The First 90 Days with a Fractional CTO: What to Expect (UK Business Timeline & Deliverables)

Last Updated: 4 November 2025 | Reading Time: 13 minutes

TL;DR - What to Expect in the First 90 Days

Q: What deliverables should I expect from a fractional CTO in their first 90 days?

A: In the first 90 days, expect: Week 1 - technical assessment and priority identification; Month 1 - comprehensive audit and 90-day roadmap; Month 2 - implementation of quick wins and strategic initiatives; Month 3 - measurable improvements in team velocity, cost optimisation, or technical decision quality. By day 90, you should have documented strategy, improved technical operations, and clear ROI visibility.

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Why the First 90 Days Matter

Last month, a Birmingham software company hired their first fractional CTO. After 60 days, the founder confided: "I don't know what they're doing or if it's working. I have no idea what I should expect by now."

Three months later, they had a comprehensive technical strategy, reduced AWS costs by £2,100/month, hired two developers successfully, and established quarterly planning processes. The problem wasn't the fractional CTO's performance - it was unclear expectations.

Most UK businesses hiring their first fractional CTO don't know what "good" looks like in the first 90 days.

This creates three problems:

• Founders can't tell if the engagement is working - no baseline for progress
• Fractional CTOs lack clear success criteria - ambiguous goals lead to misalignment
• Both parties waste time - working on wrong priorities without structured onboarding

This guide provides a week-by-week breakdown of what to expect, what deliverables should emerge, and red flags that indicate problems. Whether you're about to hire or currently 30 days into an engagement, you'll know exactly what should be happening.

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Week 1 (Days 1-7): Discovery and Assessment

What Should Happen

Day 1-3: Initial Immersion

• Access to all key systems (code repos, cloud infrastructure, project management tools)
• Introductions to entire technical team and key stakeholders
• Review of existing documentation (architecture, roadmap, past incident reports)
• Understanding of current challenges and pain points
• Initial stakeholder interviews (1-on-1 with founders, tech leads, key developers)

Day 4-7: Initial Assessment

• High-level audit of technology stack and architecture
• Review of current projects and priorities
• Assessment of team structure and capability
• Identification of immediate risks or opportunities
• Preliminary understanding of business objectives

Expected Deliverables by End of Week 1

1. Initial Assessment Summary (5-10 page document)

• Current state overview (technology, team, processes)
• 3-5 immediate priorities identified
• Critical risks flagged (if any exist)
• Quick wins identified (achievable in 30 days)
• Recommended focus areas for first 90 days

2. Stakeholder Map

• Key technical and business stakeholders identified
• Communication cadence established
• Escalation paths defined

3. Working Agreement

• Confirmed time commitment and availability
• Agreed communication channels and response times
• Success metrics for first 90 days
• Meeting schedule established (weekly check-ins, monthly strategic reviews)

Red Flags in Week 1

⚠️ Warning signs that indicate potential problems:

• Fractional CTO hasn't met with all team members by end of week 1
• No written summary or assessment by day 7
• Asking for access to systems repeatedly (blocked by process/people)
• Focusing on technical details without understanding business context
• No clear plan for next 2-3 weeks communicated
• Missing scheduled meetings or delayed in responding to messages

How to Set Them Up for Success

What you should do in Week 1:

• Grant access immediately - Have all system access ready before Day 1
• Clear calendars - Ensure key team members available for introductions
• Provide documentation - Share all relevant docs, even if incomplete or outdated
• Set clear expectations - Communicate your priorities and concerns upfront
• Be honest about problems - Don't hide technical debt or team issues

Real Example: A Leeds e-commerce company prepared a "fractional CTO onboarding pack" before Day 1: system access credentials, architecture diagrams (even rough ones), list of current projects with status, team org chart, and list of known problems. Their fractional CTO completed Week 1 assessment in 5 days instead of typical 7-10, saving 20% of first month.

