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 Responsibilities
AI-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 & Experience
Core 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 skilled 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.

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