in partnership with the Board of Directors to articulate and execute CHAPA’s mission. Rachel previously worked as the Director of Public Policy at the Alliance for Business Leadership, served as Chief of Staff to Massachusetts State Senator Susan Tucker, and was the Senior Policy Advocate at Homes for Families, a nonprofit advocacy organization working to end family homelessness. Rachel holds a Bachelor of Arts in Political Science and Peace Studies from the University of Connecticut.