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Weeks 2-4 (Days 8-30): Deep Dive and Strategy Development

What Should Happen

Week 2: Deep Technical Assessment

• Detailed architecture review and documentation
• Infrastructure audit (cloud costs, security, scalability)
• Code quality assessment (sampling, not line-by-line review)
• Technical debt inventory and prioritisation
• Development process evaluation (CI/CD, testing, deployment)

Week 3: Team and Process Assessment

• Individual developer capability assessments (informal)
• Team dynamics and collaboration patterns
• Project management effectiveness review
• Hiring needs and gaps identification
• Knowledge documentation gaps

Week 4: Strategy and Roadmap Development

• Draft 90-day tactical roadmap
• 12-month strategic technology roadmap
• Prioritized initiative list with effort estimates
• Resource requirements (hiring, tools, budget)
• Risk mitigation plans for critical issues

Expected Deliverables by End of Month 1

1. Comprehensive Technical Assessment Report (15-25 pages)

• Current State Analysis:
  • Technology stack inventory and assessment
  • Architecture strengths and weaknesses
  • Infrastructure cost analysis and optimisation opportunities
  • Security posture and vulnerabilities
  • Technical debt quantification (time/cost to address)
• Team Assessment:
  • Team structure and capability mapping
  • Skill gaps and training needs
  • Process effectiveness evaluation
  • Velocity and productivity analysis
• Recommendations:
  • Prioritized improvement areas (must-fix vs nice-to-have)
  • Quick wins (achievable in 30-60 days)
  • Strategic initiatives (3-12 month horizon)
  • Investment requirements (time, money, people)

2. 90-Day Tactical Roadmap

• Specific initiatives for next 90 days
• Week-by-week milestone plan
• Resource allocation and ownership
• Success metrics for each initiative
• Dependencies and risks identified

3. 12-Month Strategic Technology Roadmap

• Quarterly themes and objectives
• Major technology initiatives (platform improvements, migrations, etc.)
• Hiring plan (roles, timing, justification)
• Budget requirements by quarter
• Technology investment priorities

4. First Quick Wins Delivered

• At least 1-2 immediate improvements implemented
• Examples: Cost optimisation, security patch, documentation, process improvement
• Visible impact demonstrating value early

Red Flags in Month 1

⚠️ Warning signs by end of week 4:

• No comprehensive written assessment delivered
• Generic recommendations that could apply to any business
• All recommendations require 6+ months (no quick wins identified)
• Assessment focused only on technology, ignoring team/process
• No clear roadmap or priorities established
• Requesting additional time to "complete assessment" beyond 30 days
• Recommendations don't align with stated business objectives
• No measurable success criteria defined

What Good Looks Like: Real Example

A Manchester SaaS company (£3M revenue, 5 developers) received this from their fractional CTO after 30 days:

• Assessment: 22-page report identifying £3,200/month in cloud waste, 3 architectural bottlenecks limiting scalability, 2 critical security vulnerabilities, and team knowledge gaps in infrastructure
• Quick Wins Delivered: Reduced AWS costs by £1,800/month (saving identified and implemented), implemented automated security scanning (vulnerability addressed), documented deployment process (knowledge gap filled)
• 90-Day Roadmap: 8 initiatives prioritised (2 completed in month 1, 4 planned for month 2, 2 for month 3) with specific owners and dates
• 12-Month Strategy: Plan to migrate to microservices architecture (Q2-Q3), hire 2 developers (Q2), implement comprehensive monitoring (Q1), budget £85,000 for technology investments

Result: Clear direction, immediate cost savings (£1,800/month = £21,600/year), and confidence in technical leadership.

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Weeks 5-8 (Days 31-60): Execution and Team Development

What Should Happen

Strategic Execution:

• Implementation of 90-day roadmap initiatives
• Progress on quick wins identified in Month 1
• First strategic initiative kicked off (if applicable)
• Regular progress reviews and course corrections

Team Development:

• 1-on-1 coaching with tech leads or senior developers
• Process improvements implemented (if needed)
• Technical hiring support (if hiring planned)
• Knowledge sharing and documentation initiatives
• Team communication and collaboration improvements

Operational Excellence:

• Establishment of regular technical reviews
• Architecture decision records started
• Technical standards and guidelines documented
• Incident response process established (if needed)
• Technical metrics dashboard created

Expected Deliverables by End of Month 2

1. Measurable Progress on Quick Wins

• At least 3-4 quick wins from Month 1 completed or in progress
• Quantified impact (cost savings, time savings, reduced errors, etc.)
• Team visibility into improvements

2. Technical Processes Established

• Regular technical review meetings scheduled and running
• Architecture review process for major decisions
• Documentation standards and templates
• Incident management process (if applicable)
• Technical metrics being tracked

