Technical Program Manager Scrum Master Jobs in Ontario

Agile Delivery Manager 

About Upshop: 

Upshop is the foremost provider of a SaaS platform designed to streamline forecasting, ordering, production, and inventory optimization for food retailers and foodservice operators. Our unified platform simplifies and enhances daily workflows, enabling smarter, more connected operations across fresh production, inventory management, food safety, and ordering.

Trusted by over 450+ retailers and operators across 50,000+ locations globally, Upshop helps customers improve sales, reduce waste, increase operational efficiency, and advance food safety and sustainability-especially in complex, production-driven environments.

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. The role requires delivery management depth, the ability to understand the work being delivered, challenge readiness, enforce process standards, and create structure around active initiatives so Product and Engineering leadership can make timely decisions. 

The ADM / Program Manager partners closely with Product Managers, Engineering Managers, UX, Architecture, Support, and PMO to ensure teams are aligned, commitments are credible, risks are surfaced early, and execution remains predictable. 

Responsibilities 

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

Create and maintain scorecards or structured tracking views for active strategic work that requires milestone visibility, readiness tracking, or leadership oversight. 

Orchestrate cross-team delivery, ensuring alignment on sequencing, dependencies, milestones, and execution plans. 

Provide delivery visibility and forecasting across PI cycles using data, metrics, Jira, Jira Plans, and eazyBI. 

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. 

Communicate initiative status, risks, decisions needed, and progress to stakeholders and leadership. 

Ensure consistent ways of working across teams, including intake paths, issue classification, delivery hygiene, and escalation protocols. 

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. 

Qualifications 

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. 

Strong experience with Jira and Confluence required; Jira Plans / Advanced Roadmaps and eazyBI preferred. 

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. 

Active strategic work has structured visibility, milestones, owners, risks, decisions, and closure criteria. 

Leadership can clearly understand what is committed, what has changed, what is at risk, and what decisions are needed. 

Delivery risks are surfaced early with recommendations, not discovered late. 

Ways of working are consistently followed across teams. 

The role reduces ambiguity, improves predictability, and creates stronger alignment across Product and Engineering.

The estimated pay ranges for this role are as follows:

• $115,000 - 130,000 CAD

The successful candidate's starting salary will be determined based on permissible, non-discriminatory factors such as skills, experience, and geographic location.