Best Fractional CFO Services in Chicago

‍Top Chicago Fractional CFO Companies & Fractional CFOs

Chicago has long been a major center of commerce, finance, manufacturing, logistics, professional services, and entrepreneurship. From established middle-market businesses and family-owned companies to growing SaaS ventures and startups, organizations across the city need financial leadership that can keep pace with changing markets, operational demands, and growth opportunities.

Enter the fractional CFO: a flexible, strategic financial executive who brings senior-level expertise to a business without requiring the cost or commitment of a full-time CFO.

At Digital Reference, our mission is to showcase professionals more authentically and transparently. That means highlighting the independent executives doing meaningful work behind the scenes—professionals helping businesses strengthen financial operations, improve forecasting, prepare for growth, navigate transactions, and make more informed decisions.

This curated list of Fractional CFOs in Chicago highlights financial leaders supporting organizations across a wide range of industries. Some operate independently, while others lead boutique or larger finance firms—but all bring specialized experience to companies navigating growth, restructuring, optimization, or important financial transitions.

As a living list, this article will continue to evolve. We encourage you to bookmark it and return as we identify and spotlight more fractional finance professionals serving Chicago and the surrounding Midwest region.

‍

‍‍

🌟 Our Methodology - How We Built This List of Top Fractional CFO Services in Chicago

Each fractional CFO and fractional CFO company featured below has been selected through a qualitative research process based on the following criteria:

• Chicago presence (including surrounding areas across the Chicagoland region). 
• Current practice as a fractional, interim, part-time, or contract-based CFO
• Professional visibility, including a clear LinkedIn profile, company website, consulting presence, or demonstrated thought leadership
• Relevant experience working with startups, privately held businesses, professional services firms, PE-backed companies, family-owned organizations, or growth-stage ventures
• Alignment with Digital Reference’s values of transparency, authenticity, strategic thinking, and professional credibility

These are fractional CFO service providers helping Chicago businesses gain greater financial clarity—and helping founders, owners, and leadership teams make more informed, data-driven decisions.

‍

‍‍

🌟 Digital Reference's List of Best Fractional CFO Companies in Chicago

For organizations that prefer the resources and infrastructure of a firm rather than working directly with an individual fractional executive, Chicago offers a diverse range of fractional CFO providers. These companies support businesses with financial strategy, forecasting, reporting, cash-flow management, accounting oversight, fundraising, operational finance, and transaction preparation.

The firms below were selected based on their Chicago market presence, fractional or outsourced CFO capabilities, professional visibility, and experience supporting growing and established businesses. Chicago's fractional finance landscape includes both local specialists and larger providers with dedicated regional teams, giving companies flexibility in finding a model that matches their size, industry, and financial needs.

‍‍

📈 Third Road Management

Third Road Management provides fractional CFO and strategic financial leadership for businesses that need experienced finance support without committing to a full-time executive. The firm works with leadership teams to improve financial visibility, strengthen planning, and make more informed decisions around growth and performance.

Notable Services:

• Fractional CFO and financial leadership
• Financial planning and forecasting
• Business performance analysis
• Strategic planning and decision support
• Cash-flow and financial management

Third Road Management may be a strong fit for growing companies seeking practical CFO-level guidance and a more structured approach to financial decision-making.

Founded by:

John Frank, Founder & CEO. Frank brings an executive perspective to financial strategy and business management, helping companies navigate growth, improve performance, and build stronger financial foundations.

‍‍

📈 Coveted Financial Services

Coveted Financial Services provides financial management and advisory support designed to help businesses gain greater control over their financial operations. Its approach combines financial expertise with practical business guidance, giving leaders the insight they need to plan, manage performance, and pursue sustainable growth.

Notable Services:

• Financial management and advisory
• Strategic financial planning
• Business performance analysis
• Cash-flow management
• CFO-level financial guidance

Coveted Financial Services may be a good fit for organizations looking for experienced financial leadership and clearer visibility into the numbers behind their business.

Founded by:

Joe Schmidt, President & CEO. Schmidt leads the firm with a focus on helping businesses strengthen financial management and make more informed strategic decisions.

‍‍

📈 A Fractional CFO, LLC

A Fractional CFO, LLC provides flexible CFO-level financial leadership to businesses that need strategic expertise without the expense of a traditional full-time CFO. The firm focuses on helping companies improve financial planning, strengthen reporting, and use financial information more effectively as they grow.

