Long Life Learning Jessica Bailey on Impact as an Accelerant for Business Goals and Societal Benefit
When CEO of Nuveen Green Capital and repeat YGELP instructor Jessica Bailey first got into business, it was because of a fascination with the energy sector's ability to drive foreign trade and policy. She quickly identified a market gap in scaling private capital for smart financial energy solutions, and partnered with Ali Cooley to carve a unique entrepreneurial role which allowed her to bridge philanthropic and public sector leadership informed by her years at the Rockefeller Brothers Fund and Connecticut Green Bank. Today, the team Jessica has built at Nuveen has expanded its scope across the U.S. and into international regions in an effort to provide sustainable commercial real estate finance solutions which support building decarbonization.
This week, Jessica joins Kavitha in the studio to discuss how centering impact as a core KPI allows businesses to gain momentum while their competitors face headwinds, how her team's initial emphasis on passion and generalist knowledge allowed them to rapidly flourish in an ever-changing energy market, and why leading with gratitude as a CEO has made the role a long-term and satisfying endeavor. Jessica cautions CEOs not to fall into the trap of prioritizing an air of invincibility which disallows space for vulnerability and the willingness to receive reflection from colleagues. She instead describes the most capable leaders as those who embrace learning specialized business "languages," who dive into new questions and lifelong learning with enthusiasm, and who follow the "green lights" life places on their path.
Transcript
S2E4—Jessica Bailey Transcript
Links and Resources
Information on YGELP and Yale SOM Executive Education:
Resources Mentioned in Today's Episode:
- The Diary of a CEO Podcast, Steven Bartlett
- The Wisdom of the Bullfrog, Admiral William H. McRaven
- Greenlights, Matthew McConaughey
Where to Find Jessica:
About Today's Guest
Jessica Bailey is President and CEO of Nuveen Green Capital (NGC), a leading provider of sustainable commercial real estate finance.
As a pioneer of the Commercial Property Assessed Clean Energy (C-PACE) industry, Jessica co-founded Greenworks Lending in 2015 and led it to a successful acquisition by Nuveen in 2021 where the firm was rebranded to Nuveen Green Capital. Under her leadership, the firm became one of the largest C-PACE capital providers in the country. Utilizing a state-enabled policy that Jessica helped to develop, C-PACE has become a mainstream financing tool for clean energy upgrades in commercial real estate and sustainable new construction. As President and CEO of NGC, Jessica has grown the company into a national lending platform operating in over 40 states, with over $3 billion in assets under management, and a team of nearly 100 professionals. Through its nationwide distribution and originations platform, NGC has experienced double-digit annual growth since founding. Prior to starting Greenworks Lending, Jessica was with the Connecticut Green Bank from 2012 to 2014, where she played a key role in designing and leading the award-winning C-PACE program for the state – the first successful C-PACE program in the country. Earlier in her career she spent eight years at the Rockefeller Brothers Fund, a foundation based in New York where she worked to advance clean energy initiatives.
Jessica's leadership and entrepreneurship have been widely recognized. In 2025, Jessica was named a GlobeSt. "Rainmaker in CRE Debt & Equity Finance." In 2024, Jessica was recognized as a "Notable Leader in Sustainability" by Crain's New York, and was also included on Worth Magazine's Worthy 100 List, and Commercial Observer's Power 50 Finance List. She was honored as a GlobeSt. "Woman of Influence" in 2023, and she and NGC co-founder, Ali Cooley, were jointly recognized as "CRE's Best Bosses" by GlobeSt. in 2023, as well as "50 Most Important Figures of Commercial Real Estate Finance" by Commercial Observer in 2022. Jessica was named an Ernst and Young (EY) Entrepreneurial Winning Woman in 2019, and Connecticut Magazine included her on their "40 under 40" list in 2019. She was also named a "Champion of Change" by the White House in 2014.
Jessica holds a bachelor's degree from the University of Notre Dame and a master's degree from Yale University.