IT Executive Advisory · AI Strategy · Vancouver

Enterprise IT leadership at the intersection of operations, transformation, and AI.

Twenty years building and scaling technology for organizations going through transformation — IPOs, M&A integrations, 400-site global footprints, and now the AI shift that's reshaping how IT delivers value to the business.

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David Olson, IT Executive Advisor
What I Do

Three areas where I help leadership teams move faster with less risk.

01

AI Strategy & Operations

Helping CIOs and executive teams build credible AI strategies — from use case prioritization and governance frameworks to hands-on evaluation of agentic AI for IT and business operations.

02

M&A Technology Integration

End-to-end IT integration for acquisitions and divestitures: infrastructure, applications, databases, business processes. I've led integration for a $1B acquisition and scaled platforms through aggressive M&A from 12 to 400 sites without expanding the cost model.

03

Enterprise Platform Operations

Architecture, infrastructure, cloud governance, disaster recovery, and cost optimization. The unglamorous work that keeps businesses running — and the disciplines that let them scale. FinOps, ISO 27001, ITSM, and the leadership practices that make it stick.

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.

$1B
Acquisition IT integration led end-to-end
37%
Reduction in IT spend as % of revenue
200→500
Scaled a company through IPO and acquisition
12→400
Sites scaled through M&A without cost growth
Zero
Security breaches across full Copperleaf tenure
ISO 27001
Corporate-wide certification led and delivered
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 end-to-end 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, IT 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. Grew entirely through referrals. 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 with a $5M operational budget, delivering enterprise infrastructure and field technology services across 400+ sites in North America and Europe. Scaled platforms through divisional M&A from 12 to 60 to 400 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.”
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