Best Fractional CTO Services in Chicago

Chicago's Best Outsourced CTO Services, Fractional CTO, & Virtual CTO Services

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.

‍

Our Methodology: Chicago Fractional CTO, Virtual CTO Services, and Outsourced CTOs

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.

‍

Meet The Best Fractional CTO, Virtual CTO, & Outsourced CTO Services in Chicago

Yael Gomez

Yael's Website: https://www.yael-gomez.com/

Yael Gomez provides fractional CIO and CTO leadership across startups and mid-sized companies nationwide. With expertise in IT infrastructure, software engineering, data & AI, and enterprise systems, he blends innovation with operational excellence. Yael is especially valuable during transitional periods—mergers, acquisitions, scaling, exits, or platform modernization.

Highlights:
🏢 Fractional CTO/CIO for startups and mid-sized businesses
📑 Digital transformation, platform modernization, and operational alignment
💬 Systems-level thinker balancing strategy with practical execution

Yael is ideal for companies needing tech leadership during periods of significant change.

Tricia Ballad

Website: https://disentangledtech.com/

Tricia Ballad supports mission-driven startups and founder-led companies as a fractional CTO. She specializes in translating founder vision into sustainable product roadmaps while keeping ethics and user experience front and center. Tricia is particularly sought after in health, education, and nonprofit sectors.

Highlights:
🏢 Fractional CTO for founder-led and mission-driven startups
📑 Software architecture, product roadmapping, and technical coaching
💬 Skilled at guiding non-technical founders through complex decisions

Tricia is best for founders seeking clarity, structure, and tech leadership with a human touch.

Lucas Ward

Lucas Ward offers pragmatic CTO guidance to early-stage companies, focusing on lean execution, fast iteration, and aligning technology with business goals. With experience across fintech, e-commerce, and SaaS, he helps startups launch new platforms, clean up legacy systems, and scale effectively.

Highlights:
🏢 Fractional CTO for early-stage and scaling startups
📑 Architecture guidance, MVP development, and tech roadmap alignment
💬 Hands-on, roll-up-your-sleeves leadership with business-savvy

Lucas is ideal for founders who want practical, actionable technology leadership.

Scott Campbell

Scott Campbell is a trusted fractional CTO for high-growth companies. With 20+ years in engineering, architecture, and digital product development, Scott helps startups scale from prototype to acquisition while mentoring early technical hires into leadership roles.

Highlights:
🏢 Fractional CTO for startups across healthcare, logistics, and SaaS
📑 Technical pivots, platform scaling, and team leadership development
💬 Direct, collaborative, and outcome-focused advisor

Scott is a strong partner for startups seeking both technical execution and long-term team development.

Ron Richards

Ron Richards is a serial startup CTO who brings executive-level tech leadership to founder-led and growing companies. Specializing in technical due diligence, roadmap planning, and team structure evaluation, Ron thrives in high-pressure scenarios like fundraising, reorgs, or new vertical launches.

Highlights:
🏢 Fractional CTO for startups and growth-stage companies
📑 Tech strategy, team structure, and roadmap execution
💬 Calm, confident, and strategic presence during critical inflection points

Ron is ideal for companies that need steadiness and insight to turn chaos into clarity.

Sandeep Garg

Sandeep Garg provides fractional CTO services with a focus on digital transformation, AI/ML, and scaling tech in PE-backed and high-growth businesses. With prior CIO/CTO experience in startups and enterprises, he helps leadership teams modernize systems, re-architect platforms, and align technology with KPIs.

Highlights:
🏢 Fractional CTO for scaling, PE-backed, and high-growth companies
📑 Digital transformation, AI/ML, platform modernization
💬 Strategy-driven advisor blending engineering depth with business acumen

Sandeep is perfect for companies preparing for liquidity events, new funding rounds, or rapid market entry.

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 fCTO 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 Tech Leader in Chicago

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.

‍

City Spotlights of of Part-time & Fractional CTOs in the USA

Ann Arbor - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Ann Arbor Making Things Happen

Atlanta - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Atlanta Making Things Happen

Austin - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Austin Making Things Happen

Boston - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Boston Making Things Happen

Charlotte - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Charlotte Making Things Happen

Dallas–Fort Worth - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Dallas–Fort Worth Making Things Happen

Denver - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Denver Making Things Happen

Detroit - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Detroit Making Things Happen

Houston - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Houston Making Things Happen

Jacksonville - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Jacksonville Making Things Happen

Las Vegas - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Las Vegas Making Things Happen

Los Angeles - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Los Angeles Making Things Happen

Miami - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Miami Making Things Happen

Minneapolis - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Minneapolis Making Things Happen

Nashville - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Nashville Making Things Happen

Naples - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Naples Making Things Happen

New York City- Virtual CTOs & Outsourced CTO Services
Fractional CTOs in New York City Making Things Happen

Orlando - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Orlando Making Things Happen

Phoenix - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Phoenix Making Things Happen

Pittsburgh - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Pittsburgh Making Things Happen

Portland - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Portland Making Things Happen

Raleigh–Durham - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Raleigh–Durham Making Things Happen

Sacramento - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Sacramento Making Things Happen

Salt Lake City - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Salt Lake City Making Things Happen

San Antonio - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in San Antonio Making Things Happen

San Diego - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in San Diego Making Things Happen

San Francisco- Virtual CTOs & Outsourced CTO Services
Fractional CTOs in San Francisco Making Things Happen

Seattle - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Seattle Making Things Happen

St. Louis - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in St. Louis Making Things Happen

Tampa - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Tampa Making Things Happen

Washington DC - Virtual CTOs & Outsourced CTO Services
Fractional CTOs in Washington DC Making Things Happen

‍

📍 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