Senior AI Product 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. 

Position Overview 

We're looking for a Senior Product Manager, AI to lead end-to-end product delivery for complex GenAI and agentic AI engagements. This role demands deep AI fluency, hands-on prototyping ability, and the product judgment to navigate non-deterministic systems at enterprise scale. It is ideal for an experienced AI product leader who can own the full arc of an engagement — from framing the problem through shipping a production-grade agentic solution — while building trusted relationships with senior client stakeholders. 

In this role, you will work as the primary product lead on a cross-functional AI delivery team, owning the roadmap, defining agent behavior, running evals, and guiding delivery from discovery through phased rollout. You'll bring the technical depth to engage meaningfully with engineering on architecture decisions and the communication skills to frame AI tradeoffs clearly for executive audiences. 

 

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 end-to-end product delivery for complex AI and agentic AI engagements, from discovery and hypothesis framing through phased rollout and production readiness  

• Define and maintain AI product roadmaps that connect agent capabilities to measurable enterprise business outcomes  

• Lead discovery activities including user research, stakeholder interviews, and assumption testing — framing the riskiest hypotheses first and de-risking them before committing to build  

• Design and run experiments including POCs, pilot deployments, and scenario-based testing of multi-step agentic workflows, edge cases, and failure recovery  

• Define agent behavior end-to-end including system prompts, tool schemas, context management, summarization, and working memory patterns across multi-step tasks  

• Own and run evals frameworks covering task completion, reasoning quality, tool selection, failure recovery, and safety — iterating based on evidence rather than assumptions  

• Define success metrics at the agent level including task completion rate, cost per task, escalation rate, and time to resolution alongside business KPIs  

• Establish human-in-the-loop boundaries and guardrails — when the agent acts autonomously, when it escalates, and how to handle non-deterministic output  

• Bring an AI-forward mindset to your daily work, using tools like Claude, Claude Code, Cursor, and GitHub Copilot — and agentic frameworks where relevant — to move faster than traditional product 

Collaboration & Communication 

• Lead stakeholder working sessions, prioritization discussions, and risk conversations with senior client stakeholders with confidence and clarity  

• Communicate complex AI tradeoffs, agent behavior, and product decisions clearly to both technical and non-technical executive audiences  

• Build trusted relationships with client stakeholders and serve as a reliable, consultative partner throughout the engagement 

Leadership & Influence 

• Lead prioritization decisions by balancing business value, technical feasibility, cost, latency, and delivery timelines  

• Frame every request in terms of user and business outcomes, pushing back on feature-level thinking and managing AI hype cycles with realistic expectations  

• Begin mentoring junior AI PMs on the engagement, sharing knowledge on evals, agent design, and AI product delivery practices 

 

What You’ll Bring 

• 5+ years of experience in product management with hands-on experience shipping AI features or products  

• Ability to read code (Python, JavaScript, or TypeScript), evaluate architecture decisions, and make informed product tradeoffs on technical constraints  

• Deep understanding of AI concepts including LLMs, RAG, fine-tuning, prompt and context engineering, agentic systems such as planning, tool use, human-in-the-loop controls, and guardrails, and evals  

• Proven ability to prototype AI and agentic solutions using modern AI tools to validate hypotheses and de-risk product decisions (e.g., Claude, Claude Code, Cursor, GitHub Copilot)  

• Experience running evals for AI systems and iterating based on results  

• Experience defining agent behavior including system prompts, tool schemas, and human-in-the-loop boundaries  

• Strong experience working with AWS AI services in a product context (e.g., Bedrock, Lambda, SageMaker, Kendra)  

• Strong client communication skills and the ability to frame AI capabilities and limitations for non-technical executive audiences  

• Comfortable operating in ambiguous, fast-moving environments where the AI landscape evolves rapidly  

• Experience in a consulting or agency environment, familiarity with agent orchestration frameworks (LangChain, LangGraph, AWS Strands), or a software engineering background (Python, JavaScript, TypeScript) is a plus 

Helpful Extras and Unique Skills 

 

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.