Fractional CTO & Technology Leader

I help businesses build the right thing, the right way.

35+ years building software—from AI research labs to modern AI-assisted development. 9x co-founder. 4x Inc. 5000. 10x delivery speed with AI workflows.

Don Bora - Chicago Fractional CTO

About

I bring a rare combination: 15+ years of enterprise experience at companies like Bank of America, UBS, and Baxter Healthcare, balanced with 17 years as an entrepreneur building and scaling my own companies.

My career started at Motorola, and my AI journey began in 1992 at Northwestern's Institute for the Learning Sciences, an AI research lab where I built intelligent educational systems for clients including the City of Chicago, Anderson Consulting, Encyclopedia Britannica, Ameritech, and the US Department of Defense. Today, I'm on the leading edge of AI-assisted software development, leveraging modern AI tools and architectures to 10x delivery speed without sacrificing quality.

I've co-founded or helped start over 10 companies—most profitable or successfully exited. At Eight Bit Studios, we've made the Inc. 5000 list four consecutive years. This blend of enterprise discipline and startup agility means I understand both sides: the rigor large organizations need and the speed startups demand.

35+ Years in Tech
10+ Companies Founded
4x Inc. 5000
10x AI-Assisted Delivery

How I Can Help

Fractional CTO

Strategic technology leadership for established companies looking to modernize their stack, replatform legacy systems, or launch version 1.0 of a new product. I bring enterprise rigor and startup speed to guide your technology transformation.

AI-Assisted Development

From AI research labs in the '90s to modern LLM-powered workflows. I help teams adopt AI tools and architectures that dramatically accelerate delivery while maintaining code quality.

Team Building

Finding great developers is hard. I help you identify, recruit, and build engineering teams that actually deliver—drawing on decades of hiring and mentoring experience.

Advisory & Board

Technical, entrepreneurial, and business mentoring for founders and CEOs. Production risk analysis, technical audits, and strategic direction for startups and growth-stage companies.

"You work for your people as much as they work for you. Don't ever forget that."

Ventures & Experience

Current Additional Roles

Stealth Startup

Chief Technology Officer

Healthcare

Tilt 365

Fractional CTO

SaaS

1871

Expert in Residence, PYROS

Mentorship

The Josephine Collective

Member & Investor

Investment

Founded & Led

WisePatient

Co-Founder & CTO

Acquired by Sharecare

MobileMakers

Co-Founder & Chief Instructor

EdTech

Kiwi Internet Group

Owner & Sr. Engineer

Consulting

Creative Candor

Co-Founder

Consulting

Enterprise Experience

Institute for the Learning Sciences

Software Engineer

AI Research

Bank of America

VP / Sr. Software Engineer

FinTech

Baxter Healthcare

Sr. Engineer / Team Lead

Healthcare

UBS

Engineer / Team Lead / PM

Investment Banking

Teaching & Mentorship

I believe in giving back. I meet with students and young entrepreneurs to share my path and passion, hoping to give them a different perspective into software development.

Teaching

Northwestern University

Adjunct Lecturer, Medill School of Journalism

Taught iOS development curriculum to journalism students, bringing them a taste of creating digital products.

MobileMakersEdu

Co-Founder, Curriculum Author & Chief Instructor

Led the mobile bootcamp that disrupted education and helped people change their careers. Teaching here was the most humbling experience of my professional career.

1871 Startup Roadmap Program

Expert in Residence

Running Explore sessions for entrepreneurs, bringing the latest business, startup, and behavioral science research to founders early in their journey.

Uncharted Learning

Curriculum Advisor

Developing high school curriculum for iOS development as the industry evolves.

Mentoring Organizations

Code Platoon

Founding Executive Board Member

Since 2016

Chicago Tech Academy

Technology Professional

Since 2013

MATTER

Business Mentor

Since 2015

1871

Professional Mentor

Since 2019

Chicago Connectory

Professional Mentor

Since 2021

gener8tor

Professional Mentor

Since 2021

Advocate for Diversity in Tech

I'm an outspoken advocate for women and underrepresented groups in technology, seeking to bridge the technology gap by exposing the fun and creative side of programming. I frequently mentor high school and college students, participate in mock interviews, resume reviews, and power lunches. I've served on DEI and education committees at the Chicagoland Chamber of Commerce and The Executives' Club of Chicago.

Recognition

TechWeek100 Top Influencer in Chicago, 2014
Moxie Awards Mentor of the Year Nominee, 2013 & 2014
Inc. 5000 Eight Bit Studios, 4 consecutive years
Business Partner Award IL District 214 & Prospect High School

Education

New Mexico State University

BS, Computer Science

BA, Foreign Languages & Literatures

University of Erlangen-Nuremberg

Germanic Languages, Literatures & Linguistics

German (Professional Working)

Tilt 365

Laser Coaching MASTERCLASS

Certified 2022

Let's Talk

Whether you need a Fractional CTO, technical advisory, or want to explore working together—I'd love to hear from you.