Toronto, Ontario, Canada Remote (Global) Full-time USD 160,000 – 200,000 / year

lightspeedhq is hiring an Enterprise Transformation Director

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

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
  • As a global company with employees and clients outside of Quebec, fluency in English as a working language is required for this position.

Nice to Have

  • 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

Benefits

  • Flexible paid time off and remote work policies
  • Equity options, because this is your company too
  • Contributions to your pension plan. Your future matters
  • Training opportunities to grow your skills and career
  • Health and wellness credit so you feel your best
  • 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 to support growing families

Work Arrangement

Remote (Worldwide)

Team

Structure: Cross-functional transformation efforts across the business. Reports to: Chief Strategy & Transformation Officer (CSTO) and broader executive leadership team

Additional Information

  • Fluency in English as a working language is required
  • Lightspeed uses artificial intelligence–enabled tools to support certain aspects of the recruitment process; all hiring decisions are made by our recruiting and hiring teams.
  • Accommodations are available on request for candidates taking part in all aspects of the selection process.
  • This role represents an existing vacancy at Lightspeed.
  • Recruitment agencies: Lightspeed does not accept unsolicited agency resumes unless directly engaged in writing.
Required Skills
SaaSFintech
About company
lightspeedhq
Lightspeed's one-stop commerce platform helps merchants innovate to simplify, scale, and provide exceptional customer experiences. Their cloud commerce solution transforms and unifies online and physical operations, multichannel sales, expansion to new locations, global payments, financial solutions, and connection to supplier networks.
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Job Details
Department Operations
Category management
Posted a month ago