Finding the right fractional CTOs in Chicago means more than filling a seat—it's about finding someone who can cut through technical noise and move your team forward. The wrong fit costs you time, money, and momentum. This guide helps you compare top options so you can hire with confidence.
Top 10 Fractional CTOs in Chicago
Below are the profiles of the top fractional CTOs in Chicago, covering who they are and what they bring to the space.
Don Bora
Fractional CTO & Technology Leader
Chicago, United States
Focus area:
#Fractional CTO#Software Development#AI Engineering#Technology Strategy#Startup Leadership
Don Bora co-founded Eight Bit Studios and serves as a fractional CTO at Tilt 365. His career spans enterprise software, AI research, entrepreneurship, and technology leadership for growing businesses.
Bora helps founders…
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Anthony Broad-Crawford
Fractional CTO, CPO & CAIO at ABC & Company
Chicago, United States
Focus area:
#Technology Leadership#Product Strategy#Engineering Management#Digital Products#Startup Growth
Anthony Broad-Crawford is a technology and product executive who leads ABC & Company. His background includes senior leadership at SpotHero, Fooda, Within3, and other technology-driven businesses.
Across these companies, Broad-Crawford has built…
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Asim S. Mohammad
Fractional CTO at Midwest CTO Partners
Chicago, United States
Focus area:
#Data Analytics#Technology Strategy#Machine Learning#Product Architecture#Engineering Leadership
Asim S. Mohammad is a fractional CTO and technology consultant with more than 25 years of experience in data analytics, product development, and technical leadership for startups and growing companies.
Through Midwest…
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Winston Tsao
Fractional CTO & Technical Delivery Partner
Deerfield, United States
Focus area:
#Technical Architecture#Software Delivery#Cloud Systems#Engineering Leadership#Systems Integration
Winston Tsao is an independent fractional CTO and technical delivery partner with experience spanning software engineering, technology management, and executive roles at INDISTRY Media and Aspiritech.
Tsao works with agencies, consultants, and…
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Yaël Gomez
Fractional CTO/CIO at Yaël Gomez Advisory
Chicago, United States
Focus area:
#Digital Transformation#Technology Strategy#Enterprise IT#AI Implementation#Engineering Leadership
Yaël Gomez leads an advisory firm, providing fractional CTO and CIO services. He previously served as Vice President of Global IT, Integration and Intelligent Automation at Walgreens Boots Alliance.
Gomez helps organizations…
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Joe Burns
Fractional CTO & Technology Executive
Hinsdale, United States
Focus area:
#Engineering Leadership#Technical Debt#Team Building#Ecommerce Platforms#Startup Scaling
Joe Burns is a technology executive and fractional CTO who helped build TeePublic, the online marketplace acquired by Redbubble, and has led engineering teams through startup growth.
Burns helps founders and CEOs…
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Raphael R. Savastano
Founder & Principal Consultant at ROFONIC
Chicago, United States
Focus area:
#Fractional Technology Leadership#IT Strategy#Digital Transformation#ERP Systems#Business Operations
Raphael R. Savastano founded ROFONIC after more than 25 years in technology leadership. His background includes serving as CIO of a global manufacturer and directing enterprise technology transformation.
Savastano provides fractional CIO…
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Jeff Gutierrez
Founding Executive & Fractional CTO at Muralla Street
Chicago, United States
Focus area:
#Technology Strategy#Artificial Intelligence#Software Architecture#Engineering Leadership#Digital Transformation
Jeff Gutierrez provides fractional CTO, Chief AI Officer, and CIO leadership through Muralla Street. His professional work centers on building reliable software systems and leading technology organizations.
Gutierrez works across technology strategy,…
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Cindy Don
Fractional CTO
Chicago, United States
Focus area:
#Engineering Leadership#AI Adoption#Software Delivery#Team Transformation#Startup Technology
Cindy Don is a technology executive and fractional CTO with nearly two decades of experience building and leading engineering teams. Her background includes leadership roles at Pangea Money Transfer and Nautilus Labs.
…
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Robinson Cook
Founder & Fractional CTO at Def0x
Chicago, United States
Focus area:
#Startup Development#Fractional CTO#MVP Development#Software Architecture#Product Strategy
Robinson Cook founded Def0x, a fractional CTO and startup development agency. His work combines software engineering, early-stage product development, and technical leadership for founders building digital products.
Cook helps founders clarify what…
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Selection Methodology
I selected the leaders on this list based on their relevance, demonstrated expertise and impact, professional credibility, and active service offerings in the field.
I look for evidence such as leading meaningful initiatives, delivering results, providing ongoing operational leadership, developing influential ideas or practices, publishing or teaching, and other contributions that demonstrate impact.
These leaders must also be based in the area or clearly serve clients there, including through a broader regional, national, or global service area.
Further Reading
Expand your search for fractional CTOs across the nation with our city-specific guides for Atlanta and Dallas.
What’s Next?
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