Head of Product – AI Transformation

Role Overview

• Lead a phased, incremental migration of core COBOL modules to modern languages while preserving all business logic
• Use AI-assisted tools such as Claude Code to accelerate the extraction, documentation, and translation of legacy code
• Validate functional equivalence through parallel-run testing before any cutover
• Establish modern CI/CD practices and API-first patterns that make future development faster and more reliable
• Broaden the platform away from dependence on scarce COBOL expertise so that hiring and onboarding no longer constrain delivery
• Own the custom development pipeline: scope client requests, write precise specs, and work with engineering to ship on schedule
• Establish capacity visibility so client commitments are made with confidence and delays become the exception
• Partner with sales and customer success to ensure custom work is scoped and priced to reflect its true value
• Use the speed gains from modernization to systematically reduce cycle times on client work over time
• Conduct structured discovery with operators to find the highest-value AI opportunities and validate willingness to pay
• Build the business case for each initiative by quantifying the revenue uplift or cost savings the operator would realize
• Spec, ship, and measure each solution while tracking real operator outcomes post-launch
• Audit functions for high-value automation opportunities and prioritize by ROI
• Build and deploy AI agents that eliminate repetitive manual work across the business
• Train teams on effective AI tool usage and establish appropriate governance guardrails

Requirements

• 5+ years in product management or product leadership in B2B SaaS or enterprise software
• Experience managing both a core product roadmap and client-specific custom development, with the discipline to balance and prioritize across both
• Strong commercial instincts: you build business cases, deprioritize low-ROI work, and think like a GM rather than just a PM
• Familiarity with car rental, fleet, or mobility operations is strongly preferred; an understanding of where operators hurt and what they will pay to fix matters in this role
• Solid understanding of modern software architecture including APIs, cloud services, CI/CD, and microservices
• Comfortable leading legacy modernization initiatives with an understanding of the trade-offs involved and the ability to make the case for a phased approach; COBOL familiarity is a plus
• Hands-on experience with AI tools and agentic workflows with the ability to prototype quickly and engage engineering on implementation with precision
• Proven ability to drive change in established environments and influence across functions without formal authority
• Able to write a tight spec, run a sprint, hold engineering accountable to timelines, and communicate clearly to clients and executives
• Strong bias toward action: you ship things, measure them, and improve based on what you learn.

Tech Stack

• Cloud
• Microservices