Toronto, Ontario, Canada Remote (Global) Employment

lightspeedhq is hiring a Strategy Director

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

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
  • 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 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

Work Arrangement

Remote (Worldwide)

Team

Structure: cross-functional initiatives, alignment with executive leadership team. Reports to: Chief Strategy & Transformation Officer (CSTO)

You’ll enjoy

  • A flexible work environment that empowers you to do your best work
  • A culture that celebrates performance
  • The chance to make an impact in a team that’s big enough for career growth, but lean enough to make your voice heard
  • Career-defining opportunities
  • 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

Who we are

  • Powering the businesses that are the backbone of the global economy, Lightspeed's one-stop commerce platform helps merchants innovate to simplify, scale, and provide exceptional customer experiences.
  • Our 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.
  • Founded in Montréal, Canada in 2005, Lightspeed is dual-listed on the New York Stock Exchange (NYSE: LSPD) and Toronto Stock Exchange (TSX: LSPD).
  • With teams across North America, Europe, and Asia Pacific, the company serves retail, hospitality, and golf businesses in over 100 countries.

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.
  • Lightspeed does not accept unsolicited agency resumes.
  • We were founded in 2005, in Montreal’s gay village and our original members were all part of the LGBTQ+ community.
  • The ethos of our business has been about inclusion from the very beginning, and we strive to provide a workplace where everyone belongs.
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