Penny Frierson, MBA is the Director of Housing & Financial Resilience at YWCA Metropolitan Chicago, a Wife, and Supermom.
Here is how she is leading beautifully in this season:
“At the end of 2025, I was notified about a week in advance that the grant-funded program I was leading would be ending on December 31st. It was a sudden shift, but it gave me a moment to reflect on where I could have the most impact.
My background started in finance, where I worked on mortgage refinancing and originated Home Equity Line of Credits (HELOCs), and I spent nearly a decade teaching accounting and economics. I also worked in nonprofit and government spaces, including as an SBA Loan Officer, supporting individuals and small businesses in accessing capital during the COVID-19 pandemic and in response to hurricane-related disasters. Those experiences showed how critical housing and financial stability are, especially during times of crisis.
That led to stepping into my current role in February 2026, focused on housing and financial resilience. It allowed me to bring everything together... my finance background, teaching experience, and work in community and economic development, into a more comprehensive approach. The transition felt less like starting over and more like stepping into alignment with the full scope of my experience.
In addition to my formal responsibilities, I lead with a collaborative and creative mindset. I look for ways to connect people, ideas, and programs so our work is more aligned and effective.
I serve on the Leadership Caucus Planning Committee and the AI Steering Committee, contributing to strategy, programming, and how we integrate new approaches. These spaces allow me to bring ideas forward and help shape direction. My background across finance, education, government, and community work helps me work across teams and think through what actually makes sense in practice.
This season, I’ve been more thoughtful about where I spend my time and how I show up. With the transition into a new role, I’ve been intentional about being present in spaces where I can both learn and contribute, especially in conversations that connect housing, finance, and economic empowerment.
One moment that stands out is when I was able to bring multiple partners together around shared goals. That experience opened the door for stronger collaboration and ongoing communication across organizations and more opportunities to contribute and shape how we work together.
It reinforced for me how important relationships and community are, and what can happen when people come together with a clear purpose.”
Connect with Penny! Her journey reflects a thoughtful career evolution, bringing together finance, education, and community impact to advance housing and financial resilience.
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