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Aaron M.
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Aaron M.

Fractional CTO | Microsoft 365, Azure & Security | IT Strategy & AI

Head of Technology with 25+ years leading IT for NZ and UK organisations. I've delivered cloud migrations up to $5M, cut telecom costs by $96K a year, built disaster recovery programmes for healthcare and insurance, and look after 250+ business websites. What I help with • Fractional CTO / CIO: technology strategy, roadmaps, vendor and budget management • Microsoft 365, Entra ID, Intune and Azure: setup, security hardening and migrations (including Google Workspace to M365) • Cybersecurity reviews, disaster recovery and business continuity • Infrastructure: Windows Server, Remote Desktop Services, networking, VoIP / 3CX • WordPress: security hardening, hacked-site clean-up and custom plugins • AI and automation: practical AI agents and workflows (I built my own AI agent platform for WordPress) • IT training and coaching for staff and teams Selected results • Metlifecare (NZ retirement and aged care): IT Manager with budgets up to $4M; fixed a VoIP routing fault that saved $96K a year with zero capital spend, and delivered an enterprise DR programme that had stalled for years • Aioi Nissay Dowa Insurance: IT Manager; delivered a Guidewire Cloud migration valued up to $5M, working with the Japanese parent company, and introduced change, vendor and governance frameworks • Royal London Group (UK): designed multi-datacentre disaster recovery for a 900-user, 55-server site • Gencom Technology: built a new IT Services division from scratch • Tandem Studios: Head of Technology & Digital Services; launched three new service lines and delivered 250+ customer websites • My Hotel: scaled from 20 to 140+ properties and $3M revenue How I work Async-friendly, with clear written reports, documented changes and no surprises. I overlap well with Australia, the UK and Europe, and US afternoons and evenings for calls. MCSE | BSc Computer Science (University of Auckland)

🇳🇿Auckland, New Zealand$60/hr100% JSS5.00 (2)Since Aug 2020
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Earnings and projects

MRR
$584

Last 6 months ÷ 3.5 months active (since Jul 2026)

World#71,454 / 412k
🇳🇿Country#69 / 622
Revenue, last 30 days
—

Read daily since Oct 28, under 30 days

Total earnings
$2k

Billed in all: $2.3k

World#331,964 / 412k
🇳🇿Country#514 / 622
Per project
$679

$672 in the last 6 months

World#155,351 / 412k
🇳🇿Country#240 / 622
Projects, last 6 months
3

Across 4 contracts

50% fixed50% hourly
World#66,479 / 412k
🇳🇿Country#68 / 622
Projects in all
3

Across 4 contracts

50% fixed50% hourly
World#304,140 / 412k
🇳🇿Country#479 / 622

Earnings, last 30 days

$2.3k+$166 earned since Oct 28Billed in all, before Upwork's fee · drag across the chart to see what was earned in any stretch
$2.1k$2.2k$2.3kOct 28Nov 2Nov 7

Tracked from Oct 28, 2026.

Skill rankings: Top 16% in IT Infrastructure

Ranked by MRR among everyone on Upwork with the skill.

  1. #13User Technical Training61 freelancers · 🇳🇿 #1Top 21%
  2. #233CX93 freelancers · 🇳🇿 #1Top 25%
  3. #24Disaster Recovery109 freelancers · 🇳🇿 #1Top 22%
  4. #35IT Infrastructure222 freelancers · 🇳🇿 #1Top 16%
  5. #42VoIP Administration218 freelancers · 🇳🇿 #1Top 19%
  6. #75IT Consultation459 freelancers · 🇳🇿 #1Top 16%
  7. #88Cloud Migration472 freelancers · 🇳🇿 #1Top 19%
  8. #92Microsoft Intune336 freelancers · 🇳🇿 #1Top 27%