Oscar ONeill. London, Ontario, Canada.

I build AI and automation systems for real businesses.

Founder of DigitalStaff. I help small and mid-sized organizations automate repetitive work and build operations that are simpler, faster, and easier to scale.

Email me LinkedIn

Oscar ONeill standing at a mountain overlook in Banff, Alberta.

What I’m building

DigitalStaff

FOUNDER · ACTIVE SINCE 2018

My main business. An AI and automation consultancy for small and mid-sized companies. I design, build, and manage systems that take repetitive work off people’s plates. Clients include accounting firms, agriculture operations, manufacturers, and property managers across Ontario and beyond.

Personal note: fifteen years of self-employment distilled into one company—and everything I’ve learned about how small businesses actually run.

digitalstaff.ca

MyDailyCheck

FOUNDER · GROWING

An automated daily check-in service for seniors living independently. A simple phone call every day. If someone doesn’t answer, the people who care about them find out. Built because this problem deserves a solution that doesn’t cost $60 a month.

Personal note: my first consumer product, and the one that leads to the most interesting conversations.

mydailycheck.ca

More projects

MarkScanner

PRODUCT · IN PILOT

AI-assisted grading for math teachers. Scan a stack of tests, get consistent marking with a rubric, and give students better feedback in a fraction of the time. Currently in pilot with real classrooms.

markscanner.ca

YourTech Limited

COMPANY · HOLDING

The federally incorporated company behind DigitalStaff and my software products. It began as the IT business I built after Neighbourhood Nerd and has existed in its current form since 2017.

yourtechlimited.com

The story

I started fixing computers for money at 16 under the name Neighbourhood Nerd. I rode my bike to house calls, undercut Geek Squad, and learned early that people pay for problems solved, not hours worked.

That became YourTech, an IT services business handling the servers, networks, and unglamorous systems that kept small companies running. At Western, a course on automation theory gave me a framework for something I had already been circling: software can change the shape of work, not just speed it up.

I later co-founded an AI software company, built the product, and learned difficult lessons about product, partnerships, and ownership. Today I run DigitalStaff and build the practical systems I wish more small businesses had access to.

/now

Updated July 2026. Refreshed quarterly.

DigitalStaff: Building client automation for agriculture, accounting, and manufacturing; currently rewriting a large email platform in TypeScript.
Products: Growing MyDailyCheck after its first paying customers and piloting MarkScanner in real classrooms.
Away from work: Cooking, reading, biking around London, keeping a 2011 Ford Edge alive, and spoiling Mimi—the world’s most pampered miniature poodle.

How I think

Three beliefs that run through everything I build:

Free people, don’t replace them.

The goal of automation isn’t fewer people. It’s taking the repetitive work off their plates so they have time for judgment, relationships, and the work that actually needs a human.

Own the important parts.

I prefer open tools, portable systems, and infrastructure I can understand and control. Managed services are useful, but no critical system should depend on a vendor I cannot replace.

Boring is a feature.

The best automation is the kind nobody talks about because it just runs. Every day. Without drama.

Get in touch

Have a business automation problem, a product or partnership idea, or an unusual technology project? Send me a note.

Looking for automation services? Visit DigitalStaff.

oscar@digitalstaff.caLinkedIn