Head of Engineering - Stealth AI Freight Operations Startup

UP.Labs•Seattle, WA

28d

About The Position

UP.Labs is hiring a hands-on Head of Engineering for a stealth startup in the AI logistics space, building an AI platform for freight operations optimization. Freight is the lifeblood of the global economy, yet many processes are still reactive and manual with numerous hand-offs and unforeseen system disturbances. We’re here to change that with AI, data science, and agentic orchestration. Our mission is bold but simple: turn reactive freight operations into predictable, optimized results. As the first engineering leader, you’ll own architecture, data infrastructure, and team building for a platform that brings together operational efficiency, execution and optimization. You’ll remain hands-on early, build the technical foundation from scratch, and set the long-term technical direction as we scale. 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.

Requirements

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.

Nice To Haves

Familiarity with complex enterprise systems is a plus.
Knowledge of logistics or adjacent industries (nice-to-have).

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.