Director of Investments

About Proofing Station Proofing Station is an Illinois-based 501(c)(3) non-profit organization launched in 2023 with a mission to increase access to capital for entities that support the Midwest regional food and agriculture supply chain. The organization addresses enduring funding gaps for food and agriculture entities that have historically been underserved and marginalized by traditional financial institutions. The organization offers an integrated suite of financial products and technical assistance designed to support food and agriculture businesses while advancing ecological sustainability, social and racial equity, and economic resilience. Proofing Station operates with a mission-driven approach to investment, deploying capital through debt, equity, credit enhancement, and targeted grants to serve early and mid-stage enterprises that would otherwise lack access to traditional lending. Proofing Station’s core team is based in Chicago, with operations serving a geographic region that encompasses the Upper Midwest, including Minnesota, Wisconsin, Iowa, Illinois, Michigan, and Indiana. The organization works remotely as its operational model while maintaining deep connections to the food and agriculture communities it serves throughout the region. About this Role Proofing Station seeks a Director of Investments to join its growing team as a crucial hire to expand organizational capacity and bring rigorous, mission-aligned financial judgment to every investment made in Midwest food and farm businesses. The organization is looking for an experienced investment professional with demonstrated skills in analyzing, structuring, and executing deals, combined with a deep commitment to Proofing Station’s mission and the creativity to design capital solutions for underserved, early and mid-stage enterprises often not served by traditional lenders. The Director of Investments leads the assessment and structuring of every investment Proofing Station makes. Working closely with the Executive Director and the Investment Committee, the Director manages each step of the internal deal process, from financial review and readiness assessment through formal due diligence, deal structuring, the recommendation to the Investment Committee, legal negotiation, closing, and portfolio monitoring. The throughline of the role is disciplined de-risking and impact-first investing, ensuring that Proofing Station stewards its array of integrated capital to make a positive impact on Midwest food and farm businesses while maintaining rigorous processes at every stage.