VP, AI Strategy & Operations at Jobgether

, , Canada -

Full Time

Start Date

Immediate

Expiry Date

04 Oct, 26

Salary

0.0

Posted On

06 Jul, 26

Experience

10 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Strategic Leadership, Operational Excellence, AI Implementation, OKR Management, Cross-functional Leadership, Business Model Design, Unit Economics, Analytical Acumen, Sales Strategy, Organizational Design, Change Management, Executive Presence, Proptech, Automation, Agentic Tools, Performance Management

Industry

Internet Marketplace Platforms

Description

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. \n 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 \n 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? Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time. #LI-CL1

Responsibilities

Partner with the CEO to define company strategy and translate it into a measurable operating system. Oversee cross-functional teams and embed AI and automation into core business processes to drive scalability.