How to Choose the Right Fractional CTO for Your Business
You know your business needs better technology leadership. You've probably made some suboptimal tool decisions, you're not confident about security, and you're tired of reactive IT crises. You've thought about hiring a full-time CTO, but a $150,000-180,000 salary for a 25-person company doesn't make sense.
That's where fractional CTO services come in. A fractional CTO works part-time (typically 10-20 hours per week), costs 40-60% less than a full-time hire, and brings enterprise-level technology leadership to mid-sized businesses. The catch: not all fractional CTOs are the same, and choosing the wrong one will waste your money and time.
This post walks you through what to look for when hiring a fractional CTO, the right interview questions to ask, and how to evaluate whether a particular fractional CTO candidate is right for your business.
What a Fractional CTO Actually Does
Before you start evaluating candidates, you need to be clear about what role you're hiring for. The term "fractional CTO" is used broadly, and different providers offer different services.
A true fractional CTO should:
Own your technology strategy. Not just maintain existing systems, but help you make intentional decisions about where technology is going. What should your next tool upgrade be? Should you build something custom or buy off the shelf? How should your infrastructure evolve as you grow?
Evaluate and advise on tools and vendors. Should you switch from Excel to a proper database? Which CRM makes sense for your business model? Should you move to the cloud? A good fractional CTO evaluates these questions based on your specific needs, not vendor marketing.
Oversee implementation and integration. When you implement a new system, someone needs to make sure it actually works and integrates with everything else. A fractional CTO manages that process or ensures it's managed properly.
Handle security and compliance. What data do you have, where is it stored, who has access, and are you compliant with relevant regulations? A fractional CTO identifies gaps and implements controls.
Be the primary technology advisor to the CEO/Founder. You should be able to call your fractional CTO and say, "We're thinking about expanding to another location. What technology questions should we be thinking about?" and get good advice.
What a fractional CTO should NOT do:
- Day-to-day technical support (that's what managed services or a helpdesk is for)
- Server administration or network troubleshooting (that's infrastructure management)
- Software development (unless that's explicitly part of the engagement and they're qualified)
- Hands-on IT work like deploying updates or configuring individual machines
If the "fractional CTO" you're considering is spending most of their time fixing printers, they're not actually a CTO—they're an IT contractor.
What to Look For in a Fractional CTO
Before you start interviewing, know what you're looking for.
Relevant industry experience: A fractional CTO who's worked with manufacturing companies will understand different challenges than one who's worked with SaaS companies. Their experience should be somewhat relevant to your industry. A restaurant CTO should understand POS systems and hospitality technology. A healthcare company CTO should understand compliance and security in healthcare contexts.
That said, strong CTOs can transfer skills across industries. A CTO with strong financial services experience will bring excellent security practices to any business. But pure tech experience isn't enough—they should understand business contexts relevant to yours.
Track record with companies your size: Look for evidence that they've successfully advised companies in the 10-50 person range. A CTO who's spent their career at 500-person companies might not understand the constraints and pragmatism required at a 20-person company. You don't want someone who over-engineers solutions or recommends enterprise tools that are overkill for your size.
Hands-on technical depth: A fractional CTO doesn't need to be a software developer, but they should have technical depth. They should understand databases, cloud infrastructure, APIs, security concepts, and how systems integrate. They should be able to read technical documentation and make informed recommendations. If they're entirely non-technical, they'll be ineffective.
Business acumen: Technology decisions are ultimately business decisions. A good fractional CTO should ask about revenue impact, cost savings, time to market, and customer impact before recommending solutions. They should be able to explain trade-offs in business terms, not just technical terms.
Communication skills: The fractional CTO will be translating between technical and non-technical people. They need to be able to explain complex concepts clearly and actually listen to what you're trying to accomplish. You should feel like they understand your business, not like they're trying to implement their preferred tech stack.
