Senior Director, Software Development

Hi there! Thanks for stopping by

We’re looking for a Senior Director, Software Development to join our Retail team in Canada or USA. 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. You will connect business strategy to product and engineering execution, guide architectural choices, strengthen product quality, and develop the leaders who make the organization successful. You will partner closely with Product, Design, Go-to-Market, and senior company leaders to make clear decisions and deliver with focus.

What you’ll be doing:

• 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.

What you need to bring:

• 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.

Nice to have

• Experience in retail technology, wholesale, golf, commerce, SaaS, or another domain with complex operational workflows.

• Experience leading teams responsible for transactional, scheduling, inventory, payments, or other business-critical systems.

• Experience integrating product teams with shared platforms and services.

• Experience leading organizational change while maintaining delivery momentum.

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!

Be a changemaker

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

Fuel your growth. Find your people.

At Lightspeed, your growth is our priority. We invest in you with continuous learning opportunities, global mobility and benefits designed to support you—all within a driven, diverse and inclusive team that’s passionate about empowering our communities

Please note that we ask applicants to disclose any criminal convictions, and we conduct criminal record checks as part of our hiring process for this role.

At Lightspeed, we carefully consider a wide range of factors when determining compensation, including your skillset, qualifications, experience, and market data. These considerations can cause your compensation to vary. We reasonably expect the base salary for this position to be in the range of $260,000 to $290,000 USD , depending on the candidate’s location. Additionally, this role may be eligible for discretionary short-term and long-term incentives. Lightspeed also provides a variety of employee benefits including, but not limited to, medical, dental, wellness, life and disability insurance, 401K plan and match, paid parental leave top-up, and paid time off.

Please note that this salary information is solely for candidates hired to perform work within the United States, and refers to the amount Lightspeed is willing to pay at the time of this posting, which may vary depending on the candidate’s actual location. Salaries for part-time roles will be prorated based upon the agreed upon number of hours to be regularly worked.

To all recruitment agencies: Lightspeed does not accept unsolicited agency resumes. If we have not directly engaged your company in writing to supply candidates for a specific vacancy, Lightspeed will not be responsible for any fees related to unsolicited resumes.

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.

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.

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.

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.

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