Senior Delivery Manager

This is a fully remote position, open to applicants in Canada, +1 more country.

📋 Description

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

• Coordinate sprint planning, backlog refinement, and execution of deliveries across diverse teams.

• Manage staged releases, ensure production readiness, and transition processes into operations and maintenance.

• Identify and handle dependencies, risks, changes in scope, and necessary escalations.

• Define, monitor, and report on delivery KPIs to inform decision-making and tradeoffs.

• Assist with QA and UAT initiatives, ensuring that outcomes align with acceptance criteria.

• Utilize AI tools such as Claude for planning, reporting, and communications with stakeholders.

• Implement the AI Development Life Cycle throughout projects.

• Establish standards for AI-augmented delivery, including metrics, observability, and visibility tools.

• Assess agentic strategies, infrastructure, context management, latency, model risk, data readiness, and evaluation tactics.

• Collaborate with AI product managers, AI engineers, and AI/ML engineering leads on planning and ensuring production readiness.

• Set standards for AI-driven features, covering evaluation benchmarks, human-in-the-loop checkpoints, and post-launch oversight.

• Mentor delivery managers and coordinators on processes related to AI-native and agentic delivery.

• Act as a trusted advisor to clients and internal leadership concerning production-ready AI.

• Serve as the primary contact for clients, leading stakeholder, roadmap, and delivery discussions.

• Relay progress, risks, tradeoffs, ROI, milestones, and decisions to both executive and non-technical audiences.

• Collaborate with Client Partners to identify opportunities for expansion and shape subsequent projects.

• Lead both onshore and offshore distributed delivery teams.

• Mentor junior delivery managers and assist in their development plans.

• Enhance delivery practices, tools, and frameworks across various projects.

• Evaluate team strengths and weaknesses, highlight staffing needs, and identify top talent.

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

⛳️ Requirements

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

• Strong grasp of agile delivery methodologies across complex, multi-team projects, including Scrum, SAFe, and Kanban.

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

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

• Excellent communication and relationship management skills in client-facing roles.

• 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 improve delivery planning, reporting, and documentation, including Claude.

• History of leading at least one project where AI/ML or agentic capabilities were integral to the solution, including managing model risk, evaluations, and client expectations.

• Ability to establish delivery standards for AI-native projects, including evaluation criteria, human-in-the-loop checkpoints, and monitoring, and mentor other delivery managers.

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

• Comfortable establishing standards for infrastructure, context management, and latency trade-offs within agentic delivery pipelines.

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

• In-depth knowledge in one or more of the following sectors: Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing.

• Experience in delivering agentic, AI co-worker, or applied-AI projects in an enterprise environment.

• Previous experience in client-facing roles such as engagement management, consulting, or account leadership.

• Capability to lead distributed teams, mentor delivery managers, navigate ambiguity, and communicate effectively with both executive and non-technical audiences.

🏝️ Benefits

• Paid time off

• Medical insurance

• Dental insurance

• Vision insurance

• 401(k)