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About the Role
As Senior Director, Engineering – Retail, you will lead the engineering organization responsible for Lightspeedʼs Wholesale and Golf businesses. You will shape the technical strategy, operating model, and culture that enable these teams to deliver meaningful outcomes for merchants. This is a broad leadership role connecting business strategy to product and engineering execution, guiding architectural choices, strengthening product quality, and developing leaders.
Responsibilities
- Set the engineering strategy for Wholesale and Golf, translating business priorities into clear technical direction and actionable plans.
- Lead and develop a multi-team organization through strong managers and senior technical leaders.
- Partner with Product and Design to establish priorities, clarify trade-offs, and deliver customer outcomes.
- Improve the health of the engineering system through effective planning, delivery practices, quality standards, and operational discipline.
- Raise the reliability of critical merchant workflows by strengthening ownership, observability, incident learning, and risk management.
- Guide architecture and platform investments that improve product coherence, reduce unnecessary complexity, and increase team leverage.
- Create an environment where teams can move quickly without compromising technical integrity or customer trust.
- Build strong relationships across Retail and the wider company, bringing the right people together around difficult decisions.
- Hire, coach, and retain exceptional leaders and engineers; create opportunities for people to grow and do their best work.
- Communicate progress, risks, and decisions with clarity at the team, executive, and cross-functional levels.
Requirements
- Significant experience leading engineering organizations through managers and senior technical leaders.
- A track record of connecting engineering strategy to business performance and customer value.
- Experience guiding complex product and platform development across multiple teams.
- Strong technical judgment, with the ability to engage deeply in architecture, reliability, quality, and long-term maintainability.
- Experience improving delivery flow while preserving engineering standards and sustainable pace.
- A practical approach to operating in ambiguity: you create clarity, make decisions, and adjust as new information emerges.
- Strong partnership skills across Product, Design, Operations, Sales, and customer-facing teams.
- The ability to attract, develop, and retain high-performing leaders in a distributed organization.
- Clear, concise communication and the confidence to work with senior executives.
- A genuine focus on customers and the merchants who rely on our products every day.
Skills
- Retail technology
- Wholesale
- Golf
- Commerce
- SaaS
- Transactional systems
- Scheduling systems
- Inventory systems
- Payments systems
- Business-critical systems
- Integrating product teams with shared platforms and services
- Leading organizational change
- Maintaining delivery momentum
Location
- Canada
- USA
Work Type
- Flexible work environment
- Remote work policies
Experience Level
- Senior
Salary/Compensations
- $260,000 to $290,000 USD
Benefits
- Flexible paid time off
- Equity options
- Contributions to your pension plan
- Training opportunities
- Health and wellness credit
- Time off to volunteer
- Interest groups
- Employee led networks
- Social committees
- Sponsored sports teams
- Computer purchase program
- Enhanced parental leave
- Medical insurance
- Dental insurance
- Wellness insurance
- Life insurance
- Disability insurance
- 401K plan and match
- Paid parental leave top-up
About the Company
- Lightspeed is building communities through commerce, and we need people from all backgrounds and lived experiences to do that.
- 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.
- 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.
Equal Opportunity
- Lightspeed is a proud equal opportunity employer and we are committed to creating an inclusive and barrier-free workplace.
- Lightspeed welcomes and encourages applications from people with disabilities.
- Accommodations are available on request for candidates taking part in all aspects of the selection process.