Upshop

Agile Delivery Manager

Mississauga, Ontario, Canada

Sponsorship not specifiedDetected 15 days ago

AgileJiraConfluenceForecastingInventory ManagementLeadershipCommunicationCollaborationFood Safety

About the role

Role Summary The Agile Delivery Manager / Program Manager is responsible for driving delivery execution, planning discipline, and operational visibility across Product and Engineering teams.
This role ensures teams operate with clear commitments, strong delivery hygiene, consistent ways of working, and transparent visibility into scope, risks, dependencies, milestones, and progress.
This is not a traditional Scrum Master role focused only on ceremonies.

Create and maintain scorecards or structured tracking views for active strategic work that requires milestone visibility, readiness tracking, or leadership oversight.
Support Pre-PI and PI readiness by ensuring teams have clear priorities, groomed work, capacity alignment, dependencies, risks, and realistic commitments.
Challenge unclear scope, weak readiness, missing dependencies, unrealistic commitments, or ambiguous ownership before they create delivery risk.
Partner with Product and Engineering leadership to align priorities, clarify tradeoffs, and ensure delivery commitments make sense.
Manage cross-team dependencies and drive resolution of delivery blockers.
Push back when process is bypassed, including enhancements without proper intake, production defects outside agreed support flows, incorrect issue types, or unclear ownership.
Drive follow-through and closure on action items, risks, decisions, and open workstreams.
Support Inspect & Adapt, retrospectives, sprint reviews, and continuous improvement actions with measurable follow-up.
Promote collaboration, accountability, and alignment across Product, Engineering, UX, Architecture, Support, and PMO.

Bachelor's degree in business administration, management, technology, or related field.
5+ years of experience in Agile Delivery, Program Management, Technical Program Management, Delivery Operations, or similar roles in software development.
Strong understanding of Agile and SDLC methodologies, including Scrum, Kanban, SAFe, PI Planning, and backlog readiness.
Experience working across multiple Product and Engineering teams in complex delivery environments.
Experience managing cross-team dependencies, delivery risks, milestones, and execution plans.
Ability to understand technical and product work deeply enough to challenge readiness, implications, risks, and commitment credibility.
Experience creating scorecards, initiative trackers, delivery dashboards, risk logs, or leadership status views.
Strong communication skills with the ability to summarize delivery status, risks, tradeoffs, and decisions clearly.
Ability to influence without direct authority across Product, Engineering, Support, UX, Architecture, and PMO.
Comfortable enforcing process standards, challenging ambiguity, and driving alignment when ownership or intake paths are unclear.
What Success Looks Like
Teams enter PI Planning with clear priorities, realistic commitments, visible dependencies, and known risks.

Own and maintain initiative delivery tracking, including scope, milestones, progress, risks, dependencies, decisions, and overall health.

This listing is sourced directly from Upshop's careers page and normalized into a canonical job model.