Senior AI Product Engineer at Trucksmarter in San Francisco, CA

ABOUT TRUCKSMARTER Trucking moves 71% of freight in America, nearly $900 billion annually, yet the industry remains deeply fragmented and underserved by technology. TruckSmarter is fixing that, starting with the people at the center of it: truck drivers. We're a team of less than 25 building Dispatch, a vertically-integrated AI-powered product that performs many of the repetitive, time-intensive manual operations so that our users can focus on growing their business. The product is live, drivers are using it, and we're now focused on making Dispatch more powerful for the people who depend on it every day. THE ROLE We’re looking for senior software engineers to help us realize TruckSmarter’s vision of eliminating inefficiencies across the freight industry. You’ll be at the forefront of building text- and voice-based AI agents that can drive external communication, perform reasoning, execute actions, and continuously self-improve. As a senior engineer, you’ll play a critical role not only in building systems but also in shaping our technical and product strategy. You’ll mentor peers, influence architectural decisions, and help us define what best-in-class AI-driven logistics software looks like. WHAT YOU'LL DO - Partner closely with product, design, and leadership to define and evolve the architecture for agentic AI systems that scale across multiple product surfaces. - Own the design and delivery of complex features end-to-end, balancing tradeoffs between velocity, scalability, and long-term maintainability. - Lead technical discussions and architectural reviews, ensuring our systems remain robust, extensible, and secure. - Guide the integration of GenAI agents with traditional ML systems (classification, recommendation, optimization) to create hybrid intelligent workflows. - Establish engineering best practices around testing, observability, deployment, and performance monitoring for AI-driven features. - Proactively identify product and infrastructure bottlenecks, propose innovative solutions, and drive them to completion. - Mentor and coach other engineers, raising the technical bar of the team. - Stay ahead of emerging AI frameworks and technologies, evaluating and introducing them when they create real product advantage. WHAT WE'RE LOOKING FOR - 5+ years of industry experience, including leading projects end-to-end. - Demonstrated ability to design, build, and ship complex, production-grade systems. - Extremely curious about LLMs and Agentic AI architectures. - Experience in fast-paced, startup environments where you’ve had to wear multiple hats. - A track record of mentoring engineers and shaping team practices. - Bachelor’s degree in a relevant field (or equivalent practical experience). 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!