---
title: 'Senior Software Engineer - Forward Deployed at FleetWorks'
canonical: 'https://feeny.ai/job/senior-software-engineer-forward-deployed-fleetworks-chicago-tyjt9vsg5w73'
type: 'job'
last_seen: '2026-09-07'
---

# Senior Software Engineer - Forward Deployed at FleetWorks

- **Company:** FleetWorks
- **Location:** Chicago, IL
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-05-27
- **Last confirmed live:** 2026-09-07
- **Apply:** https://jobs.ashbyhq.com/fleetworks/69798d95-36c3-4292-a5de-004319cf1b31

## Job description

Every year, companies spend over a trillion dollars moving freight across the U.S. but the system for matching trucks with jobs is still slow, manual, and fragmented. FleetWorks is fixing that.

We’re building voice agents that transform the chaotic freight booking process into a modern, intelligent marketplace. Our agents replace the endless phone calls, texts, and emails and match truckers who want to get paid with loads that need to be moved.

We’re expanding our forward-deployed engineering team in Chicago, a major hub for our customers and the heart of U.S. freight operations. In this role, you’ll be embedded directly into the environments where our product meets real users. You’ll work side-by-side with operators, understand their workflows firsthand, and turn that knowledge into robust integrations and production features.

As our first Forward-deployed engineer at FleetWorks, you’ll own outcomes end-to-end: diagnosing messy real-world problems, shaping technical solutions in the field, and ensuring our AI agents perform flawlessly in live operations. If you thrive in ambiguous environments, enjoy working directly with customers, and want to see your code deliver immediate operational impact, this role is uniquely high-leverage.

Learn about our Series A here! https://www.fleetworks.ai/blog/fleetworks-launches-always-on-dispatcher-for-trucking-industry-with-17m-funding

## WHAT YOU’LL DO:

- Own customer deployments end-to-end, from initial scoping to integration design to production rollout.
- Work directly with customer operators and leaders to understand real workflows, pain points, and edge cases, translating them into clear, high-quality technical solutions.
- Build production features and integrations that allow our AI agents to operate inside complex customer environments.
- Diagnose and resolve issues in the field, often in real time and with incomplete information, owning outcomes all the way through.
- Travel 20–30% to customer sites nationwide to unblock deployments, map operational processes, and ensure successful go-lives.
- Collaborate closely with product and core engineering to shape the roadmap based on what you observe directly on the ground.
- Develop tools and reusable workflows that improve deployment speed and reduce friction for future customers.
- Operate with extreme ownership, ensuring customers experience immediate and measurable value from our platform.

## WHAT WE LOOK FOR:

- 3–6+ years of professional software engineering experience, with clear ownership of complex, production-critical systems.
- Strong command of TypeScript, Node.js, and REST API design, including debugging and integrating with external systems.
- Hands-on experience with AI-driven systems, including tuning agent behavior, refining prompts, and shaping workflow logic based on customer feedback.
- Exceptional communication and judgment, especially when balancing speed, reliability, and real-world constraints.
- Based in Chicago with willingness to travel 20–30% to customer sites.

## HOW WE'LL GET TO KNOW EACH OTHER

- Quick call with Megan, our Talent lead, for you to share your goals and motivations, what you’ve worked on that you’re proud of and to figure out together how that might fit in with what we’re working on at FleetWorks
- 45-min live-coding interview with an engineer who you'll work with if you join, so that we can get to know how you think about technical challenges
- Paid onsite work trial so that we can get to know how you work and you can get to know us
- Well talk with your references to help us understand how to best support your development at work—we might do this after you've signed your offer
- Transparent offer process that clearly outlines how we came to the compensation package we’re offering, including the current and potential value of your equity

## What we offer

- Top tier cash and equity compensation—we aim to be above 75th %ile for companies who have raised a similar amount of cash
- Competitive medical, dental, and vision benefits
- Fully covered lunches and dinners
- The opportunity to learn quickly, grow fast, and be rewarded for your contributions

## About FleetWorks

## Company Overview
- **One-liner**: FleetWorks uses AI agents to automate phone calls, emails, and negotiations between freight brokers and carriers, replacing manual load matching with an intelligent marketplace.
- **Entity Type**: Private (Series A)
- **Headquarters**: San Francisco, California, United States
- **Founded**: 2023
- **Founders**: Paul Singer and Quang Tran

## Core Business
- Primary industry/industries: Transportation, Logistics, Supply Chain, and Storage; Artificial Intelligence
- Target customers: B2B — Freight brokers, third-party logistics (3PL) firms, and carrier fleets (especially small to mid-size carriers)
- Mission or purpose statement: To rebuild the $1 trillion freight marketplace by turning a slow, manual, and fragmented system into a modern, intelligent marketplace where AI agents match jobs to trucks instantly.

