Director enterprise Jobs in Toronto, ON

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We’re looking for an Enterprise Transformation 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, driving the weekly drumbeat of execution across high-priority transformation workstreams. Lightspeed is currently undergoing a multi-year transformation focused on strengthening core growth engines and driving operational efficiency across the business. In this role, you will lead the execution of this transformation by translating strategic priorities into action, removing roadblocks, and ensuring initiatives deliver measurable impact. The ideal candidate combines strong strategic thinking with a bias toward execution and a track record of leading complex, cross-functional transformation efforts.

What you'll be doing:

• 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

What you need to bring:

• 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.

Even better if you have, but not necessary:

• 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

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

  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.