Senior Delivery Manager

Robots & Pencils

. Lead end-to-end delivery of complex, multi-phase engagements across scope, budget, timeline, and quality .

Posted 10/28/2026full-timeRemote • CanadaSenior💰 CA$170,000 - CA$220,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading complex software delivery projects, utilizing agile methodologies and AI tools to enhance planning and execution. Capable of managing distributed teams and client relationships while establishing delivery standards for AI-driven initiatives.

Highest-signal resume keywords

Agile Delivery PracticesAI Development Life Cycle (AIDLC)Client-Facing CommunicationDelivery Tooling (Jira, Confluence, GitHub, Azure DevOps)PMP, Scrum Master, SAFe Certification

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Software DeliveryTechnical Project ManagementAgile MethodologiesAI Tools UsageMulti-Platform Digital Systems DeliveryInfrastructure Standards DefinitionObservability and Success MetricsRisk ManagementDelivery KPIs TrackingCoaching Delivery Managers

Soft Skills

Relationship ManagementStakeholder CommunicationTeam LeadershipMentoringProblem Solving

Tools & Technologies

JiraConfluenceGitHubAzure DevOpsCI/CD PipelinesClaude

Certifications & Qualifications

PMPScrum MasterSAFe Certification

Industry Keywords

Consumer ProductsRetailEducationEnergyFinancial ServicesHealthcareManufacturingAI Co-WorkerApplied-AI InitiativesEngagement Management

Tech Stack

Tools & technologies

AzureCloudPMP

About the role

Key responsibilities & impact

Lead end-to-end delivery of complex, multi-phase engagements across scope, budget, timeline, and quality
Facilitate sprint planning, backlog refinement, and delivery execution across cross-functional teams
Manage phased releases, production readiness, and transitions into operations and maintenance
Identify and manage dependencies, risks, scope changes, and escalations
Define, track, and report delivery KPIs to guide decisions and tradeoffs
Support QA and UAT and ensure outcomes meet acceptance criteria
Use AI tools such as Claude for delivery planning, reporting, and stakeholder communications
Implement the AI Development Life Cycle (AIDLC) across engagements
Establish AI-augmented delivery processes and mentor delivery managers
Evaluate observability, success metrics, monitoring, model risk, data readiness, and evaluation strategy for AI-driven work
Define infrastructure standards for agentic delivery pipelines, including compute, orchestration, logging, and guardrails
Translate technical uncertainty into delivery plans and client-facing risk registers
Serve as the primary delivery contact for clients and lead stakeholder, roadmap, and delivery forums
Communicate progress, risks, tradeoffs, ROI, milestones, and decisions to executive and non-technical audiences
Partner with Client Partners to identify expansion opportunities and shape follow-on work
Lead distributed onshore and offshore delivery teams
Coach junior delivery managers and contribute to development plans
Improve delivery practices, tools, and frameworks across engagements
Assess team strengths and gaps, flag staffing needs and high-potential talent
Conduct executive interviews and contribute to go/no-go hiring decisions

Requirements

What you’ll need

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)
Track record leading at least one engagement where AI/ML or agentic capability was core to the solution, including managing model risk, evaluation, and client expectations
Ability to set delivery standards for AI-native work, including evaluation criteria, human-in-the-loop checkpoints, and monitoring, and coach other delivery managers
Track record leading a team through an agentic development/delivery process, including observability, success metrics, and status visibility
Comfortable setting standards for infrastructure, context management, and latency trade-offs in an agentic delivery pipeline
PMP, Scrum Master, SAFe, or equivalent certification preferred
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 such as engagement management, consulting, or account leadership

Benefits

Comp & perks

Paid time off
Medical insurance
Dental insurance
Vision insurance
401(k) for eligible employees
Background check conducted in accordance with local legislation
Equal employment opportunities