Staff Product Manager, AI Strategy & Delivery

Robots-&-Pencils-; Toronto; On-site; CAD 130,000 - 160,000; Full time

Job summary

Robots & Pencils is seeking a Staff Product Manager, Technical to define product strategy and lead delivery across major client engagements. You will own the full lifecycle, build trusted relationships with senior client stakeholders, and bring strategic vision with hands-on delivery discipline.

As the senior product voice on a cross-functional team, you will set direction, drive alignment, mentor other PMs, and navigate complex product challenges from discovery through delivery, including

Qualifications

• 7+ years of experience in product management, with a strong consultative background.
• Proven ability to define product strategy and vision for complex digital engagements.
• Deep experience leading discovery, road-mapping, and delivery across multi-stakeholder environments.
• Strong 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

Responsibilities

• 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

Skills

Product strategy

Client advisory

Cross-functional leadership

Executive communication

AI product discovery

Mentoring PMs

Tools

Jira

Productboard

Amplitude

Miro

Claude

Job description

Robots & Pencils is seeking a Staff Product Manager, Technical to define product strategy and lead delivery across major client engagements. You will own the full lifecycle, build trusted relationships with senior client stakeholders, and bring strategic vision with hands-on delivery discipline.

As the senior product voice on a cross-functional team, you will set direction, drive alignment, mentor other PMs, and navigate complex product challenges from discovery through delivery, including