Head of Customer Deployments

FleetWorks; San Francisco (CA); On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Equity compensation

Medical, dental, vision benefits

Lunches and dinners provided

Growth opportunities

Job summary

FleetWorks in San Francisco is seeking a Head of Deployments to own the technical customer journey from onboarding and implementation through go-live and steady-state adoption. You will scope commitments, set expectations with customers, and balance them against what engineering can deliver.

You’ll drive documentation, enablement, and scalable workflows across Product, CS, and Engineering. You’ll personally run the most important implementations, learn the product deeply, and build playbooks

Qualifications

• Experience owning implementation, solutions, or another technical customer-facing delivery role at B2B software companies.
• Excellent written and verbal communication.
• High ownership and hands-on by default.
• You understand how a business runs and care about margins.

Responsibilities

• Own Customer Deployments at the intersection of customers and engineering, including onboarding and new features.
• Manage customer implementations end to end from contract to go-live and adoption.
• Partner with engineering and product leadership to reduce required engineering effort for customer builds.
• Build documentation to help users self-serve and train customers.
• Create a cross-team project management system for Product, CS, and Engineering.
• Scope work into clear, realistic requirements and define integration work.
• Learn the product deeply and configure workflows and agents where needed.
• Own rollout and custom workflows to drive expansion with existing customers; provide enablement and training.
• Manage and develop the deployment team starting with the deployment strategist.

Skills

Implementation ownership

Customer communication

Hands-on

Ownership mindset

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 Deployments 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 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