The Chicago Community Trust is a community foundation dedicated to improving our region through strategic grant making, civic engagement and inspiring philanthropy. We are here to serve the nonprofit organizations, the generous donors and the thoughtful residents who strive to make a difference, helping their bold vision create lasting community change. We work with a number of partnerships and initiatives to accomplish this work.

We are privileged to serve our community and invite those who connect with our mission, vision, and values to explore employment opportunities with the Trust. To learn more, please visit the Trust online at

The Chicago Community Trust is an Equal Opportunity Employer.

Sr. Real Estate Advisor

  • Job Tracking ID: 512298-793093
  • Job Location: Chicago, IL
  • Level of Education: Any
  • Job Type: Full-Time/Regular
  • Date Updated: October 07, 2021
  • Starting Date: ASAP
  • Application Deadline: Until filled

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Job Description:

Position Summary

Community Desk Chicago ("the Desk") leverages private market expertise and trusted investor relationships to unlock capital for transformative real estate development. Currently based at the Chicago Community Trust ("the Trust"), the Desk was launched in 2019 as the result of a six-month study led by the Boston Consulting Group (BCG). The JP Morgan Chase Foundation (JPMCF) commissioned the study to better understand how to drive more impactful investments in communities of color.

The Desk works with catalytic real estate projects in historically underserved Black and Latinx communities to help close funding gaps based on four key beliefs including 1) strong talent and commercial development opportunities exist in communities, but face challenges accessing the necessary capital and resources, 2) communities deserve holistic development, including commercial projects that create wealth building opportunities and improve quality of life, 3) projects in communities of color should have equitable access to capital without fear of racial bias and 4) our role is to collaborate, not duplicate - partnering with the existing ecosystem to add capacity and fill gaps.

In addition to providing direct project support to community developers, nonprofits and entrepreneurs, the Desk works closing with philanthropy including the Trust and other critical stakeholders in the community development ecosystem to design and launch initiatives that increase capital flow, wealth building and real development capacity in communities. More information about the Desk can be found at

Under the direction of the Desk’s Director, the Senior Real Estate Advisor will actively manage the capital connection for community-based real estate development projects. Specifically, the advisor will assess project financial feasibility, recommend funding strategies and manage the direct connection to project funders including philanthropy, lenders and investors.

Position Responsibilities

  • Meet with community-focused nonprofits, developers and entrepreneurs to understand their development capital needs and outline potential funding strategies.
  • Leveraging relevant industry and project-based data, pressure test project assumptions related to revenue, expenses, net operating income and development costs.
  • Evaluate project feasibility based on key financial metrics including but not limited to debt coverage ratios, debt to equity ratios, cap rates and other relevant markers.
  • Model potential capital stacks and develop recommendations for target investor types and mix, based on expected social impact and financial returns of project
  • As necessary, support projects with the creation of operating pro formas, development budgets and related feasibility documentation.
  • Monitor a portfolio of projects through their development lifecycle to assist with capital resources.
  • Recommend new tools and resources to standardize the review of projects.
  • Research investment models and trends to recommend creative funding strategies for projects.
  • Support the development of an investor pool to shop investment opportunities and to help attract new capital for projects.
  • Coordinate with capital market experts to assist with deal structuring and terms.
  • Recommend pitch materials for projects to highlight feasibility, community impact and funding requirements.
  • Assist projects with completing grant applications, loan applications and other related funding documentation to secure capital.
  • Leverage the resources and network of the Trust, JPMCF, BCG and other partners to support holistic neighborhood development.
  • Codify lessons learned for knowledge sharing in the community development ecosystem.
  • Other responsibilities as identified to support the launch of new programs and initiatives.

Experience and Skills:

  • Master’s degree in finance, business administration, urban planning, real estate or community development is preferred. Bachelor’s degree in a related field of study is required.
  • 7-10 years of related work experience.
  • Demonstrated understanding and commitment to The Desk’s mission.
  • Understanding of real estate development, community development, innovative financing and complex deal flows.
  • Direct experience or working knowledge of small business financing including SBA lending
  • Ability to work collaboratively and build relationships with a variety of partners across Chicago, including The Trust, JPMCF, BCG, community residents, nonprofits, philanthropic organizations, developers, traditional investors, impact investors, financial institutions, and legal advisers.
  • Ability to self-start and approach the role with an entrepreneurial spirit.
  • Strong quantitative skill set to apply to project feasibility and capital coordination.
  • Experience with business strategy to inform investment case and pitch material preparation.
  • Experience in project management, with the ability to assess and resolve implementation issues and to establish best practices.
  • Effective listening skills and business acumen to engage with projects and key stakeholders.
  • Strong interpersonal skills, written communication, and comfort with cross-cultural communication.
  • Ability and desire to work in culturally diverse environments.
  • Direct experience underwriting, evaluating or coordinating capital requests including experience with LIHTCs, NMTCS, OZ funding, TIF and other development incentives.

Equal Opportunity Employer

The Trust is committed to creating a diverse work environment and is proud to be an equal opportunity employer. The Trust does not discriminate on the basis of race, color, national origin, sex, gender identity, religion, sexual orientation, age, disability, parental status, veteran status, or any other protected status under applicable laws. We encourage individuals of all backgrounds to apply. If you are a qualified candidate with a disability, please e-mail us at if you require a reasonable accommodation to complete this application.

History of The Chicago Community Trust

The Chicago Community Trust was founded in 1915 by Norman and Albert Harris, father and son duo of the Harris Trust and Savings Bank (now BMO Harris Bank). The Trust was the fourth community foundation ever created. There are now 750 community foundations in Canada and the U.S.

As our region’s community foundation, the Trust unites generous donors, committed nonprofits and caring residents to effect lasting change that moves our entire region forward. Our approach centers on tackling the region’s immediate needs and addressing the root causes of deep-seated issues to realize a more prosperous future for all who call metropolitan Chicago home.

For more than 100 years, donors have entrusted their philanthropic resources and visions to our stewardship. Guided by our deep knowledge of the community, we fund, lead, convene and collaborate to address the greatest and most critical needs facing the Chicago region. From the $22 million raised to help with unemployment relief in the Great Depression to spearheading an effort to help people keep their homes during the foreclosure crisis of the Great Recession to $35 million raised for the Chicago Community COVID-19 Response Fund, which supported nonprofits serving our most vulnerable neighbors, Chicagoans have put their trust in us.

In 2019, we announced we would focus our discretionary spending over the next decade on working to close Chicago’s growing racial and ethnic wealth gap. The Trust envisions a Chicago region that’s stronger and more prosperous because everyone—regardless of race, ethnicity, or zip code—has equitable access to the opportunities and resources they need to succeed and live a fulfilling life.

With assets of more than $3.7 billion, the Trust, in partnership with its donors, distributes more than $600 million in grants each year. The Trust Team seeks to match the passion and commitment of donors, grant recipients, residents, and community leaders that continue to work tirelessly to make the Chicago region one where all have the opportunity to realize their dreams.