VP, AI Strategy & Operations

Hour Consulting is hiring on behalf of our client a profitable, founder-led Canadian real-estate technology company that sits at #1 in its category, is used by millions of Canadians, and is expanding across the country. It's bootstrapped (built on real revenue rather than venture funding) and deliberately AI-native. This is a leadership-team role reporting straight to the CEO.

The role

We're seeking a VP, Strategy & Operations to run the company's operating core alongside the CEO. You'll own both the strategy and the engine that executes it across operations, sales, people, and communications acting as the connective tissue that turns a category leader into a national one. Expect to shape company strategy and OKRs, surface the problems leadership hasn't named yet, and make the tough cross-functional calls when priorities compete.

What you'll own

• Strategy with the CEO. Set direction and OKRs, frame company-level problems, and carry them from idea to operating model to measured outcome.

• The operating scorecard. Own the metrics that define execution : customer experience, compliance, sales delivery, employee experience, and the external story.

• A multi-function team. Lead and lift senior leaders across operations and technology, sales, people, and communications.

• AI woven through operations. Put AI to work across the business yourself, not as a delegated initiative.

• The hard calls. Make the high-quality executive decisions when operations, sales, people, product, and engineering pull in different directions.

What we're looking for

This is a seat for someone who has already done it at scale not someone hoping to grow into it. The strongest candidates bring:

• 8+ years of progressive leadership, 3+ at the executive level (VP / SVP / COO / Head of Strategy & Operations), with a record of rebuilding processes that scaled and leading more than one function.

• An AI-native operating style you personally use and build with AI, automation, and agentic tools, not just sponsor them.

• Sharp strategic and business foundations first-principles thinking across strategy, unit economics, market dynamics, and org design; you design the playbook, you don't just run someone else's.

• Commercial judgment and data fluency strong enough to set strategy, lead a sales function, and interrogate the numbers yourself.

• Experience operating globally across teams and time zones (North America and Asia).

• Eligibility to work in Canada without sponsorship, based in or willing to relocate to — Canada (fully remote nationwide), with excellent English.

Nice to have

• Executive experience in a Canadian brokerage, proptech, marketplace, or transaction-heavy consumer business.

• Founder or early-stage operator roots you built a function or company from zero and owned the P&L.

• Hands-on or close experience leading HR/People or Communications.

What's on offer

• Highly competitive pay, plus performance bonus and equity (calibrated to your experience).

• A leadership seat reporting to the CEO, shaping how one of Canada's standout consumer platforms operates, scales, and communicates.

• Remote-first across Canada, with generous time off.

• Full health coverage — medical, dental, life, virtual care, and travel.

• Genuine ownership and autonomy inside a lean, founder-led, AI-native team that genuinely wants the status quo challenged.