UP.Labs · 1 week ago
Head of Engineering - Stealth AI Logistics Billing Platform
United States
Full-time
Remote
Director/Executive
8+ years expUP.Labs is hiring a hands-on Head of Engineering for a stealth startup in the logistics space, building an AI-powered platform focused on freight billing, revenue integrity, and cash-flow automation. As the first engineering leader, you will own the technical foundation end-to-end and lead the engineering function while partnering closely with product and data science teams.
Responsibilities
Lead and grow the engineering function, balancing hands-on development with technical leadership and team building
Architect and own the core platform, including:
Data ingestion and normalization pipelines
AI/ML and rules-based validation layers
Scalable, secure enterprise infrastructure
Build and maintain deep integrations with enterprise systems such as TMS, ERP, billing platforms, and other operational data sources
Partner closely with Product and Data Science to translate complex, real-world billing workflows into intelligent, automated solutions
Design systems that support invoice validation, discrepancy detection, exception handling, and auditability
Establish best practices around security, CI/CD, observability, testing, and documentation suitable for enterprise finance and operations teams
Define the technical vision for AI-driven automation, explainability, and closed-loop resolution workflows
Manage and mentor distributed contributors (including nearshore/offshore teams), building a high-trust, high-output engineering culture
Deliver rapid MVP iterations while laying a durable foundation for enterprise scale and reliability
Qualification
Required
8+ years of software engineering experience, including 4+ years leading small, high-impact teams
Strong backend or full-stack background with the ability to remain hands-on
Proven experience building and scaling B2B SaaS platforms with complex data pipelines and system integrations
Deep knowledge of cloud architecture, CI/CD pipelines, observability, and distributed systems
Experience working with AI/ML systems (e.g., LLMs, rules engines, optimization or validation models)
Experience leading or managing distributed (nearshore/offshore) engineering teams
A technical leader who thrives at the intersection of data, AI, and enterprise SaaS
Deeply hands-on comfortable writing code, reviewing PRs, and making architectural tradeoffs
Experienced integrating complex, messy enterprise systems and normalizing inconsistent data
Fluent in building platforms that combine data infrastructure, applied machine learning, and workflow automation
A collaborative partner who works seamlessly with product, data science, and business stakeholders
Comfortable operating in ambiguity and scaling systems and teams from 0→1 and beyond
Preferred
Familiarity with enterprise finance, billing, or revenue systems is a strong plus
Background in logistics, supply chain, or fintech is helpful but not required
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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