Fractional CTOs in Chicago Making Things Happen in 2025

Chicago Interim Chief Technology Officers to Know

Chicago has always been a city where grit meets innovation. It’s a place where legacy industries collide with emerging tech, where scrappy startups sit next to Fortune 500s, and where engineering talent doesn’t just keep up—it quietly leads. That’s why the role of fractional CTOs in Chicago is not just growing—it’s defining how the city builds its next wave of companies.

At Digital Reference, we shine a light on the professionals who drive real business outcomes. We believe in radical transparency and radical authenticity—not just as buzzwords, but as building blocks for a better talent ecosystem. That’s why we created this blog series: to spotlight the independent CTOs, advisors, and technology leaders helping Chicago’s businesses grow smarter.

This list is a living document, and today, we’re focusing on fractional CTOs—those strategic thinkers who step into companies part-time but make full-time impact. These are the people founders call when they need more than code: they need clarity, leadership, and a roadmap.

Our methodology:

• We verify professionals are based in Chicago or actively serve Chicago-based businesses
• We prioritize those with independent or fractional service offerings
• We assess thought leadership, client impact, and platform presence

If you’re a founder, operator, or investor in the Midwest, these are the CTOs worth knowing.

Lucas Ward

LinkedIn: https://www.linkedin.com/in/lucaslward/

Lucas Ward is a deeply technical and business-savvy CTO with a track record of guiding early-stage companies through pivotal product and architecture decisions. With experience in fintech, e-commerce, and SaaS, Lucas offers fractional CTO services through his own consultancy.

Lucas is known for his pragmatic leadership style—focused on lean execution, fast iteration, and aligning tech decisions with business goals. Founders love working with him for his ability to simplify complex tech roadmaps and build MVPs that scale.

Whether you're launching a new platform or cleaning up legacy code, Lucas brings a thoughtful, roll-up-your-sleeves energy to the role of fractional CTO.

Tricia Ballad

Website: https://disentangledtech.com/

Tricia Ballad is the founder of Disentangled Tech, a Chicago-based consultancy offering fractional CTO services to mission-driven startups and founder-led businesses. Tricia has a unique approach—combining software architecture with storytelling and strategic clarity.

Her superpower? Helping non-technical founders translate vision into a sustainable product roadmap. Tricia's work is especially valued by companies in health, education, and nonprofit sectors, where tech must be both ethical and effective.

Tricia doesn't just build systems—she builds understanding. Her ability to coach founders through technical decision-making while keeping user experience front and center makes her a standout fractional CTO in the Midwest ecosystem.

Scott Campbell

LinkedIn: https://www.linkedin.com/in/campbe/

Scott Campbell has built a reputation in Chicago tech circles as a go-to fractional CTO for high-growth companies. He brings 20+ years of experience in architecture, engineering leadership, and digital product development.

Scott has helped multiple startups scale from prototype to acquisition and is a trusted advisor to founders navigating technical pivots. His style is direct, collaborative, and always focused on outcomes. With experience across healthcare, logistics, and enterprise SaaS, Scott knows how to build teams, optimize codebases, and get platforms investor-ready.

He’s also known for mentoring technical leads and helping early hires grow into leadership roles—making his engagements impactful well beyond the project at hand.

Ron Richards

LinkedIn: https://www.linkedin.com/in/rrichards1/

Ron Richards is a serial startup CTO and fractional tech leader with decades of experience in building and scaling technology teams. Ron’s background spans everything from edtech to adtech to platform engineering, and he’s known for turning chaos into clarity.

Based in Chicago, Ron offers fractional CTO services to founder-led startups and growing companies that need executive-level technology leadership. He specializes in technical due diligence, roadmap planning, and team structure evaluation.

What sets Ron apart is his calm, confident presence in high-pressure situations. Whether a startup is raising capital, undergoing a reorg, or launching a new vertical, Ron brings the steadiness—and insight—needed to keep things moving forward.

Yael Gomez

LinkedIn: https://www.linkedin.com/in/yael-gomez/

Yael Gomez is a seasoned technology executive offering fractional CIO and CTO services across multiple sectors. With a background in infrastructure, IT operations, and enterprise-scale systems, Yael’s work blends innovation with stability.

Yael brings a thoughtful, systems-level approach to every engagement—balancing digital transformation efforts with practical execution strategies. She’s an ideal partner for companies undergoing significant change, from mergers to platform modernization.

While her work spans far beyond startups, Yael’s leadership is often critical during transitional periods when businesses are rethinking their tech foundation. Based in the Chicago area, she partners with clients ranging from mid-sized businesses to nonprofits.

Sandeep Garg

LinkedIn: https://www.linkedin.com/in/sandeep-garg-tech-exec/

Sandeep Garg is a strategic technology advisor and fractional CTO with a focus on digital transformation, AI/ML, and scaling technology in private equity-backed businesses. Based in Chicago, Sandeep partners with leadership teams to assess current systems, re-architect platforms, and drive modernization initiatives.

With prior experience as a CIO and CTO in both startup and enterprise environments, Sandeep brings a rare blend of strategy, engineering depth, and business acumen. He’s particularly strong in helping tech teams scale efficiently and stay aligned with business KPIs.

For companies preparing for a liquidity event, new funding round, or rapid market entry, Sandeep offers the kind of experienced tech guidance that turns complexity into confidence.

Why Chicago Startups Rely on Fractional CTOs

The Chicago ecosystem is booming—but building tech here is not one-size-fits-all. For many companies, the full-time executive hire just doesn’t make sense at the early stage or during major transitions. Enter the fractional CTO: a flexible, high-impact solution for getting seasoned tech leadership without the C-suite price tag.

Whether it's standing up an MVP, scaling a team, or preparing for a technical due diligence process, fractional CTOs provide:

• On-demand executive expertise
• Cost-efficient leadership with flexible commitments
• A bridge between technical execution and business vision
• Guidance on hiring, roadmapping, and vendor selection

Fractional CTOs often embed deeply in teams, offering more than just advice. They help make key decisions, lead product sprints, and mentor rising engineers—without disrupting existing team dynamics.

Digital Reference: Spotlighting Real Talent

At Digital Reference, we’re rethinking what it means to build a reputation. In an industry that still relies heavily on résumés and who-you-know referrals, we’re creating a platform where professionals can:

• Showcase verified work and client impact
• Collect references once, use them forever
• Present video insights, past outcomes, and thought leadership

We believe independent professionals—like the fractional CTOs on this list—deserve more visibility and tools to tell their story. If you're hiring a tech leader or looking to expand your own consulting brand, Digital Reference is your partner in building a more human, more effective talent ecosystem.

Join the Movement or Nominate a Leader

We’re just getting started. This list will continue to grow as we meet more brilliant CTOs across the Windy City and beyond.

Know a standout fractional CTO based in Chicago? Want to see your profile here? Reach out to the Digital Reference editorial team.

📍 Whether you’re leading a product launch, scaling post-Series A, or navigating a legacy transformation, there’s a fractional CTO in Chicago who can help you make it happen.

Let’s build better. Together.

— The Digital Reference Team

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