Chicago Residential Investment Fund - CEO

Chicago Residential Investment Fund – CEO

Chicago has provided the capital and structure required to launch CRIF. The next step is rapid execution. Stakeholders expect CRIF to demonstrate early visible progress, including breaking ground on priority projects next year. As such, CRIF is seeking an entrepreneurial, technically skilled, and highly relational Chief Executive Officer to lead the organization from formation through its first generation of development, ownership, and asset management, and beyond.

The CEO will be employee number one and will shape CRIF’s strategy, operations, and identity in the field.

CRIF requires a CEO who is a builder and a real estate professional with practical experience in both market‑rate and affordable housing. This leader will build the pipeline, evaluate deals, guide negotiations, and determine which projects should move forward. They will establish evaluation tools, project intake processes, and decision frameworks that support disciplined capital deployment. They will engage directly with developers, City departments, investors, community partners, and the CRIF Board of Directors, representing CRIF with credibility and clarity.

The CEO must understand what makes a development viable, be able to evaluate opportunities quickly, and recognize which projects can be advanced with CRIF’s participation.

As employee number one, the CEO must be prepared to be an all‑in leader early on: setting vision, establishing credibility externally, and personally advancing deals, relationships, and systems before additional staff capacity is built. The CEO will partner with the Board of Directors to determine staffing needs for CRIF’s early years and will build CRIF’s internal systems, infrastructure, and workflows. The CEO will be responsible for simultaneously building and staffing the organization, and advancing deals.

They must be comfortable operating without extensive support in the early months and able to create organization‑wide structure without slowing momentum.

Key Responsibilities

• Strategic Leadership and Program Design

• Pipeline Development, Deal Evaluation, and Execution

• Organizational Development and Team Leadership

• Stakeholder Engagement and External Relations

• Portfolio and Asset Management Oversight

Required Qualifications

• Builder with Real Estate Expertise:
The CEO must bring practical, hands‑on experience with medium‑to large‑scale real estate development, ideally in both market‑rate and affordable housing contexts. They should understand financial structuring and construction considerations. Some familiarity with sustainable, high‑performance, and/or low‑carbon development is a plus. They must be able to read a deal quickly and know whether it is strong, weak, or salvageable. The most successful candidates will bring prior experience launching a new entity, fund, platform, or program from the ground up, including establishing governance, systems, and external credibility.

• Execution‑Oriented: CRIF needs a leader who works with urgency, manages ambiguity with confidence, and moves projects forward without unnecessary delay. The ideal CEO can build internal infrastructure to create consistency and continuity for impacted parties while themselves operating with very little structure, at least initially, to quickly advancing multiple deals. They stay close to the details and maintain consistent momentum.

• Sound Judgment and Analytical:
The CEO will determine which opportunities deserve CRIF’s time and capital. This requires strong financial literacy, mature judgment, and the ability to differentiate between promising and high‑risk opportunities. The CEO must be comfortable saying yes, no, or not yet based on clear analysis. Comfort operating under public scrutiny and criticism, with the judgment and temperament required to lead a high‑profile, publicly capitalized organization.

• Chicago Savvy and Relationship‑Driven:
Chicago’s development environment is shaped by neighborhood expectations, political relationships, and long‑standing community dynamics. The CEO must understand this landscape, build trust with City Council members and community, and…