[Hiring] Senior AI Product Manager @Robots and Pencils

Role Description

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.

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.

Qualifications

• 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

• A doer who sees something broken and fixes it, preferring clarity over certainty.
• A fast learner who embraces the ever-changing AI landscape.
• Direct in a way that improves the work environment through honest feedback.
• Obsessed with craft, shipping exceptional work and standing behind it.
• Built for ownership, honoring commitments and supporting teammates.
• All in, treating clients' businesses as your own and taking the work seriously.
• Resourceful in tight constraints, using them to sharpen skills.
• Glad to collaborate with others who share the same dedication.