Head of Deployments & Customer Onboarding (Equity)

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

Benefits offered by this job

Top-tier cash and equity compensation

Competitive medical, dental, andvision

Fully covered lunches and dinners

Learning and fast growth opportunities

Job summary

FleetWorks Technology in San Francisco is seeking a Head of Deployments to own the customer journey from onboarding to go-live and expansion. You will scope work, align with engineering and product, and build the playbooks that power our deployments.

You will lead the deployment team, configure workflows, train customers, create documentation, and set clear expectations with brokers. This role blends strategy with hands-on delivery in a fast-growing B2B software environment.

Qualifications

• Experience owning implementation, solutions, or another technical customer-facing delivery role at B2B software companies.
• Experience coaching customers on technical relationships and earning engineers' trust.
• Ability to learn a complex product, configure workflows, read integrations, and ask engineers the right questions.
• Strong business orientation, understanding margins, and spotting issues early.
• Excellent written and verbal communication.
• High ownership and hands-on by default.

Responsibilities

• Own Customer Deployments at the intersection of customers and engineering, including onboarding and feature rollouts.
• End-to-end ownership from contract through onboarding, go-live, and adoption.
• Partner with engineering and product to reduce engineering workload in customer builds.
• Create documentation to enable customers to self-serve.
• Build cross-team deployment tracking and manage escalations between engineering and CS.
• Translate customer requests into clear, actionable requirements for integrations and workflows.
• Learn the product deeply and be hands-on with initial configurations.
• Lead rollout and custom workflows to drive expansion and provide enablement and training.
• Manage and develop the deployment team, starting with the deployment strategist.

Skills

Implementation mgmt

Customer-facing

Technical product knowledge

Stakeholder comms

Project management

Hands-on configuration

Job description

FleetWorks Technology in San Francisco is seeking a Head of Deployments to own the customer journey from onboarding to go-live and expansion. You will scope work, align with engineering and product, and build the playbooks that power our deployments.

You will lead the deployment team, configure workflows, train customers, create documentation, and set clear expectations with brokers. This role blends strategy with hands-on delivery in a fast-growing B2B software environment.