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

Currency:

Advisor CTO

$3,600per month

~6 hours per week of dedicated time

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

How we work:

Bi-weekly strategy session with founders (90 min)
Technical stack and architecture review - are you building on the right foundation?
Code review of critical decisions and risky PRs
Candidate screening: resume review, interview structure, hire/no-hire recommendations
Infrastructure and tooling spend review - are you overpaying for cloud and third-party services?
Async access via Slack (48-hour response time)

What you walk away with:

Technical assessment report - honest evaluation of your codebase, infrastructure, and risks
Technology roadmap - prioritized recommendations for the next 6 months
Hiring scorecard - what to look for in your first 3-5 engineers

Outcome

Confidence that your technical decisions are sound and a clear plan to build on - without costly mistakes.

Month-to-month, cancel anytime

Growth CTO

Scale CTO

$11,000per month

~20 hours per week of dedicated time

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

How we work:

Everything from Growth CTO package
Daily involvement in engineering operations - standups, planning, escalations
Executive team participation - board prep, investor meetings, due diligence support
Engineering management development - coaching team leads into engineering managers
Organizational design - team topology, processes, rituals, communication structures
Vendor strategy - cloud cost optimization, service negotiations, contractor management
Technical debt strategy - refactoring roadmap balanced against product delivery

What you walk away with:

Engineering handbook - culture, standards, processes, expectations
Leveling and compensation framework - career ladders and salary bands
Engineering metrics dashboard - DORA metrics, velocity trends, code quality
Incident management playbook - on-call rotation, severity definitions, postmortem process
Technical due diligence package - investor-ready architecture and security documentation
Security and compliance assessment - SOC2, GDPR, HIPAA readiness evaluation
Engineering headcount plan and infrastructure budget forecast

Outcome

A mature engineering organization ready for due diligence and the next funding round.

3-month minimum commitment

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).