VP, AI Strategy & Operations

Role overview

This is a senior executive position within a fast-growing, AI-first company in the real estate technology space. Reporting to the CEO, you will help set the company’s direction and turn that direction into a practical operating framework that keeps execution disciplined across the business.

The role combines high-level strategy with direct operational ownership. You will partner with leaders across operations, sales, people, communications, and technology to keep priorities aligned, performance measurable, and teams moving at scale. A major part of the job is making AI, automation, and agentic tools part of everyday operations rather than a separate initiative. This role suits a decisive executive who is comfortable working in a founder-led environment and making organization-wide calls.

Key accountabilities

• Work with the CEO to define company strategy and OKRs, then convert them into an execution-ready operating model.
• Own the company-wide scorecard covering customer experience, sales results, compliance, employee experience, and communications impact.
• Lead and grow cross-functional executive leaders across operations, sales, people, communications, and technology.
• Weave AI, automation, and agentic workflows into essential business processes to improve speed and scalability.
• Make senior-level decisions when priorities compete across product, engineering, operations, and commercial areas.
• Spot systemic challenges, bring strategic gaps into focus, and drive organization-level resolution.
• Keep strategy, execution, and measurable outcomes tightly connected across all business units.

Requirements

• At least 8 years of progressive leadership experience, including 3 or more years in executive positions such as VP, SVP, COO, or Head of Strategy & Operations.
• Proven ability to lead multiple functions, scale teams, and rebuild operational systems in complex organizations.
• Strong AI-native orientation with practical, day-to-day use of AI, automation, and modern tools.
• Sharp strategic judgment with first-principles thinking across business models, unit economics, and organizational design.
• Solid commercial and analytical capability, including experience guiding sales strategy and working with complex data.
• Experience working with global, distributed teams; exposure to North America and Asia is preferred.
• Must be eligible to work in Canada without sponsorship and willing to work remotely from anywhere in Canada.
• Excellent English communication skills and strong executive presence.
• Experience in proptech, marketplaces, brokerage, or transaction-driven consumer businesses is an added advantage.
• Background as a founder or early-stage operator is highly valued.
• Exposure to HR, people operations, or corporate communications leadership is beneficial.

Perks and benefits

• Competitive executive compensation package with performance bonus and equity.
• Remote-first setup across Canada with flexibility and autonomy.
• Comprehensive health coverage, including medical, dental, life insurance, virtual care, and travel benefits.
• Generous paid time off and support for work-life balance.
• Direct reporting line to the CEO with strong strategic influence.
• Opportunity to help shape the operating model of a leading national platform in its category.
• High-ownership environment in a lean, founder-led, AI-native organization.

Eligibility

Applicants must be legally authorized to work in Canada without sponsorship and must be comfortable working remotely within Canada.

Application and hiring process

This opportunity is listed on behalf of a partner company, which handles applications and the next steps directly. Applications are reviewed using an AI-assisted matching process to identify candidates who best fit the role’s core requirements. A shortlist is then shared with the hiring company, whose internal team manages interviews, assessments, and the final hiring decision.

Privacy notice

By applying, you agree that your personal data may be processed for candidate evaluation and shared with the hiring employer in line with applicable data protection laws, including GDPR. You may request access, correction, deletion, or objection to processing at any time. AI tools may support parts of the hiring workflow, such as resume review and response analysis, but final decisions are made by humans.