Head of Engineering
Interested in this role? Contact us at careers@getoptimus.ai
About Optimus
Optimus is building the logistics industry's first AI-powered autonomous revenue engine – exclusive shipper intelligence that helps freight brokers find customers, identify expansion opportunities, and close deals automatically.
We're using cutting-edge AI to transform a $3B+ problem where 87% of brokerages aren't growing their customer base.
We just sold another venture-backed tech company and we're about to do it again.
The Opportunity
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.
What You'll Build
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
Data Engineering
- Strong with SQL, Postgres
- Ability to design and build data pipelines for messy real-world data
- Geospatial/Location Tracking data processing
AI / Machine Learning / LLMs
- Hands-on experience building LLM-powered workflows (agents, multi-step reasoning, tool use)
- Strong with prompt engineering, structured outputs (JSON), fallbacks, guardrails
- Has built ML systems in production (evaluation sets, drift detection, retraining)
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
Why Now
Large Market Opportunity
Underserved market with clear pain points and strong demand
Product-Led Growth
No onboarding friction – built for rapid adoption
Proven Leadership
Founder with successful exits and deep industry relationships, having been part of teams raising over $100M in prior ventures
Capital Efficient
Clear path to profitability with strong unit economics
Ready to Build the Future of Freight?
Interested in this role? Reach out to us at: