Senior Director, 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 Senior Director, Strategy & Operations based in Canada.

We are seeking a strategic and operational leader to help shape the future direction and execution of a rapidly growing technology organization. This role offers the opportunity to work closely with executive leadership to solve complex business challenges and drive company-wide impact. You will serve as a key connector across strategy, operations, sales, people, communications, and technology teams. The position requires exceptional judgment, cross-functional leadership, and the ability to turn strategic priorities into measurable results. You will help define operating models, improve execution, and identify opportunities that accelerate growth and scalability. This is an ideal opportunity for an entrepreneurial leader who thrives in high-ownership environments and enjoys building systems, teams, and processes from the ground up.

Accountabilities:: The Senior Director, Strategy & Operations will act as a strategic partner to executive leadership, helping define priorities, improve operational performance, and drive alignment across multiple functions. This role requires a hands-on approach to solving complex organizational challenges and building scalable processes that support long-term growth.

Partner with executive leadership to shape company strategy, define objectives and key results, and translate strategic initiatives into measurable outcomes.

Identify critical business challenges, develop solutions, and lead initiatives from problem definition through execution and impact measurement.

Own the operating scorecard by driving performance metrics related to business execution, customer experience, employee experience, compliance, and organizational effectiveness.

Lead and develop a multi-functional strategy and operations team supporting areas such as technology operations, sales, people, and communications.

Apply AI, automation, and emerging technologies across business operations to improve efficiency and enable smarter decision-making.

Act as a cross-functional leader who helps resolve competing priorities between operations, product, engineering, sales, people, and communications teams.

Provide strategic guidance to senior leaders while identifying opportunities to improve processes, collaboration, and organizational performance.

Requirements:

The ideal candidate is an experienced strategy and operations leader with a strong record of driving business transformation, managing complex initiatives, and influencing senior stakeholders across multiple functions.

7+ years of progressive leadership experience, including at least 2 years in a senior leadership position such as Senior Director, Director, or Head of Strategy & Operations.

Proven experience leading strategy, operations, or multi-functional teams within a high-growth technology company or similarly complex environment.

Strong strategic and business foundation, with expertise in market analysis, organizational design, unit economics, and commercial strategy.

AI-native mindset with hands-on experience using AI tools, automation, and emerging technologies to improve workflows and business outcomes.

Ability to lead across diverse functions, including sales, HR/people, communications, compliance, and operations, without requiring deep functional specialization in each area.

Strong commercial judgment and data fluency, with the ability to understand revenue drivers, sales performance, business metrics, and operational insights.

Excellent problem-solving, decision-making, and stakeholder management skills, with the ability to influence senior leaders and drive alignment.

Experience working across global teams and multiple time zones.

Eligibility to work in Canada without sponsorship, with excellent written and verbal English communication skills.

Preferred experience in real estate technology, marketplaces, brokerage environments, or other transaction-driven platforms.

Entrepreneurial experience as a founder, co-founder, or early-stage operator is highly valued.

Experience leading people, communications, or organizational development functions is considered an advantage.

Benefits:

Highly competitive compensation package with performance-based bonus opportunities aligned with experience.

Opportunity to directly influence the strategy, operations, and growth of a leading technology platform.

Close partnership with executive leadership and the opportunity to contribute to company-wide decisions.

Fully remote role available across Canada with flexible working arrangements.

Generous vacation time to support work-life balance.

Comprehensive health coverage, including medical, dental, life insurance, virtual care, and travel benefits.

High level of ownership and autonomy within a lean, innovative, and AI-focused organization.

Opportunity to challenge existing ways of working and build scalable solutions in a fast-moving environment.

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