Staff Software Engineer, TruckSmarter
AI Products
$210-240k
Offers Equity
All-in-one platform serving truck drivers
Be an early applicant
All-in-one platform serving truck drivers
21-100 employees
Be an early applicant
$210-240k
Offers Equity
21-100 employees
Company mission
To empower truck driver's lives and by doing so, build the future of the industry.
Role
Who you are
- 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 the job involves
- 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
- 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
- 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
- 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
Our take
The massive rise in eCommerce means that truck drivers are at an all-time demand, but the trucking industry massively lags behind many others in technological advancements. TruckSmarter delivers a free platform that allows truckers, carriers, and dispatchers to search and book loads, streamlining the entire trucking process.
The trucking industry has been historically fragmented, with truckers wasting countless hours searching for their next gig, followed by more time waiting to be loaded or unloaded – which can be very detrimental to truckers who are often paid per mile. Trucksmarter digital trucking platform addresses all these problems. It stands out from the competition by being a free-to-use service. It makes its revenue by offering truckers same-day payments for each load, in exchange for a small percentage of their fee, rather than charging to use the load board itself.
TruckSmarter has raised an impressive amount of funding from top investors and names in the industry, showing respect for and interest in its solution. The investment will be used to add more finance and banking tools to the company’s driver ecosystem.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
70% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Sep 2025
$16m
LATE VC
Sep 2022
$25m
SERIES B
Total funding: $85m
Company benefits
- 100% of premiums, 75% for dependents
- Unlimited PTO
- Monthly wellness stipend
- Parental leave
- Relocation support to move to SF or Chicago
- 401(k) program
Company HQ
Yerba Buena, San Francisco, CA
Leadership
Daniel Kao
(Co-Founder & CEO)Investor & Advisor. Former General Manager, Shipper Platform & Head of Customer Success at Uber Freight. Co-founded Sharespace and Open Canal.
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