Head of Product – AI Transformation
Aspire Software
full-time
Posted on:
Location Type: Remote
Location: United States
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Job Level
Tech Stack
About the role
- 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.
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
COBOLAI toolsCI/CDAPIscloud servicesmicroserviceslegacy modernizationproduct roadmap managementcustom developmentautomation
Soft Skills
commercial instinctsinfluence without authoritycommunicationprioritizationchange managementspec writingagile methodologyclient engagementteam trainingaction-oriented