For 20 years I ran IT at the enterprise level, as CIO, CTO, and VP of IT. Now I bring that same leadership to small and mid-size businesses that need strategic IT direction but can't justify a full-time executive.
Most growing businesses hit a wall around 20–250 employees: the IT decisions get serious, the risk gets real, and the people who got you here aren't built for the strategic calls ahead. I've been the person making those calls at enterprise scale for three decades.
I led IT through a company's growth from $100K to $25M in revenue, delivering 3,255% shareholder value along the way. I've personally run 150+ Microsoft 365 and hybrid-cloud migrations. I hold CEH and Security+ certifications, so the security side isn't theoretical: it's operational.
Crawford IT is the practice I built to put that experience to work for businesses that need it most. It's intentionally part-time: senior focus, right-sized scope, no bloated retainers. You get the CIO judgment without the executive overhead.
Strategy, security, and cloud are where growing businesses get hurt. Here's where the experience runs deepest.
Multi-year roadmaps aligned to business goals, budget reality, and risk tolerance, prioritized by ROI, not by vendor preference.
Security programs, risk registers, and compliance readiness (HIPAA, SOC 2) built by someone who's owned them operationally.
150+ migrations. Architecture, license consolidation, cost control, and the cleanup work nobody got around to after go-live.
IT translated into business terms for founders, boards, and leadership teams. Vendor-agnostic, executive-grade, decision-ready.
Contract review, spend optimization, and the discipline to say no to tools you don't need, keeping IT aligned to the business.
Incident response planning, risk registers, and the calm that comes from having lived through the scenarios you're worried about.
The most expensive thing in IT isn't a tool: it's a wrong decision made early and lived with for years. My job is to make sure that doesn't happen to you.
Thirty minutes, no pressure. You'll get a senior CIO's read on where your IT stands, whether or not we end up working together.
Book a free strategy call