Remote / Hybrid • CST Timezone

Fractional CTO in Chicago

Expert technical leadership for Chicago startups. CTO services in CST timezone. Build, scale, and transform your product without full-time CTO costs.

Why Chicago Startups Choose Fractional CTO

Chicago is the third-largest US city and one of the leading tech hubs in the Midwest. The city is home to a thriving startup ecosystem with strong presence in FinTech, E-commerce, Enterprise SaaS, Food Tech, and Logistics. With proximity to major Fortune 500 corporations, Chicago startups have unique access to enterprise clients and partnerships.

However, the Chicago market has its nuances: while engineering salaries are lower than coastal cities, they're still significant ($240K-$380K for a CTO). Competition for senior talent is growing, and investors expect technical maturity at coastal levels. For many startups, a full-time CTO in the early stages is an unaffordable luxury.

Challenge

Challenges for Chicago Startups

CTO salaries of $240K-$380K make full-time hiring expensive
Growing competition for senior technical talent
Need to meet enterprise standards for B2B sales
Scaling challenges after fundraising

Integration with large corporate systems (legacy, compliance)
CTO salaries of $240K-$380K make full-time hiring expensive
Growing competition for senior technical talent

Need to meet enterprise standards for B2B sales
Scaling challenges after fundraising
Integration with large corporate systems (legacy, compliance)

How Fractional CTO Helps Solve These Challenges

Access to experienced CTO without Chicago salary premiums ($150K-$300K+ savings annually)
Start immediately—no 3-6 month hiring process
Scalable architecture from day one
Expertise in building distributed teams with remote-first focus
Experience integrating with corporate systems

What I do

Build Your MVP

Turn your startup idea into a working product

Tech stack selection for Midwest talent market
Launch in 3-4 months with scalable foundation
Enterprise-ready architecture for B2B

Scale Your Product

Grow from seed stage to Series A

Handle 10x growth without downtime
Technical debt management and refactoring
Prepare for Chicago VC due diligence

AI Transformation

Integrate AI/ML into your startup

LLM integrations and GPT-based solutions
ML systems for competitive advantage
Strategy, implementation, and MLOps

Technology Audit

Technical assessment before fundraising

Code quality and architecture review
Prepare for Midwest VC due diligence
Risk map and recommendations

Technical Due Diligence for Investors

For investors evaluating startups

Comprehensive technical risk assessment
Team and product scalability analysis
Reports for investment committees

Team Building

Hire your first 5-10 engineers

Navigate Midwest talent market
Build hybrid teams (local + remote engineers)
Establish engineering culture

Pricing

Packages for Chicago Startups

Contract Length:

Currency:

Advisor CTO

$3,600per month

6 hours per week, 24 hours per month

For early-stage startups with an MVP or an idea that need oversight and support without full-time involvement.

2 strategic sessions per month (90 minutes each)
Technical stack and architecture audit
Slack support (48-hour response time)
Hiring support: candidate reviews and recommendations

What's included:

6-month technical roadmap
Architecture guidelines document

Outcome:A clear plan and recommendations for technology and team development without the overhead of a full-time CTO.

Contract term:1 month

Growth CTO

Scale CTO

$12,000per month

≈3 days per week, 80 hours per month

Series A+ startups with 15-20+ engineers preparing for the next funding round.

Everything from Growth CTO package
Participation in executive meetings and investor discussions
Building engineering management team (leads, engineering managers)
Due diligence support for fundraising
Organizational design: team structure, processes, rituals
Technical debt strategy and refactoring roadmap
Vendor and partner negotiations (AWS, third-party services, contractors)

What's included:

Engineering handbook and team culture code
Leveling and compensation framework
Engineering metrics dashboards (DORA, velocity, code quality, etc.)
Incident management and on-call rotation

Outcome:A mature engineering organization with clear processes, metrics, and a culture of product ownership.

Contract term:from 6 months

How Remote Work with Chicago Startups Works

Time overlap: 6 hours daily overlap with 9am-6pm CST—sufficient for meetings and calls. Outside this window, available asynchronously via Slack and email for uninterrupted workflow.
Communication rhythm: Weekly strategic calls with founders. Bi-weekly team syncs. Daily communication via Slack. Emergency availability for critical issues.
In-person visits: Quarterly visits to Chicago available for Scale CTO packages and above. Available for board meetings and investor presentations (remote or in-person).