Head of Solutions Engineering

FleetWorks • Chicago, IL

9d

About The Position

FleetWorks is hiring a Head of Solutions Engineering to own the technical customer journey, from onboarding and implementation through custom builds that support customers’ core business. The role works with freight brokers, whose operations vary, to translate their needs into realistic projects that engineering can deliver while setting and managing expectations on both sides.

The person in this role will personally lead the company’s most important implementations and develop a playbook based on what they learn. They will own deployments and customer implementations end to end, partner with Product and Engineering to improve delivery, and build the systems, training, and documentation that help customers adopt the product and use it more independently. The role will also manage and develop 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 where you can coach others.
• A track record that earns the trust of engineers.
• Technical ability to learn a complex product deeply, configure workflows, read an integration, and ask engineers the right questions.
• Strong operational instincts, 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 build the first version personally.

Responsibilities

• Own customer deployments at the intersection of customers and engineering, including onboarding, new product features, and rollouts.
• Lead 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 creating documentation that helps users self-serve.
• Build a project management system used across Product, Customer Success, and Engineering to track the status of customer builds.
• Own escalations between Engineering and Customer Success.
• Scope customer requests into clear, realistic requirements and manage expectations.
• Scope integrations with customers and partners.
• Learn the product deeply and configure workflows and agents hands-on, identifying when one-off solutions should become product features.
• 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.
• Personally run important implementations and develop an implementation playbook from experience.

Benefits

• Top-tier cash and equity compensation, targeting 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: Senior
• Education Level: No Education Listed