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 Staff Product Manager, Technical to define product strategy and lead delivery across major client engagements. This role is ideal for a seasoned product leader who can own the full product lifecycle, build trusted relationships with senior client stakeholders, and bring both strategic vision and hands‑on delivery discipline to the engagements they support.

In this role, you will work as the senior product voice on a cross‑functional team, setting direction, driving alignment, and owning outcomes from discovery through delivery. You'll partner closely with client leadership, mentor other PMs, and bring the experience and judgment to navigate the most complex product challenges.

Why This Role Matters Staff Product Managers are the bridge between what the client needs and what the team builds at Robots & Pencils. On the engagements you lead, you set the direction,



frame the right problems, and make the trade‑off calls that decide whether the product is great or just done. We ship production‑ready AI in 30 to 45 days; that pace holds only when someone keeps the customer in the room, sweats the details, and refuses to let speed beat clarity.

What You’ll Do Craft & Delivery

Define product strategy and vision for major client engagements, setting direction in alignment with client goals and business outcomes

Own the product roadmap end‑to‑end, driving prioritization across business value, technical constraints, and delivery timelines

Lead complex discovery and problem framing with senior client stakeholders, ensuring the right problems are defined before solutions are built

Define product success metrics and use data to evaluate outcomes, inform priorities, and drive continuous improvement

Drive cross‑functional alignment across engineering, design, delivery, and strategy to keep complex engagements moving

Bring an AI‑forward mindset to your daily work, using tools like Claude to drive product discovery, research synthesis, and documentation at speed

Build and maintain trusted advisor relationships with client leadership, serving as a reliable strategic partner on product direction

Communicate strategy, tradeoffs, and recommendations clearly and confidently at the executive level





Lead complex stakeholder working sessions, workshops, and decision‑making forums across large, multi‑stakeholder organizations

Leadership & Influence

Establish product delivery standards and practices on the engagements you support

Mentor senior and mid‑level PMs, helping them grow their product thinking, client skills, and delivery impact

Act as a technical escalation point on complex product, scope, and prioritization challenges

What You’ll Bring

7+ years of experience in product management, with a strong consultative background

Demonstrated ability to define product strategy and vision for complex digital engagements

Deep experience leading discovery, road‑mapping, and delivery across multi‑stakeholder environments

Solid executive communication and client advisory skills

Track record of driving cross‑functional alignment and influencing without authority

Experience defining and tracking product success metrics

High accountability, ownership, and follow‑through

Proficiency with product tools across discovery, road‑mapping, and delivery (e.g., Jira, Productboard, Amplitude, Miro)

Deep applied experience with AI tools to drive product discovery, research synthesis, and documentation at speed (e.g., Claude)

Prior exposure to building or shipping AI/ML products

A point of view on where AI is changing product management — and an appetite to keep moving up that learning curve as the firm does

Helpful Extras and Unique Skills

Comfort prototyping with AI tools to validate product hypotheses (e.g., Claude, Claude Code, Cursor, GitHub Copilot), de‑risking decisions before engineerin

📌 Staff Product Manager, Technical (Toronto)
🏢 Robots and Pencils
📍 Toronto