Senior Delivery Manager

🔥 15 hours ago

🌐 Canada, United States – Remote

🇨🇦 Canada – Remote 🇺🇸 United States – Remote

💵 $160k - $190k / year

⏰ Full Time

🟠 Senior

👔 Manager

👻 Ghost score 6%

What it means: how likely this posting is sitting open without active hiring.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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Robots & Pencils

WebsiteLinkedInAll Job Openings

51 - 200 employees

🤖 Artificial Intelligence

🤝 B2B

☁️ SaaS

💰 Venture Round on 2022-04

Artificial Intelligence • B2B • SaaS

Robots & Pencils is a digital innovation firm that specializes in developing digital strategies and products utilizing mobile, web, and frontier technologies to drive transformation for businesses. They focus on areas such as mobile development, product design, UX research, artificial intelligence, machine learning, and organizational change management. With a commitment to blending creativity with technology, they aim to unlock data insights and enhance product innovation, ultimately delivering excellent customer experiences and helping brands gain a competitive edge.

📋 Description

• Lead end-to-end delivery of complex, multi-phase engagements 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 • Identify and manage dependencies, risks, scope changes, and escalations • Define, track, and report delivery KPIs to guide decisions and tradeoffs • Support QA and UAT and ensure outcomes meet acceptance criteria • Use AI tools such as Claude for delivery planning, reporting, and stakeholder communications • Implement the AI Development Life Cycle across engagements • Model and coach AI-augmented delivery processes • Partner with AI product managers and engineers on observability, model risk, data readiness, evaluation strategy, infrastructure, orchestration, logging, and guardrails • Define success metrics and standards for AI-augmented and agentic delivery processes • Build or direct status-visibility tooling for complex AI-driven pipelines • Evaluate context-management and latency trade-offs and determine when agentic approaches are unsuitable • Own delivery approaches for AI-native and agentic engagements and translate technical uncertainty into client-actionable plans and risk registers • Define “definition of done” standards for probabilistic and AI-driven features • Coach delivery managers and coordinators • Serve as the primary delivery contact for clients and build trusted relationships • Lead stakeholder sessions, roadmap alignment discussions, and delivery forums • Communicate progress, risks, and tradeoffs to executive and non-technical audiences • Partner with Client Partners to identify expansion opportunities and translate delivery progress into business impact • Lead distributed onshore and offshore delivery teams • Coach junior delivery managers and contribute to development plans • Improve delivery practices, tools, and frameworks • Assess team strengths and gaps and flag staffing needs and high-potential talent • Conduct executive interviews and contribute to go/no-go hiring decisions

🎯 Requirements

• 5+ years of experience in software delivery, technical project management, or engineering leadership • Strong understanding of agile delivery practices across complex, multi-team engagements, including Scrum, SAFe, and 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 such as Jira, Confluence, GitHub, Azure DevOps, and CI/CD pipelines • Familiarity with cloud-native architectures and AI-enabled platforms • Demonstrable usage of AI tools to enhance delivery planning, reporting, and documentation, such as Claude • Track record leading at least one engagement where AI/ML or agentic capability was core to the solution, including model risk, evaluation, and client expectations • Ability to set delivery standards for AI-native work, including evaluation criteria, human-in-the-loop checkpoints, and monitoring, and coach other delivery managers • Track record leading a team through an agentic development/delivery process, including observability, success metrics, and status visibility • Comfort setting standards for infrastructure, context management, and latency trade-offs in agentic delivery pipelines • Instinct for spotting engagement growth opportunities and credibility with clients to advance those conversations • PMP, Scrum Master, SAFe, or equivalent certification preferred • Vertical depth in one or more of Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing is helpful • Experience delivering agentic, AI co-worker, or applied-AI initiatives in enterprise is helpful • Prior client-facing experience in engagement management, consulting, or account leadership is helpful • Successful completion of a background check may be required

🏖️ 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