Hire a
Fractional CTO
Complete guide to finding, vetting, and hiring the perfect fractional Chief Technology Officer for your business.
Where to Find Fractional CTOs
Six proven channels for finding pre-vetted, experienced fractional technology leaders.
Fractional Job Boards
Platforms like Fractional.Quest with pre-vetted fractional executives actively looking for engagements.
LinkedIn Search
Search for CTOs using hashtags #FractionalCTO, #PortfolioCTO, or "Fractional CTO" in titles.
Fractional Executive Networks
Agencies and networks that match companies with fractional technology leaders.
VC & Founder Referrals
Ask your investors, advisors, or founder network who they've used or heard of.
Tech Communities
Slack groups (CTO Craft, Engineering Leadership), tech meetups, or Stack Overflow.
Tech Conferences
Attend QCon, DevOps conferences, or engineering leadership events.
Pro Tip: Use multiple channels in parallel. The best fractional CTOs are often working with 2-3 companies and may not be actively looking—referrals help you reach them.
What to Look For in a Fractional CTO
Not all experienced engineers make good fractional CTOs. Here's what separates the best from the rest.
1. Relevant Tech Stack Experience
Have they built systems with your tech stack? A CTO experienced with enterprise Java won't be ideal for a Python/React startup. Look for experience with similar architectures, cloud platforms, and development methodologies.
Portfolio of similar tech stacks, architecture decisions at your scale, knowledge of modern dev practices
Only worked with legacy systems or completely different tech paradigms
2. Company Stage Experience
Have they scaled engineering at your stage? A CTO from a 500-person company won't know how to prioritize at a 5-person startup. Look for experience at companies 1-2 stages ahead of you.
Built teams from scratch, scaled from 5 to 50 engineers, experience at Series A/B companies
Only worked at large enterprises or never scaled a team past 10 people
3. Architecture & System Design
Can they design scalable, maintainable systems? Great fractional CTOs can whiteboard architecture, explain trade-offs, and make decisions about build vs buy, monolith vs microservices, and tech debt.
Clear architecture thinking, can explain past decisions and trade-offs, pragmatic about technology choices
Dogmatic about specific technologies or can't explain architectural decisions
4. Team Leadership & Hiring
Have they built and led engineering teams? A fractional CTO needs to hire, mentor, and manage people—not just write code. They should have hired at least 10-20 engineers and managed teams of 5-20 people.
Built teams from scratch, hiring process expertise, coaching/mentorship stories, structured engineering culture
Never managed people or prefers to code alone
5. Business & Product Alignment
Can they translate business needs to technology strategy? Great CTOs understand product roadmaps, revenue models, and can prioritize features that matter. They should speak business language.
Experience with product teams, can explain how tech decisions impact revenue, prioritization frameworks
Purely technical mindset, dismissive of business constraints
6. Fractional Working Model Fit
Do they know how to work fractionally? This requires discipline, clear communication, and asynchronous collaboration. Ask how they manage multiple clients, stay organized, and make impact in 2 days/week.
Works with 2-4 companies currently, systems for time management, clear communication cadence
First fractional engagement or working with 6+ companies (spread too thin)
Interview Questions to Ask
These questions separate strategic CTOs from hands-on engineers.
🎯 Architecture & Technical Questions
- "Walk me through how you designed the architecture at [Company X]. What trade-offs did you make?"
Listen for: Clear reasoning, awareness of trade-offs, pragmatic decision-making - "How would you approach our current tech debt? What would you prioritize?"
Listen for: Balance between perfect and good enough, business-aware prioritization - "How do you decide between building vs buying? Give me an example."
Listen for: Framework for decision-making, awareness of total cost of ownership - "Tell me about a system that failed under load. What did you learn?"
Listen for: Comfort with failure, post-mortem culture, continuous improvement
📊 Delivery & Process Questions
- "How do you measure engineering productivity? What KPIs do you track?"
Listen for: DORA metrics, cycle time, deployment frequency, not just story points - "How do you balance new features vs tech debt vs reliability?"
Listen for: Clear allocation strategy (e.g., 70/20/10), business-aware trade-offs - "Walk me through your release process. How do you ship safely?"
