What to Expect in Your First 90 Days with a Fractional CTO

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.