Senior Delivery Manager

This is a fully remote position, open to applicants in Canada.

📋 Description

• Oversee comprehensive delivery of intricate, multi-phase projects, ensuring alignment of scope, budget, timeline, and quality.

• Facilitate sprint planning, backlog refinement, and execution of delivery across interdisciplinary teams.

• Manage staged releases, ensure production readiness, and facilitate transitions into operations and maintenance.

• Identify and address dependencies, risks, scope modifications, and escalations.

• Define, monitor, and report on delivery KPIs to inform decisions and trade-offs.

• Assist in QA and UAT processes to ensure outcomes align with acceptance criteria.

• Leverage AI tools such as Claude for planning, reporting, and stakeholder communications related to delivery.

• Implement the AI Development Life Cycle across projects and establish standards for delivery.

• Model and mentor AI-enhanced delivery processes for delivery managers.

• Collaborate with AI product managers and engineers on observability, model risk, data readiness, evaluation strategy, infrastructure, context management, latency, monitoring, and production readiness.

• Establish success metrics for AI-augmented delivery, focusing on quality, rework, review overhead, and velocity.

• Create or direct status-visibility tools for complex AI-driven workflows.

• Decide when agentic approaches are inappropriate and advocate for those decisions with clients.

• Define completion criteria for AI-driven features, which include evaluation thresholds, human-in-the-loop checkpoints, and post-launch monitoring.

• Act as the primary delivery liaison for clients, leading stakeholder interactions, roadmap discussions, and delivery forums.

• Communicate progress, risks, and trade-offs effectively to both executive and non-technical audiences.

• Collaborate with Client Partners to identify expansion opportunities and translate delivery progress into business value.

• Lead distributed onshore and offshore teams while mentoring junior delivery managers.

• Enhance delivery practices, tools, and frameworks across all engagements.

• Evaluate team strengths and gaps, highlight staffing needs, and identify high-potential talent.

• Conduct executive interviews and contribute to go/no-go hiring decisions.

⛳️ Requirements

• A minimum of 5 years of experience in software delivery, technical project management, or engineering leadership.

• Strong grasp of agile delivery methodologies in complex, multi-team environments, including Scrum, SAFe, or Kanban.

• Experience managing distributed teams across both onshore and offshore settings.

• Proven track record in delivering complex, multi-platform digital systems within agile frameworks.

• Strong skills in client-facing communication and relationship management.

• Familiarity with delivery tools such as Jira, Confluence, GitHub, Azure DevOps, and CI/CD pipelines.

• Knowledge of cloud-native architectures and AI-enabled platforms.

• Demonstrated experience using AI tools to enhance delivery planning, reporting, and documentation, including Claude.

• A solid record of leading at least one engagement where AI/ML or agentic capabilities were essential, covering model risk, evaluation, and client expectations.

• Capable of establishing delivery standards for AI-native projects, including evaluation criteria, human-in-the-loop checkpoints, and monitoring, while also mentoring other delivery managers.

• Proven experience leading a team through an agentic development/delivery process, focusing on observability, success metrics, and status visibility.

• Comfort in setting standards for infrastructure, context management, and latency trade-offs in agentic delivery pipelines.

• PMP, Scrum Master, SAFe, or equivalent certification is preferred.

• Additional valuable experience includes in-depth knowledge in Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing; experience in enterprise agentic/AI co-worker/applied-AI delivery; and prior experience in client-facing engagement management, consulting, or account leadership.

• Strong qualities of ownership, eagerness to learn, direct feedback, attention to detail, resourcefulness, composure under pressure, and commitment to clients.

🏝️ Benefits

• 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