Fractional CFOs in Chicago Making Things Happen in 2025

Chicago Interim Chief Financial Officers to Know

Chicago is a city that thrives on business grit and financial ingenuity. From legacy industries to emerging startups, the Windy City is home to businesses navigating complex challenges—and behind many of those operations is a fractional CFO making sense of the numbers, optimizing operations, and guiding the financial narrative.

At Digital Reference, our mission is to create a more transparent, authentic, and efficient talent ecosystem. That means highlighting not just the roles people play, but the value they bring. This blog is part of our living series designed to spotlight the professionals working behind the scenes to help companies scale smarter.

Today, we’re introducing you to a standout roster of fractional CFOs based in Chicago. These independent financial leaders are driving clarity and growth across sectors—from e-commerce and SaaS to service-based companies and social impact ventures.

Our Methodology

We selected each individual featured in this list based on:

• Proven experience offering fractional or interim CFO services
• A presence in Chicago or surrounding cities
• Public-facing thought leadership, consulting platforms, or a track record of service
• Demonstrated alignment with the principles of transparency, operational rigor, and authenticity

This list will evolve. If you’re a founder or executive looking for CFO leadership in the Midwest, consider this your starting point. If you’re a CFO doing great work in the region, get in touch—we’re always updating.

Featured Fractional CFOs

Chris Gwinn

https://midwestcfo.com/about-us/
Chris Gwinn is the founder of Midwest CFO and brings a powerful combination of data-driven decision-making and business acumen to his client work. Specializing in fractional CFO and exit readiness services, Chris supports CEOs in achieving profitability, scale, and strategic clarity.

Specialties:

• Exit planning and transaction readiness
• Operational efficiency and KPI design
• Profitability analysis and systems optimization

His practical and collaborative approach makes him a go-to advisor for small and midsize business leaders.

James Dillion

https://www.linkedin.com/in/james-dillion/
James Dillion is a strategic finance professional with a background in both private equity and operational finance. As a fractional CFO, he supports companies navigating growth, cost restructuring, and due diligence.

Specialties:

• Financial modeling and M&A support
• Operational budgeting
• Investor relations and board reporting

He brings the poise and precision needed to manage financials at every stage of a company’s lifecycle.

Kimberly Stanley

https://kimberlyandcompany.io/
Founder of Kimberly & Company, Kimberly Stanley is a dynamic CFO who blends finance with culture-building. Her boutique firm works with founders to drive clarity, financial storytelling, and team alignment.

Specialties:

• Women- and minority-led businesses
• Startup and founder coaching
• Fractional CFO services with embedded team support

Kimberly is known for making finance both inclusive and empowering for leadership teams.

Lowell Mora

https://www.linkedin.com/in/lowellmora/
Lowell brings decades of operational leadership experience to his work as a fractional CFO, helping companies build financial discipline and drive performance.

Specialties:

• Growth-stage operations
• KPI-driven forecasting and scenario planning
• Turnaround support and cash flow management

His impact is felt most in businesses ready to scale but in need of financial clarity to do so.

Rachael Brinker

https://khulas.com/
Rachael is the founder of KhulA Consulting, a firm offering strategic financial leadership to mission-driven organizations and startups. Her work lives at the intersection of financial acumen and social impact.

Specialties:

• Nonprofit and social enterprise finance
• Financial operations strategy
• Equity-focused budgeting and growth planning

Rachael brings a sharp lens for both numbers and values—helping her clients build financial models rooted in impact.

Rich Smolen

https://www.smolenconsultingcfo.com/
Rich is the principal at Smolen Consulting CFO, where he provides fractional CFO services to business services companies under $50M in revenue. Known for his clarity and thoroughness, Rich partners with CEOs to professionalize their finance function.

Specialties:

• Budget development and strategic planning
• Cash flow improvement
• Profitability optimization for SMBs

His quiet, steady leadership is often exactly what teams need to make bold moves with confidence.

Sarah Britt

https://www.linkedin.com/in/sarah-britt-4504b37/
Sarah offers fractional CFO services to founders and leadership teams in transition—whether navigating scale, restructuring, or early growth.

Specialties:

• Financial operations cleanup
• Interim finance team leadership
• Modeling and forecasting

She brings grounded energy to businesses building their first finance foundation.

Tom Dillon, CFA

https://www.linkedin.com/in/tom-dillon-cfa/
Tom provides CFO advisory services to SaaS, eCommerce, and SMB clients through a modern lens. He combines traditional finance with a startup-friendly mindset to guide his clients through ambiguity.

Specialties:

• Digital business finance modeling
• Cost of acquisition (CAC) and lifetime value (LTV) analysis
• FP&A and growth-stage metrics

Tom is a sharp operator with a strategic mind—well suited for businesses focused on high-performance growth.

Tony Olivito

https://www.linkedin.com/in/tonyolivito/
Tony is a hands-on CFO with a background in media, finance, and high-growth environments. As a fractional executive, he builds systems that make finance a strategic asset rather than a reporting function.

Specialties:

• Media and content business finance
• Dashboard creation and automation
• Revenue forecasting and reporting transparency

His mix of creativity and analytics makes him a rare and valuable leader across industries.

Bill Raspe

https://www.linkedin.com/in/williamraspe/
Bill leads Bright Future CFO Services and specializes in helping businesses prepare for exits and M&A activity. With a calm demeanor and deep experience, he helps owners see the full picture.

Specialties:

• Business sale and acquisition readiness
• Cash flow and forecasting
• Exit strategy consulting

Bill is especially helpful for founders considering transitions—and needing a partner who’s been there before.

Why Fractional CFOs Matter More Than Ever

In today’s economic landscape, companies can’t afford to treat finance as an afterthought. Whether it's managing cash runway, pricing strategy, or investor reporting, strategic financial leadership is non-negotiable.

Fractional CFOs bring C-suite strategy at a part-time cost, allowing growing companies to:

• Understand their burn and profitability
• Make investment-ready decisions
• Forecast with confidence
• Communicate clearly with internal and external stakeholders

In cities like Chicago, where a rich mix of startups, mid-sized firms, and mission-driven orgs all coexist, fractional leaders are the glue between operational hustle and sustainable growth.

Digital Reference: A Platform for Work That Speaks for Itself

At Digital Reference, we empower professionals to build structured portfolios of their work, backed by verification and radical authenticity. For leaders like the ones featured above, we believe:

• Your expertise should be findable
• Your impact should be documentable
• Your work should travel with you

That’s why we create space for independent leaders—especially in fractional roles—to be seen, celebrated, and connected to opportunity.

Want to Be Featured?

If you’re a fractional CFO in the Chicago area and believe your work aligns with this community, we want to hear from you. This is a living list—meant to evolve, expand, and reflect the real work being done by fractional leaders across the region.

We’re proud to amplify the professionals behind the spreadsheet magic.

– The Digital Reference Team

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