Executive Director

Who We Are

Of the households that own commercial real estate, just 1% hold 81% of its total value. That is the foundation underneath every storefront, every shopping center, every block. And in low- and moderate-income neighborhoods, decades of disinvestment and extractive ownership means that the people who live on those blocks almost never share in the financial upside of the property they shop at and work in. TREND is changing that, one shopping center at a time.

TREND Community Development Corporation (TREND CDC) is a 501(c)(3) nonprofit founded in 2019 to complement the mission of TREND, a social enterprise focused on revitalizing urban commercial corridors and closing the racial wealth gap. Together, they form the TREND enterprise, united by a shared goal: strengthening neighborhoods through inclusive economic development.

TREND acquires shopping centers in low- and moderate-income neighborhoods, transforms them into vibrant community hubs, and creates opportunities for local residents and small-dollar investors to co-own these assets. To date, TREND co-owns six shopping centers in partnership with 462 local and small-dollar investors.

TREND CDC is the philanthropic and programmatic engine behind that work — leading investor communications and advancing programs including small business support, commercial corridor planning, climate-positive improvements, and creative placemaking.

We're a lean team by design. Whoever takes this role will shape it.

The Role

We are looking for an Executive Director who can own TREND CDC end-to-end: strategy, fundraising, programs, operations, communications, and team. You will report to the Board of Directors and work in close partnership with Chicago TREND's CEO to align the nonprofit's programs and capital with the real estate strategy. You will inherit an active grants portfolio, a board of seasoned community development leaders, and an organization with momentum. This is a build-the-next-chapter role, not a maintain-the-org one. The infrastructure is in place. The relationships are warm. The pipeline is real. What we need now is someone who can grow the nonprofit's capacity, deepen its identity, and unlock the next tier of funding and programs as the portfolio expands into new markets.

Why TREND CDC

A model that works. Six shopping centers, 462 community investors, four cities, a published playbook, and a roadmap to double in size. The theory of change is no longer theoretical.

Real impact on real blocks. Our community investors are people who watched their neighborhood's shopping center decline over decades and now own a piece of its revival. When you close a grant, hire a contractor, or launch a program, you can see and feel that impact at the property.

A small team with an outsized footprint. You will not spend your year in planning meetings. You will ship programs, close grants, and build the organization. Your work will be cited in think tank pieces, in funder rooms, and in city halls.

A leadership table with national influence. The next Executive Director will step into a uniquely high-leverage ecosystem of investors, operators, funders, and institution builders shaping the future of inclusive ownership, impact investing, and community development nationally.

You will partner closely with Lyneir Richardson, founding CEO of TREND and a nationally recognized leader in equitable commercial real estate development. Lyneir has built a reputation for turning ambitious ideas into investable, executable models at national scale, with deep relationships across leading foundations, developers, city leaders, and impact investors.

You will work with Chinwe Onyeagoro, current Board Chair of TREND CDC, fintech founder, and nationally respected strategist known for building high-growth companies and moving institutions toward bold action. Chinwe brings deep relationships across venture capital, technology, and community financial markets, and creates access to networks and opportunities that can materially expand TREND CDC's reach and influence.

You will work alongside Bob Weissbourd, TREND’s co-founder and one of the most respected thinkers in community development finance and economic inclusion. His network spans major foundations, policy circles, and civic leadership nationally. Access to Bob means access to conversations and relationships that most organizations spend decades trying to enter.

What You'll Actually Work On

Strategy and leadership. Set the strategic direction of TREND CDC and lead the organization through its next phase of growth. Partner with the Board on governance, with Chicago TREND on enterprise alignment, and with the field on thought leadership.

Fundraising and funder relations. Own the fundraising strategy across foundations, corporations, public-sector grants, and donor-advised funds. Steward relationships with national funders (Surdna, Kresge, Robert Wood Johnson, MacArthur, McKnight, and others) and build new ones.

Programs and impact. Conceive, launch, and oversee programs that bring the real estate strategy to life: small business support, creative placemaking, commercial corridor planning, public safety partnerships, climate-positive improvements, and community investor education.

Community investor relations. Steward the experience of 462-and-growing community investors. Lead quarterly reports, webinars, and engagement. Build the education materials that bring first-time commercial real estate investors into the model with confidence.

Operations, finance, and compliance. Own the annual budget, cash projections, annual audit, tax filings, and federal, state, and local compliance. Strengthen related-party governance with Chicago TREND, including service agreements, segregation of duties, and inter-entity documentation.

Communications and external affairs. Build TREND CDC's public voice as distinct from and complementary to Chicago TREND. Oversee the website, social channels, reports, and presentations that translate the work for funders, partners, and the broader field.

Your First 90 Days

Days 1–30: Get oriented. Meet the Board, the Chicago TREND leadership team, and the Development and Operations Associate. Visit the shopping centers. Get to know the grants portfolio, financial systems, compliance landscape, and current programs. Sit in on community investor calls. Read every funder relationship file.

Days 30–60: Get your hands on the work. Take ownership of in-progress proposals and reports, and meet directly with three to five priority funders. Lead your first quarterly Board meeting. Support two community investment vehicle launches with the Chicago TREND team.

Days 60–90: Set the direction. Present your strategic priorities to the Board. Bring in your first major new funding opportunity. Begin building out the team and contractor bench needed to deliver against the next portfolio expansion.

What We're Looking For

Must-haves:

• 7–10+ years of progressive nonprofit leadership, including 3–5 years in an executive role (ED, COO, VP, or equivalent)
• A real fundraising track record — existing relationships and a history of personally closing six- and seven-figure grants
• Working knowledge of community development, commercial real estate, urban planning, or small business development
• Experience managing a Board of Directors, including governance, committee work, and Board cultivation
• Strong financial acumen across budgeting, reporting, audit oversight, and grant management
• Comfort with related-party governance and compliance
• Excellent written and verbal communication across funder, investor, and civic audiences
• Entrepreneurial and flexible — comfortable building in a lean organization

Strong signals

• Led an organization through a phase of growth
• Experience in shared-equity, cooperative, or community ownership models
• Built a fundraising engine from the ground up
• Worked at the intersection of a nonprofit and an affiliated for-profit or social enterprise
• Network in racial wealth gap, commercial real estate, or community development funder worlds

Details

Location: Remote-first with regular travel to Chicago, Baltimore, Columbus, and Minneapolis. Compensation: Competitive salary plus health insurance, 401(k) matching, unlimited PTO, and performance bonuses. Reports to: TREND CDC Board of Directors, in close partnership with the CEO of Chicago TREND. Supported by: Development and Operations Associate

To Apply

Please submit a resume and cover letter to ***email_hidden***. Applications reviewed on a rolling basis; priority consideration by Friday, June 26, 2026.