[Hiring] Senior Delivery Manager @Robots and Pencils

Role Description

As a Senior Delivery Manager, you are the senior delivery authority on a cross-functional engagement: owning execution from kickoff through release, leading distributed onshore-and-offshore teams, and serving as the primary delivery partner to the client. You bring the judgment to navigate ambiguity, the discipline to keep complex programs on track, and the instinct to make every engagement a foundation for the next one.

What You’ll Do

• Delivery
  • Lead end-to-end delivery of complex, multi-phase engagements, ensuring alignment across scope, budget, timeline, and quality to meet delivery commitments and achieve successful outcomes.
  • Facilitate sprint planning, backlog refinement, and delivery execution across one or more cross-functional teams.
  • Manage phased releases, production readiness, and transitions into operations and maintenance models.
  • Identify and proactively manage dependencies, risks, scope changes, and escalations before they become blockers.
  • Define, track, and report delivery KPIs, using data to guide decisions, manage delivery health, and inform tradeoffs across scope, timeline, and budget.
  • Support QA and UAT efforts, ensuring quality is validated and outcomes meet agreed acceptance criteria.
  • Bring an AI-forward mindset to your daily work, using tools like Claude to enhance delivery planning, reporting, and stakeholder communications.
• AI Enablement
  • Help implement the AI Development Life Cycle (AIDLC) across your engagements, and set the standard other delivery managers follow for standing it up.
  • Use AI yourself day-to-day, and set the standard for how your engagements run an AI-augmented delivery process.
  • Know observability for agentic and AI-driven work well enough to partner credibly with an AI product manager and AI engineers across your engagements.
  • Define what “success” looks like for an AI-augmented delivery process and set the metrics standard across your engagements.
  • Build — or direct the building of — status-visibility tooling for complex AI-driven pipelines, using AI yourself.
  • Understand context management and latency trade-offs deeply enough to make the call on when an agentic approach is the wrong tool for a client’s needs.
  • Set the standard for what infrastructure an agentic delivery pipeline needs — compute, orchestration, logging, guardrails.
  • Own the delivery approach for AI-native and agentic engagements.
  • Work with AI product managers and AI engineers to set the standard for what a “definition of done” looks like for probabilistic or AI-driven features.
  • Coach delivery managers and delivery coordinators you mentor on the difference between shipping an AI product and running an agentic development process.
  • Serve as a credible voice with clients and internal leadership on what “production-ready AI” actually requires.
• Collaboration & Communication
  • Serve as the primary delivery contact for clients, building trusted relationships through transparency, consistency, and clear communication.
  • Lead stakeholder working sessions, roadmap alignment discussions, and delivery forums with confidence.
  • Communicate progress, risks, and tradeoffs clearly to executive and non-technical audiences.
  • Partner with Client Partners to spot expansion opportunities inside the engagement.
  • Translate delivery progress into business impact for client stakeholders.
• Leadership & Influence
  • Lead distributed delivery teams across onshore and offshore locations, fostering accountability, collaboration, and delivery excellence.
  • Coach junior delivery managers with concrete feedback and stretch opportunities.
  • Foster a culture of transparency, continuous improvement, and high performance across the engagement.
  • Contribute to improving delivery practices, tools, and frameworks across engagements.
  • Assess team strengths and gaps on your engagements, and partner with Client Partners to flag staffing needs.
  • Conduct executive interviews for engineers, designers, and other roles joining your engagements.

Qualifications

• 5+ years of experience in software delivery, technical project management, or engineering leadership.
• Strong understanding of agile delivery practices across complex, multi-team engagements (e.g., Scrum, SAFe, 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 (e.g., Jira, Confluence, GitHub, Azure DevOps, CI/CD pipelines).
• Familiarity with cloud-native architectures and AI-enabled platforms.
• Demonstrable usage of AI tools to enhance delivery planning, reporting, and documentation (e.g., Claude).
• Track record leading at least one engagement where AI/ML or agentic capability was core to the solution.
• Able to set delivery standards for AI-native work across an engagement or practice.
• Track record leading a team through an agentic development/delivery process yourself.
• Comfortable setting the standard for the infrastructure, context-management, and latency trade-offs an agentic delivery pipeline needs.
• PMP, Scrum Master, SAFe, or equivalent certification preferred.
• Instinct for spotting where an engagement can grow, and the credibility with clients to bring those conversations forward.

Helpful Extras and Unique Skills

• 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 that informs growth conversations.

You’ll Do Well Here if You Are

• A doer.
• A fast learner who knows you don't know everything.
• Direct in a way that makes the work better.
• Obsessed with craft.
• Built for ownership.
• All in.
• Resourceful when the budget, timeline, or team is tight.
• Calm when it gets hot.
• Glad to be in the room with people who care as much as you do.

Benefits

• Comprehensive package of benefits including paid time off, medical/dental/vision insurance, and 401(k) to eligible employees.

Salary Range

The salary range for this role is $170,000 CAD - $220,000 CAD. This range may be modified in the future based on various factors.