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, ensuring adherence to scope, budget, timeline, and quality standards.

• Facilitate sprint planning, backlog refinement, and execution of delivery across diverse cross-functional teams.

• Manage staged releases, readiness for production, and transitions into operational maintenance.

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

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

• Support Quality Assurance (QA) and User Acceptance Testing (UAT), ensuring outcomes meet the established acceptance criteria.

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

• Implement the AI Development Life Cycle throughout various engagements.

• Model and guide AI-enhanced delivery processes.

• Collaborate with AI product managers and engineers on observability, model risk, data readiness, evaluation strategies, infrastructure, orchestration, logging, and guardrails.

• Establish success metrics and standards for AI-enhanced and agentic delivery processes.

• Develop or oversee status visibility tools for complex AI-driven pipelines.

• Evaluate context management and latency trade-offs, determining when agentic approaches may not be suitable.

• Own the delivery strategies for AI-native and agentic engagements, translating technical uncertainties into actionable client plans and risk registers.

• Define "definition of done" criteria for probabilistic and AI-driven features.

• Mentor delivery managers and coordinators.

• Act as the primary delivery contact for clients, fostering trusted relationships.

• Lead stakeholder sessions, roadmap alignment discussions, and delivery forums.

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

• Collaborate with Client Partners to identify opportunities for expansion and translate delivery achievements into business impacts.

• Guide distributed teams, both onshore and offshore, in their delivery efforts.

• Mentor junior delivery managers and contribute to their development plans.

• Enhance delivery practices, tools, and frameworks.

• Assess team strengths and gaps, identifying staffing needs and high-potential talent.

• Conduct executive interviews and assist in 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 projects, including Scrum, SAFe, and Kanban.

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

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

• Excellent client-facing communication and relationship management abilities.

• 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 use of AI tools to enhance delivery planning, reporting, and documentation, such as Claude.

• Experience leading at least one engagement where AI/ML or agentic capability was central to the solution, encompassing model risk, evaluation, and client expectations.

• Capability to set delivery standards for AI-native work, including evaluation criteria, human-in-the-loop checkpoints, and monitoring while coaching other delivery managers.

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

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

• Instinct for identifying opportunities for engagement growth and credibility with clients to advance these discussions.

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

• Depth of expertise in one or more sectors, including Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing, is advantageous.

• Experience in delivering agentic, AI co-worker, or applied-AI initiatives within enterprises is beneficial.

• Prior client-facing experience in engagement management, consulting, or account leadership is a plus.

• Successful completion of a background check may be a requirement.

🏝️ Benefits

• 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