Director, Strategy

Lightspeed Commerce, Inc.•Montreal, QC

8d•CA$160,000 - CA$190,000•Remote

About The Position

Lightspeed is seeking a Strategy Director to join their team. This role will partner with the Chief Strategy & Transformation Officer (CSTO) and executive leadership to shape enterprise strategy and lead the annual strategic planning process. The position is crucial for defining priorities, guiding decisions, and driving alignment as Lightspeed enters a new phase of growth and transformation. The ideal candidate will have strong strategic thinking skills and a proven ability to lead complex, cross-functional initiatives from inception to completion.

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

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 growth opportunities
Flexible paid time off and remote work policies
Equity options
Contributions to pension plan
Training opportunities
Health and wellness credit
Time off to volunteer
Interest groups, employee led networks, social committees to sponsored sports teams
Computer purchase program
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