3. Team Support and Development

• Regular 1-on-1s with technical leads
• Technical hiring progress (if applicable): job descriptions, candidate pipeline, interviews conducted
• Team skill development plan in progress
• Improved team communication and collaboration

4. Strategic Initiative Progress

• At least 1 major initiative from roadmap actively underway
• Clear ownership and timeline
• Regular progress updates
• Blockers identified and being addressed

5. Monthly Strategic Review Completed

• Written update on progress against 90-day roadmap
• Metrics dashboard showing improvements
• Adjusted priorities based on learnings
• Next 30-day focus areas clearly defined

Red Flags in Month 2

⚠️ Warning signs by end of week 8:

• No visible progress on quick wins from Month 1
• Still "assessing" or "planning" without execution
• No regular meeting cadence established
• Team doesn't know what fractional CTO is working on
• No documented processes or improvements
• Promises made but not delivered without clear explanation
• Fractional CTO not visible to team (remote without engagement)
• No metrics or progress tracking established

What Good Looks Like: Real Example

A Bristol fintech company (£2M revenue, 4 developers) at end of Month 2:

• Quick Wins Delivered: Reduced cloud costs by £2,400/month (from £4,800 to £2,400), implemented CI/CD pipeline (deployment time from 3 hours to 15 minutes), documented all key systems, established incident response process
• Processes Established: Weekly technical reviews, architecture decision log, fortnightly 1-on-1s with both developers, monthly strategic reviews with founder
• Strategic Progress: Hired 1 senior developer (fractional CTO led interviews), kicked off security audit project, started API documentation initiative
• Team Impact: Developer velocity increased 25% (features delivered per sprint), reduced production incidents from 4/month to 1/month, team satisfaction scores improved

Result: Clear ROI visible (£2,400/month savings + improved velocity), team feels supported, strategic initiatives progressing.

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Weeks 9-12 (Days 61-90): Optimization and Long-term Planning

What Should Happen

Roadmap Completion:

• Completion of 90-day roadmap initiatives (or clear progress with adjusted timelines)
• Measurable outcomes documented
• Lessons learned captured
• Success stories communicated to stakeholders

Process Maturation:

• Established processes running smoothly without constant oversight
• Team taking ownership of new practices
• Documentation complete and maintained
• Metrics and dashboards regularly reviewed

Strategic Planning:

• Next quarter (Q2) roadmap developed
• Refinement of 12-month strategy based on first 90 days
• Budget planning for next quarter/year
• Hiring plan updated (if applicable)

Relationship Transition:

• Shift from intensive onboarding to sustainable ongoing engagement
• Reduced time commitment if appropriate (from setup mode to maintenance mode)
• Established patterns and expectations clear to all

Expected Deliverables by End of Day 90

1. 90-Day Results Report

• Summary of all initiatives completed
• Quantified outcomes and ROI:
  • Cost savings achieved (cloud, tools, efficiency)
  • Time savings (deployment, processes, reduced incidents)
  • Quality improvements (reduced bugs, improved performance)
  • Team improvements (velocity, satisfaction, capability)
  • Risk reduction (security, technical debt, documentation)
• Case studies of key wins
• Challenges encountered and how addressed
• Recommendations for next 90 days

2. Updated 12-Month Strategic Roadmap

• Refined based on first 90 days learnings
• Clear priorities for Q2, Q3, Q4
• Resource requirements updated
• Budget requirements detailed
• Success metrics defined for each quarter

3. Next Quarter (Q2) Detailed Plan

• Specific initiatives with owners and timelines
• Dependencies and risks identified
• Resource allocation plan
• Success criteria for each initiative

4. Established Operating Rhythm

• Regular meeting schedule and cadences
• Communication patterns established
• Decision-making frameworks documented
• Escalation paths clear
• Team knowing when and how to engage fractional CTO

5. Measurable Business Impact

• At least £10,000-30,000 in quantified value delivered (cost savings + productivity gains)
• Improved team velocity (15-30% typical)
• Reduced incidents or technical issues
• Successful hires made (if hiring was priority)
• Strategic technology decisions made confidently

Red Flags at Day 90

⚠️ Serious warning signs by end of 90 days:

• Cannot quantify any value delivered (no cost savings, no productivity gains, no improvements)
• Still in "assessment" or "planning" phase
• No documented processes or standards established
• Team unclear on what fractional CTO has accomplished
• Original roadmap largely undelivered without good explanations
• No regular operating rhythm established
• Fractional CTO still figuring out what to work on
• No measurable improvement in any area (cost, velocity, quality, team capability)
• Relationship feels transactional rather than strategic partnership

If seeing 3+ of these red flags at Day 90, it's time for a serious conversation about fit and expectations.

