Delivery Manager

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.  

About the role

We're looking for a Delivery Manager to own execution across digital product engagements, keeping teams aligned, delivery on track, and clients informed. This role is ideal for an experienced delivery practitioner who thrives in a fast-paced, collaborative environment and takes pride in shipping quality software on time. 

 We are standing up an AI Pod for a managed services provider (IT, cybersecurity, cloud/infrastructure), beginning with a 3-week Sharpening Sprint and moving into a 3-month build engagement. The Delivery Manager runs the operating rhythm of the engagement — scheduling sessions, capturing artifacts and decisions, managing the sprint cadence, and ensuring the prioritized AI roadmap is delivered on schedule. During the Pod phase, this person owns weekly alignment sessions, sprint planning, and the 30-day readouts with stakeholders, and acts as the connective tissue between the R&P pod team and the client. 

Why this role matters  

At Robots & Pencils, we design AI systems for a human world. Our name says it all. Robots and pencils means engineering paired with creativity, because every agent we ship has to work for real people in real workflows. That balance is baked into how we operate.  
  
Every role here contributes directly to that mission. Here, you shape how AI systems integrate into enterprise operations, how teams move at real velocity, and how products create measurable impact for clients and the people they serve. We ship production-ready AI in 30 to 45 days. That pace demands people who take ownership, lead with craft, and care deeply about what they put their name on.  

What You’ll Do  

Craft & Delivery  

• Own day-to-day delivery execution for an engagement, keeping scope, timeline, and quality consistently on track and ensuring delivery commitments are met 
• Facilitate sprint planning, backlog refinement, standups, and retrospectives in close partnership with the Product Manager  
• Identify and manage dependencies, risks, and scope changes proactively throughout the delivery lifecycle  
• Track and report delivery progress, KPIs, and blockers to the team and client stakeholders  
• Support QA and UAT efforts, ensuring quality is validated and issues are resolved before release  
• Bring an AI-forward mindset to your daily work, using tools like Claude to enhance delivery planning, reporting, and documentation 

Collaboration & Communication  

• Act as the operational bridge between the client and the delivery team, ensuring clarity and alignment on both sides  
• Communicate progress, risks, and tradeoffs clearly to technical and non-technical audiences  
• Participate in client-facing meetings and working sessions, building trust through consistency and transparency while identifying opportunities to deliver additional client value 

Leadership & Influence  

• Foster a culture of accountability, collaboration, and continuous improvement within the delivery team  
• Take full ownership of delivery responsibilities end-to-end and follow through with consistency  
• Bring a calm, solutions-focused presence when navigating pressure, ambiguity, and competing priorities 
• Share learnings and best practices with peers to improve delivery consistency across teams 

What you’ll bring  

• 3+ years of experience in software delivery, project management, or a related role  
• Solid understanding of agile delivery practices including Scrum and Kanban  
• Experience facilitating sprint ceremonies and managing delivery execution for cross-functional teams  
• Strong communication skills across technical and non-technical audiences  
• Experience working directly with clients or external stakeholders  
• Familiarity with delivery tooling (e.g., Jira, Confluence, GitHub)  
• Demonstrable usage of AI tools to enhance delivery productivity and documentation (e.g., Claude)  
• PMP, Scrum Master, SAFe, or equivalent certification preferred  
• Experience in a consulting or agency environment is a plus 

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.  
• 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.  

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.