Flexibility and pragmatism: Growing businesses operate in constraints—budget constraints, time constraints, people constraints. A good fractional CTO works within those constraints instead of insisting on the ideal solution. They might recommend using a spreadsheet for two more years instead of buying a $40,000 software system, because you don't have the ROI case yet.
Interview Questions for Fractional CTO Candidates
When you're talking to potential fractional CTOs, ask these questions:
About Their Background and Experience
"What's your background? What roles have you held before offering fractional CTO services?"
A real CTO should have held senior technical leadership roles. They might have been a VP of Engineering, a CTO at a startup, an architect at a larger company, or a technology consultant. Listen for depth of responsibility, not just job titles. You want someone who's made technology decisions that affected the business, not someone who's just been a senior engineer.
"What industries have you worked in? Which feels most relevant to my business?"
A good answer acknowledges what's relevant and what you'll need to learn about your business. A bad answer pretends all industries are the same or suggests their experience is irrelevant.
"How many companies your size have you advised? What was your role?"
You want specifics. They should be able to describe 3-5 previous clients of similar size and explain what they did to help. If they've mostly worked at large companies, ask how they adapt to the smaller company context.
About Their Process and Approach
"Walk me through how you'd approach your first 90 days with a company like mine."
This is the most important question. A good fractional CTO should describe:
- Assessment phase: Understanding current technology, business goals, pain points, and risks
- Strategy phase: Identifying priority initiatives and creating a roadmap
- Implementation phase: Execution of the highest-priority initiatives
They should be curious about your specific situation and not assume one answer fits all companies. If they give you a generic answer about "best practices," that's a red flag.
"How do you handle situations where the business wants to move fast and technical best practices suggest moving slow?"
You want someone who understands trade-offs. A good answer acknowledges that sometimes you need to move fast, but explains how to do that responsibly—maybe by taking technical debt on purpose (knowing you'll pay it back), or by scoping differently, or by focusing engineering effort where it matters most.
"How do you stay current with technology? What are you learning about right now?"
Technology changes constantly. A good fractional CTO should be actively learning and staying current. They might mention specific certifications they're pursuing, technologies they're experimenting with, or books/podcasts they follow. If they seem static or stuck in older technologies, that's a concern.
About Their Understanding of Your Business
"Based on what you know about [your industry], what technology challenges do you typically see companies like mine facing?"
A knowledgeable fractional CTO should be able to speak to common challenges in your industry. They should ask good questions to understand if your business faces those challenges too.
"What's your opinion on build vs. buy? How do you make that decision?"
This reveals their philosophy. A good answer is nuanced—sometimes you should build (when you have specific competitive advantage from custom software), sometimes you should buy (when off-the-shelf solves 80% of the problem). A bad answer is ideological in either direction.
"Tell me about a time you recommended a solution that turned out to be wrong. How did you handle it? What did you learn?"
Everyone makes mistakes. You want someone who learns from them. A good answer shows humility and a process for correcting course quickly.
About Engagement and Support
"How many hours per week are you typically available? How do we communicate? What's the response time if I have an urgent question?"
You want clarity on time commitment and availability. Most fractional CTOs should be available 10-20 hours per week, with a defined schedule or on-call arrangement for urgent issues. If they're vague, ask directly: "If my website goes down and I need advice immediately, can I reach you?"
"How do you work with our existing IT person/team? What's the relationship?"
If you have in-house IT staff, the fractional CTO should work well with them, not around them. Ask how they approach collaboration and knowledge transfer. A fractional CTO who creates silos or doesn't share knowledge with your team is problematic.
"What tools do you use for collaboration and documentation? How will I track progress?"
You should have visibility into what's happening. There should be regular check-ins, documented decisions, and a shared roadmap. If they're vague about this, they might be the kind who does work in a black box and presents you with opinions.
About Cost and Terms
"What's your pricing model? How do you bill?"
