Few professionals embody the intersection of leadership, service, and finance as gracefully as Courtney Olson, Senior Vice President and Managing Director of Business Banking at First Bank Chicago. As a standout member of Angeles Investors, Olson has made a name for herself as a community development lending expert in Chicago, shaping the trajectory of small businesses and nonprofits through her innovative, people-first approach to finance.
With over 20 years of experience in nonprofit lending, treasury services, and business advisory, Olson continues to impact the financial landscape in Illinois, especially for Hispanic entrepreneurs and women-led organizations. Her career offers a blueprint for how community banking in Chicago can fuel positive transformation for both the private and nonprofit sectors.
A Career Rooted in Impact and Business Strategy
Courtney Olson’s journey in banking began with a clear mission: to empower people through personalized financial solutions. Her early years as Vice President at NorthSide Community Bank set the stage for a multifaceted career in commercial lending, deposits, and customer relationship development. It was there that she began to hone her specialization in cash flow management for small businesses, working closely with business owners and CFOs to identify financial pain points and opportunities.
At First Bank of Highland Park, Olson advanced to senior leadership, where she championed holistic banking strategies for nonprofits. Her advisory approach to clients, balancing technical knowledge with relationship-building, solidified her as a go-to resource for companies navigating complex economic conditions. Over time, she developed a reputation as a treasury management advisor for nonprofits, someone who could demystify banking for organizations with mission-driven goals.
Current Leadership: Transforming Banking Solutions at First Bank Chicago
Now serving as SVP and Managing Director at First Bank Chicago, Olson leads a dedicated team focused on nonprofit banking services in Illinois, business lending, and treasury operations. Her signature offering lies in constructing financial strategies for mission-driven organizations, solutions that reflect both fiscal discipline and social responsibility.
Olson’s unique role requires her to work with nonprofit leaders, often helping them overcome the same cash flow challenges faced by their for-profit counterparts. She tailors her strategies by offering nonprofit lending programs that align with organizational goals, whether for capacity expansion or operational sustainability.
What sets Olson apart is her dual commitment to affordable housing finance leadership in Chicago and scalable business support. As a voting member of the Multifamily Loan Committee at the Community Investment Corporation, she plays a pivotal role in underwriting deals that impact neighborhood revitalization and equitable housing development.
Angel Investing & Community Mentorship with Angeles Investor
As a member of Angeles Investors, Olson exemplifies the power of financial leadership in angel investing circles. Her contributions go far beyond monetary investment—she brings business banking insights for CFOs, mentoring early-stage founders on how community banks support nonprofits and private ventures alike.
Olson’s dedication to uplifting Hispanic and Latinx entrepreneurs is both personal and professional. She uses her platform to advocate for banking support for Hispanic entrepreneurs, offering her strategic expertise to help founders scale and attract responsible capital.
Whether participating in pitch sessions or guiding startups through financial planning, Olson bridges the gap between access and opportunity—living proof that empowering women through financial leadership isn’t just aspirational, it’s operational.
Thought Leadership: Financial Empowerment Through Service
A strong proponent of integrating community development lending into mainstream banking models, Olson continues to raise the standard for what a community development lending expert in Chicago can achieve. Her efforts with the Center for Enriched Living (CEL) and other nonprofits reflect a deep-seated belief in giving back to the communities she serves.
Recognition has followed. In 2024, Olson was honored by the Illinois Bankers Association as a Woman of Impact—an acknowledgment of her excellence in treasury management, commitment to nonprofits, and broader financial leadership. Her philosophy is simple: “Use your skills to lift others.” For Olson, that includes driving access to financial solutions for nonprofit organizations that often operate on limited margins and big missions.
Her insights have helped reshape how banks view mission-aligned financing. Through treasury management, Olson teaches that nonprofits aren’t just charitable institutions; they’re strategic economic players in need of customized banking models.
Join a Movement of Impact with Angeles Investors
If you’re inspired by professionals who combine technical expertise with community stewardship, look no further than Courtney Olson. Her membership in Angeles Investors is not just a credential, it’s a call to action. By supporting banking support for Hispanic entrepreneurs and scaling financial strategies for mission-driven organizations, Olson champions a model of economic empowerment that resonates across sectors.
Whether you’re a founder in need of cash flow management for your small business, a nonprofit navigating complex compliance rules, or an investor seeking high-impact opportunities, connecting with leaders like Olson through Angeles Investors is your next smart move.
A Legacy of Finance, Service, and Leadership
Courtney Olson’s influence spans from bank boardrooms to community centers, from corporate strategy to nonprofit missions. Her work in nonprofit banking services in Illinois, her leadership in affordable housing finance in Chicago, and her ability to deliver holistic banking strategies for nonprofits define her as a change-maker in every sense of the word.
By aligning financial excellence with community development, Olson has carved a path for others to follow. For those navigating the intersections of business, mission, and impact, Courtney Olson is the advisor, mentor, and investor you want in your corner.
Share this article:
Join our dynamic community at Angeles Investors and unlock access to diverse opportunities and valuable connections. Whether you’re an experienced investor or just starting, our platform provides the resources and support you need to grow and succeed. Explore the benefits of membership and become part of a thriving network dedicated to fostering growth and innovation. View membership options here: https://angelesinvestors.com/membership/
