Head of Product & AI Transformation

Valsoft Corporation

2d•Remote

About The Position

Thermeon is a market-leading rental management system (RMS) with a global base of car rental operators who have trusted us for decades. We go beyond standard software by building custom workflows for each client, creating deep loyalty and long-term relationships that competitors struggle to displace. We are now at an exciting inflection point. AI has fundamentally changed what is possible in how software is built and what it can do for end users. This role exists to lead that transformation: modernize our platform to unlock greater development speed and capability, build agentic tools and workflows that clients will value and pay for, and bring AI-powered efficiency to every function across the business. The right person is as comfortable in a customer conversation, uncovering operator pain points as they are working with an engineering team on a modernization roadmap. They see the platform and the business opportunity as inseparable.

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
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

Nice To Haves

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
COBOL familiarity is a plus

Responsibilities

Codebase Modernization
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
Custom Development Throughput
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
Agentic Product Development
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
Internal AI Transformation
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