AI Operations Manager – Right Hand to CEO (Run Multi-Business Ops with AI)

I'm the CEO of a multi-business group (HVAC & energy services in Canada and Florida, real estate, financing, short-term rentals) and I run most of my operations with AI today — Claude, GPT, and automation tools do the heavy lifting, with me as the operator. I'm hiring the person who takes the operator seat. This is NOT a VA role and NOT a traditional assistant role. You will manage the business day-to-day by driving AI to do the work, verifying its output, and holding our managers accountable — so I can focus on growth, acquisitions, and strategy. THE ROLE — TWO HALVES 1) Run the operating system: - Own my inbox and open-loop register: every commitment tracked to verified completion - Run the weekly operating meeting with our managers (sales, ops, finance, service) — you run it, I attend monthly - Keep a scorecard per manager: numbers owned, commitments made, commitments kept - Send me a short daily brief: max 3 decisions needed, risks, anomalies. If nothing needs me, say exactly that - Chase contractors, vendors, lawyers, insurers, and lenders so I never have to send a reminder again 2) Execute through AI: - Use Claude/GPT/automation tools as your primary workforce: drafting, research, tracking, reporting, document prep - I will record my workflows; you replicate them, then improve them - Build and maintain a prompt & workflow library so every recurring task is documented and repeatable - Verify every AI output before it ships — you are the judgment layer, not a copy-paste layer WHAT YOU WILL ACTUALLY OWN We run several separate legal entities across HVAC and energy services in Canada and Florida, real estate, financing, and short-term rentals. A key operations person recently left the business, and his workload is the clearest picture of this job: - Weekly commission and agent payroll prep, pay advances, bonuses and deductions, reconciled and queued for my approval in our internal portal (you never move money, approvals stay with me) - Daily dispatch coordination for the remote team and confirming coverage - Outbound calling infrastructure: VoiceDrop campaigns, phone number reputation, caller ID registration, DIDs and call routing - Lead imports, lead source history, and distribution to the sales floor - Vendor and subscription management: renewals, domains, billing cards, and evaluating vendor proposals before they reach me - Portal and product coordination: collecting bugs and requests, prioritizing them with our developers, and verifying a fix actually shipped before anyone calls it done - Consolidating daily reporting from department managers into one operating picture - Insurance renewals, vendor contracts, and document organization across the entities - Marketing execution and ad spend reporting - Hiring coordination (you will run our future Upwork hires end to end) - Some personal and family logistics Variety is the job. REQUIREMENTS - Proven experience managing operations or supporting a CEO/founder across multiple business areas at once - Real, hands-on AI fluency: you use Claude or GPT daily to produce finished work, and you can show it - Experience running a meeting cadence and holding managers accountable (EOS/L10, scorecards, or similar a plus) - Excellent written and spoken English; comfortable on calls with lawyers, bankers, insurers, and contractors - North American time zone availability required. Canadian candidates strongly preferred (our HQ is Ottawa; familiarity with Canadian business context is a real advantage). Exceptional candidates elsewhere in the Americas considered - Quiet professional home office, reliable high-speed internet - Full time, ~40 hrs/week, long-term. Contract-to-hire. HOW WE'LL HIRE Shortlisted candidates complete a PAID 3-hour trial before any interview: you'll redo a real task from my screen recording using AI, show your prompts and your verification steps, and run a short mock manager check-in. The trial decides, not the interview. Fast process — target is an offer within 2 weeks. HOW TO APPLY — READ CAREFULLY Start your application by describing ONE real workflow you automated or ran with AI: what the manual version was, what you built or did, and how you verified the output before it shipped. Applications without a specific, concrete example will be archived unread. Then briefly cover: (1) the most demanding founder/executive you supported and what you owned, (2) your experience holding managers or vendors accountable, (3) your timezone and availability. If you're the person who closes loops without being chased, brings me decisions instead of problems, and treats AI as your workforce — I want to hear from you.