Head of Engineering

About the role Head of Engineering Company Tread is the AI-native operating system for the $660B construction materials logistics market: the aggregate, asphalt, and concrete behind every road, bridge, and building in the country. Our customers run the gamut: enterprise producers and contractors that supply the world's largest infrastructure projects, alongside the family-owned hauling fleets that have moved the material this work depends on for generations. They're the operators who actually build the roads, bridges, and buildings around us. Most of the work still happens on paper tickets, phone calls, and disconnected scale houses. We're building the software they run on. We crossed $1Bn in monthly delivered load value on the platform in March 2026. We're at ~$XM ARR, and growing fast. Our enterprise customers reconcile real money, real freight, and real P&L against our data every day. Tread is the most important software they use. We're a Series A company backed by Mucker Capital. We're in growth mode. If you are fulfilled by ownership and a life-changing outcome, let's connect. Role We're looking for a hands-on engineering leader who can help define and operate the next generation of our AI-native engineering system, partnering directly with the CEO to evolve how software is built at Tread. You will partner directly with the CEO on building the category-defining operating system for construction materials logistics. The team you lead today is under 10 engineers shipping at aggressive velocity. We're investing heavily in an AI-driven SDLC - which you will help drive - with the product specs, architecture documentation, code review, and quality gates in place to make ~100% AI-generated code work. We've operated this way since March 2026. The successful candidate will already have experience operating an AI-first engineering organization where coding agents are responsible for a significant portion of production software delivery. They should be able to describe: - how work flows from specification through implementation using agents - how architecture, code quality, and correctness are reviewed - how evaluation frameworks prevent regressions and hallucinations - how AI integrates into CI/CD and release management - where human judgment remains essential We are not looking for someone who is simply enthusiastic about AI. We're looking for someone who already operates an AI-native engineering organization and can install that operating system at Tread. Tread is also a financial system of record. We move freight, we move money, and our customers reconcile their business against our platform. Correctness, reliability, and trust are non-negotiable. In this role, you will: - Own engineering execution across product engineering, platform, data, payments, AI infrastructure, internal developer tooling, and the AI-native software development lifecycle. - Recruit top-tier talent and raise our bar for excellence. Push the team to strike the balance between speed and a reliable product. Have the hard conversations early. - Drive the AI-native SDLC forward. Personally invest in the shared skills library, namespaced agent review pipelines, devcontainers, CI, and cloud agent infrastructure that lets a small team operate at scale. - Design and continuously improve evaluation systems for AI-generated software, including quality gates, benchmark suites, regression testing, rollout strategy, rollback procedures, and model performance monitoring. - Set technical direction across the Rails API, data layer, payments business logic, and clients. - Make build-vs-buy and platform-investment calls that balance speed with long-term use. - Own platform reliability and trust posture: uptime, data integrity, payment accuracy, security, and incident response. - Partner closely with the CEO on the product roadmap and serve as a key thought partner. The roadmap includes deepening AI agents into customer workflows and embedding fintech throughout the app (instant funding, ACH for B2B payments, financing). Requirements - 7-12 years building software, with demonstrated engineering leadership in high-growth startups (Seed-Series B/C) or founder experience. - Background in hypergrowth startups. Ideally Seed through Series C, or founder experience. - Fluent and opinionated about AI-native engineering. You've personally built or operated production engineering workflows where AI agents participate throughout the software lifecycle, including specification, implementation, testing, code review, evaluation, deployment, and maintenance. - Strong engineering judgment around speed vs. correctness. You know where to intentionally optimize for rapid iteration, where correctness is non-negotiable, and how to build systems that recover safely when things fail. - Experience operating payments or financial systems at scale. - Deep technical credibility. Comfortable discussing architecture, distributed systems, AI infrastructure, eval Compensation Base salary is set at $220,000. An annual bonus target of $40,000 is available based on performance. Equity compensation valued at $100,000 (2026) is offered. What You'll Do Architect the AI-native SDLC so specs become verified code through agents. Design intake workflows that transform tickets, calls, and scales into structured data. Build review gates where agents and humans jointly ensure quality and safety. Ship with CI systems that route changes through tests, rollbacks, and monitoring. Establish partner interfaces that connect hauling fleets to our execution platform. Champion evaluation suites that catch regressions and model drift early. Guide payments and rails logic so money moves accurately with every load. Maintain reliability practices that keep uptime, data integrity, and trust intact. Translate CEO vision into a product roadmap for embedded fintech and agents. Recruit engineers who operate AI-native workflows and elevate the entire team. Nice to Have Experience founding or scaling a company from seed through series C. Skills & Tools Rails API, Postgres, React, GCP, Kubernetes, Gitlab CI, Datadog, Sentry, PagerDuty. Practical Notes Hours may vary; travel