Strategy Director
About The Position
We’re looking for a Strategy Director to join our team at Lightspeed. This role will serve as a key partner to Lightspeed’s Chief Strategy & Transformation Officer (CSTO) and broader executive leadership team to shape enterprise strategy and lead the annual strategic planning process. As Lightspeed enters its next phase of growth and a multi-year transformation, this role will play a critical part in defining priorities, guiding decision-making, and driving alignment across the business. The ideal candidate brings strong strategic thinking and a track record of leading complex, cross-functional initiatives from concept through execution.
Requirements
- Strong structured problem-solving skills, with the ability to tackle complex and ambiguous business challenges
- Demonstrated experience leading enterprise-level strategic initiatives or workstreams in fast-paced environments
- Ability to influence senior executives and drive alignment across functions
- Strong business judgment, with the ability to connect insights to strategic implications
- Excellent communication skills, with the ability to synthesize complex topics into clear, executive-level messaging
- High level of ownership, accountability, and ability to operate independently
- Fluency in English as a working language is required for this position.
Nice To Haves
- 7–10+ years of experience in strategy consulting, corporate strategy, or a related field
- Experience working directly with executive leadership on strategic decision-making and planning
- Advanced degree (e.g., MBA) or equivalent experience
- Experience in SaaS, fintech, or other high-growth, technology-driven environments
Responsibilities
- Lead enterprise strategic planning, including owning the annual planning process and ongoing strategic review cadences
- Partner closely with the CSTO and executive leadership team to shape strategic priorities and inform key business decisions
- Structure complex, ambiguous business problems and develop data-driven insights to guide enterprise direction
- Drive development of business cases, strategic plans, and executive-ready recommendations to support leadership decision-making
- Lead cross-functional initiatives, aligning stakeholders on priorities, driving execution, and delivering against defined business outcomes
- Act as a strategic mentor and coach to junior team members, elevating capabilities in problem solving, analysis, and stakeholder engagement
Benefits
- Flexible work environment
- Culture that celebrates performance
- Career-defining opportunities
- Flexible paid time off and remote work policies
- Equity options
- Contributions to your pension plan
- Training opportunities to grow your skills and career
- Health and wellness credit
- Time off to volunteer and give back to your community
- Interest groups, employee led networks, social committees to sponsored sports teams
- Computer purchase program to get your personal MacBook
- Enhanced parental leave
- Medical insurance
- Dental insurance
- Wellness insurance
- Life insurance
- Disability insurance
- RRSP plan and match
- Paid parental leave top-up
- Paid time off
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Number of Employees
501-1,000 employees
