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 - $190,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading complex, multi-phase software delivery engagements with a strong focus on AI-augmented processes and agile methodologies. Proven ability to manage distributed teams, communicate effectively with clients, and implement delivery standards for AI-native projects.

Highest-signal resume keywords

Agile Delivery PracticesAI-Augmented Delivery ProcessesClient-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 Tools UsageDelivery Standards SettingComplex Digital Systems DeliveryObservabilitySuccess Metrics DefinitionInfrastructure StandardsContext Management

Soft Skills

Relationship ManagementCoachingStakeholder CommunicationTeam LeadershipProblem Solving

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 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 across engagements
Model and coach AI-augmented delivery processes
Partner with AI product managers and engineers on observability, model risk, data readiness, evaluation strategy, infrastructure, orchestration, logging, and guardrails
Define success metrics and standards for AI-augmented and agentic delivery processes
Build or direct status-visibility tooling for complex AI-driven pipelines
Evaluate context-management and latency trade-offs and determine when agentic approaches are unsuitable
Own delivery approaches for AI-native and agentic engagements and translate technical uncertainty into client-actionable plans and risk registers
Define “definition of done” standards for probabilistic and AI-driven features
Coach delivery managers and coordinators
Serve as the primary delivery contact for clients and build trusted relationships
Lead stakeholder sessions, roadmap alignment discussions, and delivery forums
Communicate progress, risks, and tradeoffs to executive and non-technical audiences
Partner with Client Partners to identify expansion opportunities and translate delivery progress into business impact
Lead distributed onshore and offshore delivery teams
Coach junior delivery managers and contribute to development plans
Improve delivery practices, tools, and frameworks
Assess team strengths and gaps and 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, 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
Comfort setting standards for infrastructure, context management, and latency trade-offs in agentic delivery pipelines
Instinct for spotting engagement growth opportunities and credibility with clients to advance those conversations
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 is helpful
Experience delivering agentic, AI co-worker, or applied-AI initiatives in enterprise is helpful
Prior client-facing experience in engagement management, consulting, or account leadership is helpful
Successful completion of a background check may be required

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