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Senior Delivery Manager
Robots & Pencils
Calgary, CAN
Full Time
Senior
6 days ago
Agile DeliveryScrumSAFeKanbanJiraConfluence
Free
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About the Role
Robots & Pencils seeks a Senior Delivery Manager to lead end-to-end delivery of complex AI engagements, managing distributed onshore and offshore teams. The role involves owning execution from kickoff through release, serving as the primary delivery partner to clients, and ensuring production-ready AI delivery.
Key Skills for This Role
Agile DeliveryScrumSAFeKanbanJiraConfluence
Responsibilities
- Lead end to end delivery of complex, multi phase engagements, ensuring alignment across scope, budget, timeline, and quality
- Facilitate sprint planning, backlog refinement, and delivery execution across one or more cross functional teams
- Manage phased releases, production readiness, and transitions into operations and maintenance models
- Identify and proactively manage dependencies, risks, scope changes, and escalations before they become blockers
- Define, track, and report delivery KPIs, using data to guide decisions, manage delivery health, and inform tradeoffs
- Support QA and UAT efforts, ensuring quality is validated and outcomes meet agreed acceptance criteria
- Bring an AI forward mindset to daily work, using tools like Claude to enhance delivery planning, reporting, and stakeholder communications
- Serve as the primary delivery contact for clients, building trusted relationships through transparency, consistency, and clear communication
- Lead stakeholder working sessions, roadmap alignment discussions, and delivery forums with confidence
- Communicate progress, risks, and tradeoffs clearly to executive and non technical audiences
- Partner with Client Partners to spot expansion opportunities inside the engagement and help shape the case for what’s next
- Lead distributed delivery teams across onshore and offshore locations, fostering accountability, collaboration, and delivery excellence
Requirements
- 5+ years of experience in software delivery, technical project management, or engineering leadership
- Strong understanding of agile delivery practices across complex, multi team engagements (e.g., Scrum, SAFe, Kanban)
- Experience managing distributed teams across onshore and offshore locations
- Proven ability to deliver complex, multi platform digital systems in agile environments
- Strong client facing communication and relationship management skills
- Experience with delivery tooling (e.g., Jira, Confluence, GitHub, Azure DevOps, CI/CD pipelines)
- Familiarity with cloud native architectures and AI enabled platforms
- Demonstrable usage of AI tools to enhance delivery planning, reporting, and documentation (e.g., Claude)
- PMP, Scrum Master, SAFe, or equivalent certification preferred
Full Job Posting
Position Overview
- As a Senior Delivery Manager, you are the senior delivery authority on a cross functional engagement: owning execution from kickoff through release, leading distributed onshore and offshore teams, and serving as the primary delivery partner to the client.
- You bring the judgment to navigate ambiguity, the discipline to keep complex programs on track, and the instinct to make every engagement a foundation for the next one.
What You’ll Do
- Lead end to end delivery of complex, multi phase engagements, ensuring alignment across scope, budget, timeline, and quality to meet delivery commitments and achieve successful outcomes
- Facilitate sprint planning, backlog refinement, and delivery execution across one or more cross functional teams
- Manage phased releases, production readiness, and transitions into operations and maintenance models
- Identify and proactively manage dependencies, risks, scope changes, and escalations before they become blockers
- Define, track, and report delivery KPIs, using data to guide decisions, manage delivery health, and inform tradeoffs across scope, timeline, and budget
- Support QA and UAT efforts, ensuring quality is validated and outcomes meet agreed acceptance criteria
- Bring an AI forward mindset to your daily work, using tools like Claude to enhance delivery planning, reporting, and stakeholder communications
- Serve as the primary delivery contact for clients, building trusted relationships through transparency, consistency, and clear communication while identifying opportunities to expand value within the engagement
- Lead stakeholder working sessions, roadmap alignment discussions, and delivery forums with confidence
- Communicate progress, risks, and tradeoffs clearly to executive and non technical audiences
- Partner with Client Partners to spot expansion opportunities inside the engagement (scope, follow on work, new use cases) and help shape the case for what’s next
- Translate delivery progress into business impact for client stakeholders (ROI, milestones, decisions) so executives see ongoing value, not just status
What You’ll Bring
- 5+ years of experience in software delivery, technical project management, or engineering leadership
- Strong understanding of agile delivery practices across complex, multi team engagements (e.g., Scrum, SAFe, Kanban)
- Experience managing distributed teams across onshore and offshore locations
- Proven ability to deliver complex, multi platform digital systems in agile environments
- Strong client facing communication and relationship management skills
- Experience with delivery tooling (e.g., Jira, Confluence, GitHub, Azure DevOps, CI/CD pipelines)
- Familiarity with cloud native architectures and AI enabled platforms
- Demonstrable usage of AI tools to enhance delivery planning, reporting, and documentation (e.g., Claude)
- PMP, Scrum Master, SAFe, or equivalent certification preferred
- Experience in regulated environments (e.g., utilities, government, finance) is a plus
- Instinct for spotting where an engagement can grow, and the credibility with clients to bring those conversations forward with Client Partners
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