10 Years of Breaking Barriers for Women in Commercial Real Estate Finance

Nuveen Green Capital co-founders Jessica Bailey and Ali Cooley discuss their career paths as women in traditionally male-dominated industries.

As we enter Women’s History Month and Nuveen Green Capital celebrates its 10th anniversary since its founding, our co-founders, President and CEO, Jessica Bailey and Chief Investment Officer, Alexandra (Ali) Cooley, reflect on their journey to becoming leaders within the commercial real estate (CRE) and finance industries. Not only are they pioneers of the C-PACE industry, but they have also disrupted the predominantly male-dominated industries of finance and CRE in which they’ve operated.

As President and CEO, Jessica led NGC’s expansion from a small startup, Greenworks Lending, to a high-growth firm acquired by $1 trillion+ asset manager, Nuveen in 2021. Jessica has helped expand the C-PACE platform to 40 states, while achieving double digit origination growth each year, deploying over $3.3 billion in private capital to C-PACE projects across the country. 

As Chief Investment Officer, Ali develops and leads NGC’s investment strategy, including capital markets, finance, credit, portfolio, and asset management. She oversaw the C-PACE industry’s first securitization of C-PACE-backed assets, as well as the largest 144A securitization of C-PACE assets, followed by two more securitizations.¹ In addition, she spearheaded the groundbreaking launch of the Nuveen CPACE Lending Fund, a new, first-of its kind fund, designed to give insurers access to a diversified portfolio of C-PACE’s energy efficient, climate resilient, water conservation and renewable energy projects.

Where are you from originally?

JB: Oak Park, Illinois - just outside of Chicago

Ali: Westport, Connecticut

What was your first job?

JB: When I graduated college, I got a fellowship in Washington, DC that didn’t pay nearly enough to actually live in DC, so I started hostessing at one of the busiest DC restaurants. They didn’t take reservations, so my job was to try to keep people waiting and happy. I think everyone should work in the service industry at some point because it was incredibly humbling, and I learned a ton. You’ve got to manage the waitlist, lighten the mood of hungry, cranky people, and try to keep people from leaving. Let’s just say I probably gave out the most free drinks of any hostess! But this early ability to balance and juggle perhaps served as early training for the future leadership roles I took on. 

Ali: My first job was in high school starting a company with my best friend that made jewelry and sold it to retail stores on Westport’s growing main street. I have always had a creative and entrepreneurial streak, so this was perhaps an early sign that I was meant to start a business! 

What brought you to commercial real estate finance?

Ali: I started off in management consulting but went to business school because I wanted to pivot into enabling clean energy projects. That led me to the Connecticut Green Bank after graduation, where I learned about C-PACE from Jessica and became convinced that this public-private financing mechanism was scalable and could provide financing benefits, while aiding in decarbonization. 

JB: It’s probably not the most common route… but it was from public policy. An early job working for the Rockefeller Brothers Fund tasked me with supporting policies to reduce carbon emissions. I quickly realized that a huge percentage of emissions came from buildings, and then realized that the lack of attractive financing for energy reducing upgrades to real estate was a huge market failure. C-PACE emerged as a solution to the challenge, and we were off to the races!

How did you go about scaling a first successful C-PACE program?

Ali: It is hard to believe, but we actually wrote part of our first plan on a napkin. We started out small by testing the waters in Connecticut. While we saw early evidence of scalability in our home state, we had our work cut out for us to build this into something larger! Each stakeholder of our business – from policy makers to borrowers to capital markets – had to be educated in lockstep to ensure we built the business sustainably.

JB: When I think back to those early days, the image of a stool with three uneven legs comes to mind. Our job was to keep the stool level while adding to each of the three legs – expanding the policy, selling the product to commercial real estate owners, and raising capital to lend through C-PACE programs. Right-scaling growth among those three key stakeholders was critical to building the industry and our company within it.

What are some challenges you faced and overcame in the industry?

Ali: Early on, we saw evidence of demand for C-PACE as an investment platform, but it was challenging to wedge the door open because the asset class was so new, and our team came from the public sector. Once we did, though, we were able to explain what we knew was a tremendous opportunity to make a positive impact on the CRE industry, while providing significant returns. 

JB: There was no playbook for us to follow because we were trying to build a company in an industry that didn’t really exist. The white space was sometimes overwhelming. Ali and I literally had to convince people that this industry would exist and that we were the right team to win within it. Ali and I stood out as two of very few females in CRE finance, in structured credit, and in clean energy. This almost became like a superpower for us. We were sometimes met with a tone of dismissiveness by men who would suggest that they could “take it from here, ladies.” There was a lot of eyerolling when Ali and I would get into the elevator after those meetings – but they really served as fuel for us to keep pushing forward. 

Advice for aspiring women?

Ali: Find the right people to partner with and surround yourself. Working with Jessica has been a tremendous benefit, because while we are very different people with different approaches – we have similar values, vision and mindsets. Our skillsets complement one another and together we have been able to accomplish more together. We also had a phenomenal group of initial investors, who were generous with their time and focus; this enabled us to leverage significant relevant experience as we were building the business.

JB: As Ali says, it’s all about the people. One of the most crucial early decisions we made was to surround ourselves with the right people who we trusted and who trusted us.  Many of our colleagues were -and are- women, but we also have some outstanding men who have been with us since the start. We have also made a point of putting capable people in roles outside of their backgrounds or experience, which has led to business breakthroughs resulting from their perspectives. Don’t wait for “the grownups” to enter the room – the truth is no one has a blueprint of what success looks like.  

Is there anything that you would do differently?

JB: While we have been able to navigate numerous challenges, including the pandemic and the financial crisis, all while “building this plane as we fly it,” I think I would tell my younger self that it is ok to try a couple directions, even if one of them proves to be wrong. Our former COO and one of our first employees had a phrase, “always forward, but never straight.” That about sums up how we broke the barriers to get C-PACE from an idea to an asset class. The learning is often gained by going down a path that may not work at the outset or have been right for the business. It makes you more knowledgeable – and a stronger leader. 

Ali: I have evolved as a leader in terms of my ability to focus on the things that matter. As a finance specialist, one can get immersed in detail, whereas much of the success in this field is tied to listening to your team, reading/hearing differing views and synthesizing the information at hand to move forward while balancing many important initiatives. One thing I would do differently would be to focus more effort on managing myself – I realized through this process that I make much clearer decisions when I’m calmer and able to focus my effort on what really matters. I’d rely on the team more if I were to go back - which is easy to say now, because in hindsight, it’s clear we have built an incredible team!