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 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
Valsoft Corporation is an operating group that acquires and builds mission-critical software businesses for the long term, operating through subsidiaries including Aspire Software and Dockmaster Software. The company serves diverse vertical markets including higher education, public sector, and marine industries with specialized software solutions. Valsoft provides operational expertise, stability, and resources to support the growth and innovation of its portfolio companies. Key products include Dockmaster, the marine industry's comprehensive marina management software platform founded in 1983, and Orbit, a cloud-based software lifecycle management solution for IT asset management in higher education and public sector organizations.
