Senior Delivery Manager

Robots & Pencils

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

Posted 11/9/2026full-timeRemote • CanadaSenior💰 CA$170,000 - CA$220,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in leading complex, multi-phase software delivery engagements with a strong focus on AI-augmented processes, agile methodologies, and stakeholder communication. Capable of managing distributed teams and establishing delivery standards while ensuring alignment with client expectations and business impact.

Highest-signal resume keywords

Agile Delivery PracticesAI Tools UsageClient-Facing CommunicationDelivery Tooling ExperienceTeam Leadership

ATS Keywords

Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Software DeliveryTechnical Project ManagementAgile MethodologiesMulti-Platform Digital SystemsAI Development Life CycleDelivery KPIs TrackingObservabilityModel Risk ManagementEvaluation StrategyCloud-Native Architectures

Soft Skills

Strong OwnershipAttention to DetailResourcefulnessCalm Under PressureDirect Feedback

Tools & Technologies

JiraConfluenceGitHubAzure DevOpsCI/CD Pipelines

Certifications & Qualifications

PMPScrum MasterSAFe

Industry Keywords

Consumer ProductsRetailEducationEnergyFinancial ServicesHealthcareManufacturing

Tech Stack

Tools & technologies

AzureCloudPMP

About the role

Key responsibilities & impact

Lead end-to-end delivery of complex, multi-phase engagements, aligning 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 across engagements and establish delivery standards
Model and coach AI-augmented delivery processes for delivery managers
Partner with AI product managers and engineers on observability, model risk, data readiness, evaluation strategy, infrastructure, context management, latency, monitoring, and production readiness
Define success metrics for AI-augmented delivery, including quality, rework, review overhead, and velocity
Build or direct status-visibility tooling for complex AI-driven pipelines
Decide when agentic approaches are unsuitable and defend those decisions to clients
Establish definitions of done for AI-driven features, including evaluation thresholds, human-in-the-loop checkpoints, and post-launch monitoring
Serve as the primary delivery contact for clients and lead stakeholder, roadmap, and delivery forums
Communicate progress, risks, and tradeoffs to executive and non-technical audiences
Partner with Client Partners on expansion opportunities and translate delivery progress into business impact
Lead distributed onshore/offshore teams and coach junior delivery managers
Improve delivery practices, tools, and frameworks across engagements
Assess team strengths and gaps, flag staffing needs, and identify 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, including Scrum, SAFe, or 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 such as Jira, Confluence, GitHub, Azure DevOps, and CI/CD pipelines
Familiarity with cloud-native architectures and AI-enabled platforms
Demonstrable usage of AI tools to enhance delivery planning, reporting, and documentation, such as Claude
Track record leading at least one engagement where AI/ML or agentic capability was core to the solution, including model risk, evaluation, and client expectations
Able 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 agentic delivery pipelines
PMP, Scrum Master, SAFe, or equivalent certification preferred
Helpful extras include vertical depth in Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing; enterprise agentic/AI co-worker/applied-AI delivery experience; and prior client-facing engagement management, consulting, or account leadership experience
Strong ownership, learning, direct feedback, attention to detail, resourcefulness, calm under pressure, and client commitment

Benefits

Comp & perks

Paid time off
Medical insurance
Dental insurance
Vision insurance
401(k) for eligible employees
Equal employment opportunities
Background check conducted in accordance with local legislation
Current employer will not be contacted without your permission