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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.
Mark Joseph
With decades of experience in B2B SaaS and enterprise growth strategies, Mark Joseph is one of Chicago's most versatile revenue leaders. As a fractional CRO, he’s not just about high-level strategy—he’s known for jumping into the weeds to rebuild sales processes, coach underperforming teams, and identify scalable revenue opportunities.
His experience includes leadership roles in both early-stage startups and mature organizations. What makes Mark unique is his pragmatic, data-driven approach that blends CRM optimization with human-centered leadership. A natural problem solver, Mark helps clients shift from reactive selling to proactive go-to-market strategy.
Liz Kammel Tilatti
A founder-turned-fractional executive, Liz Kammel Tilatti brings a rare mix of creative marketing insight and revenue operations savvy. As the former CEO of a successful fashion-tech company, she understands the intersection of growth, brand building, and customer experience better than most.
Her strength lies in translating storytelling into revenue results. Companies work with Liz when they’re seeking more than pipeline volume—they want strategic clarity. Her work often includes helping companies reposition their offering, rebuild their GTM strategy, and craft revenue playbooks that reflect today’s buyer behavior.
What sets Liz apart? Her ability to build trust quickly with marketing and sales teams, and her deep roots in both the startup and investor communities in Chicago.
Doug Miller
Doug Miller is a veteran CRO and revenue strategist who focuses on helping mid-market companies tackle scale-stage challenges. With a track record across SaaS, logistics, and services businesses, Doug brings structured thinking to organizations that are hitting their first or second big growth wall.
His expertise includes revenue forecasting, sales team restructuring, and aligning sales and marketing teams under unified KPIs. Doug often plugs in for 3–6 month engagements where his goal is to build the right team, process, and reporting framework before handing off a clean playbook.
Known for his calm leadership and no-fluff communication style, Doug is a go-to for companies that need grown-up revenue thinking—fast.
John Rospenda
John Rospenda is a go-to-market operator with experience scaling sales and partnerships teams across North America. With a background in financial services and fintech, John works particularly well with companies trying to sell into complex, regulated environments.
Clients appreciate John's cross-functional mindset: he doesn’t just think sales, he thinks product, customer success, and finance. He helps leadership teams design compensation structures, model out CAC-to-LTV, and operationalize demand generation.
Looking for someone who can bridge the gap between board expectations and frontline execution? John’s your guy.
Jeff Lundal
Jeff Lundal has deep roots in enterprise sales, having worked with Fortune 500 clients and led teams through multiple industry transformations. As a fractional CRO, he brings executive presence and process discipline to fast-moving organizations.
What makes Jeff unique is his passion for aligning GTM strategy with company mission. He’s helped multiple clients transform underperforming sales departments into high-trust, high-conversion machines—often without expanding headcount.
Jeff is especially effective in high-stakes moments: product launches, post-funding revenue acceleration, and geographic expansion efforts.
Why It Matters: The Rise of Fractional CROs in Chicago
Chicago's business DNA is a blend of industrial grit and emerging innovation. From fintech to food tech, local companies are facing an increasingly competitive market—and they need revenue leaders who can help them scale with speed and intentionality.
Fractional CROs allow founders and CEOs to bring in seasoned leadership without long-term overhead. But the real value? These leaders come in ready to make decisions. They’ve done this before. They know how to set strategy Monday and run a team call Tuesday. In an era where speed to market can make or break a business, that experience is priceless.
What to Look for in a Fractional CRO
When choosing a fractional CRO, look for:
- Industry Fit: Does their experience match your business model?
- Stage Alignment: Are they comfortable with the chaos of early stage? Or do they specialize in post-Series B scale?
- Hands-On Approach: Will they just advise? Or will they actually run point on deals and pipeline reviews?
- Data Fluency: Do they know your KPIs cold? Can they build the dashboards that matter?
Related Reading from Digital Reference
- Top Outsourced COO Agencies in the USA
- Ray Dalio’s Baseball Cards & Digital Reference
- Revenue Consultants & Sales Experts: What Do They Do?
About Digital Reference
At Digital Reference, we are building a more transparent and efficient professional talent ecosystem. Our platform is home to verified references, curated talent lists, and deep-dive insights across industries. We help consultants, executives, and operators showcase their work—and we help businesses discover and engage with them faster.
Want to be featured? Start by creating a profile and requesting a few reference videos. We’re setting out to collect the dots—then connect them.
This blog will continue to evolve. If you know a great fractional CRO in Chicago we should highlight, reach out to our editorial team at hello@digitalreference.co.
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