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