Description
Resource needs to work in PST hours.
Remote across Canada.
Might require travel to U.S.
Annual Compensation – Up to CAD 135K per year plus benefits (depending upon experience and domain expertise)
FTE, Permanent (can consider contract)
This is a hands-on ownership role for a practitioner who has led complex, multi-workstream programs in dynamic retail or enterprise technology environments. You will be the program management thread across two geographically and operationally distinct markets, responsible for aligning regional teams, managing cross-locale dependencies, and driving structured delivery through each phase of the rollout from planning and pilot through deployment and hypercare.
What You’ll Do
Program Ownership & Delivery
- Own end-to-end program execution across all workstreams and regions, from discovery and scoping through go-live and post-deployment stabilization.
- Define and maintain a consolidated program plan with milestones, dependencies, and critical path across engineering, product, hardware, and regional operations teams.
- Manage launch readiness activities including go/no-go criteria, cutover planning, rollback strategy, deployment sequencing, and post-launch monitoring protocols.
- Own the program-level risk register; identify, escalate, and actively mitigate risks before they become delivery blockers — across all workstreams and regions simultaneously.
- Coordinate hardware logistics and device provisioning timelines (where applicable) in alignment with software release schedules and program milestones.
Financial Estimation, Forecasting and Actualization
- Own the program-level financial picture — including initial cost estimation, ongoing forecast maintenance, and actuals tracking through each phase of the program.
- Partner with Finance and governance teams to ensure spending is accurately represented, variances are explained, and budget assumptions are revisited as scope or sequencing evolves. Bring early, proactive visibility to spending risk before it surfaces in formal reviews; do not wait for a governance checkpoint to flag a forecast that is trending in the wrong direction.
- Maintain financial reporting that gives leadership a clear, honest view of where the program stands against plan — across procurement, licensing, implementation effort, and deployment costs.
Multi-Region Coordination
- Serve as the primary program management point of contact for all regional teams, ensuring region-specific requirements, compliance needs, and operational constraints are embedded in the plan.
- Manage the structural complexity of a multi-region program: time zone alignment, localization requirements, staggered deployment sequencing, and region-specific change management needs.
- Identify and surface cross-locale dependencies early — including shared platform capabilities, vendor relationships, and infrastructure components — and manage them proactively.
- Partner with regional leadership and in-market stakeholders to navigate local operational requirements, site readiness protocols, and workforce impacts tied to the technology transition.
Cross-Functional Coordination
- Partner with Product Management, Engineering, QA, Enterprise Architecture, Field Operations, and Technology teams to align on scope, sequencing, and success metrics.
- Coordinate with Legal, Compliance, Finance, and IT infrastructure teams to ensure regional regulatory requirements, data privacy standards, and change management obligations are integrated into program execution.
- Facilitate program rituals where applicable — quarterly planning, sprint reviews, steering committee check-ins, dependency syncs, regional stand-ups, and retrospectives — with discipline and focus across all stakeholder groups.
- Manage vendor and hardware partner relationships as they relate to program schedule, device delivery, and field support readiness.
Technical Engagement
- Engage meaningfully in technical discussions around platform architecture, system configuration, hardware integration, data processing pipelines, and middleware dependencies — even without deep prior domain experience.
- Translate product and business requirements into executable technical workstreams; surface gaps in scoping before they emerge in execution.
- Review system integration specifications, ADRs, and environment readiness assessments with enough depth to identify downstream risks to program timelines.
- Understand the difference between configuration and customization decisions in the context of a platform swap, and escalate appropriately when scope creep threatens delivery.
Stakeholder Communication
- Produce executive-quality program status reporting: clear, concise, and honest about program health across all workstreams and regions without burying risks in activity summaries.
- Manage expectations for both internal leadership and regional business stakeholders around deployment timelines, feature availability, known limitations, and go-live readiness.
- Run structured decision-making forums when competing regional priorities, resource constraints, or technical trade-offs require leadership alignment.
- Communicate proactively across time zones, ensuring all regional stakeholders are never operating on stale program information.
What You’ll Bring
Required Experience
- 5–8 years of experience in Technical Program Management, with at least 3 years leading complex, multi-workstream programs at an enterprise or large-scale technology company.
- Demonstrated experience owning end-to-end program delivery — not just participating in programs. Able to speak to specific programs you led, decisions you navigated, and outcomes you drove.
- Proven ability to manage programs with significant geographic and operational complexity — multi-site deployments, multi-region rollouts, or programs requiring coordination across internationally distributed teams.
- Strong working knowledge of enterprise software delivery cycles, including agile and scaled agile frameworks (SAFe, LeSS, or equivalent).
- Experience managing cross-functional programs where engineering, product, operations, and field teams all have active work in flight simultaneously.
- Comfort working in environments where you are ramping on a new technical domain quickly; proven ability to ask the right questions, absorb context rapidly, and drive clarity without waiting for perfect information.
Skills & Competencies
- Ability to build and maintain detailed program plans in tools such as Jira, Asana, Smartsheet, or equivalent — with structured milestone tracking, dependency mapping, and risk registers.
- Strong analytical and structured problem-solving skills; able to decompose ambiguous problems and drive to action in a fast-moving environment.
- Excellent written and verbal communication; able to adjust register from engineering stand-ups to executive steering committees, and to operate effectively across cultural and linguistic contexts.
- Proven ability to hold timelines and delivery commitments without being the person who just escalates — you bring solutions alongside the flag.
- Comfortable navigating ambiguity in program scope; able to impose structure without imposing rigidity, especially during the early phases of a technology transition.
- Cross-cultural fluency or experience managing programs with internationally distributed business stakeholders is a meaningful asset for this role.
Nice to Have
- Prior experience with the relevant technology domain, retail or enterprise systems, or hardware/software deployment programs at scale.
- Familiarity with device management platforms, MDM solutions, or hardware provisioning and deployment workflows at scale.
- Experience managing systems integrations, compliance requirements, or technology change management in complex operational environments.
- Background in solutions engineering, implementation consulting, or technical project management at an enterprise software or technology company.
- PMP, PMI-ACP, SAFe Program Consultant (SPC), or equivalent certification.
- Familiarity with SOC 2, PCI-DSS, or similar compliance frameworks as they relate to enterprise data systems.