Listen for: CI/CD, feature flags, rollback procedures, monitoring - "Tell me about a major project that went off track. How did you course-correct?"
Listen for: Early warning systems, stakeholder communication, pragmatic solutions
👥 Team & Leadership Questions
- "How would you structure our engineering team? What roles would you hire first?"
Listen for: Alignment with product roadmap, clear hiring priorities, team topology thinking - "How do you evaluate engineering candidates? What signals do you look for?"
Listen for: Structured interview process, beyond just coding ability - "Tell me about a time you coached an underperforming engineer to success."
Listen for: Mentorship approach, patience, structured feedback - "How do you stay effective working 2 days/week vs embedded full-time?"
Listen for: Async communication, clear frameworks, delegation and trust
🔍 Business & Product Questions
- "How do you work with product managers? What's your ideal relationship?"
Listen for: Partnership mindset, healthy tension, clear ownership boundaries - "How do you estimate engineering effort for product planning?"
Listen for: Realistic estimating, confidence intervals, clear communication - "When have you said 'no' to a feature request? How did you handle it?"
Listen for: Business reasoning, alternative solutions, stakeholder management - "Are you open to converting to full-time if we scale significantly?"
Listen for: Flexibility, transparency about preferences, long-term thinking
The Fractional CTO Hiring Process
From first conversation to start date in 2-4 weeks.
Brief
Tell us about your needs, company stage, and what you're looking for in a fractional executive.
Match
We curate a shortlist of pre-vetted fractional executives who match your specific requirements.
Meet
Interview your top candidates. We handle scheduling and provide interview frameworks.
Start
Your fractional executive begins within days. We support onboarding and ongoing success.
Brief
Tell us about your needs, company stage, and what you're looking for in a fractional executive.
Match
We curate a shortlist of pre-vetted fractional executives who match your specific requirements.
Meet
Interview your top candidates. We handle scheduling and provide interview frameworks.
Start
Your fractional executive begins within days. We support onboarding and ongoing success.
Timeline Breakdown
Week 1: Define & Source
- • Define tech stack requirements (Day 1-2)
- • Post on job boards, ask for referrals (Day 2-3)
- • Review candidates, shortlist 5-10 (Day 4-7)
Week 2-3: Interview & Select
- • First-round interviews (45-min calls)
- • Second round: architecture deep dive
- • Reference checks (2-3 calls)
- • Make offer and negotiate terms
Week 4: Onboard & Start
- • Contract signing and admin setup
- • Share codebase access, docs, architecture
- • First week: codebase review, team intros
- • Begin audit and roadmap work
First 90 Days: Deliver
- • Month 1: Audit, quick wins, roadmap
- • Month 2: Process improvements, hiring plan
- • Month 3: Scale, architecture decisions
- • Decide to extend or part ways
Contract Terms & Structure
Standard terms for fractional CTO engagements.
Standard Contract Template
Engagement Model
- Day rate: £900-£1,600 per day (based on experience)
- Commitment: 1-3 days per week (specify exact days)
- Monthly retainer option: £4,000-£6,500 for predictable billing
Term & Notice
- Initial term: 3-month trial period
- Renewal: Auto-renew to 12-month rolling contract after trial
- Notice period: 30 days either side (standard)
Scope of Work
- Responsibilities: Tech strategy, architecture decisions, team leadership, hiring
- Deliverables: Architecture docs, tech roadmap, weekly async updates
- Exclusions: Day-to-day coding (unless scoped), attending all standups
IP & Confidentiality
- IP ownership: Company owns all code and documentation
- Confidentiality: Standard NDA terms, survives termination
- Non-compete: Usually not applicable (fractional works with multiple companies)
Payment Terms
- Invoicing: Monthly in arrears or bi-weekly
- Payment terms: Net 15 or Net 30
- Expenses: Pre-approved expenses reimbursed separately
Optional: Equity
- Advisory shares: 0.25-0.5% for long-term engagements (12+ months)
- Vesting: Quarterly or annual vesting
- Cash reduction: If equity included, day rate may reduce 10-15%
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