Strategy Director (SaaS)

TL;DR

Strategy Director (SaaS): Shaping enterprise strategy and leading the annual strategic planning process with an accent on cross-functional alignment and data-driven decision-making. Focus on structuring complex business problems and driving multi-year transformation initiatives.

Location: Must be based in Ontario, Canada

Salary: $160,000 - $190,000 CAD

Company

Cloud commerce platform providing unified online and physical operations for retail, hospitality, and golf businesses.

What you will do

• Lead enterprise strategic planning and own the annual planning process and review cadences.
• Partner with the CSTO and executive leadership to shape strategic priorities and inform business decisions.
• Structure complex, ambiguous business problems and develop data-driven insights to guide enterprise direction.
• Develop business cases and executive-ready recommendations to support leadership decision-making.
• Lead cross-functional initiatives, aligning stakeholders on priorities and driving execution.
• Mentor and coach junior team members in problem solving, analysis, and stakeholder engagement.

Requirements

• Strong structured problem-solving skills for tackling complex and ambiguous business challenges.
• Demonstrated experience leading enterprise-level strategic initiatives in fast-paced environments.
• Ability to influence senior executives and drive alignment across different functions.
• Excellent communication skills for synthesizing complex topics into executive-level messaging.
• Fluency in English as a working language.
• Must be based in Ontario, Canada.

Nice to have

• 7–10+ years of experience in strategy consulting or corporate strategy.
• Experience working directly with executive leadership on strategic planning.
• Advanced degree (e.g., MBA) or equivalent experience.
• Experience in SaaS, fintech, or other high-growth technology environments.

Culture & Benefits

• Flexible work environment with remote work policies.
• Equity options and contributions to a pension plan.
• Health and wellness credit and enhanced parental leave.
• Professional training opportunities to grow skills and career.
• Computer purchase program for a personal MacBook.
• Time off to volunteer and give back to the community.