UP.Labs · 1 month ago
Head of Engineering - Stealth AI Freight Operations Startup
United States
Full-time
Remote
Director/Executive
8+ years expUP.Labs is a company focused on building high-growth technology startups, and they are seeking a hands-on Head of Engineering for a stealth startup in the AI logistics space. The role involves leading the engineering team, owning the architecture and data infrastructure, and building a platform that optimizes freight operations with AI and data science.
Venture Capital & Private Equity
Responsibilities
Lead and grow the engineering team, balancing hands-on development with strategic leadership
Architect and own the core platform, including data pipelines, AI/ML integration layers, and scalable enterprise infrastructure
Build robust integrations with existing TMS, telematics and other enterprise freight systems to ingest and operationalize complex logistics data
Partner with Product and Data Science to translate messy real-world workflows into intelligent agentic solutions
Drive best practices around security, CI/CD, observability, testing, and documentation
Establish the technical vision for AI-driven demand forecasting, predictive placement, and closed-loop execution
Manage and mentor distributed contributors (including nearshore/offshore teams) to build a high-performance engineering culture
Deliver quick MVP iterations while laying the foundation for enterprise scale
Qualification
Required
8+ years in software engineering, including 4+ years leading small, high-output teams
Strong backend or full-stack background and ability to remain hands-on
Proven experience scaling B2B SaaS platforms with real-time data pipelines and system integrations
Expertise in cloud architecture, CI/CD pipelines, observability, and distributed systems
Experience working with AI/ML platforms (e.g., predictive models, optimization engines, LLMs)
Experience leading or managing distributed teams (nearshore/offshore)
A technical leader who thrives at the intersection of AI, data, and enterprise SaaS
Hands-on and detail-oriented, comfortable writing code, reviewing PRs, and guiding architecture
Skilled at integrating complex enterprise data systems (TMS, telematics and other operational enterprise systems)
Experienced building products that combine data infrastructure with LLMs and applied machine learning
A collaborative partner who can work closely with product, data science, and business stakeholders
Capable of thriving in ambiguous, high-growth startup environments and scaling teams from 0→1 and beyond
Preferred
Familiarity with complex enterprise systems is a plus
Knowledge of logistics or adjacent industries (nice-to-have)
Benefits
Equity ownership in a high-growth venture with global impact.
We reward our entire team and ecosystem of partners with meaningful equity.
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
Company data provided by crunchbase