What Good Looks Like: Real Example

A London marketplace startup (£1.5M revenue, 6 developers) at Day 90:

Quantified Outcomes:

• Cloud costs reduced from £5,200/month to £3,100/month (£2,100/month = £25,200/year savings)
• Deployment time reduced from 4 hours to 30 minutes (saving 14 hours/month = £3,500/month developer time)
• Production incidents reduced from 8/month to 2/month (saving ~20 hours/month = £5,000/month)
• Hired 2 developers successfully (avoided 1 potential bad hire = £50,000 saved)
• Developer velocity increased 35% (features per sprint from 8 to 11)
• Total quantified value in 90 days: £83,200 (£25,200 annual savings + £50,000 hiring risk avoided + £8,500/month productivity gains)
• Investment: £18,000 (£6,000/month × 3 months)
• ROI: 362% in first 90 days

Processes Established:

• Weekly technical reviews (now run by tech lead with fractional CTO attending monthly)
• Architecture decision records (10 decisions documented)
• Incident response process (followed for 6 incidents, average resolution time down 65%)
• Hiring process for technical roles (used to successfully hire 2 developers)
• Quarterly strategic planning process

Strategic Direction:

• 12-month roadmap with clear priorities
• Q2 plan with 6 initiatives (all with owners and timelines)
• Technology budget approved (£120,000 for year)
• Hiring plan (2 more developers in Q2-Q3)

Relationship: Fractional CTO now in sustainable 2-day/month engagement (reduced from 3 days during intensive 90-day period), team operating independently with strategic guidance as needed.

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Success Metrics: How to Measure Progress

Week 1 Success Criteria

• ✅ Initial assessment document delivered
• ✅ All stakeholder meetings completed
• ✅ 3-5 priorities identified
• ✅ Working agreement and schedule established

Month 1 Success Criteria

• ✅ Comprehensive technical assessment delivered (15-25 pages)
• ✅ 90-day roadmap documented with specific initiatives
• ✅ 12-month strategic roadmap created
• ✅ At least 1-2 quick wins delivered
• ✅ Clear success metrics defined

Month 2 Success Criteria

• ✅ 3-4 quick wins completed or in progress
• ✅ Regular meeting cadence established and running
• ✅ At least 1 strategic initiative actively underway
• ✅ Technical processes documented and adopted
• ✅ Measurable progress visible to team

Month 3 (Day 90) Success Criteria

• ✅ £10,000-30,000+ in quantified value delivered
• ✅ 90-day roadmap substantially complete
• ✅ Next quarter plan documented and approved
• ✅ Established operating rhythm with team
• ✅ Measurable improvements in velocity, quality, or cost
• ✅ Team confident in technical direction

How to Track Progress

Weekly Check-ins (15-30 minutes):

• What was accomplished this week?
• What's planned for next week?
• Any blockers or challenges?
• Quick review of any urgent issues

Monthly Strategic Reviews (60-90 minutes):

• Progress against 90-day roadmap
• Quantified outcomes delivered
• Updated metrics dashboard
• Adjusted priorities for next month
• Discussion of strategic questions or decisions

90-Day Review (2-3 hours):

• Comprehensive results presentation
• ROI analysis and quantified outcomes
• Review of what worked and what didn't
• Refined 12-month strategy
• Next quarter detailed plan
• Discussion of ongoing engagement model

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Common Blockers and How to Address Them

Blocker 1: Slow Access to Systems and Information

Impact: Delays Week 1 assessment by 1-2 weeks, pushes all subsequent deliverables

Solution:

• Prepare access credentials before Day 1
• Have IT/admin ready to provision access immediately
• Use temporary read-only access if full access requires approval process
• Provide documentation even if incomplete

Blocker 2: Team Resistance or Lack of Engagement

Impact: Fractional CTO can't get accurate information, team won't adopt recommendations

