Staff AI Product Engineer

TruckSmarter is building the operating system for the people who move the world’s freight.

Trucking is a massive, dynamic network: hundreds of thousands of carriers, tens of thousands of brokers, volatile prices, uncertain supply and demand, real-world constraints, and decisions made in minutes. Building products for it requires solving hard problems at the intersection of AI, mathematics, distributed systems, and product engineering working together.

We are looking for engineers who are excited by problems that do not have established patterns or obvious solutions. We value intellectual honesty, independent thinking, technical excellence, urgency, and ownership.

You will join a small team with experience building and scaling products at DoorDash, Uber Freight, LinkedIn, Affirm, Typeface, Flexport, Coinbase, and Strava.

You will be given an important, ambiguous problem and expected to understand it deeply, formulate it precisely, explore possible approaches, and build a solution that works in the real world

• Work directly with customers to uncover the real problem, not merely the requested feature.

• Turn ambiguous objectives into models, algorithms, system designs, and measurable success criteria.

• Build intelligent decision systems using optimization, probability, machine learning, information retrieval, graph algorithms, and related techniques.

• Turn sophisticated mathematical and technical capabilities into products that are simple and intuitive to the people using them.

• Design scalable, low-latency, fault-tolerant systems that operate across long-running and highly concurrent workflows.

• Raise the technical standards through rigorous thinking, clear communication, thoughtful design reviews, and high-quality implementation.

Examples of the problems our engineers work on include:

• Building autonomous agents that can create plans, execute them over hours or days, react to rapidly changing market conditions, and know when an objective has been achieved or is no longer possible.

• Searching and personalized ranking hundreds of thousands of freight opportunities against multiple, sometimes competing constraints in under a second.

• Designing systems that balance exploration of new strategies with exploitation of approaches known to work.

• Resolving incomplete, ambiguous, or contradictory information about locations, loads, companies, people, times, and prices.

• Coordinating concurrent workflows while enforcing fairness, resource limits, permissions, and safety constraints.

• We care more about intellectual ability, technical depth, and demonstrated achievement than about matching a rigid checklist.

  You’ll be a strong fit if you:

  • Have an exceptional foundation in computer science, mathematics, statistics, physics, operations research, or another quantitative field.

  • Decompose messy, ambiguous problems into precise, tractable ones.

  • Move naturally between mathematical reasoning and production engineering.

  • Have built technically demanding systems, algorithms, infrastructure, or products.

  • Evaluate ideas rigorously through proofs, simulations, prototypes, benchmarks, experiments, and production data.

  • Learn unfamiliar domains quickly, communicate precisely, and want substantial ownership.

  • Communicate complex ideas precisely and can collaborate productively with other highly capable people.

  You might come from a technology company, quant firm, research lab, ambitious startup, or rigorous academic program. Pedigree matters far less than how you think and what you’ve built.

• You want to work with people who will challenge you.

• You want difficult problems with real-world consequences.

• You want the freedom and responsibility to find the right answer—not simply implement a spec.

• And you want to build systems that can reshape how a massive industry operates.

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.

• 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!