I've been doing IT long before the iPhone.
I built macOS deployment automation from scratch and ran DigginIT, a Canadian Apple-focused managed services company, for nearly two decades. Back then, there was nothing to buy and you had to write it yourself.
From there I ran Apple platform engineering at Morgan Stanley, built endpoint platform engineering at Shopify, and grew the Apple practice at Wipro fifteen times over, all under audit and at Fortune 500 scale, years before Goodland existed.
None of those jobs go to a stranger. A bank vets you before it hands over its fleet, and a client keeps an MSP for two decades only if the work holds up. The through-line of my career is that people trusted me with their IT, and it kept being the right call.
Now it's just me. If your fleet is out of anyone's control, your AI policy doesn't exist yet, or you need something built, ask me.
// the short version
- Since
- 2000. I was automating Mac deployment before Jamf shipped.
- Ran fleets at
- Morgan Stanley, Shopify, and Wipro, before Goodland.
- Built
- DigginIT, a Canadian Apple MSP. Founded it and ran it for nearly two decades.
- Certified
- Jamf 400. Apple Certified Support Professional.
- Spoke at
- JNUC, twice. Published by Jamf.
// what i do
Six things, and I do all of them myself.
Advice and building get equal weight, because advice is worthless if nobody ever ships the thing. Most people start with one of these and add the rest later. I write the policy, deploy the fleet, and build the tool myself, where most consultants only do one of the three.
Advisory
- Apple & full-stack IT
- Zero-touch Mac deployment, MDM, device lifecycle. I was building this before Jamf existed. I'll set it up so you stop thinking about it. Intune and cross-platform too.
- AI governance
- A policy, an approved tool list, and usage tracking. Before someone pastes a client file into a chatbot. Mapped to PIPEDA and whatever confidentiality rules your profession actually has.
- IT automation
- Onboarding, offboarding, resets, provisioning. Scripted and documented, so your ops keep running the week your admin quits.
Build
- Product engineering
- Custom progressive web apps on AWS Amplify. They install from the browser and work offline. Role Radar and PokerRun are two I built and still run.
- Data feeds
- Scrapers that turn Canadian public data into structured feeds. CanadaBuys for federal procurement, CanadaJobs for postings. Available as JSON, CSV, or API.
- MCP feeds
- The same feeds as Model Context Protocol servers, so your AI agents can query live Canadian data with one line of config.
If the thing you need isn't on this list, ask anyway. If I can't help I'll tell you, and I'll usually know who can.
// built & shipped
Working software, live in production.
Two web apps you can use right now, a Canadian procurement feed live on Apify, and another still in build.
Role Radar
LIVEA personal job-hunt sweep that surfaces the right role and walks you through it. An installable PWA on AWS Amplify, fed by CanadaJobs.
roleradar.bot ↗PokerRun
LIVEHost or join poker-run events for motorcycles, boats, or anything. Visit checkpoints, draw cards, build the best hand. Free to organize.
pokerrun.fun ↗CanadaBuys
Federal and Local procurement tenders
CanadaJobs
Job postings, deduped, going back 6 months
Rows in the two feeds above are examples, not live data. Role Radar and PokerRun are live right now.
// mcp feeds · private beta
Give your AI agents live Canadian data.
The feeds will run as Model Context Protocol servers. Add one line to Claude, Cursor, or any MCP client and your agent can query procurement tenders and job postings directly, no scraping or glue code. The package is not published yet, so the config below is what it will look like. Ask me for early access.
- ▸Typed tools: search, filter, and fetch records
- ▸Same nightly data as the JSON, CSV, and API feeds
- ▸Hosted by us, or self-hosted in your stack
// about · the long version
Twenty-five years of Apple IT.
I founded DigginIT and ran it for nearly two decades. It was a Canadian Apple-focused managed services company. We were writing macOS deployment automation from scratch before Jamf and zero-touch enrollment existed, because there was nothing to buy. If you wanted it, you wrote it.
From there I moved into Apple platform engineering at large, regulated employers. I was Vice President of Apple Platform Engineering at Morgan Stanley, running an on-premises Jamf Pro deployment against mSCP, NIST 800-53, and CIS baselines, and reporting compliance posture straight to IT leadership. I did endpoint platform engineering at Shopify, on a global fleet of 15,000+ devices across macOS, Windows, iOS, and Android. Then at Wipro I helped build and lead the Apple engineering practice, growing it into a major practice, ran more than a dozen endpoint and security proof-of-concepts as the pre-sales architect, and governed device management for 50,000+ machines across Fortune 500 clients.
I've published technical work with AWS, Wipro, and Amaris, and spoken twice at JNUC, Jamf's own conference. Goodland is me. You get the person who did all of that on every engagement, not an account manager and a junior with a runbook. When a job genuinely needs more hands, I bring in senior people I've worked with for years.
Here's the part the resume doesn't say outright: all of that ran on trust. The work I like best has always been sitting down with an owner or an IT lead, figuring out what they actually need, and becoming the person they stop worrying about it with. Clients stayed with DigginIT for years at a stretch, and employers kept handing me bigger fleets. Twenty-five years in, I'm still not done earning it.
And about the name: Goodland is an apple. A hardy variety developed right here in Manitoba, bred to come through a prairie winter and fruit again the next year. Given what I do for a living, it seemed like the right one to borrow.
Credentials
- ✓Jamf Certified Expert (Jamf 400)
- ✓Apple Certified Support Professional
- ✓Enterprise MDM with Microsoft Intune
- ✓AWS Cloud & Solutions Architecture
- ✓Microsoft Azure OpenAI
- ✓Google Vertex AI
- ✓ISACA Member
// let's talk
Tell me what's slowing your IT down, or what you want to build.
Send me a note and I'll set up a 30-minute call. No cost, no pitch. We talk through where you're stuck and what to do about it. And it's me you'll be talking to, start to finish.
Prefer email? chris@goodland.consulting