Solution:

• Communicate clearly to team why fractional CTO is being engaged (not replacing anyone, here to support)
• Involve team in assessment process (ask for their input on problems and priorities)
• Celebrate quick wins publicly (show value to team)
• Have fractional CTO build relationships with team early (not just management)

Blocker 3: Unclear or Changing Priorities

Impact: Fractional CTO works on wrong things, wasted time and effort

Solution:

• Establish clear success criteria in Week 1
• If priorities change, have explicit conversation and adjust roadmap
• Use monthly strategic reviews to course-correct
• Document agreed priorities and revisit regularly

Blocker 4: Insufficient Time Commitment

Impact: Progress slower than expected, deliverables delayed

Solution:

• Be realistic about time needed for first 90 days (often higher than steady-state)
• Consider 3-4 days/month for first 90 days, then reduce to 2-3 days ongoing
• Clarify expectations upfront about deliverable timelines based on time commitment
• If critical work needed, consider temporary increase in hours

Blocker 5: Expecting Hands-On Implementation

Impact: Misalignment between expectations and fractional CTO role

Solution:

• Clarify that fractional CTO provides strategic guidance, not implementation
• Ensure you have team to execute recommendations
• If need hands-on work, consider additional technical consultant or developer hire
• Focus fractional CTO time on high-leverage activities (strategy, architecture, hiring, decisions)

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Setting Your Fractional CTO Up for Success

Before Day 1: Preparation Checklist

✅ Access and Accounts

• Code repository access (GitHub, GitLab, etc.)
• Cloud infrastructure access (AWS, Azure, GCP - read-only initially)
• Project management tools (Jira, Asana, Linear, etc.)
• Communication tools (Slack, Teams, email)
• Documentation systems (Notion, Confluence, Google Docs)
• Monitoring and analytics tools

✅ Documentation Gathered

• Architecture diagrams (even if rough or outdated)
• Technology stack list
• Current roadmap or backlog
• Recent incident reports or post-mortems
• Team org chart
• Any existing technical strategy documents

✅ Stakeholder Alignment

• Team informed about fractional CTO engagement
• Key stakeholder calendars cleared for intro meetings
• Clear communication about fractional CTO's role and objectives
• Expectations set internally about timeline and deliverables

✅ Success Criteria Defined

• Clear business objectives fractional CTO should support
• 3-5 priority problems to solve
• Success metrics you'll use to evaluate engagement
• Budget and resource constraints communicated

During First 90 Days: Your Role

Week 1:

• Be available for questions and context
• Facilitate introductions to team
• Provide honest assessment of challenges
• Review and provide feedback on initial assessment

Weeks 2-4:

• Review and approve 90-day roadmap
• Ensure team cooperating with assessment
• Provide business context for technical decisions
• Remove blockers fractional CTO identifies

Weeks 5-12:

• Hold team accountable for executing roadmap
• Participate in monthly strategic reviews
• Provide feedback on progress
• Communicate wins to broader organization
• Make decisions when fractional CTO needs direction

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When to Be Concerned vs When to Be Patient

Be Concerned If (Address Immediately):

• ❌ No written deliverables by end of Month 1
• ❌ Cannot articulate what they're working on or why
• ❌ Missing scheduled meetings or consistently late responses
• ❌ Team doesn't know who they are or what they're doing
• ❌ No progress visible after 60 days
• ❌ Cannot quantify any value by Day 90
• ❌ Constantly changing focus without completing anything
• ❌ Making recommendations that conflict with business objectives

Action: Have direct conversation immediately. Review engagement terms and expectations. Consider 30-day improvement plan or transition out.

Be Patient When:

• ✅ Progress slower than expected due to complexity you didn't anticipate
• ✅ Recommendations challenging but clearly well-reasoned
• ✅ Quick wins taking longer but for good reasons (dependencies, resource constraints)
• ✅ Team adoption of new processes taking time (normal change management)
• ✅ Fractional CTO identifying more problems than expected (thorough assessment)
• ✅ Strategic initiatives require more planning than anticipated

Key difference: Good fractional CTOs communicate proactively about delays, provide clear reasoning, adjust plans accordingly, and still deliver documented progress. Poor fractional CTOs go silent, make excuses, or promise future deliverables without interim progress.