Common models: monthly retainer for a set number of hours, hourly billing, or project-based fees. Understand what's included and what's not. Do security reviews cost extra? Does vendor evaluation? Tool implementation?
"What's the minimum engagement? Can we start with a 3-month trial?"
You want to test the relationship before committing long-term. Any fractional CTO should be willing to do a shorter initial engagement.
"If I need extra hours one month because we're implementing a new system, how does that work?"
You want flexibility. A good model includes some flexibility to burst to higher hours when needed.
Red Flags to Watch For
As you evaluate fractional CTO candidates, watch for these red flags:
They push a specific technology stack. If they're trying to convince you to move everything to Kubernetes, or to embrace some other specific technology before understanding your needs, that's a bad sign. A good CTO recommends based on your needs, not their preferences.
They guarantee they can cut your costs by 30% without understanding your business. Anyone making big claims before deep assessment is overselling.
They're vague about their previous experience. A real CTO can speak specifically about companies they've worked with (respecting NDAs, of course) and concrete problems they've solved. Vagueness suggests they haven't actually done it.
They seem more interested in the title than the work. Some people want to call themselves CTO because it sounds prestigious. A good fractional CTO is interested in problem-solving, not prestige.
They don't ask you many questions. A first conversation should be mostly them asking about your business, goals, challenges, and team. If they're mostly talking about themselves, they're not ready to advise on your situation.
They guarantee specific outcomes. Technology outcomes depend on execution, team buy-in, and external factors. Anyone guaranteeing specific results (like "this will increase revenue by 40%") isn't being realistic.
They want a long-term contract with an exit penalty. You should have the flexibility to exit if the relationship isn't working. If they're requiring a 12-month commitment with penalties, be cautious.
How to Structure the Evaluation
Here's a process:
Step 1: Phone Screen (30 minutes) Have a brief conversation with 2-3 candidates. Ask about their background and get a sense of their communication style. Most conversations will quickly reveal if someone isn't a fit.
Step 2: Deeper Conversation (60 minutes) With your finalists (probably 1-2 people), have a longer discussion. Walk through your current situation, challenges, and goals. Ask the interview questions above. See if they ask good clarifying questions.
Step 3: Reference Calls Ask for references from 2-3 previous clients. Specifically ask: "Did this person actually improve your technology over time? Would you hire them again? Are there any weaknesses we should know about?"
Step 4: Paid Pilot Engagement (3 months) Start with a 3-month engagement at a set monthly rate. Define what success looks like. At the end of 3 months, assess: Are you getting value? Do you trust their judgment? Do they understand your business? If yes, continue. If no, thank them and move on.
The cost of a 3-month pilot ($4,000-6,000 for a fractional CTO) is far less than the cost of hiring someone full-time and having it not work out.
What Success Looks Like
After 3-6 months with a good fractional CTO, you should see:
- Clear technology roadmap that connects to business goals
- Priorities clarified (what to tackle first, what to delay)
- Vendor relationships established or improved
- One or two meaningful technology improvements implemented
- Your team feeling more confident about technology direction
- Reduction in reactive IT crises
- Better tool decisions being made
- Understanding of what compliance and security needs look like for your business
You should feel like you have a trusted advisor who understands your business and is helping you make better technology decisions.
Ready to Find Your Fractional CTO?
If you've assessed your technology leadership needs and decided a fractional CTO is right for your business, we'd like to help. Sandbar Systems has been serving as fractional CTO to small and mid-sized businesses for 15+ years. We specialize in working with companies in the 15-75 person range across industries including hospitality, professional services, e-commerce, and manufacturing.
In our initial conversation, we'll understand your business, assess your current technology situation, and discuss what fractional CTO services would look like for you. We offer flexible engagements starting with a 3-month pilot so you can evaluate the fit.
Call us: (804) 510-9224 | Email: info@sandbarsys.com
We're based in the Outer Banks/NC and Richmond VA, but we work with clients nationwide. Let's see if we're a fit for your business.