Strategy Director

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Are you actively looking for a new opportunity? Or just checking the market? Well… you might just be in the right place!

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.

What you'll be doing:

• 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

What you need to bring:

• 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.

Even better if you have, but not necessary:

• 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

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

Plus benefits designed to keep you happy, healthy and fulfilled.

• 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

We know that people are more than what’s on their CV. If you’re unsure that you have the right profile for the role... Hit the ‘Apply’ button and give it a try!

At Lightspeed, we carefully consider a wide range of factors when determining compensation, including your skill set, qualifications, experience, and market data. These considerations can cause your compensation to vary. We reasonably expect the total compensation for this position to be in the range of $160,000 - $190,000 CAD. Lightspeed also provides a variety of employee benefits including, but not limited to, medical, dental, wellness, life and disability insurance, RRSP plan and match, paid parental leave top-up, and paid time off.Please note that this compensation information is solely for candidates hired to perform work within Ontario and reflects the amount Lightspeed is willing to pay at the time of this posting. This role represents an existing vacancy at Lightspeed. 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.