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After 90 Days: Transitioning to Ongoing Engagement

Evaluate the Engagement

Questions to ask yourself at Day 90:

• Has measurable value been delivered? (cost savings, productivity gains, successful hires, strategic decisions made)
• Do I have more confidence in our technical direction?
• Has the team improved? (velocity, capability, processes)
• Do I have clear visibility into technology status and roadmap?
• Has technical risk been reduced?
• Is the relationship working well? (communication, alignment, trust)

If 5-6 yes: Excellent engagement - continue and adjust time commitment as needed

If 3-4 yes: Good engagement with room for improvement - discuss concerns and refine

If 0-2 yes: Poor fit - consider transitioning out or major reset of expectations

Adjust the Ongoing Model

After intensive 90-day onboarding, typical adjustments:

• Reduce time commitment: If engaged at 4 days/month for first 90 days, might reduce to 2-3 days/month ongoing
• Shift focus: From setup/assessment to ongoing strategic guidance and execution support
• Empower team: Fractional CTO has established processes that team now owns, reduces need for constant oversight
• Quarterly planning: Establish rhythm of quarterly strategic planning with monthly check-ins

Long-term Success Pattern

Months 4-6: Execute Q2 roadmap, refine processes, continue delivering value

Months 7-12: Established partnership, predictable value delivery, strategic planning cycles

Year 2+: Ongoing strategic guidance, adapt as business grows, potential transition planning to full-time CTO when appropriate

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Final Checklist: Are You On Track?

End of Week 1:

• [ ] Initial assessment document received
• [ ] 3-5 priorities identified
• [ ] Regular meeting schedule established
• [ ] Team has met fractional CTO

End of Month 1:

• [ ] Comprehensive technical assessment (15-25 pages) delivered
• [ ] 90-day roadmap documented
• [ ] 12-month strategic roadmap created
• [ ] At least 1-2 quick wins delivered
• [ ] Clear success metrics defined

End of Month 2:

• [ ] 3-4 quick wins completed or in progress
• [ ] Technical processes established and documented
• [ ] Strategic initiative actively underway
• [ ] Regular cadence running smoothly
• [ ] Team seeing visible progress

End of Day 90:

• [ ] £10,000-30,000+ in quantified value delivered
• [ ] 90-day roadmap substantially complete
• [ ] Next quarter plan approved
• [ ] Measurable improvements visible
• [ ] Team confident in technical direction
• [ ] Sustainable operating rhythm established

If you can check 80%+ of these boxes, your fractional CTO engagement is on track for success.

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Ready to Start Your Fractional CTO Engagement Right?

Book a free 30-minute consultation to discuss your first 90 days.

We'll help you:

• Set realistic expectations for your first 90 days based on your situation
• Define success criteria and deliverables specific to your business
• Create an onboarding plan that accelerates value delivery
• Establish metrics to track progress effectively

Our fractional CTOs deliver an average of £35,000 in quantified value in the first 90 days through cost optimisation, improved velocity, and better technical decisions.

Book Your Free Consultation →

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About Grow Fast

Grow Fast provides fractional CTO services to UK businesses at the £1-10M revenue stage. We've helped 15+ businesses successfully navigate their first 90 days and establish sustainable technical leadership.

Our approach: We establish clear expectations from Day 1, deliver documented progress weekly, and ensure measurable value by Day 90. Our fractional CTOs average 250%+ ROI in the first 90 days through cost optimisation, improved productivity, and better technical decisions.

Related Services:

• Fractional CTO: Part-time strategic technical leadership for growing businesses
• AI Audit: Identify £50K+ in efficiency opportunities through practical AI implementation
• Managed Projects: Fixed-price delivery for specific technical projects

Read more in this series:

• Day 1: How Much Should You Budget for a Fractional CTO? (Complete UK Breakdown)
• Day 2: Fractional CTO vs Consultant vs Interim CTO (Which Your Business Needs)
• Day 3: 7 Signs You're Ready for a Fractional CTO (And 3 Signs You're Not)
• Day 4: The First 90 Days with a Fractional CTO (You're reading this)

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This guide is based on 15+ successful fractional CTO engagements with UK businesses, analysis of first 90-day outcomes, and established best practices for technical leadership onboarding. All examples are from real engagements with identifying details changed. Data current as of November 2025.