Head of Customer Deployments
Fleetworks · San Francisco
About this role
## Head of Customer Deployments FleetWorks is fixing how freight brokers match trucks with jobs—by building a faster, less fragmented system. As **Head of Customer Deployments**, you’ll own the technical customer journey from onboarding and implementation through custom builds that power customers’ core business. ### What You’ll Do - Own **Customer Deployments** at the intersection of customers and engineering (onboarding, new product features, rollouts, etc.). - Own customer implementations **end to end**: contract signature → onboarding → go-live → 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 for self-serve. - Build a **project management system** used across Product, CS, and Engineering to track customer build status; own escalations between engineering and CS. - **Scope the work** and manage expectations—turn customer requests into clear, realistic requirements engineering can build against. - Learn the product deeply: get hands-on early (configure workflows/agents) and determine when a one-off should become a product feature. - Own rollouts and custom workflows that drive expansion with existing customers, including enablement, training, and documentation. - Manage and develop the deployment team, starting with the **deployment strategist**. ### What We Look For - Experience owning implementation/solutions or another **technical customer-facing delivery** role at B2B software companies. - Ability to manage technical customer relationships at a level where you can **coach others**, with a track record engineers trust. - Technical depth to learn a complex product, configure workflows, read integrations, and ask the right questions. - **Operator mindset**: understand how the business runs, care about customer margins, and spot issues early. - Excellent written and verbal communication. - High ownership and hands-on by default—prefer doing the first version yourself over delegating a plan. ### What We Offer - **Top-tier cash and equity** (aiming above the 75th percentile for similarly funded companies) - Competitive **medical, dental, and vision** benefits - Fully covered **lunches and dinners** - Opportunity to learn quickly, grow fast, and be rewarded for your contributions
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