Oscar ONeill. London, Ontario, Canada.

I like figuring things out with people.

I’m a business owner, software builder, and enthusiastic process nerd. I run DigitalStaff, where I help people make better use of AI and automation, and I build a few products of my own.

I love getting into the inner workings of businesses: how things happen, what makes work difficult, and what we can do about it. A good conversation can turn into a plan, a working piece of software, and a whole new set of possibilities. That’s my kind of afternoon.

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

How this all started

My first encounter with automation was in RuneScape, when I was twelve, on the family computer. I downloaded a botting program, left it mining virtual rocks overnight, and woke up to a bank full of digital gold. Discovering that a computer could play the game for me while I slept made quite an impression.

Years later, I built my own RuneScape bot from scratch. It fought scorpions, caught and cooked fish, and ate them to heal after battle. I was very pleased with it. Then my bot got stuck in a corner, immobile and mute, and attracted the attention of a moderator, who immediately pegged my character as a bot and banned me. Oops!

I still think about that first overnight botting session, going to sleep and dreaming of digital rocks. Not much has changed for me since then. The stuff I automate has changed (it’s a lot more professional now, I swear!), but the satisfaction is exactly the same. Read the full RuneScape story(opens in a new tab)

At sixteen, I started Neighbourhood Nerd, my first small business: fixing computers and riding my bike to house calls. That grew into YourTech, where I supported the technology small businesses depended on. Working with those businesses got me interested in the work happening around their computers: the repeated tasks, the inefficiencies, and the workarounds people had learned to live with.

I finished my Bachelor of Arts in Media, Information and Technoculture at Western University in 2017 and founded DigitalStaff in 2018. Now I run DigitalStaff and build the practical systems I wish more small businesses had access to.

What working with me is like

I ask a lot of questions. I like seeing how people work and understanding the little decisions they make along the way. The offhand remarks and digs at the software they use tell me a lot about which problems to solve.

There’s usually some joking, some showing and telling, and a plan taking shape between us.

From there, I turn what we’ve learned into a clear plan, build a working version, and bring it back for feedback. I want people to recognize their own work and their own needs in the software, and to feel comfortable telling me what needs to change.

I use AI to explore ideas, learn, organize information, and write software. Working with AI coding agents to build really useful software for my customers has increased how much I can help. It’s never a one-off task either. I keep working on and improving the code collaboratively with the people who use the system.

I love the breadth of it: business conversations, process design, software, and the practical work of getting something useful into people’s hands.

What I’m building

MyDailyCheck

FOUNDER · GROWING

An automated daily phone check-in for seniors living independently, with alerts to the people who care about them when a check-in is missed.

mydailycheck.ca(opens in a new tab)

MarkScanner

PRODUCT · IN PILOT

Helps math teachers create, scan, and mark paper math tests so they can focus on the other important parts of the job, like helping students reach their full potential.

markscanner.ca(opens in a new tab)

YourTech Limited (opens in a new tab) is the company behind DigitalStaff and my software products. The computer-repair business grew up.

Away from the screen

Updated September 2026

Lately I’ve been trying to recreate the food I ate in Czechia, Austria, and Hungary on a recent trip: schnitzel, dumplings, and goulash. Pan-frying schnitzel and spooning hot oil over it, I felt like I was on Hell’s Kitchen. I could practically hear Gordon Ramsay calling me a donut for leaving it in the pan too long. After a day of digital work, making something real and delicious is refreshing.

I like fixing my car, biking, and playing flag football. I’m one of the few players wearing the requisite mouthguard, mostly because I would like to keep eating schnitzel with my original teeth.

My reading leans heavily toward science fiction, especially elaborate time-travel stories like Recursion by Blake Crouch, plus anything by Andy Weir. I love the ambitious problem-solving in The Martian. Could I survive stranded on Mars? Probably not. With full-time access to the latest AI model I might manage to grow my own potatoes, but the whole lack-of-oxygen situation would still need addressing.

Closer to home, there’s Mimi, my mom’s miniature poodle, who I dognap every so often and thoroughly spoil.

Say hello

I love hearing about what people are working on, particularly if there’s an interesting problem involved. Business ideas, collaborations, questions about my work, and good science-fiction recommendations are all welcome.

Looking for automation services? Visit DigitalStaff.(opens in a new tab)