Head of Engineering - AI Logistics Billing Platform

Head of Engineering - AI Logistics Billing Platform Remote Portfolio roles Remote Full-time Company Overview:

Groundtruth, a Vantora (formerly UP.Labs) portfolio company is hiring a hands-on Head of Engineering. Groundtruth is building an AI-powered platform focused on freight billing, revenue integrity, and cash-flow automation.

Freight billing today is fundamentally broken. Complex contracts, fragmented systems, and manual, error-prone workflows lead to disputes, revenue leakage, delayed payments, and significant overhead. This company exists to change that by unifying fragmented data into a single source of truth, validating invoices automatically, and identifying discrepancies in real time, turning revenue chaos into predictable outcomes.

As the first engineering leader, you will own the technical foundation end-to-end: architecture, data infrastructure, AI integration, and team building. You’ll stay hands-on early, build from first principles, and define the long-term technical direction as the platform scales to enterprise adoption.

You’ll also have access to the UP.Partners ecosystem, a world-class team across product, engineering, design, analytics, marketing, legal, talent, finance, and venture capital - to help accelerate execution.

In This Role, You Will

* 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 d