HouseSigma — the highest-rated real estate app in Canada — is hiring a VP, Strategy and Operations to lead the operating backbone of the company alongside the CEO: strategy, brokerage operations, sales, HR, and PR. This is a full-time, permanent role with the flexibility to work from anywhere in Canada.

How We Hire

Before anything else about the role, here’s how we think about who fits at HouseSigma. If these don’t resonate with you, this likely isn’t the right fit — regardless of how strong your experience is.

Our North Star Behaviour

Solve problems deeply with ownership, and collaborate to multiply impact.

We think of every challenge at HouseSigma as a stone that needs moving. Each person owns their stones end-to-end — from understanding the problem, to designing the solution, to shipping it. We don’t rely on handoffs to explain stalled progress. We collaborate as a force multiplier, not a dependency chain.

Read more about how we work: North Star Behaviour & Performance Philosophy

Our Values

The traits we look for in every teammate, and how we evaluate ourselves:

  • Responsibility and extreme accountability — We take end-to-end ownership of our projects and follow through, because taking accountability earns trust and freedom.
  • Deep and independent thinking — We use first-principles thinking to go beyond surface-level answers, ask the “why” repeatedly, and reason from those fundamentals to get to the truth.
  • Logical and fact-driven judgment — We make decisions based on evidence and clear thinking, not assumptions or gut feel.
  • Judgment and courage — We act decisively in ambiguity, using sound judgment and the courage to make and own hard calls.
  • Growth mindset and hard-work appreciation — We stay curious, keep improving, and respect the consistent effort required to build something great.
  • Direct, transparent, and constructive communication — We communicate clearly, give feedback that helps, and say directly to someone the same thing we would say about them.
  • Superstar and dream-team mindset — We set a high bar for individual excellence and collaborate in ways that elevate the whole team.
  • High agency and initiative — We step up without waiting to be asked, move quickly, and proactively improve processes and outcomes.
  • Passion and craftsmanship — We care deeply about the work, treat our role as a craft, and keep refining quality over time.

Read more about our values: About Us

This Role: North Star Behaviour Applied to Strategy and Operations

The VP, Strategy and Operations owns four functions that hold the company together day to day: Brokerage Technology, Sales, Human Resources, and Content & PR. The job is to solve company-level problems deeply, with ownership, and to multiply the impact of the senior leaders already running each function. This role exists as the connective tissue between departments and is expected to make high-quality executive-level judgments that are transferable across the company.

What “Solve problems deeply with ownership” looks like here

  • Partner with the CEO on company strategy, OKRs, and the problem set — and surface the strategic problems leadership hasn’t named yet
  • Take a company-level problem and own it end-to-end — frame it, design the solution, ship the operating model, and measure the result
  • Hold final accountability for operational KPIs — agent experience, compliance, sales execution, employee experience, external narrative
  • Make the cross-functional calls when operations, product, engineering, sales, people, and PR priorities collide

What “Collaborate to multiply impact” looks like here

  • Lead the Director of Brokerage Technology, Senior Director of Sales, Director of Human Resources, and Head of Content and PR — sharpen their thinking, and elevate the bar across all four functions, while collaborating with other cross-functional teams to elevate company outcomes
  • Collaborate with the CEO and senior leaders to elevate company outcomes

What We’re Looking For

Strong candidates will be able to point to clear evidence of the North Star Behaviour and the HouseSigma values in their past work. Beyond that:

  • Broad senior leadership experience and an AI-native mindset. You’ve led strategy, operations, or a multi-function executive seat at a high-growth, tech company. You’ve personally rebuilt processes that scaled, not just managed them, with an AI-native mindset, where you’re engaging AI as a primary, collaborative partner rather than just an automated tool.
  • Strong business and strategic foundations. Grounded in core business theory — strategy, unit economics, market dynamics, organizational design — with a track record of using those frameworks to design and execute commercial strategy from first principles, not just operate within someone else’s playbook.
  • Comfort across multiple functions. You don’t need to be the deepest expert in HR, PR, sales, or brokerage compliance — but you can lead senior leaders in each, set direction, and call out gaps.
  • Commercial judgment. You understand revenue, pipeline, and unit economics well enough to set commercial strategy, lead a sales function and pressure-test commercial decisions.
  • Systems thinking. Upstream causes, downstream effects, and where the leverage actually sits.
  • Data comfort. You can pull and interpret data deeply without waiting for a dashboard and apply insights fluidly to impact business outcomes.
  • Experience operating in a global, cross-team environment (the HouseSigma team currently resides in North-America + China)

Nice to Have

  • Direct executive level experience inside a Canadian real estate brokerage, proptech, or marketplace
  • Entrepreneurial experience highly preferred. Founder, co-founder, or early-stage operator background — someone who has built a function, product line, or company from zero and carried full P&L or outcome accountability.
  • Managing broker designation, or willingness to obtain one
  • Direct or adjacent experience leading HR or Communications functions

How We Evaluate

Your resume gets you in the door. Your build gets you the job.

Instead of a traditional executive interview loop, we ask selected candidates to complete a Builder Challenge — a real problem from HouseSigma’s domain that you analyze, design a solution for, prototype, and present. This is how we identify people who embody our North Star Behaviour in practice — not just in conversation — and understand your AI-native mindset and capabilities.

Interview Process

  • Prescreen Interview
  • Builder Challenge (invitation only). Deliverables: problem ticket, solution document, operating/technical design, working prototype.
  • Interview with senior leadership. Challenge walkthrough, values alignment, mutual fit.

Additional interviews as required.

What You Can Expect from Us

  • A seat shaping how Canada’s leading real estate platform operates, scales, and communicates
  • Direct partnership with the CEO and senior leadership
  • Health benefits including health, dental, life, virtual health care, and travel coverage
  • Remote-friendly work environment: anywhere in Canada
  • Highly competitive compensation and generous vacation time
  • A team that actually wants you to challenge how things are done

Base salary range: CAD approximately $250,000 – $500,000, plus performance bonus and stock options (final offer determined based on skills and experience)

About HouseSigma

HouseSigma is a leading real estate technology platform, listings portal, and brokerage based in Canada. Our mission is to empower consumers with more knowledge to make better real estate decisions, and we use data and technology to provide transparency in the market. We were the first in Canada to make sold prices publicly available, and we use proprietary data and AI to give users real-time insights into market trends and home valuations. We now have more than two million registered users and more than five million monthly web visits. HouseSigma’s platform and brokerage services have a TrustPilot rating of 4.9/5, and we are the highest-rated Canadian real estate app on both the iOS Store and Google Play Store.

HouseSigma is an equal opportunity employer. If you require accommodation at any stage of the recruitment process, please let us know and we will work with you to meet your needs.

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