Head of Engineering - AI Logistics Billing Platform

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 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.

Who You Are:

• 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.