Fractional CROs in Chicago Making Things Happen in 2025

Chicago Interim Chief Revenue Officers to Know

At Digital Reference, we believe that the future of work is more agile, authentic, and efficient—and nowhere is that more apparent than in the growing ecosystem of fractional executives. In a city like Chicago, known for its gritty business culture and innovation-driven economy, fractional Chief Revenue Officers (CROs) are helping startups scale, corporations pivot, and founders rethink how they build out their revenue engines.

Our goal in building curated content like this is simple: to shine a light on the professionals who are shaping the talent economy by working differently. This is not just a list of names—this is a pulse check on what modern leadership looks like in a city that knows how to hustle.

Each executive featured below is independent, entrepreneurial, and strategically oriented. Many run their own shops or consultancies. All were selected based on digital presence, professional credibility, and regional visibility in the Chicago business ecosystem. We looked at factors like client feedback, past roles, thought leadership, and specialization within B2B, SaaS, finance, and operations-heavy industries.

How We Built This List - Fractional CRO Services

At Digital Reference, we specialize in recognizing the independent leaders who help businesses unlock revenue, build scalable systems, and align go-to-market teams. For this Chicago edition, we evaluated Fractional CROs using a blend of quantitative and qualitative criteria to ensure a balance of strategic expertise and local relevance:

📍 Chicago-based or regionally active
📈 Proven record of revenue leadership and business transformation
🧠 Expertise in GTM alignment, forecasting, enablement, and RevOps strategy
🗣 Presence in the ecosystem—through advisory roles, education, or thought leadership

These are the operators' founders' trust when it's time to scale smarter, fix the pipeline, or build infrastructure for the next stage.

Featured Fractional CRO Service Providers

Mark Joseph

🔗 LinkedIn

Mark is a Chicago-based revenue strategist with experience leading sales transformation across enterprise tech and services firms. As a fractional CRO, he focuses on pipeline optimization, scalable sales models, and aligning revenue orgs with business outcomes. Known for his sharp GTM planning and ability to shift culture quickly, Mark helps companies transition from founder-led chaos to data-driven consistency.

💠 Signature Strengths
📈 Revenue planning and forecasting
📊 GTM execution and roadmap design
📘 Mid-market and enterprise sales leadership
🔍 Sales culture transformation

Liz Kammel Tilatti

🔗 LinkedIn

Liz is a proven founder and revenue executive who brings product-savvy insights to CRO engagements. With deep experience in retail tech, SaaS, and early-stage growth, Liz helps companies define monetization strategies, segment audiences, and sharpen positioning. Her cross-functional leadership style connects marketing, sales, and customer success to build cohesive revenue engines.

💠 Signature Strengths
📘 Monetization and pricing strategy
📈 Sales process creation and team alignment
🔗 Founder-to-scale revenue transitions
💡 Customer segmentation and product positioning

Doug Miller

🔗 LinkedIn

Doug is a results-focused interim revenue leader with a track record of helping organizations expand into new markets and drive sustainable ARR growth. He blends RevOps structure with agile execution, delivering clarity across sales cycles, enablement programs, and performance dashboards.

💠 Signature Strengths
📊 Revenue operations and data enablement
📘 Sales team structure and process clarity
📈 New market entry strategy
🔍 Dashboarding and performance metrics

John Rospenda

🔗 LinkedIn

John helps B2B SaaS and services companies turn GTM complexity into streamlined execution. With experience across private equity-backed firms and venture-stage startups, he designs scorecard-aligned sales programs, reduces friction in the sales cycle, and ensures sales and marketing stay aligned on outcomes.

💠 Signature Strengths
📈 PE-backed GTM execution
📊 Scorecard alignment and sales incentives
📘 Conversion optimization
🔗 Marketing and sales team alignment

Jeff Lundal

🔗 LinkedIn

Jeff is a strategic commercial executive who brings decades of experience leading sales and partnerships across health tech, logistics, and enterprise software. His fractional CRO work emphasizes strategic partnerships, long-cycle deal acceleration, and revenue expansion through channel ecosystems.

💠 Signature Strengths
📘 Channel partnerships and alliances
📈 Strategic account growth
🔍 Long-cycle B2B deal optimization
📊 GTM partnerships and integrations

Why This List Matters

This list isn’t just a roll call of talented executives—it’s a curated resource for Chicago founders, CEOs, and revenue leaders who need strategic support without the overhead of a full-time hire. The Fractional CROs featured here reflect the dynamic needs of a growing business ecosystem, offering adaptable, high-impact leadership exactly when and where it’s needed most.

In Chicago’s competitive and often capital-efficient market, revenue challenges don’t wait. These professionals bring senior-level go-to-market expertise to early and growth-stage companies, helping them refine product-market fit, implement scalable sales systems, and unify marketing, sales, and customer success under one cohesive revenue strategy.

More than just interim operators, these CROs are systems builders. They’ve led inside SaaS startups, fintech disruptors, B2B services firms, and operationally intensive businesses across the Midwest. They know how to create accountability, introduce process clarity, and turn inconsistent sales motions into reliable revenue engines.

Each name on this list was selected for their ability to lead with both strategy and empathy—delivering results, building infrastructure, and elevating the teams they work alongside. From River North to the West Loop, these leaders are shaping the future of revenue in one of the country’s most resilient business hubs.

If you're in Chicago and looking to drive smart, sustainable growth, these are the people you want in your corner.

A Note from Digital Reference

We believe great revenue leadership doesn’t have to be full-time to be transformational. Whether you’re a founder building your first GTM engine or an executive team rethinking your approach to scale, we’re here to help spotlight the Fractional CROs driving results behind the scenes.

Want to recommend someone for this list? Get in touch.
Want to be part of this conversation? You’re already in the right place.

Learn More

• How to Hire a Revenue or Sales Consultant
  
  
• Revenue Consultants vs. Sales Experts: What Do They Do?
  
  
• What Are Revenue Professionals and What Do They Do?
  
  
• Find Fractional CROs Near Me
  
  

At Digital Reference, we help Fractional CROs stand out in a competitive market. Our platform supports executive operators, GTM architects, and RevOps leaders with structured, verified insights that elevate visibility and build trust.

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If you're a Fractional CRO ready to grow your reputation and attract better opportunities, join Digital Reference today and take ownership of your professional narrative.

Written by the Digital Reference editorial team. We spotlight the people behind the pipelines—empowering the operators, strategists, and builders who drive revenue forward.