Head of Engineering

Get AI-powered advice on this job and more exclusive features.

Join as the founding engineering leader to build cutting-edge AI systems and data infrastructure that power intelligent freight insights 'll architect machine learning pipelines and predictive models that define the technical foundation of a company targeting $125M ARR in 5 years.

AI/ML Systems

Architect next-generation AI systems with advanced predictive models for shipper behavior, intelligent targeting, and automated deal scoring

Data Infrastructure

Process millions of shipment records across 500K+ companies at scale

Product Platform

Serve 20,000+ potential freight broker customers with a scalable platform

Strategic Integrations

Build integrations with major TMS systems and strategic partners

What We're Looking For

• Product & Startup Mindset
• Comfort with ambiguity; builds MVPs quickly
• Strong product intuition — able to turn data and ideas into customer-facing insights
• Experience in early-stage startups ready for scale
• Pragmatic, fast, iterative, and relentlessly resourceful
• Curious and has the ability to learn on the job to use the right tool for the job

Backend / Full Stack

• Can design and build APIs
• Can build UI and application including dashboards and actionable features
• Experience with Python or MVC frameworks
• Understands distributed systems, event-driven workflows, caching, and logging
• Strong with SQL, Postgres
• Ability to design and build data pipelines for messy real-world data
• Hands‑on experience building LLM‑powered workflows (agents, multi‑step reasoning, tool use)
• Strong with prompt engineering, structured outputs (JSON), fallbacks, guardrails

Recruiting & Leadership

• Ability to recruit and close awesome engineers on Day 1
• Proven track record of attracting top‑tier technical talent in competitive markets
• Experience building and mentoring high‑performing, distributed engineering teams
• Strong personal network of engineers to tap into immediately
• Experience managing engineering budgets and resource allocation

Director

Full‑time

Engineering and Information Technology

Transportation, Logistics, Supply Chain and Storage

Referrals increase your chances of interviewing at Optimus by 2x

Apply BELOW