Senior Delivery Manager

🔥 15 hours ago

🌐 Canada, United States – Remote

🇨🇦 Canada – Remote 🇺🇸 United States – Remote

💵 $160k - $220k / 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 efforts 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 • Establish AI-augmented delivery standards, metrics, observability, and status-visibility tooling • Evaluate agentic approaches, infrastructure, context management, latency, model risk, data readiness, and evaluation strategy • Partner with AI product managers, AI engineers, and AI/ML engineering leads on delivery planning and production readiness • Define standards for AI-driven features, including evaluation thresholds, human-in-the-loop checkpoints, and post-launch monitoring • Coach delivery managers and coordinators on AI-native and agentic delivery processes • Serve as a credible voice with clients and internal leadership regarding production-ready AI • Act as primary delivery contact for clients and lead stakeholder, roadmap, and delivery forums • Communicate progress, risks, tradeoffs, ROI, milestones, and decisions to executive and non-technical audiences • Partner with Client Partners to identify expansion opportunities and shape follow-on work • Lead distributed onshore and offshore delivery teams • Coach junior delivery managers and contribute to development plans • Improve delivery practices, tools, and frameworks across engagements • Assess team strengths and gaps, flag staffing needs, and identify 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 • Comfortable setting standards for infrastructure, context-management, and latency trade-offs in agentic delivery pipelines • 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 • Experience delivering agentic, AI co-worker, or applied-AI initiatives in enterprise • Prior career experience in client-facing roles such as engagement management, consulting, or account leadership • Ability to lead distributed teams, coach delivery managers, manage ambiguity, and communicate with executive and non-technical audiences

🏖️ Benefits

• Paid time off • Medical insurance • Dental insurance • Vision insurance • 401(k)