Staff AI Product Engineer

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

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!