Principal Product Manager - AI Assistant

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Principal Product Manager - AI Assistant based in Canada.

As Principal Product Manager, AI Assistant, you will lead the strategy and evolution of a high-impact AI-powered marketing companion designed to transform how small and mid-sized businesses engage with digital marketing. You will own the product roadmap and full lifecycle, from discovery and prioritization through execution, launch, and iteration. Working at the intersection of AI, UX, data, and business strategy, you will turn customer needs into intuitive and valuable experiences. You will drive adoption, engagement, customer acquisition, and retention through measurable product improvements. This is a highly visible role requiring strong cross-functional leadership and the ability to navigate ambiguity. You will also mentor other product managers and help establish best practices for building impactful AI products.

Accountabilities

• Lead the strategic roadmap for the AI Assistant, positioning it as a differentiated, industry-leading marketing companion for SMB customers.
• Own the full product lifecycle, including product vision, feature definition, prioritization, execution, launch, measurement, and continuous iteration.
• Drive adoption and engagement by understanding customer workflows, identifying friction points, and creating AI-powered experiences that deliver meaningful value.
• Partner closely with engineering, design, analytics, research, marketing, sales, and customer success to align stakeholders and translate product capabilities into customer and business outcomes.
• Define success metrics and develop compelling business cases for AI investments, with a clear focus on ROI, customer acquisition, retention, and product growth.
• Use customer insights, behavioral data, and experimentation to identify high-impact opportunities and guide product decisions.
• Represent the AI Assistant vision in company-level strategy discussions and ensure alignment with broader platform priorities.
• Mentor and support other product managers, sharing best practices for developing, launching, and scaling AI-powered products.

Requirements

• 8+ years of product management experience, including at least 2 years owning AI- or ML-powered products in production.
• Demonstrated experience taking products from established offerings to best-in-class experiences within competitive markets.
• Strong customer intuition, particularly around SMB users, their workflows, constraints, priorities, and expectations.
• Practical understanding of LLM-powered products, AI capabilities, UX considerations, and common limitations, with the ability to connect technical possibilities to business outcomes.
• Strong analytical skills and a data-driven approach to product decisions, including the ability to investigate product performance and extract actionable insights from large datasets.
• Proven ability to lead teams through ambiguity, make high-quality decisions under pressure, and maintain a strong bias toward shipping, learning, and iteration.
• Excellent communication and storytelling skills, with the ability to explain complex AI concepts and product trade-offs clearly to both technical and executive audiences.
• Strong cross-functional leadership skills and the ability to build alignment and influence without relying solely on formal authority.
• Experience mentoring or leading other product managers and helping teams improve their product practices.
• A strong product and UX sensibility, with clear judgment around what makes AI experiences genuinely useful, intuitive, and engaging rather than superficial.
• Experience with email marketing, marketing automation, Product-Led Growth, onboarding, monetization, or retention is an asset.
• A technical background is considered a plus.

Benefits

• Base salary range of $148,782-$185,977 USD, with the specific offer influenced by experience, education, skills, and work location.
• Potential eligibility for additional bonus or on-target compensation, depending on the role and compensation structure.
• Health and welfare benefits, including comprehensive healthcare support.
• Paid leave and competitive paid time off.
• Flexible work arrangements within a remote-first environment.
• Opportunities for professional development, coaching, stretch assignments, and career growth.
• Inclusive and collaborative culture with programs supporting diversity, belonging, and employee development.
• Accessibility accommodations available throughout the hiring process for candidates who require individualized support.