Delivery Manager

Location: Remote in US or Canada | Travel: Regular

Company Overview

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.
We’ve earned the trust of leaders across Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, and Manufacturing and more, and earned a reputation as the nimble alternative to traditional global systems integrators. Founded in 2009, with delivery centers in Canada, the United States, Eastern Europe, and Latin America, we are smaller, faster, and more senior by design. Our teams average 15+ years of experience. We move fast, sweat the details, and build things that actually ship.

Position Overview

As a Delivery Manager, you own delivery on a cross-functional project: leading the team from kickoff through release, coordinating onshore and offshore contributors, and serving as a key delivery partner to the client. You bring the discipline to keep work on track, the judgment to navigate everyday trade-offs, and the ownership to make sure the project lands.

Why This Role Matters

Delivery Managers are where Robots and Pencils’ promise of “production-ready AI in 30 to 45 days” turns into actual project plans, sprint cadences, and shipped work. On the projects you run, you set the pace of delivery, the discipline behind it, and the trust that builds when the team consistently ships on time. The work moves only as fast as someone is willing to own the plan, surface trade-offs early, and keep the team pulling in the same direction.

What You’ll Do

Craft & Delivery

• Lead end-to-end delivery of cross-functional projects, 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 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
• Serve as the primary delivery contact for clients, building trusted relationships through transparency, consistency, and clear communication
• Lead stakeholder working sessions and delivery forums with confidence
• Communicate progress, risks, and tradeoffs clearly to executive and non-technical audiences
• Support Senior Delivery Managers and Client Partners in identifying opportunities to expand value within the engagement

Leadership & Influence

• Lead delivery teams across onshore and offshore locations, fostering accountability, collaboration, and delivery excellence
• Mentor delivery coordinators and team members on your project, sharing knowledge and supporting their growth
• Foster a culture of transparency, continuous improvement, and high performance across the engagement
• Contribute to improving delivery practices, tools, and frameworks across engagements
• Participate in interviews for project team members and contribute input to hiring decisions

What You’ll Bring

• 3+ years of experience in software delivery, technical project management, or engineering leadership
• Strong understanding of agile delivery practices (e.g., Scrum, Kanban)
• Experience managing distributed teams across onshore and offshore locations
• Ability to deliver 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)
• Scrum Master or equivalent certification preferred
• Experience in regulated environments (e.g., utilities, government, finance) is a plus

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 (engagement management, consulting, account management) that builds client trust

You’ll Do Well Here if You Are

• A doer. You see something broken and fix it. You'd rather move on clarity than wait for certainty.
• A fast learner who knows you don't know everything. The AI landscape changes weekly. You're senior enough to know better and curious enough to keep learning anyway.
• Direct in a way that makes the work better. You give honest feedback. You'd rather have the hard conversation than blow smoke.
• Obsessed with craft. You know genius is in the details. You ship exceptional, not perfect, and you don't put your name on work you wouldn't stand behind.
• Built for ownership. You honor commitments, admit mistakes fast, and back your teammates when a decision costs something. No handoffs, no finger-pointing.
• All in. You treat clients' businesses like your own. You take the work seriously without taking yourself seriously.
• Resourceful when the budget, timeline, or team is tight. Constraints don't slow you down. They sharpen you.
• Calm when it gets hot. When scope, timeline, and stakeholders pull in three directions, you slow the room down enough to make the right call. You’d rather raise the hard trade-off in week two than absorb it in week eight.
• Glad to be in the room with people who care as much as you do. Our teams average fifteen-plus years of experience. We hire people who push each other to do better work.

The below range reflects the range of possible compensation for this role at the time of this posting. We may ultimately pay more or less than the posted range. This range may be modified in the future. An employee's position within the salary range will be based on several factors including, but not limited to, relevant education, qualifications, certifications, experience, skills, seniority, geographic location, performance, shift, travel requirements, sales or revenue-based metrics, any collective bargaining agreements, and business or organizational needs. The salary range for this role is $130.000 USD - $165.000 USD ($109.000 CAD - $137.000 CAD) and we offer a comprehensive package of benefits including paid time off, medical/dental/vision insurance and 401(k) to eligible employees. An offer of employment may be conditional upon successful completion of a background check in accordance with local legislation and our candidate privacy notice. Your current employer will not be contacted without your permission. We are committed to ensuring equal employment opportunities for all job applicants and employees. Employment decisions are based upon job-related reasons regardless of an applicant's race, color, religion, sex, sexual orientation, gender identity, age, national origin, disability, marital status, genetic information, protected veteran status, or any other status protected by law.