R

Senior Delivery Manager

Canada
Full Remote
This Job is No Longer Active This position is no longer accepting applications

Lead end-to-end delivery of complex AI co-worker engagements from kickoff to release, managing distributed onshore-offshore teams and ensuring production readiness. Serve as primary client contact, building trusted relationships and translating delivery progress into business impact. Requires 5+ years of software delivery experience, strong agile practices, and AI tool proficiency.

Key Highlights
Own execution of cross-functional engagements from kickoff through release
Manage distributed teams across onshore and offshore locations
Deliver production-ready AI in 30-45 days with measurable client results
Lead stakeholder communication and expansion opportunities
Key Responsibilities
Craft and deliver complex, multi-phase engagements ensuring alignment 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 models
Identify and proactively manage dependencies, risks, scope changes, and escalations
Define, track, and report delivery KPIs using data to guide decisions and manage delivery health
Support QA and UAT efforts ensuring quality meets agreed acceptance criteria
Lead stakeholder working sessions, roadmap alignment discussions, and delivery forums
Communicate progress, risks, and tradeoffs clearly to executive and non-technical audiences
Partner with Client Partners to spot expansion opportunities and shape the case for follow-on work
Translate delivery progress into business impact for client stakeholders (ROI, milestones, decisions)
Lead distributed delivery teams 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
Contribute to improving delivery practices, tools, and frameworks across engagements
Assess team strengths and gaps and partner with Client Partners to flag staffing needs
Conduct executive interviews for engineers, designers, and other roles joining engagements
Serve as essential voice in go/no-go hiring decisions across the firm
Technical Skills Required
Agile delivery practices Delivery tooling (Jira, Confluence, GitHub, Azure DevOps) Cloud-native architectures AI tools (Claude)
Benefits & Perks
Remote work
Nice to Have
Vertical depth in 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 (engagement management, consulting, account leadership)
Experience in regulated environments (utilities, government, finance)

Job Description

Robots & Pencils is an applied AI engineering firm building the next frontier of business architecture. We design and ship AI co-workers that integrate into enterprise operations and deliver measurable results for our clients. We're all in on AWS, combining deep UX capability with senior engineering talent to get AI into production fast and keep it there.
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