Oscar ONeill
Director of AI & Automation, Founder of DigitalStaff Building the Future of Business Automation, One Solution at a Time
Helping Businesses Achieve More Through Automation
My passion is helping people take advantage of the latest and greatest automation and AI technologies. I enjoy all aspects of this work, especially collaborating and building strong, lasting relationships where I guide business owners on their automation journey.
As the founder and Director of AI & Automation at DigitalStaff, I lead a team of people and robots with the ultimate goal of helping you achieve more by transforming your business to be more efficient, innovative, and profitable. We specialize in creating business automation solutions that are customized to your exact requirements, turning the time lost on mundane activities into opportunities for strategic achievements and business expansion.
Since 2018, DigitalStaff has helped over 35 companies across diverse industries—from First Nations government and healthcare to finance, intellectual property, retail, and construction. We've automated everything from financial job costing and human resource reporting to medical document filing, solving real-world business challenges with technology.
What sets me apart is my commitment to truly understanding your business. I don't just write code—I take the time to learn about your goals, challenges, and unique requirements so I can provide the best guidance. My approach blends deep automation expertise with a genuine understanding of business process optimization, ensuring that the solutions we create don't just work technically, but drive real value for your organization.
Operating from the traditional territories of the Anishinabek, Haudenosaunee, and Lunaapéewak peoples (London, Ontario), I'm committed to being here for the long haul—building lasting partnerships based on transparency, trust, and exceptional results.
Impact & Experience
A decade of entrepreneurship and innovation in technology and automation
Education
Bachelor of Arts
Media, Information & Technoculture
Western University, 2017
This interdisciplinary program combined technical knowledge with a deep understanding of how technology shapes society, culture, and business—a perfect foundation for understanding and solving modern business challenges.
Professional Highlights
- ✓ Built and led multiple successful businesses over 10+ years
- ✓ Experience in hiring and training teams of professionals
- ✓ Marketing and business development expertise
- ✓ Startup ecosystem leadership at Western University
- ✓ Continuous learning and staying current with emerging technologies
The Path to DigitalStaff
From teenage tech enthusiast to leading Canada's premier business automation agency
Neighbourhood Nerd
First venture into IT services, teaching customers computer skills and troubleshooting hardware and software problems. Set up and maintained wireless networks for residential and small business customers.
Entrepreneurship Leadership
Interned at Propel Entrepreneurship and BizInc at Western University, promoting entrepreneurship across campus and improving event attendance. Campus Outreach Coordinator at Startup London, connecting organizations and growing the startup community.
YourTech London
Founded and directed YourTech London, providing personalized IT solutions and consulting for small businesses. Coached intermediate computer skills, repaired systems, and built a passionate team of professionals.
Western University Graduate
Graduated with Bachelor of Arts in Media, Information & Technoculture, combining technical knowledge with understanding of how technology shapes society.
DigitalStaff Founded
Recognizing the growing importance of automation in business, pivoted the company to specialize in software automation and AI, rebranding as DigitalStaff.
Director of AI & Automation
Leading DigitalStaff to help 35+ companies automate tasks like financial job costing, human resource reporting, and medical document filing. Managing cloud-hosted SQL databases, 24/7 automation solutions, and a growing team.
Expertise & Approach
Technical capabilities combined with a partnership mindset
Custom Automation
AI Integration
Process Re-engineering
Cloud Operations
Innovation Focus
Long-term Partnership
How We Work Together
Connect & Understand
Plan Together
Build & Implement
Support & Evolve
Beyond Business
The person behind the automation solutions
Interests
- 📚 Reading science fiction
- 💻 Programming and technology
- 🚴 Cycling (even in the rain!)
- 🧠 Learning new things
Core Values
- 💡 Innovation and creativity
- 🤝 Reliability and honesty
- ✨ Kindness and empathy
- 🎯 Helping others succeed