Notable Services:

• Fractional CFO services
• Financial planning and forecasting
• Cash-flow management
• Financial reporting and analysis
• Strategic business advisory

A Fractional CFO, LLC may be a strong fit for small and growing businesses that need hands-on financial leadership as their operations become more complex.

Founded by:

Russ Cramer, Principal & Fractional CFO. Cramer provides hands-on CFO support focused on helping business leaders better understand their financial position and make stronger decisions around growth and performance.

‍‍

📈 Pivot Capital LLC

Pivot Capital LLC provides strategic advisory and financial guidance for businesses facing important growth, capital, and corporate development decisions. Its approach combines financial analysis with broader strategic thinking to help leadership teams evaluate opportunities and navigate periods of change.

Notable Services:

• Strategic financial advisory
• Growth and capital planning
• Financial analysis and modeling
• Corporate development support
• Business and investment strategy

Pivot Capital may be particularly relevant for companies facing capital decisions, strategic transitions, or growth opportunities that require an investment-oriented perspective.

Founded by:

Rakesh Parikh, Managing Director. Parikh brings an investment and strategic advisory perspective to his work, helping businesses evaluate financial opportunities and make more informed decisions around growth and capital.

‍

📈 Warrior Group

Warrior Group provides fractional CFO and strategic business support for companies that need experienced financial leadership without adding a full-time executive. The firm takes a hands-on approach to helping business leaders improve financial visibility, strengthen operations, and connect financial performance with broader business objectives.

Notable Services:

• Fractional CFO services
• Financial strategy and planning
• Cash-flow management and forecasting
• Business performance analysis
• Strategic operational support

Warrior Group may be a strong fit for business owners seeking an engaged financial partner who can connect day-to-day financial management with long-term growth strategy.

Founded by:

Donny Mashiach, Fractional CFO, Founder & CEO. Mashiach combines CFO-level financial guidance with entrepreneurial leadership, working closely with businesses to improve financial decision-making and overall performance.

‍‍

🌟 Digital Reference's List of Best Fractional CFOs in Chicago

‍

📊 Chris Gwinn

As the founder of Midwest CFO, Chris Gwinn combines data-driven financial strategy with practical business leadership. His work as a fractional CFO focuses on helping CEOs improve profitability, strengthen operations, and prepare their companies for successful exits.

Notable Expertise:

• Exit planning and transaction readiness
• KPI development and operational efficiency
• Profitability analysis and financial systems optimization

Chris is a strong fit for small and midsize businesses seeking greater financial clarity, operational discipline, and strategic direction.

‍‍

📊 James Dillion

James brings a blend of private equity experience and hands-on operational finance to his fractional CFO work. He partners with companies navigating growth, restructuring, and complex financial decisions, bringing a measured approach to both strategy and execution.

Notable Expertise:

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

James is well suited for organizations entering periods of growth, transformation, or increased investor and stakeholder scrutiny.

‍‍

📊 Kimberly Stanley

Founder of Kimberly & Company, Kimberly Stanley takes a people-centered approach to CFO leadership. She combines financial strategy with culture-building, financial storytelling, and founder coaching, helping leadership teams better understand and communicate their numbers.

Notable Expertise:

• Women- and minority-led businesses
• Startup and founder financial coaching
• Fractional CFO leadership and embedded team support

Kimberly is particularly valuable for founders looking to make finance more accessible, collaborative, and empowering across the organization.

‍‍

📊 Lowell Mora

With decades of operational leadership experience, Lowell Mora brings a performance-focused perspective to fractional CFO work. He helps growing businesses establish stronger financial discipline while using forecasting, KPIs, and scenario planning to support better decisions.

Notable Expertise:

• Growth-stage operations and financial leadership
• KPI-driven forecasting and scenario planning
• Turnaround strategy and cash flow management

Lowell is a strong partner for businesses that have momentum but need greater financial structure and visibility to scale sustainably.

‍‍

📊 Rachael Brinker

Rachael Brinker is the founder of KhulA Consulting, where she provides strategic financial leadership to startups and mission-driven organizations. Her work brings together financial rigor and social impact, helping organizations build systems that support both sustainability and purpose.

Notable Expertise:

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

Rachael is an excellent fit for organizations that want to build financially sustainable models without losing sight of their mission or values.

