indeed
Senior Delivery Manager
Robots & Pencils
Toronto, CAN
Full Time
Senior
1 weeks ago
Software DeliveryAgileScrumSAFeKanbanJira
Free
Job Fit Check
Base Career helps you apply smarter for this job.
?%
Ready to ScanKey skills for this role
Software DeliveryAgileScrum
About the Role
Robots & Pencils is hiring a Senior Delivery Manager to lead end-to-end delivery of complex AI engagements. You will manage distributed teams, facilitate agile ceremonies, and serve as the primary delivery partner to clients.
Key Skills for This Role
Software DeliveryAgileScrumSAFeKanbanJira
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 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
- 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
- Translate delivery progress into business impact for client stakeholders (ROI, milestones, decisions)
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
- Experience in regulated environments (e.g., utilities, government, finance) is a plus
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 Craft & Delivery
- 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.
What You'll Do Collaboration & Communication
- 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 Do Leadership & Influence
- Lead distributed delivery teams across onshore and offshore locations, fostering accountability, collaboration, and delivery excellence.
- Coach junior delivery managers with concrete feedback and stretch opportunities, contributing to their development plans.
- Foster a culture of transparency, continuous improvement, and high performance across the engagement.
- Contribute to improving delivery practices, tools, and frameworks across engagements.
- Assess team strengths and gaps on your engagements, and partner with Client Partners to flag staffing needs and high potential talent for the firm.
- Conduct executive interviews for engineers, designers, and other roles joining your engagements, and serve as an essential voice in go/no go hiring decisions across the firm.
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.
Helpful Extras and Unique Skills
- Vertical depth in one or more of Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing.
- Experience delivering agentic, AI co worker, or applied AI initiatives in enterprise.
- Prior career experience in client facing roles (engagement management, consulting, account leadership) that informs growth conversations.
You'll Do Well Here if You Are
- A doer. You see something broken and fix it. You'd rather move on clarity than wait for certainty.
- A fast learner who knows you don't know everything. The AI landscape changes weekly. You're senior enough to know better and curious enough to keep learning anyway.
- Direct in a way that makes the work better. You give honest feedback. You'd rather have the hard conversation than blow smoke.
- Obsessed with craft. You know genius is in the details. You ship exceptional, not perfect, and you don't put your name on work you wouldn't stand behind.
- Built for ownership. You honor commitments, admit mistakes fast, and back your teammates when a decision costs something. No handoffs, no finger pointing.
- All in. You treat clients' businesses like your own. You take the work seriously without taking yourself seriously.
- Resourceful when the budget, timeline, or team is tight. Constraints don't slow you down. They sharpen you.
- Calm when it gets hot. When scope, timeline, and stakeholders pull in three directions, you slow the room down enough to make the right call. You'd rather raise the hard trade off in week two than absorb it in week eight.
- Glad to be in the room with people who care as much as you do. Our teams average fifteen plus years of experience. We hire people who push each other to do better work.
Apply for this job in 1 click
Skip the repetitive application forms
Install the Base Career Chrome Extension and autofill job applications across major job boards with your profile.
Trusted by over 500,000 job seekers on Base Career
More from this employer
More jobs at Robots & Pencils
Senior Delivery Manager
Calgary, CAN
SeniorFull Time
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, se
6 days agoView →
Product Manager
Vancouver, UAE
Fulltime
Robots & Pencils is an applied AI engineering firm building the next frontier of business architecture. We design and ship AI co-workers that integrate into enterprise operations and deliver measurable results for our cl
1 months agoView →