Aspire Software

We never stop building. A vertical acquisition software company that owns, operates and manages a diverse portfolio.

Head of Product – AI Transformation

Product ManagerProduct ManagerFull TimeRemoteTeam 1,001-5,000H1B No SponsorCompany SiteLinkedIn

Location

United States

Posted

10 days ago

Salary

Not specified

Bachelor Degree5 yrs expEnglishCloudMicroservices

Job Description

• 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

Job 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.

Related Job Pages

More Product Manager Jobs

Senior Product Manager

ISACA

In pursuit of digital trust

Product Manager10 days ago
Full TimeRemoteTeam 201-500Since 1969H1B No Sponsor

Sr. Product Manager driving strategy and execution for ISACA products

United States
$98.7K - $148.0K / year

Product Manager II

Jobgether

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best! Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time. #LI-CL1 We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

Product Manager10 days ago
Full TimeRemote

This role involves significantly impacting the integral area of fraud analytics, contributing to the enhancement of crucial insights that safeguard communities and industries. Collaborating within a dynamic global team, your responsibilities will encompass understanding customer ...

United States

Senior Product Manager – Agentic AI

Autodesk

How the world gets designed and made. #MakeAnything

Product Manager10 days ago
Full TimeRemoteTeam 10,001+Since 1982H1B No Sponsor

Lead AI-powered platform experiences for Autodesk's design ecosystem

Cloud
California + 3 moreAll locations: California, New York, Massachusetts, Washington
$128K - $228.7K / year

Senior Product Manager, Payments Platform

Instacart

Instacart invites the world to share love through food. This is how homemade is made.

Product Manager10 days ago
Full TimeRemoteTeam 1,001-5,000Since 2012H1B Sponsor

This role involves leading a key segment of Instacart’s payments platform, focusing on alternative and emerging tenders and stored value. Own the end-to-end strategy and roadmap for the payments platform. Translate complex payments problems into structured plans. Partner closely ...

United States