LightSpeed Retail

Enterprise Transformation Manager / Senior Manager

LightSpeed Retail$125K — $170K *
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • Strong problem-solving skills linking strategy to execution
  • Experience leading cross-functional initiatives in fast-paced environments
  • Proactive driver of execution, not just coordination
  • Strong stakeholder management and influence over senior executives
  • Excellent communication skills for executive decision support
  • Solid business acumen connecting initiatives to strategy
  • Fluency in English as a working language is required

Responsibilities

  • Drive transformation initiatives from start to finish, ensuring measurable outcomes
  • Translate strategic priorities into actionable execution plans
  • Maintain momentum and progress across transformation workstreams
  • Collaborate with teams to align priorities and unblock issues
  • Identify and resolve risks and dependencies to keep projects on track
  • Track progress against milestones and value targets
  • Lead high-stakes workstreams and mentor team members at the Senior Manager level

Benefits

  • Flexible paid time off and remote work policies
  • Equity options to share in the company's success
  • Pension plan contributions for your future
  • Training opportunities for skills and career growth
  • Health and wellness credits for personal well-being
  • Time off for community volunteering
  • Employee-led interest groups and social activities
  • Computer purchase program for personal tech needs
  • Enhanced parental leave for growing families
Full Job Description
We're looking for an Enterprise Transformation Manager or Senior Manager to join our team at Lightspeed. This role will serve as a key member of Lightspeed's Transformation Management Office (TMO) and report to Lightspeed's VP of Enterprise Transformation, driving the weekly drumbeat of execution across multiple 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 help bring strategy to life by translating priorities into action, removing roadblocks, and ensuring initiatives deliver measurable impact. The ideal candidate combines strong strategic thinking with a bias toward execution and experience navigating complex, cross-functional environments.

**we are looking to bring someone on at either the Manager or Senior Manager level. Your specific title and total rewards package will be tailored based on your unique background, expertise, and how you show up during the interview process.

What you'll be doing:
  • Drive high-priority transformation initiatives from concept through execution, ensuring accountability and delivery of measurable outcomes
  • Translate strategic priorities into actionable plans, bringing strategy to life through clear execution plans, ownership, and outcomes
  • Act as the drumbeat behind execution across transformation workstreams, maintaining momentum and ensuring consistent progress week over week
  • Partner closely with the broader transformation team, workstream leads and initiative owners, and other cross-functional teams to align priorities, drive accountability, and unblock critical issues
  • Proactively identify risks, dependencies, and roadblocks, and take action to resolve them and keep initiatives on track
  • Track progress against key milestones and value targets, ensuring initiatives deliver measurable financial and operational impact
  • If joining at the Senior Manager level, you'll take the lead on our most intricate, high-stakes workstreams with significant independence, while also mentoring the TMO team and acting as a key partner to senior leadership

What you need to bring:
  • Strong structured problem-solving skills, with the ability to connect strategy to execution and drive outcomes
  • Demonstrated experience leading complex, cross-functional initiatives in fast-paced, matrixed environments
  • Proven ability to operate with a bias toward action and act as a driver of execution, not just a coordinator
  • Strong stakeholder management skills, with the ability to influence senior executives and drive cross-functional alignment without direct authority
  • Excellent communication skills, including experience synthesizing insights and supporting executive-level decision-making
  • Strong business acumen, with the ability to connect initiative progress to broader strategic priorities
  • 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:
  • Experience working on or within large-scale transformation programs or enterprise-wide initiatives
  • Experience in SaaS, fintech, or other high-growth, technology-driven environments
  • For the Manager level: 2-4 years of experience in consulting, strategy, business operations, or a related field
  • For the Senior Manager level: 5+ years of experience in consulting, strategy, business operations, or a related field, with a proven track record of independently leading large-scale initiatives

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 $125,000 - $170,000 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.

Where to from here?

Obviously, this has to be mutually beneficial: we want you to step into a role you love, and we want to offer you a place you're proud to come to every day. For a glimpse into our world check out our career page here.

About LightSpeed Retail

LightSpeed Retail is a cloud-based point-of-sale and e-commerce software provider for retailers and restaurateurs. The company was founded in 2005 by Dax Dasilva and is headquartered in Montreal, Canada. LightSpeed Retail's platform allows businesses to manage their inventory, process transactions, and analyze sales data. The company's mission is to help businesses grow by providing them with the tools they need to succeed. LightSpeed Retail has raised over $290 million in funding from investors such as Caisse de dépôt et placement du Québec, iNovia Capital, and Accel Partners.
Learn more about LightSpeed Retail
Size
1,000 employees
Market Cap
$18.4 billion
Industry
Founded
2005
5 Year Trend
+48.5%

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