VP, AI Strategy & Operations

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a VP, AI Strategy & Operations based in Canada.

This is a senior executive leadership role at the core of a high-growth, AI-native organization operating in the real estate technology space. You will work directly with the CEO to define company strategy and translate it into a clear, measurable operating system that drives execution across all business functions. The role blends strategic leadership with hands-on operational ownership, requiring someone who can shape direction while also ensuring flawless delivery across teams. You will oversee cross-functional leaders spanning operations, sales, people, communications, and technology, ensuring alignment and performance at scale. A key part of your mandate is embedding AI into the operational fabric of the organization, not as an initiative, but as a way of working. This is a high-impact role designed for a proven executive who thrives in fast-moving, founder-led environments and is comfortable making decisive, organization-wide calls.

In this role, you will act as the CEO’s strategic and operational partner, owning both company direction and execution across key business functions.

• Define company strategy and OKRs in close partnership with the CEO, translating vision into execution-ready operating models
• Own the company-wide operating scorecard, including customer experience, sales performance, compliance, employee experience, and communications impact
• Lead and develop cross-functional executive teams across operations, sales, people, communications, and technology
• Embed AI, automation, and agentic tools into core business processes to improve efficiency and scalability
• Make high-impact executive decisions across competing priorities in product, engineering, operations, and commercial functions
• Identify systemic issues, surface strategic gaps, and drive resolution at the organizational level
• Ensure alignment between strategy, execution, and measurable outcomes across all business units

Requirements:

The ideal candidate is a seasoned executive with a proven track record of operating at scale and leading multiple functions in complex organizations.

• 8+ years of progressive leadership experience, including 3+ years in executive roles (VP, SVP, COO, or Head of Strategy & Operations)
• Demonstrated success leading and scaling multiple business functions and rebuilding operational systems
• Strong AI-native mindset with hands-on experience using AI, automation, and modern tooling in day-to-day operations
• Excellent strategic thinking with strong first-principles reasoning across business models, unit economics, and organizational design
• Strong commercial and analytical acumen with the ability to lead sales strategy and interpret complex data
• Experience operating across global teams and distributed environments (North America and Asia preferred)
• Eligibility to work in Canada without sponsorship and willingness to work remotely across Canada
• Exceptional communication skills and executive presence in English
• Background in proptech, marketplaces, brokerage, or transaction-heavy consumer businesses is a plus
• Founder or early-stage operator experience is highly valued
• Exposure to HR, people operations, or corporate communications leadership is an advantage

Benefits:

• Highly competitive executive compensation package including performance bonus and equity
• Fully remote-first role across Canada with flexibility and autonomy
• Comprehensive health benefits including medical, dental, life insurance, virtual care, and travel coverage
• Generous paid time off and work-life balance support
• Executive leadership seat reporting directly to the CEO with significant strategic influence
• Opportunity to shape the operating model of a leading national platform in its category
• High ownership environment within a lean, founder-led, AI-native organization