Senior Product Manager Enterprise Ai & System Mo

Senior Product Manager – Enterprise AI & System Modernization
Location: Toronto, ON (Hybrid – 3 Days Onsite per week)Position Type: Full-Time, PermanentBenefits & Perks
100% Employer-Paid Health & Dental Benefits (after 3 months)4 Weeks Paid VacationEmployee Stock Ownership Plan (ESOP) eligibility after tenure milestoneAbout the Organization
Our client is a leading commercial equipment manufacturers' representative in North America, with 20 locations across Canada and the US. Their technology solutions division develops the enterprise applications, business intelligence tools, and digital platforms that empower engineering, sales, service, and operations teams across the business. The organization is making a bold, long-term investment in technology to transform its operations. They are modernizing their core enterprise system while simultaneously building an Enterprise AI Platform from the ground up.Role Mandate & Overview
We are seeking a Senior Product Manager to drive this dual-track technology strategy. This is a high-profile, strategic individual contributor role reporting to the Director of Product / Business Solutions (Product Owner). As a trusted advisor, you will define product goals, shape roadmaps, and manage backlogs across two core pillars: Enterprise AI Platform (75% Focus): Architect and build a ground-up AI platform integrating LLMs, retrieval-augmented generation (RAG), and intelligent agents to power workflow automation across all 20 business units. Core System Modernization (25% Focus): Modernize the core business platform—which powers proposals, sales quoting, order management, and field technician service modules—and transition functionality away from legacy ERP dependencies. You will lead through influence, partnering with an internal System Architect, dedicated AI engineering squads, Enterprise Delivery teams (including 19 Project Management Business Analysts and QA Analysts), and cross-functional business leaders.Key Responsibilities
Enterprise AI Roadmap & Execution (75%): Evaluate, prioritize, and validate generative AI, RAG, and AI agent use cases. Oversee LLM vendor evaluations, integration patterns, cost/latency controls, hallucination safeguards, and responsible AI guardrails.Core Application Modernization (25%): Map functional migration plans for the core enterprise application. Evaluate legacy modules (sales, quoting, technician service, commissions) to determine what to retain, refactor, or replace with AI-driven workflows.Backlog & Prioritization: Maintain a single, prioritized backlog aligned with business strategy. Define epics, business context, and acceptance criteria. Make day-to-day product execution decisions while presenting strategic trade-offs to leadership.Voice of the User & Domain Mastery: Develop a deep understanding of commercial rep and distribution workflows (engineering design, proposals, equipment distribution, maintenance). Translate user pain points into precise product requirements.Cross-Functional Leadership: Direct four dotted-line Business Analysts and work alongside QA and Engineering leads to deliver measurable outcomes, tracking post-launch adoption, efficiency gains, and ROI metrics.What We Are Looking For (Requirements)
Senior Product Management Experience: 5+ years of enterprise/B2B SaaS product management experience with a track record of driving complex products from concept to production.Deep AI Platform Knowledge: 2+ years leading product vision for enterprise AI or generative AI capabilities (multi-model LLMs, RAG, vector search, embeddings, agentic workflows, API integrations, and model evaluation metrics) beyond simple feature add-ons.Complex System Modernization: Experience modernizing legacy enterprise systems or ERP-integrated environments, navigating technical debt, and managing phased migration roadmaps.Proven Prioritization & Product Discovery: Strong mastery of product discovery methodologies (RICE, OKRs, Jobs-to-be-Done) and data-driven prioritization. Candidates must demonstrate their framework during the interview process.Complex Business Domain Appreciation: Respect for domain complexity and a background working on deep, multi-faceted business products (e.G., Legal AI, HealthTech, FinTech, Logistics, Transportation, Construction, or Supply Chain).Communication & Influence: Outstanding stakeholder management skills with the ability to translate complex AI concepts into clear business terms for executive leadership.Education: Bachelor’s degree in Computer Science, Engineering, Business, or equivalent technical/business experience.Nice-to-Have Qualifications: Hands-on experience with tools like JIRA, ClickUp, SQL, or reporting tools. Familiarity with Model Context Protocol (MCP), APIs, and middleware data pipelines. Background in commercial HVAC, equipment distribution, construction engineering, or manufacturing.AI may be used to support certain administrative aspects of our recruitment process. However, all applications and resumes are reviewed by qualified human reviewers, and all screening and hiring decisions are made solely by the hiring team. The posted salary range reflects expected compensation for this role in accordance with Ontario pay transparency requirements. Actual compensation will be determined based on the successful candidate’s experience, skills, and qualifications and may fall anywhere within the range.
#J-18808-Ljbffr