‍‍

📊 Rich Smolen

As principal of Smolen Consulting CFO, Rich Smolen provides fractional CFO support to business services companies, particularly those generating less than $50 million in revenue. His approach centers on clarity, financial discipline, and practical planning that helps CEOs make confident decisions.

Notable Expertise:

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

Rich is a strong choice for business owners looking to professionalize their finance function and create a stronger foundation for growth.

‍‍

📊 Tom Dillon, CFA

Tom Dillon brings a modern, growth-oriented perspective to CFO advisory work across SaaS, eCommerce, and small and midsize businesses. He combines traditional financial expertise with startup-friendly thinking, helping companies turn complex metrics into actionable decisions.

Notable Expertise:

• Digital business financial modeling
• CAC and LTV analysis
• FP&A and growth-stage performance metrics

Tom is particularly well suited for businesses focused on high-performance growth, recurring revenue, and data-driven decision-making.

‍‍

📊 Tony Olivito

Tony Olivito brings experience across media, finance, and high-growth environments to his work as a fractional CFO. His approach focuses on building financial systems, dashboards, and reporting processes that transform finance from a back-office function into a strategic resource.

Notable Expertise:

• Media and content business finance
• Financial dashboards and automation
• Revenue forecasting and reporting transparency

Tony is a strong fit for companies that need better financial visibility without sacrificing speed, creativity, or operational flexibility.

‍‍

📊 Bill Raspe

Bill Raspe leads Bright Future CFO Services and specializes in helping business owners prepare for exits, acquisitions, and other major transitions. His calm, experienced approach gives owners greater visibility into their financial position and helps them prepare for what comes next.

Notable Expertise:

• Business sale and acquisition readiness
• Cash flow management and forecasting
• Exit strategy and transaction planning

Bill is especially valuable for founders and owners preparing for a major transition and looking for experienced financial guidance along the way.

‍

‍‍

Using Digital Reference to Find the Best Fractional CFO Services in Chicago For Your Needs

Chicago’s diverse business landscape calls for fractional CFOs who can bring strategic clarity without the cost of a full-time executive. Whether a company is preparing for growth, restructuring operations, managing cash flow, or planning an exit, fractional CFOs provide the financial leadership needed to navigate complex decisions with confidence.

They’re not just number crunchers. They’re:

• Strategists who connect financial decisions to business goals
• Translators who turn complex financial data into actionable insights
• Architects who build scalable systems, forecasts, and processes

At Digital Reference, we believe in professional storytelling backed by structured data, verification, and social proof. Our platform gives fractional leaders a place to:

• Showcase their experience through structured, verified portfolios
• Share references and testimonials that build trust
• Present their expertise and thought leadership in a credibility-focused format

This guide is one of the ways we help professionals show the work behind the title and make their expertise easier for organizations to discover.

Looking to hire a fractional CFO in Chicago?

Bookmark this list. Looking to become one? Let Digital Reference help you build a professional digital footprint with purpose.

This is a living list, and we’re always looking to highlight more fractional CFOs making an impact across Chicago and the surrounding business community. If you are—or know—a standout Chicago-based fractional CFO, reach out to Digital Reference.

We’re building the infrastructure that makes talent visible, verifiable, and more human.‍

‍

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

Fractional CFO Services in Australia

Top Outsourced CFO Agencies in Australia
Explore a list of top fractional CFO firms in Australia offering part-time financial leadership to startups and growth-stage companies.

Fractional CFO Services in Canada

Top Outsourced CFO Agencies in Canada
A curated directory of top Canadian firms offering outsourced and fractional CFO services, with a strong emphasis on affordability and financial clarity.

Fractional CFO Services in India

Top Outsourced CFO Agencies in India
India's growing ecosystem of financial leadership includes cost-effective, high-impact CFO services for scaling companies.

Fractional CFO Services in the United Arab Emirates (UAE)

Top Outsourced CFO Agencies in the UAE
A roundup of leading part-time CFO firms in Dubai and beyond, offering strategic support for regional and international ventures.

Fractional CFO Services in the United Kingdom (UK)

Top Outsourced CFO Agencies in the UK
From London to Leeds, this list highlights some of the best interim CFO providers for UK-based startups and SMEs.

Fractional CFO Services in the United States (USA)

Top Outsourced CFO Agencies in the USA
A national view of leading firms offering fractional CFO services to startups, family businesses, nonprofits, and more.

‍

Take a Dive into Our Regional 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