UP.Labs · 2 weeks ago
Head of Product - Stealth AI Logistics Billing Platform
United States
Full-time
Remote
Director/Executive
10+ years expUP.Labs is launching a stealth startup in the logistics and freight space, building an AI-powered platform focused on billing, revenue integrity, and cash-flow automation for enterprise logistics operators. The Head of Product will own product vision, strategy, and execution from 0→1, working closely with engineering, data science, and early customers to create a category-defining platform.
Responsibilities
Own and articulate the end-to-end product vision for an AI-driven freight billing and revenue automation platform
Translate the company’s mission into a clear roadmap that balances near-term customer value with long-term platform scalability
Define the initial product wedge (billing accuracy, exception management, cash-flow acceleration) and guide expansion into a broader revenue intelligence platform
Work directly with early enterprise logistics customers to deeply understand billing workflows, disputes, and exceptions
Rapidly test, learn, and iterate based on real-world usage and feedback
Partner closely with engineering and data science to build:
Automated invoice validation
Real-time discrepancy and exception detection
Intelligent workflows for resolution and reconciliation
Ensure AI-driven outputs are explainable, auditable, and trusted by finance and operations teams
Make pragmatic tradeoffs that deliver quick wins while laying the foundation for a scalable, enterprise-grade platform
Design products that integrate seamlessly with existing enterprise systems (e.g., TMS, ERP, billing, and operational data sources)
Drive adoption across multiple stakeholders, including finance, operations, and executive leadership
Navigate complex enterprise buying, onboarding, and rollout environments
Act as a founder-level leader, aligning executives, investors, and customers around product strategy
Start as a hands-on builder (user research, workflows, PRDs), then recruit and grow a high-performing product organization
Serve as the internal and external voice of product as the company scales
Qualification
Required
10+ years of product leadership experience in enterprise SaaS
A proven 0→1 product builder who has taken enterprise SaaS products from concept to MVP to market traction
Demonstrated experience building data-first or AI-powered platforms from the ground up
Strong technical fluency and ability to partner deeply with engineering and data science teams
Experience in logistics, supply chain, fintech, or complex B2B operational platforms (billing or revenue systems a strong plus)
Experience balancing short-term delivery with long-term platform architecture
Comfort navigating enterprise sales cycles, implementations, and customer adoption
Comfortable working in messy, real-world workflows involving contracts, data fragmentation, and operational exceptions
Fluent in AI and data-driven systems, with experience applying ML, rules engines, or intelligent automation to complex processes
A strong communicator and storyteller who can earn trust across engineers, executives, and enterprise customers
Entrepreneurial, decisive, and comfortable operating with ambiguity
Benefits
Meaningful equity ownership in a high-growth venture with enterprise-scale potential
Company
UP.Labs
UP.Labs is a first-of-its-kind venture lab unlocking the future of transportation and mobility.
11-50 employees
Funding
Current Stage
Early StageLeadership Team
André Rabold
Head of Engineering & Venture CTO
Keith Rives
CTO, Stealth Retail Data Science Startup
Recent News
2026-01-11
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