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AI Product Lead

  • Toronto, Ontario, Canada
  • Remote
  • Posted Sep 1, 2026
  • 1 position

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Employment type
Full-time
Experience level
Senior · 5+ years
Posting language
English
Working hours
40 hours per week
Location requirements
Country, Canada

Job summary

The AI Product Lead is responsible for identifying, building, and scaling AI-powered solutions that drive measurable business outcomes. This role involves direct customer engagement to validate prototypes and leading cross-functional teams to deliver high-impact product features.

Job details

Role Overview The AI Lead is responsible for identifying, building, validating, and scaling AI-powered product solutions that drive real customer and business outcomes. This role is hands-on and AI-first. An AI Lead does not operate through documents, tickets, or handoffs. They build working solutions using AI, engage directly with customers, and iterate rapidly based on real-world feedback. The AI Lead does everything an AI Product Engineer does - plus owns customer discovery, validation, prioritization, and measurable impact. About Us Dockmaster is a leading provider of innovative marina software solutions, dedicated to equipping our customers with the tools that streamline operations, improve operational efficiency while driving revenue growth. Our largest customer concentration is in North America but are quickly expanding to have a global presence. Core ResponsibilitiesAI-First Product Building · Build working product solutions using AI as the primary execution medium · Rapidly prototype, iterate, and refine solutions to validate ideas early · Use AI agents for requirements analysis, design exploration, implementation, and testing · Move from problem understanding to working solution without reliance on legacy SDLC rituals Customer Discovery & Engagement · Engage directly with customers to understand workflows, pain points, and unmet needs · Use live demos and working prototypes to drive customer conversations · Validate solutions through real usage, not assumptions or opinions · Build trust by clearly explaining AI behaviour, limitations, and tradeoffs Problem Framing & Opportunity Identification · Frame problems clearly and precisely before execution · Identify new AI-powered solution opportunities and revenue potential · Evaluate ideas based on impact, feasibility, and learning velocity · Use experimentation to discard weak ideas quickly Outcome Ownership · Define success in terms of adoption, retention, efficiency, and revenue impact · Prioritize initiatives based on outcomes, not feature volume · Continuously assess whether solutions are creating real value · Own the full lifecycle from idea to impact Cross-Functional Leadership · Work closely with AI Product Engineers and AI Developers within AI Pods · Align engineering, design, and data efforts around outcomes · Communicate clearly with internal stakeholders · Represent the product externally with credibility and clarity What This Role Is Not · Not a backlog or roadmap-only role · Not a handoff-based product manager · Not a requirements writer detached from execution Required Skills & ExperienceCore Capabilities · Strong ability to build working software using AI tools · Proven experience rapidly prototyping and iterating on product ideas · Deep understanding of probabilistic AI systems and guardrails · Ability to reason about systems end-to-end Product & Business Acumen · Experience engaging directly with customers · Ability to identify business and revenue opportunities · Strong product judgment and taste · Comfort prioritizing under uncertainty Communication & Leadership · Ability to explain complex AI behavior clearly and honestly · Strong storytelling grounded in real system behavior · Comfortable leading through influence rather than authority Why Join Dockmaster? At Dockmaster, you’ll have the opportunity to make a significant impact on our growth while working alongside a passionate team dedicated to transforming the marina management industry. This is a key leadership role, reporting directly to the CEO, with ample opportunity for professional growth, strategic influence, and direct impact on the company's success. What We Offer: · Competitive salary and bonus structure based on performance. · Health insurance, 401(k) with company match, and paid time off. · Opportunities for professional development and career advancement. #Dockmaster

What you’ll do

The AI Product Lead is responsible for identifying, building, and scaling AI-powered solutions that drive measurable business outcomes. This role involves direct customer engagement to validate prototypes and leading cross-functional teams to deliver high-impact product features.

Requirements

Candidates must have strong experience in building working software using AI tools and a proven ability to rapidly prototype and iterate on product ideas. The role requires deep understanding of probabilistic AI systems and the ability to effectively communicate complex technical concepts to stakeholders.

Benefits

• Competitive salary • Bonus structure • Health insurance • 401(k) with company match • Paid time off

Listed skills

  • Data analysis · Preferred
  • Stakeholder Management · Preferred

Other relevant skills

Identified from the job description. Confirm important requirements above.

  • AI product development
  • Rapid prototyping
  • Customer discovery
  • Probabilistic AI systems
  • Product strategy
  • Stakeholder management
  • Cross-functional leadership
  • System design
  • Data analysis
  • Requirement analysis
  • Agile methodology
  • Product lifecycle management
  • Technical communication
  • Business acumen
  • AI agents
  • Influencing Skills
  • Software Solutions
  • Operational Efficiency
  • Influencing Without Authority
  • Workflow Management
  • Time Off Management
  • AI Agents
  • Artificial Intelligence
  • Business Acumen
  • Management
  • Communication
  • Engineering Design Process
  • Leadership
  • Innovation
  • Problem Solving
  • Operations
  • Product Engineering
  • Product Management
  • Systems Development Life Cycle
  • Prototyping
  • Relationship Building
  • Requirements Analysis
  • Revenue Growth
  • Prioritization
  • Honesty
  • Artificial Intelligence Infrastructure

Job areas

  • Technology
  • Software
  • Management & Leadership
  • Data & Analytics
  • Consulting
  • AI Product Manager
  • Artificial Intelligence Engineer (General)
  • Software Developers

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