Senior Director, 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 senior leadership role reporting straight to the CEO.

The role

We're seeking a Senior Director, Strategy & Operations to help lead the company's operating backbone alongside the CEO — across strategy, brokerage operations, sales, people, and communications. You'll act as the connective tissue between departments, drive company-level problems end to end, and multiply the impact of the senior leaders already running each function. Expect to help 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. Partner on company strategy and OKRs, frame company-level problems, and carry them from idea to operating model to measured outcome.

• The operating scorecard. Drive the metrics that define execution — agent experience, compliance, sales delivery, employee experience, and the external narrative.

• A multi-function team. Lead and lift the strategy & operations team across four functions — brokerage technology, sales, people, and content & PR.

• AI woven through operations. Put AI to work across the business yourself, engaging it as a primary, collaborative partner rather than a delegated initiative.

• The hard calls. Make the high-quality operating decisions when operations, product, engineering, sales, people, and PR priorities collide.

What we're looking for

Strong candidates show clear evidence of deep, ownership-driven problem-solving and cross-functional judgment in their past work. Beyond that, the strongest bring:

• Broad senior leadership experience — 7+ years of progressive leadership, 2+ at a senior leadership level (Senior Director / Director / Head of Strategy & Operations), having led strategy, operations, or a multi-function team at a high-growth tech company, including leading senior leaders.

• An AI-native operating style — you personally use and build with AI, automation, and agentic tools, engaging AI as a collaborative partner rather than just an automated tool.

• Strong business and strategic foundations — grounded in strategy, unit economics, market dynamics, and org design, with a track record of using those frameworks to help shape and execute commercial strategy.

• Comfort across multiple functions — you can lead senior leaders in HR, PR, sales, and brokerage compliance, set direction, and call out the gaps, without needing to be the deepest expert in each.

• Commercial judgment and data fluency — you understand revenue, pipeline, and unit economics well enough to help set commercial strategy, support a sales function, and pull and interpret data yourself.

• Experience operating globally across teams and time zones (the team currently spans North America and China).

• Eligibility to work in Canada without sponsorship, based in — or willing to relocate to — Canada (the role is fully remote nationwide), with excellent written and spoken English.

Nice to have

• Direct experience inside a Canadian real-estate brokerage, proptech, or marketplace.

• Entrepreneurial roots (highly preferred) — founder, co-founder, or early-stage operator who built a function, product line, or company from zero and carried outcome accountability.

• A managing broker designation, or willingness to obtain one.

• Direct or adjacent experience leading HR/People or Communications functions.

How they hire

Our client hires for what you can build, not just what's on your résumé. Instead of a marathon of panel interviews, shortlisted candidates take on a Builder Challenge — a real problem from the business that you scope, design, prototype, and present (using AI is expected and encouraged). It's a true two-way audition: you get a feel for the actual work and the team before you ever say yes.

The process: a first conversation with Hour Consulting → the Builder Challenge (by invitation) → a working session with senior leadership → references and final discussions.

What's on offer

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

• A seat shaping how one of Canada's leading real-estate platforms operates, scales, and communicates, in direct partnership with the CEO and senior leadership.

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

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

• Genuine ownership and autonomy inside a lean, founder-led, AI-native team that actually wants how things are done challenged.

Hour Consulting Corporation is an executive search and HR consulting firm. Our client is an equal-opportunity employer and provides accommodations at any stage of the hiring process on request.