Group Product Manager, AI & Data

Work arrangement

• This is a hybrid position based out of Rightsline's Toronto, Ontario office.

Role overview

AI product ownership

• Personally run discovery, write PRDs, build prototypes, and ship AI products into production.
• Reimagine customer workflows and maintain a high bar for UX, trust, confidence, exception handling, and human oversight.
• Own the MCP integration surface for model, tool, and Rightsline capability contexts.
• Set the AI product vision, multi-quarter roadmap, evaluation discipline, and LLMOps foundation.

Strategy and monetization

• Set build-versus-leverage-versus-partner decisions across proprietary and third-party AI.
• Run Jobs to Be Done discovery, customer validation, design-partner programs, and early access programs.
• Own pricing, packaging, monetization, product-led growth experiments, and AI financial attribution.
• Own adoption, revenue, retention, ARR, customer value, and other AI product scorecard metrics.

Team and cross-functional leadership

• Manage a Senior Product Manager from day one and set standards for PRDs, prototypes, launches, and evaluations.
• Build the AI and Data product management team as the product line expands.
• Partner with product, engineering, revenue, marketing, and client expansion leaders on architecture and go-to-market.

Experience and qualifications

• 7–10 years of product management experience in B2B enterprise SaaS.
• Direct individual-contributor management experience is required.
• Personally shipped at least one Agent-class AI product from zero to production, adoption, and measurement.
• Fluency with LLM patterns, MCP, evaluations, prompt design, RAG, human-in-the-loop workflows, model selection, and LLMOps.
• Hands-on daily use of Claude, Codex, Cursor, or comparable AI development tools.
• Experience with Jobs to Be Done discovery and structured customer interviews.
• Experience with enterprise software pricing, packaging, and monetization.
• Analytics, reporting, BI, or embedded data product experience is a strong plus.
• Strong understanding of accuracy, explainability, permissions, privacy, auditability, security, and trust in enterprise AI.
• Excellent written and verbal communication.

What Rightsline offers

• The role offers significant organizational impact, executive visibility, growth opportunities, and collaboration with cross-functional teams.
• The company provides a competitive compensation and benefits package.