Staff Software Engineer, AI Products

About TruckSmarter

Logistics is one of the single largest industries in the world. Globally, logistics is an $8–$12 trillion dollar industry and in the US alone, ~ $2 trillion, representing ~10% of GDP. A single percent of improvement drives profound change to every corner of the world—from the cost of goods, to the livelihoods of local communities, to even the impact on our environment.

To reshape the industry, at TruckSmarter, our focus is first on truck drivers. Trucks move 71% of freight in America (~$900bn annually) & the trucking industry represents nearly 6% of the full-time jobs in the country. Every item you see has sat on a truck at one point on its journey to you. Yet, despite the industry’s enormous scale and importance, it remains deeply fragmented and structurally misaligned.

Our mission is to fix that—and we need your help.

The Role

We're looking for a Staff Software Engineer to help help define and build the next generation of TruckSmarter’s AI-native products. This is a high-impact, high-ownership role for an engineer who can lead through architecture, execution, and influence—shipping end-to-end while shaping the technical direction and leveling up the team.

You’ll build systems that are secure, scalable, and low-latency, and you’ll help set the standards for how we design, deploy, and improve agentic AI products in production.

In this role, you will:

• Partner with product, design, and engineering to turn ambiguous problems into clear technical plans and scalable architectures.

• Own the end-to-end design and delivery of complex, cross-cutting features (product + infrastructure + reliability).

• Define and evolve the architecture for agentic AI systems (text + voice) that can reason, take actions, and self-evaluate.

• Build and integrate GenAI agents with traditional ML systems to power hybrid intelligent workflows.

• Establish and raise the bar for quality, observability, and performance across our products and AI model behavior (monitoring, evaluation pipelines, iteration loops).

• Make crucial architectural decisions that will influence feature development for years—balancing speed with long-term maintainability.

• Lead technical reviews and provide high-leverage feedback through code reviews, design docs, and system-level guidance.

• Mentor and unblock other engineers; help the team move faster by improving systems, tooling, and execution patterns.

• Continuously experiment with new technologies and frameworks—introducing them when they create durable product advantage.

You should be comfortable navigating the uncertainties of a startup environment, be flexible to shifting priorities, and be driven by hard technical and product problems.

What Excites You

• Working directly with users to deeply understand problems and ship pragmatic solutions.

• End-to-end ownership: idea → architecture → implementation → launch → iteration.

• Building real-world products using agentic AI architectures, not demos.

• Solving messy problems with systems thinking—simplifying without losing extensibility.

• A collaborative startup environment where you can drive strategy and execution.

• Playing a meaningful role in cultivating engineering culture and technical standards.

• Work cross-functionally with the team to shape product strategy.

What Excites Us

• 8+ years of industry experience building and shipping production software (or equivalent depth of impact), including leading large projects end-to-end.

• Drivers, not passengers

• A track record of architecting scalable systems and making principled tradeoffs across product, reliability, and velocity.

• Informed opinions about LLMs, agent behavior, and evaluation—and the rigor to validate them in production.

• Experience thriving in fast-moving environments with shifting priorities and imperfect information.

• Demonstrated ability to mentor engineers and influence without relying on org structure.

What Success Looks Like

• Craft — You build high-quality, reliable software that delights end users.

• Ownership — You drive high-impact initiatives to production and iterate based on outcomes.

• Leadership — You raise the bar for the team through mentorship, architectural clarity, and technical standards.

Working Model: TruckSmarter offers an in-office collaborative culture. This role is based in our downtown San Francisco office 5 days/week.

We’d love for you to join us on this journey and are excited to review your application!