---
title: 'Head of Solutions Engineering at FleetWorks'
canonical: 'https://feeny.ai/job/head-of-solutions-engineering-fleetworks-san-francisco-h1yzjgkjwk7d'
type: 'job'
last_seen: '2026-11-02'
---

# Head of Solutions Engineering at FleetWorks

- **Company:** FleetWorks
- **Location:** San Francisco, CA
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-10-31
- **Last confirmed live:** 2026-11-02
- **Apply:** https://jobs.ashbyhq.com/fleetworks/071c9585-0355-466c-a673-74b269f8141e

## 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. Our customers are freight brokers, and every one of them runs a little differently. Getting a new customer from signed contract to a working, adopted product means learning how they operate, deciding what we're building for them, keeping the project moving across their team and ours, and managing expectations on both sides. Today that work is spread across customer success, engineering, and the founders. We’re looking for a Head of Solutions Engineering to own the technical customer journey through onboarding & implementation and custom builds that power our customers’ core business. You'll personally run our most important implementations and write the playbook from what you learn. You'll be the person who scopes what we're committing to, sets expectations with the customer, and balances them against what engineering can deliver.

## What You'll do

- Own Customer Deployments at the intersection of of customers and engineering. This includes onboarding as well as new product features, rollouts, etc
- You’ll own customer implementations end to end: from contract signature through onboarding, go-live, and steady-state adoption.
- Partner with engineering and product leadership on changes that reduce engineering’s role in customer builds
- Work with Product to train and enable customers, including building documentation that will help users self-serve.
- Build a project management system that can be used across Product, CS, and Engineering to keep up to date on current status of customer builds. Be the owner of escalations between engineering and CS.
- Scope the work and manage expectations. Turn what a customer wants into clear, realistic requirements engineering can build against. Scope how integrations work, with customers and with partners.
- Learn the product deeply. Get hands-on enough to configure workflows and agents yourself at the start, and know when a one-off should become a product feature.
- Own the rollout and the custom workflows that drive expansion with existing customers. This also includes enablement, training, and documentation that lets customers get more value without waiting on us.
- Manage and develop the deployment team, starting with our deployment strategist.

## What We Look For

- Experience owning implementation, solutions, or another technical customer-facing delivery role at B2B software companies.
- Experience managing technical customer relationships at a level where you could coach others on it, and a track record that engineers will trust.
- Technical enough to learn a complex product deeply, configure workflows, read an integration, and ask engineers the right questions.
- Operator's instincts. You understand how a business runs, you care about your customer's margins, and you spot issues before they become a problem.
- Excellent written and verbal communication.
- High ownership and hands-on by default. You'd rather do the first version yourself than write a plan for someone else to execute.

## 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)

## Other roles at FleetWorks

- [Head of Customer Deployments](https://feeny.ai/job/head-of-customer-deployments-fleetworks-san-francisco-y36phczk4hf8) — San Francisco, CA
- [Senior Product Manager](https://feeny.ai/job/senior-product-manager-fleetworks-san-francisco-tspj1jk9b2xf) — San Francisco, CA
- [Product Manager](https://feeny.ai/job/product-manager-fleetworks-san-francisco-rgmhkvxj7303) — San Francisco, CA
- [Senior Backend Software Engineer](https://feeny.ai/job/senior-backend-software-engineer-fleetworks-chicago-tscxjvva06yh) — Chicago, IL
- [Senior Software Engineer](https://feeny.ai/job/senior-software-engineer-fleetworks-chicago-ryd849hefk51) — Chicago, IL
- [Senior Backend Software Engineer](https://feeny.ai/job/senior-backend-software-engineer-fleetworks-san-francisco-hr5m4m3a3zq7) — San Francisco, CA
- [Senior Product Engineer](https://feeny.ai/job/senior-product-engineer-fleetworks-san-francisco-38465cmkdwm6) — San Francisco, CA
- [Get In Touch](https://feeny.ai/job/get-in-touch-fleetworks-san-francisco-k2r0w7w0tjad) — San Francisco, CA
- [Head of Solutions Engineering](https://feeny.ai/job/head-of-solutions-engineering-humanoid-us-boston-z7hbc2kqw1he) — US Boston, MA
- [Head of Solutions Engineering](https://feeny.ai/job/head-of-solutions-engineering-flow-engineering-san-francisco-0ktjn5wz77p0) — San Francisco, CA