Head of Customer Deployments

FleetWorks • Chicago, IL

5d

About The Position

FleetWorks is hiring a Head of Deployments to own the technical customer journey, including onboarding, implementation, and custom builds that support customers’ core business. The role bridges customers and engineering, translating customer needs into realistic requirements while setting expectations about what engineering can deliver.

The Head of Deployments will personally lead important implementations, develop a deployment playbook based on lessons learned, and build systems for tracking customer work across Product, Customer Success, and Engineering. The role also includes enabling customers to use the product independently, identifying when custom work should become a product feature, and managing and developing the deployment team, initially including a deployment strategist.

Requirements

• Experience owning implementation, solutions, or another technical customer-facing delivery role at a B2B software company.
• Experience managing technical customer relationships at a level sufficient to coach others.
• A track record that earns the trust of engineers.
• Technical aptitude to learn a complex product, configure workflows, understand integrations, and ask engineers informed questions.
• Strong operational judgment, understanding of how a business runs, care for customer margins, and ability to identify issues early.
• Excellent written and verbal communication.
• High ownership and a hands-on approach; willingness to do initial work directly.

Responsibilities

• Own customer deployments, including onboarding and new product features and rollouts.
• Manage implementations end to end, from contract signature through onboarding, go-live, and steady-state adoption.
• Personally lead important customer implementations and develop a playbook based on experience.
• Partner with engineering and product leadership on changes that reduce engineering's involvement in customer builds.
• Work with Product to train and enable customers and create documentation that supports self-service.
• Build and own a project management system that tracks customer-build status across Product, Customer Success, and Engineering.
• Manage escalations between Engineering and Customer Success.
• Scope customer requests into clear, realistic requirements and manage customer expectations.
• Scope integrations with customers and partners.
• Learn the product deeply and configure workflows and agents hands-on; identify when a one-off solution should become a product feature.
• Own rollouts and custom workflows that drive expansion with existing customers.
• Provide enablement, training, and documentation so customers can get more value independently.
• Manage and develop the deployment team, starting with the deployment strategist.

Benefits

• Top-tier cash and equity compensation, intended to be above the 75th percentile for companies that have raised a similar amount of cash.
• Competitive medical, dental, and vision benefits.
• Fully covered lunches and dinners.
• Opportunity to learn quickly, grow fast, and be rewarded for contributions.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed