The Fractional CTO Playbook for PE-Backed Companies
The 90-day playbook I run at every new PE portfolio company. Discovery, stabilization, and value creation — in that order.
I have run this playbook at enough portfolio companies to know what works. The first 90 days are everything.
Why Fractional
PE-backed companies in the $20M–$100M revenue range rarely need a full-time CTO. They need someone who has seen the movie before—who can walk in on Day 1, assess the landscape, and start creating value by Day 30. That is the fractional model.
The 90-Day Framework
Days 1–30: Discovery
The goal is simple: understand everything, change nothing.
- Infrastructure audit — Azure Migrate for full discovery. What is running, where, and what does it cost?
- License audit — Microsoft 365 Admin Center for license utilization. Who has what, and is anyone actually using it?
- People mapping — Who knows what? Where are the single points of failure?
- Technical debt inventory — Azure DevOps for codebase analysis, dependency mapping, and security posture.
Deliverable: a 10-page assessment with prioritized recommendations and cost estimates.
Days 31–60: Stabilization
Fix the things that are on fire.
- Identity consolidation — Get everyone onto Microsoft Entra ID with MFA. Non-negotiable.
- Backup and DR — If backups are not tested, they do not exist. Azure Backup and Azure Site Recovery.
- Security baseline — Microsoft Defender for Cloud across all workloads. Conditional access policies. Privileged Identity Management.
Deliverable: a security posture report showing before/after risk scores.
Days 61–90: Value Creation
Now we build.
- Data unification — Microsoft Fabric to consolidate the data estate. One source of truth for the operating partner.
- AI pilot — Pick the highest-impact, lowest-risk use case. Usually customer support or internal knowledge management with Copilot.
- Roadmap — A 12-month technology roadmap tied directly to the PE value creation plan.
Deliverable: a board-ready technology roadmap with quarterly milestones and investment requirements.
Why Microsoft
The answer is pragmatic, not religious. Microsoft's ecosystem is the only one that covers identity, productivity, data, AI, and infrastructure in a single licensing agreement. For PE portfolio companies that need speed and simplicity, it is the fastest path to value.
The ROI
Across my engagements, the fractional CTO model generates 3–5x ROI within the first year. The savings come from license optimization, vendor consolidation, and avoided incidents. The value creation comes from data-driven decision-making and AI augmentation of core workflows.