Head of Customer Deployments

present of AI; San Francisco (CA); On-site; USD 140,000 - 190,000; Full time

Job summary

FleetWorks in San Francisco/Chicago is seeking a Lead-level Customer & Solutions professional to own the end-to-end path from signed contract to a live, adopted product for freight brokers.

You will turn vague customer wishes into clear scope for engineers, set up AI workflows and integrations, spot issues early, and later grow a small deployment team.

Qualifications

• Experience running technical implementations for B2B software companies.
• Ability to translate messy customer wishes into clear engineering scope.
• Trusted by both customers and internal teams to deliver.
• Hands-on enough to configure workflows and set up deployments.

Responsibilities

• Own end-to-end deployment from contract to live product for freight brokers.
• Set up AI workflows and agent configurations in production environments.
• Spot trouble early and guide a small deployment team.
• Lead and coach a deployment team as it grows.

Skills

B2B software implementations

Scope engineering builds

AI workflows configuration

Stakeholder trust

Team coaching

Tools

AI workflow tools

Job description

Customer & Solutions · San Francisco / Chicago · Full-time · Lead level

This role owns the whole path from signed contract to a live, adopted product for freight brokers, each of whom works a little differently. A strong candidate has run technical implementations at B2B software companies, can turn messy customer wishes into clear scope that engineers can build, and is trusted by both sides. They should be hands‑on enough to set up workflows themselves, spot trouble early, and later lead and grow a small deployment team.

How it fits the AI era

The product itself is AI that handles broker calls and load booking, so much of this job is configuring AI workflows and agents and deciding when a one‑off request should become a real feature. AI can speed up documentation, setup and status tracking, which supports the goal of needing less engineering time per customer. What stays human is judging what a customer really needs, setting honest expectations, building trust with engineers and brokers, and caring about the customer's margins.

How it builds AI experience

Someone in this role would gain close, daily experience configuring AI agents and workflows for real freight operations, and seeing where they work well and where they need human handling. Building that experience beforehand could mean setting up automations with any AI agent or workflow tool and writing down what worked. Learning how freight brokers book loads and talk to carriers would also help a lot, since that is the work the product automates.

Worth showing

• Led B2B software implementations
• Scoping custom builds for engineers
• Configuring workflows and integrations
• Customer playbooks and documentation
• Coaching and managing a team

This is our own read, written from the employer's posting and the company's Spotlight. The employer's posting is the source of truth for the role.

About FleetWorks

AI-powered freight automation platform that automates broker telephone calls, carrier communications, and load booking operations.