Full-Time

Senior Software Engineer

AI Products

Posted on 10/30/2025

TruckSmarter

TruckSmarter

51-200 employees

Consolidated load board and broker access

Compensation Overview

$170k - $220k/yr

San Francisco, CA, USA

Hybrid

Category
Software Engineering (2)
,
Required Skills
Machine Learning
Observability
Requirements
  • 5+ years of industry experience, including leading projects end-to-end.
  • Demonstrated ability to design, build, and ship complex, production-grade systems.
  • Bachelor’s degree in a relevant field (or equivalent practical experience).
Responsibilities
  • 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.
Desired Qualifications
  • 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.

TruckSmarter is a free digital platform for owner-operators and small trucking businesses that combines a load board, real-time load information, credible broker listings, fuel price data, bidding and booking, document uploads, and factoring loads in one dashboard. It works by aggregating trucking-related services so users search for loads, compare brokers, track fuel prices, and arrange bookings, with revenue coming from partnerships through commissions or referral fees. It differentiates itself with a free, centralized hub plus direct human support and a user-friendly interface that saves time compared to using multiple sites. Its goal is to streamline trucking operations for owner-operators, helping them find loads faster, save on fuel, access reliable broker information, and grow their independent businesses.

Company Size

51-200

Company Stage

Late Stage VC

Total Funding

$135M

Headquarters

San Francisco, California

Founded

2021

Simplify Jobs

Simplify's Take

What believers are saying

  • OTR acquisition sharpens focus on AI dispatching post-2025 divestiture.
  • $16M Series C from a16z and Founders Fund fuels Dispatch expansion.
  • Sapp Bros. partnership boosts fuel reservations 230% in one month.

What critics are saying

  • OTR acquisition eliminates 30-40% factoring revenue within 6-12 months.
  • Convoy and Uber Freight AI displace Dispatch in 12-24 months.
  • Broker consolidation by XPO shrinks load inventory in 12-18 months.

What makes TruckSmarter unique

  • Dispatch AI integrates SONAR data for real-time spot rates in chat interface.
  • TCS partnership embeds route-level fuel pricing and 51¢/gallon discounts.
  • Free load board consolidates broker loads for owner-operators only.

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Benefits

Competitive salary & equity

100% of premiums, 75% for dependents

Unlimited PTO

Monthly wellness stipend

Desk budget

Parental leave

Relocation support to move to SF or Chicago

401(k) program

Growth & Insights and Company News

Headcount

6 month growth

1%

1 year growth

1%

2 year growth

1%
readmagazine.com
Nov 19th, 2025
OTR Solutions Acquires TruckSmarter Factoring & Banking

OTR Solutions acquires TruckSmarter factoring & banking. OTR Solutions has announced the acquisition of TruckSmarter's factoring and banking division, a strategic move that strengthens both companies' ability to deliver specialized value to carriers across the freight industry. Under the agreement, OTR Solutions will take over all TruckSmarter factoring and business banking operations, ensuring a seamless one-to-one transition for existing clients, who will immediately gain access to OTR's Truly Instant Funding, nationwide support, and intelligent financial platform designed to keep carriers paid and protected around the clock. Meanwhile, TruckSmarter will sharpen its focus on accelerating its AI-driven dispatching and load board technology. Leaders from both companies emphasized their shared commitment to providing carriers with best-in-class tools: "TruckSmarter has built a reputation for empowering carriers through technology, and we're proud to be the partner they trust to continue supporting their clients' success," said Fritz Owens, CEO of OTR Solutions, while TruckSmarter CEO Dan Kao noted OTR's "speed, reliability, and commitment to carriers." The acquisition unites OTR's expertise in factoring, fuel, and business banking with TruckSmarter's strengths in freight visibility and automation, creating a more connected and efficient ecosystem. OTR leaders added that the partnership reflects a broader mission to drive innovation, collaboration, and long-term success for carriers and brokers industry-wide.

FreightCaviar
Sep 8th, 2025
Exclusive: TruckSmarter Goes All In on AI with $16M Raise and Launch of Dispatch – We Went To SF to See it For Ourselves

TruckSmarter raises $16M and launches Dispatch, an AI assistant to help carriers book loads faster. We visited their SF office to see what’s driving the momentum.

FreightCaviar
Sep 8th, 2025
TruckSmarter Raises $16M, Launches AI Dispatch

TruckSmarter has raised $16M, led by Socium Ventures with support from a16z, Founders Fund, Bain Capital Ventures, and Thrive Capital. They have launched Dispatch, an AI assistant aimed at helping carriers book loads more efficiently. The company is leveraging its popular app and technical talent in San Francisco to enhance its position as a leading freight platform.

Yahoo Finance
Jul 16th, 2024
TruckSmarter’s financial services secure $50M debt facility

The digital trucking platform partners with CoVenture for up to $100 million in debt to accelerate its financial services. The post TruckSmarter’s financial services secure $50M debt facility appeared first on FreightWaves.

PR Newswire
Jul 15th, 2024
Trucksmarter Announces $50 Million In Debt Financing To Continue Empowering Drivers Across The Trucking Industry

Financing will enable the company to expand its suite of financial services to make drivers' lives easierSAN FRANCISCO, July 15, 2024 /PRNewswire/ -- TruckSmarter, a digital platform designed to assist owner-operators and trucking companies in optimizing their operations, today announced the close of a $50 million debt facility, with the option to scale to $100 million, led by CoVenture. The funding will allow TruckSmarter to continue to scale its suite of financial services to further empower truck drivers to build, manage, and grow their businesses.TruckSmarter leads the industry in offering driver-first solutions, serving as a one-stop shop of financial services for truck drivers, owner-operators, and fleets. With TruckSmarter, truck drivers have access to a 100% free load board, transparent freight factoring, fuel discounts, and banking services. Designed and built for truck drivers, the app streamlines their workflows, quickens payment processes, and gives owners easier access to the capital they need to run their businesses."The pandemic reminded the world just how critical the trucking industry is to our daily lives and why maintaining a healthy supply chain is key," said Daniel Kao, co-founder and CEO of TruckSmarter. "In order to transform the logistics industry, we must focus on its backbone – truck drivers. TruckSmarter is committed to providing tailored products and tools to truck drivers that streamline their day-to-day operations, increase earnings, make their lives easier, and, in turn, improve all of our lives.""Amid challenges for the trucking industry over the past several years, TruckSmarter has demonstrated how technological innovation and its commitment to drivers is pivotal when developing a disruptive solution that addresses industry needs," said Lei Tie, Managing Director of CoVenture

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