If you are planning to mail a check by the end of the year, please note that the U.S. Postal Service has updated its rules, and machine postmarks will now be applied when mail is processed at regional processing centers (not at the local drop off point). To ensure your check is postmarked in time to be eligible for a 2025 charitable deduction, we recommend requesting a manual postmark in person at a post office or using certified/registered mail. Click here for more details on giving dates and deadlines.
Lindsey Doolittle is the director of impact investments for The Chicago Community Trust.
In this role, Lindsey leads impact investing at the Trust—driving strategy, guiding investment selection and monitoring, and working closely with financial institutions and donors to ensure investments are both financially sound and deliver meaningful community impact.
Prior to joining the Trust, Lindsey was a Director at the U.S. International Development Finance Corporation (DFC) where she managed a portfolio focused on catalyzing capital for underserved small and medium enterprises, women-led businesses, and climate-smart ventures in emerging markets. Before that, she held several roles at HOPE International—overseeing its Data Analytics division and building the risk management program for its microfinance institution in the Dominican Republic, where she lived. She spent the early years of her career as a forensic accountant and financial consultant at PricewaterhouseCoopers.
Lindsey holds a master’s degree in public policy from the University of Chicago and bachelor’s degrees in finance, business management, and Spanish from the University of Virginia.
