Senior Delivery Manager

Robots & Pencils

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

Posted 10/8/2026full-timeRemote • Canada, United StatesSenior💰 $160,000 - $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 implementing AI-driven solutions. Capable of managing distributed teams and fostering client relationships while ensuring adherence to delivery standards and performance metrics.

Highest-signal resume keywords

Agile Delivery PracticesAI-Driven SolutionsClient-Facing CommunicationDelivery Tooling ExperienceDistributed Team Management

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Software DeliveryTechnical Project ManagementAgile MethodologiesAI Development Life CycleMulti-Platform Digital SystemsDelivery Standards SettingModel Risk EvaluationObservability MetricsInfrastructure ManagementEvaluation Criteria Definition

Soft Skills

Relationship ManagementCoachingCommunicationLeadershipProblem-Solving

Tools & Technologies

JiraConfluenceGitHubAzure DevOpsCI/CD PipelinesClaude

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 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 efforts 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
Establish AI-augmented delivery standards, metrics, observability, and status-visibility tooling
Evaluate agentic approaches, infrastructure, context management, latency, model risk, data readiness, and evaluation strategy
Partner with AI product managers, AI engineers, and AI/ML engineering leads on delivery planning and production readiness
Define standards for AI-driven features, including evaluation thresholds, human-in-the-loop checkpoints, and post-launch monitoring
Coach delivery managers and coordinators on AI-native and agentic delivery processes
Serve as a credible voice with clients and internal leadership regarding production-ready AI
Act as 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 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, and 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
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 agentic delivery pipelines
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
Ability to lead distributed teams, coach delivery managers, manage ambiguity, and communicate with executive and non-technical audiences

Benefits

Comp & perks

Paid time off
Medical insurance
Dental insurance
Vision insurance
401(k)