Fractional COOs in Chicago Making Things Happen in 2025

Chicago Interim Chief Operating Officers to Know

When it comes to scaling businesses with precision and purpose, Chicago has long been a powerhouse for talent, grit, and execution. But today’s fast-growing companies need more than just hustle—they need operational leadership that’s flexible, seasoned, and deeply aligned with the demands of modern growth. Enter the fractional COO.

A fractional Chief Operating Officer (COO) is a senior executive brought in on a part-time or interim basis to help founders and executive teams optimize operations, improve strategy, and drive outcomes. Whether launching a new business unit, navigating a funding round, or transforming legacy systems, fractional COOs provide high-level expertise—without the full-time overhead.

At Digital Reference, we’re reimagining how professionals document, validate, and amplify their contributions to the organizations they serve. That means creating space for fractional leaders to be seen, celebrated, and connected. This curated list of fractional COOs in Chicago showcases individuals who are not only making an impact behind the scenes—they’re pushing businesses forward across industries.

Our Methodology

We selected this group through a thoughtful process of research and community input, using the following criteria:

• Active fractional or interim COO or operations leadership role
• Based in Chicago or surrounding areas with clients in the region
• Operate as solo consultants, small firms, or boutique leadership advisors
• Have visible experience in operations, growth strategy, process design, and leadership development
• Align with the Digital Reference mission of radical authenticity, structured professional storytelling, and a more transparent talent ecosystem

These are the operators who help founders sleep at night—and help teams scale with confidence.

Meet the Fractional COOs Powering Chicago’s Growth

Mark Scrimenti

As founder of Vivid Path Consulting, Mark Scrimenti delivers fractional COO services with a sharp focus on people, processes, and performance. With deep experience in e-commerce, marketing, and operations, he helps founders scale sustainably.

The Digital Reference Team had the opportunity to sit down 1on1 with Mark to ask him a few questions about his fractional work.

Here's what we learned:

What’s your typical approach to fractional engagements?

"Every engagement starts with listening. I work closely with founders and leadership teams to understand their vision, uncover root issues, and prioritize the work that will unlock growth without creating unnecessary complexity. I believe operations should serve the business – not the other way around – so I design systems that are simple, scalable, and aligned with your strategy and culture. I often start with a strategic planning sprint, then move into rolling up my sleeves to lead key initiatives, coach internal leaders, and build the infrastructure for sustained success."

What type of clients are you the best fit for?

"I’m a great fit for founder-led companies – especially in e-commerce, SaaS, or professional services – who have product-market fit and a solid team, but are hitting growth ceilings due to operational inefficiencies, unclear roles, or lack of alignment. If you're at a stage where the founder can no longer be the glue holding everything together, that’s often when I can make the biggest impact. My clients are mission-driven, growth-minded, and ready to evolve from hustle to healthy scale."

What type of clients are the best fit for you?

"I do my best work with leaders who value clarity, culture, and continuous improvement. I’m not the COO for companies chasing growth at any cost – I work best with clients who care about building great businesses and great places to work. If you're open to reflection, willing to change, and believe that strong operations are about more than just KPIs and dashboards, we’ll get along well."

When it comes to Ops what are your specialties?

"My specialties include strategic planning, organizational design, team development, and systems implementation. I’m especially skilled at translating vision into execution – creating clarity around roles, priorities, and rhythms so that everyone knows where they’re headed and how to get there. I’m also a certified System & Soul™ coach, which allows me to integrate structured operational frameworks with leadership and culture-building strategies."

What else should your clients know about you?

"I’m equal parts strategist and builder. I’ve led $100M+ operations, built startups from scratch, and coached dozens of leadership teams through transformation. But I’ve also been in the trenches – as a writer, marketer, product manager, and people leader. That range gives me empathy, curiosity, and perspective – so I can zoom out to see the big picture and zoom in to get the details right. I’m here to help you scale what’s working, fix what’s not, and build the kind of company you’re proud to lead."

Why He Stands Out to the Digital Reference Team:

• Offers fractional COO, strategic planning, and org design services
• Works with e-commerce brands, DTC companies, and creative teams
• Balances business growth with leadership development and team clarity

Mark is ideal for fast-moving teams Mark is ideal for fast-moving, purpose-driven teams who need a thoughtful operator who can scale systems without sacrificing soul.

Jesse Hallock

Founder of Arabona, Jesse Hallock is a fractional COO and operations strategist who brings clarity and structure to purpose-driven organizations. His work spans startups, nonprofits, and service-based businesses seeking intentional growth.

Why He Stands Out:

• Expertise in financial modeling, process mapping, and operational audits
• Works closely with clients to implement repeatable systems and workflows
• Prioritizes relationship-building alongside performance improvement

Jesse is best known for bringing both heart and systems to his clients—leading with curiosity, accountability, and structure.

