Staff AI Product Engineer

ABOUT TRUCKSMARTER Trucking powers the American economy, moving 71% of the nation’s freight and representing nearly $900 billion in annual spend. Yet despite its scale, the industry still runs on fragmented systems, phone calls, emails, tribal knowledge, and manual coordination. TruckSmarter is changing that, starting with the people at the center of it all: truck drivers and small carriers. We’re a team of fewer than 25 building Dispatch, an AI-powered operating layer for freight. Think Claude Code for trucking. Dispatch helps carriers navigate a constantly changing freight market, reason through complex tradeoffs, and execute operational workflows on their behalf. The product is live, drivers are using it, and we’re now focused on making Dispatch dramatically smarter and more capable. THE ROLE This is a high-ownership, high-influence engineering role on a team of fewer than 15 engineers. You'll report to the Head of Engineering and work directly with our CEO on the most technically ambitious work we're doing. With our small team, there's no bureaucracy between you and impact. You'll define how we architect and scale our core systems, mentor engineers who want to learn from you, and ship software that real truck drivers depend on every day. For those currently at a larger organization, this role offers significantly increased scope, more challenging problems, and a direct influence on product strategy. WHAT YOU'LL DO - Partner with product, design, and engineering to turn ambiguous problems into clear technical plans and scalable architectures - Own end-to-end design and delivery of complex, cross-cutting features across product, infrastructure, reliability, and AI-powered systems. - Define and evolve the architecture for core systems and AI platforms that are fast, resilient, and built to scale - Raise the bar for quality, observability, performance, and iteration - Make architectural decisions that influence how we build for years, balancing speed with long-term maintainability - Lead technical reviews and give high-leverage feedback through code reviews, design docs, and system-level guidance - Mentor and unblock engineers; help the team move faster by improving systems, tooling, and execution patterns WHAT WE'RE LOOKING FOR - 8+ years building and shipping production software, including leading large projects end-to-end - A track record of architecting scalable systems and making principled tradeoffs across product, reliability, and velocity - Demonstrated ability to mentor engineers and influence without relying on org structure - Comfort navigating fast-moving environments with shifting priorities and imperfect information WORKING MODEL We work in-person 5 days a week at our downtown San Francisco office. We believe the best products get built when people are in the same room. Fast feedback loops, real collaboration, and a team that genuinely enjoys working together. If that's how you do your best work, you'll fit right in. WE OFFER - Full health, dental and vision coverage - Daily catered lunch provided in-office, plus dinner covered for anyone working past 6:00pm - Commuter benefits - Flexible PTO - 401k - Commuter benefits We’d love for you to join us on this journey and are excited to review your application!