Staff Technical Program Manager in Winnipeg

We're looking for a Staff Technical Program Manager to join our Product & Technology Operations team and own how we build the Product Development Lifecycle (PDLC) into a shared execution model across Product, Engineering, and Design. You will own how work flows from idea to impact across the organization - one language for how work moves, one set of metrics leaders can trust, and one standard for what 'good' looks like at every stage of PDLC. This is a founding role for the function. You'll define the model, align stakeholders around it, and prove out its value as you build.

What you’ll be doing:

• Define the execution model
• Design a PDLC framework that works across Product, Engineering, and Design and across all Lightspeed products.
• Define what good looks like at each stage of PDLC, including the artifacts, checkpoints, and exit criteria teams should use.
• Build the measurement system
• Establish metrics that give leaders a trustworthy, holistic view of how work is flowing and where it's getting stuck.
• Design the framework so it measures the system and surfaces bottlenecks, not individual performance.
• Build in exception tracking so blocked or off-track work is visible early.
• Drive adoption
• Partner with Product, Engineering, and Design leaders across every vertical to align on the model and earn genuine buy-in and adoption.
• Navigate real differences across verticals and business units without forcing false consistency where it doesn't make sense.
• Bring structure to ambiguity - resolve open questions as they surface rather than waiting for a perfect spec.
• Build an AI-first PDLC
• Define what humans own versus what AI agents own at each stage of PDLC, keeping judgment, accountability, and anything irreversible or customer-facing with humans.
• Partner with Engineering to identify where AI agents can accelerate delivery, build pilots, and measure their ROI and impact on speed.
• Ensure human checkpoints are genuine decisions, not rubber stamps, as adoption scales.
• Evolve the model
• Treat the framework as a living system - review it periodically and adjust based on what's actually working.
• Report on program health and progress to senior leadership.

What you need to bring:

• Experience designing or significantly evolving a delivery framework, execution model, or program management system - not just operating one someone else built.
• Experience leading cross-functional organizations through operational change, including turning skepticism into genuine adoption.
• A track record of building measurement systems from ambiguous or inconsistent data, and knowing which problems to solve first versus defer.
• Experience partnering with Engineering on applied AI or automation, including how to evaluate and measure whether it's actually accelerating delivery, not just novel.
• Strong executive communication skills - able to represent program health, risk, and trade-offs credibly to senior leadership.
• Demonstrated ability to influence and align senior stakeholders across Product, Engineering, and Design without formal authority over them.
• Comfort operating with significant ambiguity and independently structuring a path forward rather than waiting for direction.

As a global company with employees and clients outside of Quebec, fluency in English as a working language is required for this position.

You'd Be Great At This Role If You...

• Enjoy building something from a blank page rather than optimizing an existing system.
• Can hold a strong point of view on 'what good looks like' while staying open to what the data and teams tell you.
• Get energized aligning stakeholders with different views, perspectives, and backgrounds.
• Think in systems and flow, not individual tickets or teams.
• 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.

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.

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.

Lightspeed is building communities through commerce, and we need people from all backgrounds and lived experiences to do that.