Marisa Mann

Marisa Mann is a strategic visionary and founder of Uplift All, delivering fractional CXO and advisory services to mid-market, impact- and outcome-driven organizations. Backed by 30+ years at Accenture, JPMorgan, Kin+Carta and Gartner, she spearheads transformative digital and AI initiatives, fortifies risk and compliance ecosystems, and galvanizes executive teams to achieve measurable, sustainable growth.

Why She Stands Out:

• Strategic Ecosystem Navigator: Aligns technology, operations and compliance to accelerate scale
• Impact-Driven Innovator: Leverages clear metrics and AI to boost top- and bottom-line results
• Coaching-Informed Leader: Builds resilient, high-performing teams through empathy and structure

Marisa is a go-to leader for organizations navigating complexity at the intersection of growth and inclusion.

Valentina Mendoza

https://www.myntplanning.com/about

As the founder of Mynt Planning, Valentina Mendoza helps impact-driven organizations build clarity through operational structure and strategic roadmaps. With experience across nonprofits, startups, and corporate strategy, Valentina offers fractional COO services designed to help leaders translate vision into action.

Why She Stands Out:

• Deep expertise in goal setting, strategic planning, and executive collaboration
• Specializes in mission-led businesses and high-growth teams
• Brings a values-aligned approach to operations, finance, and communications

Valentina is an ideal partner for teams who want rigor without rigidity—someone who can co-create structure while preserving culture.

Josh Chapman

https://greengranite.co/

Co-founder of Green Granite, Josh Chapman brings a builder’s mindset to operations. He’s a hands-on fractional COO who works with startups and scaling businesses to develop resilient teams, scalable systems, and sustainable growth.

Why He Stands Out:

• Brings a tech-forward and systems-led approach to organizational design
• Deep focus on founder enablement, leadership coaching, and culture
• Combines COO services with strategic advisory and org development

Josh thrives in environments where the vision is strong but the execution needs support—and he helps make that vision a reality.

Jennifer Ludwig Clark

https://www.linkedin.com/in/jenniferludwigclark/

With a robust background in executive operations and nonprofit leadership, Jennifer Ludwig Clark provides interim and fractional COO support to teams in transition. Her leadership style is collaborative, systems-focused, and grounded in impact.

Why She Stands Out:

• Specializes in interim executive management, process design, and organizational change
• Strong experience in fundraising operations, board relations, and program execution
• Works across nonprofit and mission-driven for-profit sectors

Jennifer is often brought in during periods of strategic realignment or leadership shifts, helping organizations stabilize and move forward with clarity.

Why Chicago Is Built for Fractional Leadership

Chicago has always been a city that blends business acumen with Midwestern practicality. Its economy spans industries—finance, healthcare, logistics, food, and tech—making it fertile ground for companies in various growth stages. And as remote work and agile teams become the norm, the fractional executive model is thriving.

Fractional COOs are in high demand because:

• Companies need senior leadership without full-time costs
• Startups need flexibility during growth and fundraising cycles
• Nonprofits and mission-driven orgs need experienced operators on a project basis

The leaders on this list represent the best of what Chicago has to offer: smart, capable, values-aligned operators who know how to get things done.

What Makes a Great Fractional COO?

The best fractional COOs combine versatility with vision. They are:

• Operational generalists with deep expertise in at least one domain
• Comfortable moving between strategy and execution
• Quick to build trust with founders and teams
• Fluent in the language of culture, KPIs, and cash flow
• Structured thinkers who leave organizations better than they found them

They bring order to chaos, clarity to complexity, and calm to uncertainty.

The Digital Reference Viewpoint

At Digital Reference, we’re building a platform that enables professionals to own their story—not just tell it. For fractional leaders, that means:

• Capturing verified work outcomes and client feedback
• Organizing experience into a structured, professional portfolio
• Building trust and discoverability in a transparent, reputation-driven ecosystem

We believe that the future of executive talent is modular, mission-aligned, and measurable—and that platforms like ours are how we’ll get there.

Final Thoughts

The rise of fractional leadership isn’t just a trend—it’s a signal that organizations are seeking better, more flexible, and more values-aligned ways to grow.

The fractional COOs featured here—Valentina Mendoza, Marisa Mann, Josh Chapman, Jesse Hallock, Jennifer Ludwig Clark, and Mark Scrimenti—aren’t just keeping the wheels turning. They’re building the systems that drive long-term success.

Whether you're a founder preparing for a new phase, a nonprofit in transition, or a scaling company that needs strategic operations—this list is your starting point.

Explore their work. Reach out. And when you're ready to document your leadership story or hire someone who can move your mission forward—start with Digital Reference.

– The Digital Reference Team

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