Head of Product & AI Transformation

The Opportunity

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.

What You’ll Own

1. Codebase Modernization

This is the primary mandate. The goal is a modern, maintainable codebase that any strong developer can contribute to, enabling us to hire more easily, move faster, and build the integrations and agentic features that clients increasingly expect.

• 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

2. Custom Development Throughput

Client-funded custom development is core to our business model and a key driver of retention. This role is accountable for making that engine run more efficiently through tighter scoping, faster execution, and reliable 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

3. Agentic Product Development

With a more capable platform in place, the next priority is building AI-powered tools and workflows that operators will pay for. This means going deep into how rental businesses actually operate across fleet management, reservations, check-in, yield management, and damage workflows, then identifying where agentic solutions create measurable financial outcomes.

• 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

Target opportunity areas include:

• Yield and rate optimization agents that maximize revenue per available vehicle

• Fleet utilization and rebalancing agents that prevent idle-vehicle revenue loss

• Check-in and check-out automation that reduces counter time and staffing costs

• Predictive maintenance agents that reduce unplanned downtime

• Upsell and cross-sell agents that present the right offer at the right moment in the customer journey

• Damage detection and claims automation that closes revenue leakage

4. Internal AI Transformation

Apply the same AI-first lens internally. Functions across Product, Engineering, Sales, Customer Success, Finance, and Operations all have workflows that can be automated or materially accelerated.

• 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

What You Bring

Product & Domain Experience

• 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

Technical Depth

• 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

Leadership

• 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

What Success Looks Like

At 6 months: a modernization pilot is underway with a clear phased roadmap behind it; the custom development pipeline is running more predictably; operator discovery has produced a prioritized agentic opportunity map with at least one solution in development.

At 12 months: modernization is measurably reducing development cycle times; at least one client-facing agentic solution has shipped with documented operator ROI; release delays to clients are materially reduced; internal AI automations are live across multiple functions.

Why This Role

• A proven platform with a loyal global customer base and a well-supported mandate to modernize and grow

• Real executive backing and a genuine scope to match the ambition of the title

• A small, senior team where your decisions have outsized impact

• Remote-first and North America-based with competitive compensation

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