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 - Chicago Fractional CFO Services

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 in Chicago

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.

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. Digital Reference is here to help - need more insight into the world of Finance Professions? - Check out below:

• What are Finance Professionals?
• Do I need a Finance or Accounting Consultant?
• Deep Dive into Finance Executive Responsibilities
• Outsourced CFO Services in the US
• US-Based Financial Advisors
• City Directories of Fractional CFOS
• Save some money -> Outsourced CFO services in India & Outsourced CFO services in Canada

If there is other content that you think we're missing that would help make Finance more authentic and transparent, let us know at hello@digitalreference.co . Thanks for reading! Keep work human!

Explore our International Directories of Part-Time, Fractional, and Virtual CFO Services

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Top Outsourced CFO Agencies in India
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Fractional CFO Services in the United Kingdom (UK)

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Fractional CFO Services in the United States (USA)

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Take a Dive into OurRegional Guides to Fractional & Part-Time CFO Talent

Looking for financial leadership that fits your stage and budget? These city-by-city guides highlight vetted, independent fractional CFOs helping companies grow smarter, operate leaner, and plan with confidence.

Fractional CFOs in Ann Arbor Making Things Happen

Ann Arbor’s deep tech and academic ecosystem is supported by a growing cohort of CFOs who understand innovation, grants, and founder-led finance.

Fractional CFOs in Atlanta Making Things Happen

Atlanta-area fractional CFOs bring sharp financial discipline to fast-growing tech, logistics, and consumer brands across the Southeast.

Fractional CFOs in Austin Making Things Happen

In a city known for startups and scale-ups, these CFOs help Austin companies make smart capital decisions and operationalize growth.

Fractional CFOs in Dallas-Fort Worth Making Things Happen

From fundraising prep to financial operations, these DFW-based CFOs bring high-impact expertise to Texas’s most diverse business hub.

Fractional CFOs in Denver Making Things Happen

Denver’s startups and PE-backed firms are increasingly turning to fractional finance leaders who can help bridge vision and execution.

Fractional CFOs in Detroit Making Things Happen

Detroit’s resurgence is being shaped by finance professionals who know how to manage transformation—from legacy to modern systems.

Fractional CFOs in Houston Making Things Happen

Houston-based fractional CFOs offer clarity and control to companies navigating scale in healthcare, logistics, energy, and services.

Fractional CFOs in Los Angeles Making Things Happen

LA’s creative and tech-driven economy benefits from fractional CFOs who understand cash flow, venture expectations, and brand finance.

Fractional CFOs in Miami Making Things Happen

Miami’s capital influx and startup energy are backed by fractional CFOs helping local companies stay lean, fundable, and focused.

Fractional CFOs in Nashville Making Things Happen

Nashville-based CFOs are powering healthcare, SaaS, and creative businesses with the structure and insight needed for sustainable growth.

Fractional CFOs in New York City Making Things Happen

NYC fractional CFOs bring Wall Street discipline to Main Street startups—from fintech and fashion to media and SaaS.

Fractional CFOs in Phoenix Making Things Happen

Phoenix companies are tapping into a new class of CFOs ready to support capital planning, margin strategy, and finance ops at scale.

Fractional CFOs in San Francisco Making Things Happen

In the heart of venture capital and product-led growth, these SF-based CFOs are helping startups move from story to sustainability.

Fractional CFOs in Tampa Making Things Happen

Tampa’s startup and services economy is supported by CFOs bringing strategic clarity to e-commerce, healthtech, and founder-led orgs.

Fractional CFOs in Washington DC Making Things Happen

DC’s nonprofits, govtech, and professional services firms benefit from fractional CFOs who understand compliance, complexity, and growth.

Careers are long, but life is short. Let’s build a more transparent and efficient financial consulting industry—together. Explore your options. Ask the right questions. And build your team—with transparency and trust.

– The Digital Reference Team

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