Enterprise Transformation Director

Lightspeed Commerce, Inc. • Toronto, ON

4d • Hybrid

About The Position

Lightspeed is seeking an Enterprise Transformation Director to join their team. This role is crucial for partnering with the Chief Strategy & Transformation Officer (CSTO) and executive leadership to drive high-priority transformation initiatives. Lightspeed is currently engaged in a multi-year transformation aimed at enhancing core growth and improving operational efficiency. The Director will be responsible for translating strategic goals into actionable plans, removing obstacles, and ensuring initiatives deliver tangible results. The ideal candidate will possess strong strategic thinking, a focus on execution, and a proven history of leading complex, cross-functional transformations.

Requirements

• Strong structured problem-solving skills, with the ability to connect strategy to execution and drive enterprise outcomes
• Demonstrated experience leading large-scale, cross-functional transformation initiatives in fast-paced, matrixed environments
• Proven ability to influence senior executives and drive alignment across functions without direct authority
• Strong ownership mindset, with the ability to drive execution and accountability across complex organizations
• Excellent communication skills, including experience synthesizing insights and supporting executive-level decision-making
• Strong business and financial acumen, with the ability to connect initiative progress to broader strategic and financial outcomes
• Fluency in English as a working language is required

Nice To Haves

• 7–10+ years of experience in consulting, strategy, transformation, or business operations
• Experience leading or operating within enterprise-wide transformation programs
• Advanced degree (e.g., MBA) or equivalent experience
• Experience in SaaS, fintech, or other high-growth, technology-driven environments

Responsibilities

• Lead the execution of Lightspeed’s enterprise transformation, driving high-priority initiatives from concept through execution and value delivery
• Translate strategic priorities into actionable plans, ensuring clear milestones, ownership, and accountability across transformation workstreams
• Establish and maintain the drumbeat of execution, ensuring consistent progress, visibility, and momentum week over week
• Partner closely with the CSTO and executive leadership team to align priorities, drive accountability, and enable decision-making
• Identify and resolve cross-functional risks, dependencies, and roadblocks, ensuring initiatives remain on track and deliver expected outcomes
• Drive visibility into transformation progress, including tracking against key milestones, value targets, and business impact

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

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Number of Employees: 501-1,000 employees