Mar 13, 2025
A practical guide for companies considering or onboarding a fractional CTO
Hiring a Fractional CTO is a strategic move for companies that need senior technology leadership without the full-time commitment. But what does that relationship actually look like in the first 90 days? Whether you're a startup building your first product or a growing company looking to scale, this guide outlines what to expect—and how to make the most of it.
Day 1–30: Discovery & Assessment
The first month is all about understanding your business, your team, and your technology landscape.
Key Activities:
Stakeholder Interviews – Meeting with founders, department heads, and key team members to understand goals, pain points, and expectations.
Tech Stack Audit – Reviewing your current infrastructure, codebase, tools, and processes.
Team Evaluation – Assessing the skills, structure, and dynamics of your engineering team (in-house or outsourced).
Business Alignment – Understanding your product roadmap, customer needs, and growth strategy.
Deliverables:
A clear picture of your current state
Identification of major risks, gaps, and opportunities
A prioritized list of quick wins and long-term initiatives
Day 31–60: Strategy & Roadmapping
With a solid understanding of your environment, the Fractional CTO begins to define a strategic path forward.
Key Activities:
Technology Roadmap – Creating a 6–12 month plan that aligns tech initiatives with business goals.
Process Improvements – Recommending changes to development workflows, deployment practices, or team structure.
Tool & Vendor Recommendations – Evaluating or selecting platforms, frameworks, or partners.
Budget & Resource Planning – Helping you allocate resources effectively and plan for future hiring or scaling.
Deliverables:
A documented technology roadmap
Recommendations for process and tooling improvements
A plan for scaling infrastructure and/or team
Day 61–90: Execution & Momentum
Now it’s time to put the plan into action and build momentum.
Key Activities:
Team Leadership – Leading standups, mentoring developers, and helping with hiring or onboarding.
Project Oversight – Ensuring key initiatives are moving forward on time and on budget.
Metrics & Reporting – Establishing KPIs and reporting structures to track progress.
Stakeholder Communication – Keeping leadership aligned and informed.
Deliverables:
Active execution of roadmap initiatives
Improved team performance and morale
Clear visibility into progress and outcomes
Making the Most of the Relationship
To get the most value from your Fractional CTO:
Be transparent about your goals, challenges, and constraints.
Empower them to make decisions and lead.
Stay engaged—this is a partnership, not a handoff.
Thinking about bringing on a Fractional CTO?
Colayre offers flexible, high-impact tech leadership tailored to your stage and strategy. Let’s talk about how we can help you scale smarter.