Head of AI Operations.

ABOUT ME & MY COMPANIES
My name is Lisa. I'm a Canadian entrepreneur based in Alberta, and I've been building businesses for over a decade. The anchor company in my portfolio is Ed's Auto Salvage, an automotive recycling operation that's been running for nearly 50 years in Westlock, Alberta. Beyond that, I own a real estate and mini-storage portfolio, a horizontal directional drilling company, and additional operating businesses across Alberta.
These are not startups. They are established, profitable, essential-service businesses with real teams and real customers. Now I'm ready to build the technology layer they've never had, and I'm looking for one exceptional person to help me do it.
THIS IS NOT A TRADITIONAL VA ROLE
I am not looking for someone to manage my calendar, answer emails, or do data entry. I need someone who can build systems, AI-powered systems that change how my businesses operate at a fundamental level. If you are someone who is genuinely fascinated by AI, loves designing workflows, and wants to see your work have real impact across multiple industries, keep reading.
WHAT YOU'LL BUILD
A company-wide knowledge base in Notion across all five businesses. AI assistants trained on our actual documents, SOPs, and operating procedures. Automations in ---------- that eliminate repetitive manual work. Searchable knowledge bases in NotebookLM built from company documents. Prompt libraries for management and frontline staff. Onboarding and training systems using Loom and Notion. Workflows across automotive recycling, real estate, storage, and construction operations. A process for identifying and documenting automation opportunities across all departments.
TOOLS WE USE
AI: ChatGPT, Claude, NotebookLM, Notion AI. Automation: ---------- . Operations: Notion, Microsoft 365, Slack, Loom.
WHAT I'M LOOKING FOR
I need someone senior, someone who has already built real things with these tools and can lead this work from day one. I'm not looking for someone to train from scratch. That said, AI moves fast. I need a partner who enjoys staying at the edge of what's possible, learns new tools quickly, and brings ideas I haven't thought of yet. The best version of this role is a genuine collaboration, not a task list. You must be able to document clearly, communicate proactively, and work independently without constant direction.
THE OPPORTUNITY
This starts as a full-time role with an intense build phase. The first six months we move fast, building core systems across all five companies. After that, you become the person who owns, maintains, and evolves what you built. I'm not looking for a contractor. I'm looking for the person who owns this function permanently. If you do this well, you won't just be an implementer. You'll be the person who designed the AI backbone of a multi-company operation. That's a credential that defines a career.
COMPENSATION & SCHEDULE
$1,200–$1,400 USD per month based on experience. Paid weekly via Wise. Full-time, 40 hours per week. Fully flexible schedule, work when you work best, as long as deliverables are met. No required overlap with Canadian business hours, fully async. 13th month equivalent paid at year end.
HOW TO APPLY
Do not send a generic cover letter. I will not read it. Start your message with the words "Systems First" then tell me three things. One, an automation or AI system you have built, what it did, what tools you used, and what the result was. Two, which tool in our stack you know best and one specific thing you have built with it. Three, your available start date. Applications that do not follow these instructions will not receive a response. I read every qualified application personally.