VP, AI Strategy & Operations
Accountabilities: 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
How Jobgether works: We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best! Why Apply Through Jobgether?
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