Oscar ONeill - Director of AI & Automation

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

7+
Years Leading DigitalStaff
Since 2018
35+
Companies Served
Across multiple industries
10+
Years in Tech
Since 2011
6+
Industries
First Nations government, healthcare, finance, IP, retail, construction
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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.

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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

👨‍💻
2011–2015

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.

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2013–2016

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.

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2015–2018

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.

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2017

Western University Graduate

Graduated with Bachelor of Arts in Media, Information & Technoculture, combining technical knowledge with understanding of how technology shapes society.

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2018

DigitalStaff Founded

Recognizing the growing importance of automation in business, pivoted the company to specialize in software automation and AI, rebranding as DigitalStaff.

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2018–Present

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

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Custom Automation

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AI Integration

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Process Re-engineering

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Cloud Operations

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Innovation Focus

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Long-term Partnership

How We Work Together

01
💬

Connect & Understand

02
📋

Plan Together

03
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Build & Implement

04
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Support & Evolve

Beyond Business

The person behind the automation solutions

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Interests

  • 📚 Reading science fiction
  • 💻 Programming and technology
  • 🚴 Cycling (even in the rain!)
  • 🧠 Learning new things
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Core Values

  • 💡 Innovation and creativity
  • 🤝 Reliability and honesty
  • Kindness and empathy
  • 🎯 Helping others succeed

Ready to achieve more with automation and AI?