Available now · accepting fractional IT leadership and project engagements for Q2 & Q3 2026
Fractional IT Leadership · Interim Technology Executive · Vancouver

Senior IT leadership, when you need it, for as long as you need it.

Twenty years running enterprise technology through IPOs, M&A integrations, 400-site global rollouts, and corporate-wide ISO 27001 certification. Now available to mid-market companies, PE-backed portfolios, and growth-stage SaaS that need executive-grade IT leadership — including strategic partnership through the agentic-AI transition the whole industry is working through.

David Olson, Fractional IT Executive
Service Menu

Eight ways I help companies build IT that actually scales.

Every engagement is scoped to the problem in front of you. Some clients bring me in to lead IT two days a week. Others need a three-week assessment before their next board meeting, or a senior hand on an M&A integration. Here's what I do.

Flagship

Fractional & Interim IT Leadership

Bring me in to lead IT — one to three days a week — owning strategy, team leadership, vendor management, board reporting, and the hard calls. Ideal for companies that have outgrown their IT manager or are between permanent leaders. Call the role whatever fits internally; I bring the authority and operating rigor of a full-time executive.

Engagement: 3–12 months · 90-day minimum
AI & Agents

AI Strategy Partnership

Strategic partnership through the agentic-AI transition: AI use-case portfolio, governance baseline, data-readiness assessment, minimum production standard for agents, and cross-functional alignment across finance, legal, security, and business. For CIOs and executives who need to move AI from pilot theater to a credible operating plan — and want a senior IT partner working the transition with them, not selling yesterday's playbook.

Engagement: 4–8 weeks + ongoing advisory retainer
M&A

M&A Technology Integration

End-to-end IT integration for acquisitions and divestitures — infrastructure, applications, databases, business processes. And technology due diligence for PE firms and corporate development teams who need a trusted senior read on the target.

Engagement: 1–3 weeks for DD · 3–9 months for integration
Strategy

IT Strategy & Roadmap

Current-state assessment, gap analysis, and a 12–36 month technology roadmap with a real budget model and an executive presentation that lands. For companies about to scale, modernize, or raise.

Engagement: 3–6 weeks, fixed fee
Risk & Compliance

Cybersecurity & Compliance

Risk assessments, framework gap analysis (SOC 2, ISO 27001, HIPAA, NIST), remediation roadmaps, policy libraries, and ongoing advisory through audit prep. I've led a corporate-wide ISO 27001 certification end to end, zero breaches across full tenure.

Engagement: 2–8 weeks + optional oversight retainer
Cloud & Infrastructure

Cloud Strategy & FinOps

Cloud readiness, phased migration plans, vendor selection across AWS, Azure, and GCP, and FinOps discipline to get the spend under control. Proven at scale — I've cut IT as a percentage of revenue by 37% without slowing delivery.

Engagement: 3–6 weeks for strategy · ongoing execution oversight available
Assessment

IT Assessments & Audits

A fast, executive-ready read on your IT environment: infrastructure, security posture, application portfolio, vendor spend, team structure, compliance gaps. Prioritized remediation plan included. Low commitment, high insight.

Engagement: 1–3 weeks, fixed fee
Operations

Vendor, Team & Org Design

Vendor evaluation, RFP management, and contract negotiation — often on a savings-share model. Plus IT team org design: structure, roles, hiring plans, and the management practices that make it stick as you grow.

Engagement: 2–6 weeks per engagement
How to Engage

Three ways to start working together.

Most clients enter at the Quick-Look, step up to a Roadmap, and end at a Retainer. Some jump straight to ongoing IT leadership if they're in transition or crisis. All three are scoped for mid-market budgets.

Package 01

The IT Quick-Look

Fixed-fee engagement / scoped to your environment

A one-week executive assessment. Low-risk entry point, often the start of something larger.

  • Infrastructure, security & apps review
  • Vendor spend and team structure audit
  • Prioritized remediation plan
  • Executive-ready findings report
Start a Quick-Look
Package 03

Fractional IT Leadership

Monthly retainer / scoped to days per week

Ongoing leadership of your IT function, one to three days per week. Executive presence and operating authority without the full-time hire.

  • Strategy execution & team leadership
  • Vendor oversight & budget discipline
  • Security, risk & board-level reporting
  • 90-day minimum, 30-day rolling after
Discuss a retainer
Track Record

I've owned the full technology mandate at scale — reporting to the CEO, running the team, making the call when it's hard. The same hand, now at your table.

$1B
Acquisition — led IT integration end to end
37%
Reduction in IT spend as % of revenue
200→500
Scaled a company through IPO and acquisition
12→60
Sites scaled without cost model expansion
Zero
Security breaches across full tenure
ISO 27001
Corporate-wide certification led & delivered
Who I Work With

Built for companies in transition.

Mid-market companies
(100 – 1,000 employees)

Big enough to have real IT complexity. Too small to justify a full-time IT executive salary. The sweet spot for fractional leadership.

PE-backed portfolio companies

Between IT leaders, under operating-partner pressure to professionalize, or mid-integration. I've lived this cycle from the inside.

Growth-stage SaaS
(Series B – D)

Outgrowing the first IT hire. Need governance, security, SOC 2 or ISO readiness, and the cloud discipline to scale without runaway cost.

Companies in transition

M&A integration, leadership departure, compliance deadline, rapid scaling, post-incident cleanup. Urgency is where I do my best work.

Twenty Years Of

Doing the job I'm now offering to do for you.

2024 – 2025

Senior Director, IT PMO

IFS — Industrial AI, ERP & Enterprise Software · London HQ · 90+ countries

Rebuilt IT governance and delivery capability at a 7,000-person international software company. Ran IT integration of Copperleaf into IFS across infrastructure, applications, databases, and business processes.

2019 – 2024

Head of IT (Director, Technology Experience)

Copperleaf Technologies · Asset Management SaaS · Reported to CEO

Owned the full IT operations mandate: cloud and on-premise infrastructure, databases, cybersecurity, service delivery, disaster recovery. 38-person team, $11M budget. Scaled through IPO (2021) and $1B IFS acquisition (2024). ISO 27001 certified. Zero breaches.

2005 – 2019

Owner & Operator

Granite Mind IT Solutions · Vancouver, BC

Fourteen years running managed IT services for BC-based SMBs. Infrastructure, networks, server and database administration, end-user support across Mac, Windows, and Linux environments.

1997 – 2005

Director of Network Services

Iron Mountain Inc. · $2.1B Revenue · 10,000 Employees · Seattle, WA

Oversaw a distributed team of 35, delivering enterprise infrastructure and field technology services across 60 sites in North America, and then 400. Scaled platforms through divisional M&A from 12 to 60 sites without expanding the cost model.

Perspective
“The question isn't how do we enable IT with AI. It's how do we reimagine the business around AI. That's a fundamentally different conversation, and it's the one CIOs need to own. If we don't claim that strategy, someone else at the table will.”
Let's Talk

Tell me what's on your plate.

First call is 30 minutes, no pitch, no obligation. I'll either be the right hand for the problem or I'll tell you who is.

Based In
Vancouver, British Columbia · serving clients across Canada & US