Head of Engineering
Optimus
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Join as the founding engineering leader to build cutting-edge AI systems and data infrastructure that power intelligent freight insights at scale. You'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
Seniority level
Director
Employment type
Full‑time
Job function
Engineering and Information Technology
Industries
Transportation, Logistics, Supply Chain and Storage
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