Vice President, Advisory Services

THE ORGANIZATIONChicago TREND ("TREND") is a mission-driven real estate platform advancing inclusive commercial ownership and neighborhood revitalization in historically underinvested communities. The organization acquires, improves, and manages neighborhood shopping centers while creating opportunities for local residents to participate in ownership through innovative Community Investment Vehicles. TREND combines disciplined real estate execution with a commitment to community wealth-building, ensuring that revitalization creates long-term economic participation rather than simply physical improvements.Is this the next step in your career Find out if you are the right candidate by reading through the complete overview below.To complement the for-profit platform, TREND established TREND Community Development Corporation (TREND CDC), a separate 501(c)(3) nonprofit partner. TREND CDC secures philanthropic and public funding, delivers small business advisory programming, supports community investor engagement, and advances national field-building in inclusive commercial real estate. The two entities operate independently from a governance standpoint but are strategically aligned in mission and execution.TREND is now entering its next stage of growth. As the organization expands geographically and deepens its real estate portfolio, it is also scaling its advisory services platform. TREND operates in an entrepreneurial, high-trust environment that values creativity, accountability, and results, and seeks leaders who can help institutionalize its model while preserving its mission-driven DNA.For more information, visit: OPPORTUNITYAdvisory Services represents a central growth engine for Chicago TREND. The Vice President, Advisory Services will build and lead a revenue-generating advisory platform that translates TREND's inclusive ownership model into scalable engagements across multiple U.S. markets. The near-term expectation is to generate approximately $2M in annual advisory revenue, with early opportunities already in development. Existing offerings include programs such as FITT, which supports franchise entrepreneurs, and Buy Back the Block Lab, which trains organizations pursuing inclusive commercial real estate projects. Advisory engagements may be structured as direct contracts with TREND or funded through grants via TREND CDC. In practice, both serve as revenue pathways supporting the broader enterprise.This is a true executive player-coach role. The Vice President will shape strategy, originate opportunities, strengthen fundraising and earned revenue streams, and build external partnerships while ensuring disciplined execution across advisory initiatives. The role sits at the intersection of real estate, capital, community development, and fundraising, requiring a leader who is equally comfortable in strategic conversations with funders and investors as in hands-on program design and delivery.For the right leader, this represents a rare opportunity to help define and scale a national model for inclusive commercial ownership.The RoleThe Vice President, Advisory Services is a senior executive leader responsible for building, scaling, and institutionalizing TREND's advisory services platform as a core growth engine of the organization.Reporting directly to the Chief Executive Officer, the Vice President will serve on the senior leadership team and work closely with the COO of TREND CDC, the VP of Finance & Operations, and real estate leadership.This is not a program oversight role. It is a platform-building mandate. The Vice President will define the advisory business model, expand revenue pathways, develop new advisory offerings, and ensure the portfolio of initiatives operates as a cohesive and scalable enterprise aligned with TREND's real estate strategy.TREND operates in a largely remote environment with travel across active and emerging markets. Current markets include Chicago, Baltimore, Columbus, Newark, Selma, and Minneapolis.Key responsibilities include:Strategic Partnership & Platform Innovation• Architect and execute a multi-year growth strategy for Advisory Services aligned with TREND's geographic and portfolio expansion.• Define the business model, operating structure, and service offerings for the advisory platform, identifying new advisory opportunities that extend TREND's inclusive ownership model into new markets and sectors.• Design scalable advisory engagements that can be packaged, priced, and delivered consistently across geographies.• Continuously assess market demand and funder priorities to shape a differentiated and competitive suite of advisory services.• Position TREND as a national thought leader in inclusive commercial ownershipRevenue & Capital Development• Co-own with the TREND CEO advisory revenue performance, including pipeline development, proposal strategy, pricing, negotiation, and closing.• Build and manage direct relationships with philanthropic funders, public agencies, and strategic partners, leading funder conversations and securing advisory engagements aligned with their priorities.• Originate and sell advisory engagements that respond to both market demand and funder priorities.• Partner with TREND CDC leadership to align philanthropic capital strategy with enterprise growth, while maintaining personal accountability for revenue outcomes.• Expand revenue streams across earned revenue, contract engagements, and grant-supported advisory work.Program Delivery & Operational Discipline• Oversee execution across advisory initiatives, ensuring rigor in planning, budgeting, partner coordination, and impact measurement.• Institutionalize operating standards and performance management across the advisory portfolio.• Align advisory initiatives directly with TREND's real estate strategy and community ownership objectivesExternal Leadership & Cross-Entity Alignment • Serve as a national ambassador for TREND's inclusive ownership model, representing the organization across capital, policy, and community environments.• Build strong relationships across funders, investors, community partners, and ecosystem collaborators.• Lead effectively across TREND and TREND CDC structures, balancing governance boundaries with operational alignment.• Strengthen coordination and accountability across the enterprise as the organization scales.Professional ExperienceThe successful candidate will bring:• 10+ years of progressive leadership experience across community development, commercial real estate, economic development, small business ecosystems, or adjacent sectors.• Demonstrated success building or scaling a business line, advisory practice, or multi-program platform.• A personal track record of fundraising and capital development, including building funder relationships, securing multi-year support, and closing revenue-generating engagements tied to defined targets.• Experience navigating public-private-nonprofit intersections with sophistication and political acuity.• Exceptional executive presence, communication capability, and relationship-building strength.• Strong operational leadership skills, with experience building systems and managing delivery in lean, entrepreneurial environments.• Strong program management capability, including developing workplans, coordinating partners, delivering services, and tracking outcomes.• The ideal candidate combines entrepreneurial drive with disciplined execution. They are imaginative yet pragmatic, visionary yet grounded, and comfortable being measured by outcomes.Why This Role MattersTREND stands at a pivotal moment in its growth.Advisory Services represents both a revenue diversification strategy and a powerful multiplier of TREND's mission. Through this platform, TREND has the opportunity to extend its inclusive ownership model into new markets, influence broader industry practices, and accelerate community wealth-building beyond its direct real estate portfolio.The Vice President, Advisory Services will play a central role in shaping this next chapter.CULTURAL ALIGNMENTThe successful candidate will thrive in a mission-driven, entrepreneurial environment characterized by urgency, creativity, collaborative problem-solving, and service-oriented leadership. xijylhu TREND values leaders who act decisively, push boundaries thoughtfully, operate with a win-win mindset, and bring intensity and courage to advancing inclusive economic growth.To explore this opportunity, please contact:Nanda at the Bigwin Group

Created: 2026-04-03