Principal Technical Program Manager We're looking for a Principal Technical Program Manager to join our Product & Technology Operations team and own how we manage, optimize, and scale cloud, vendor, and AI spend across the organization.

You will define the FinOps strategy itself - not just run an existing cost program, but decide what gets optimized, in what order, and why. Cloud and vendor cost management has an established playbook that we want to scale and automate; AI spend does not. You'll be defining and building FinOps for AI, while also evolving existing practice into a more automated system.

This is a very senior technical IC role. You'll bring enough technical depth to build or directly shape the automations, dashboards, and optimization recommendations yourself, and enough strategic judgment to influence how leadership thinks about cost trade-offs and how we partner with Finance, Procurement and other functions on all things vendor management and optimizations.

What You’ll Be Doing Define the FinOps strategy

Own the strategy for cloud, vendor, and AI cost management across the organization - not just the execution of an existing roadmap.

Continuously reassess what to optimize, in what order, and why, based on where spend and risk are actually concentrated.

Build the framework for managing AI cost, an area with no established industry playbook yet.

Drive cost optimization with technical depth

Analyze cloud usage, vendor contracts, and AI spend to identify inefficiencies and develop strategies to reduce unnecessary cost.

Build or directly shape the dashboards, automations, and monitoring systems that make cost visible and actionable, at a technical depth equivalent to a Senior Engineer.





Propose specific technical optimizations, not just process recommendations, and know when a suggestion requires deeper engineering partnership.

Apply hands-on experience building and automating with AI, not just directing others to do it.

Lead the program across the organization

Oversee and in some cases execute multiple cost-optimization initiatives simultaneously.

Own the reporting structure - cost attribution, monitoring, and alerting - and use it to tell leadership a clear, trustworthy story about spend and savings.

Partner with FP&A; to define and establish key cost metrics giving leadership a sharper financial lens on cost efficiency.

Manage cross-functional dependencies, risk, and change across SRE, Engineering, Data, FP&A;, and Procurement teams.

Influence at the executive level

Bring insights on feasibility, timelines, risk, and cost trade-offs directly to senior and executive stakeholders, shaping decisions that affect real budget and infrastructure choices.

Balance centralized cost management standards with the autonomy individual business units need to operate effectively.

Proactively surface issues and advocate for change across products and teams, rather than waiting to be asked.

Mentorship

Partner with Delivery Ops leadership on TPM career development, best practices,



and the foundation of the broader TPM function.

Mentor other TPMs, helping raise the technical and strategic bar across the team.

What You Need To Bring

Experience owning both the strategy and execution for a cloud, vendor or AI cost optimization program - not just executing one someone else designed.

Deep knowledge of the AI vendor landscape - pricing models, contract structures, and the specific optimization levers and nuances that differ from traditional cloud cost management.

Technical depth in cloud architecture, cost management, and optimization techniques strong enough to build or directly evaluate dashboards and automation yourself.

Experience navigating an area with no established playbook, building the framework as you go rather than applying a known model.

A track record of running large, cross-organizational programs spanning multiple business units.

Strong executive communication skills - able to translate complex technical and cost trade-offs into decisions leadership can act on.

Demonstrated ability to influence senior stakeholders and drive change across an organization without formal authority over them.

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 growth opportunities, but lean enough to make your voice heard

Career-defining opportunities

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 yo

📌 Principal Technical Program Manager (Winnipeg)
🏢 Lightspeed Commerce
📍 Winnipeg