## Products & Services
- **AI-Powered Freight Automation Platform**: A voice-first and email-capable AI assistant that automates the manual work of freight brokerage operations. The platform handles three core functions:
    - **Load Booking**: Automates outbound calls to carriers to share load details, negotiate rates, and book loads.
    - **Load Tracking**: Proactively calls drivers for status updates, detects live issues, and relays updates back to brokers.
    - **Appointment Scheduling**: Handles calls and emails to facilities to set or reschedule appointment times.
- **Always-On AI Dispatcher**: A recently launched feature that acts as a persistent, automated dispatcher, continuously working to match available trucks with loads without human intervention.

## Market Standing
- **Valuation/Market Cap**: Not disclosed
- **Key Metric: Total Funding**: $17.5M
- **Funding History**:
    - **Pre-Seed (Sep 2023)**: $500,000 led by Y Combinator
    - **Series A (Oct 2025)**: $17.0M led by First Round Capital (Bill Trenchard), with participation from Y Combinator, Saga Ventures, and LFX Venture Partners.
- **Notable Investors/Partners**: First Round Capital, Y Combinator, Saga Ventures, LFX Venture Partners. Key customer/adoption includes Uber Freight.
- **Growth Signals**:
    - Onboarded over 10,000 carriers and dozens of brokers within the first six months of 2025.
    - Headcount grew 115.4% year-over-year to 21 employees.
    - Actively hiring for 13+ open positions, primarily senior engineering and customer-facing roles.

## Competitive Advantages
- **SME Founder DNA**: Founder Paul Singer was a Product Manager at Uber Freight, giving the team deep, first-hand domain expertise in freight brokerage operations and the pain points of the industry.
- **Nuanced AI for a Complex Industry**: The platform uses specialized AI models designed to handle the complexity and nuance of freight, such as booking appointments, negotiating prices, and remembering driver preferences (e.g., facilities requiring steel-toed boots, desire to be home by Friday).
- **Focus on Change Management**: The company emphasizes not just building AI agents, but also helping large, established brokers implement the technology effectively, a key learning from the founder's time at Uber Freight.

## Strategic Focus
- **Commercial Expansion**: Using the $17M Series A to grow the sales and customer success teams to bring on more brokers and carriers.
- **Product Development**: Continuing to build and improve the "always-on" AI dispatcher and other core AI agents to increase automation rates and handle more complex edge cases.
- **Hiring**: Aggressively hiring senior engineering talent (Product Engineers, Forward Deployed Engineers) and senior customer-facing roles (Account Executives, Customer Success Managers) to scale the platform and support customer growth.

## Why Work Here
- **High-Impact Stage**: As a Y Combinator (S23) graduate with fresh Series A funding, the company is in a rapid growth phase, offering early employees significant ownership and influence over the product and culture.
- **Cutting-Edge AI in a Legacy Industry**: Employees get to work on applied AI problems (voice, text, multi-agent systems) that directly solve real-world problems in a massive, trillion-dollar market.
- **Founding Team**: The team is led by repeat founders with experience at top-tier tech companies (Uber Freight, Airbnb) and backed by elite investors (First Round Capital, YC).
- **Engineering Culture**: The active job postings heavily favor senior technical roles, suggesting a high bar for engineering talent and a focus on building a strong engineering culture.
- **Work Policy**: Positions are listed in San Francisco, CA, and Chicago, IL, with some roles likely being hybrid or in-office.
- **Compensation**: Senior engineering roles are listed with a salary range of $160K - $240K, indicating competitive compensation for the Bay Area.

## Sources
1. [fleetworks.ai](https://www.fleetworks.ai/)
2. [techcrunch.com](https://techcrunch.com/2025/10/14/fleetworks-raises-17m-to-match-truckers-with-cargo-faster/)
3. [ycombinator.com](https://www.ycombinator.com/companies/fleetworks)
4. [linkedin.com](https://www.linkedin.com/company/fleetworksai)
5. [jobs.ashbyhq.com](https://jobs.ashbyhq.com/FleetWorks)

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