Senior Implementation Lead

Overview

Truckbase is building the modern transportation management system for specialized and growing trucking companies. Our customers run complex operations—heavy haul, open deck, specialized freight, brokerage, and other transportation businesses where implementation requires much more than configuring a few settings.

We’re looking for an experienced Implementation Lead to own complex customer implementations from kickoff through successful go-live.

This is a highly customer-facing, hands-on role. You’ll work directly with operations leaders, executives, dispatchers, accounting teams, and drivers to understand how their businesses operate, configure Truckbase around their workflows, migrate data, coordinate integrations, train teams, and guide customers through change.

You’ll also help us continuously improve how we implement Truckbase.

What you'll do

• Own customer implementations end-to-end, from sales handoff through go-live and stabilization
• Lead discovery with customers to understand their existing systems, workflows, requirements, and business processes
• Translate complex operational needs into practical configurations and implementation plans within Truckbase
• Manage implementation timelines, dependencies, risks, customer expectations, and executive communication
• Coordinate data migrations, integrations, accounting setup, and other technical implementation work with our product and engineering teams
• Conduct remote and onsite customer training for operations, dispatch, accounting, administrative, and leadership teams
• Become an expert in both the Truckbase product and the workflows of specialized trucking companies
• Identify product gaps and work closely with product and engineering to distinguish true requirements from workflow or configuration challenges
• Help develop implementation playbooks, templates, training materials, and repeatable processes that allow us to scale
• Serve as a trusted advisor to customers during one of the most important transitions in their business

What we're looking for

• 5+ years of experience in B2B software implementation, professional services, solutions consulting, or a similar customer-facing role
• Experience independently managing complex software implementations with multiple stakeholders
• Strong project-management skills and the ability to keep customers and internal teams accountable to deadlines
• Excellent communication skills, including confidence working directly with executives and operational teams
• Strong analytical ability—you enjoy understanding how businesses work and solving messy operational problems
• Comfort learning technical concepts and working with data migrations, integrations, APIs, and accounting or operational systems
• Ability to balance customer needs with product constraints rather than simply saying yes to every request
• High ownership and comfort operating in a fast-moving startup environment
• Willingness to travel regularly for customer implementations and training, typically approximately one customer trip per month
• Experience in transportation, logistics, ERP/TMS software, accounting systems, or other operationally complex industries is helpful but not required.

What success looks like

• Within your first several months, you’ll be able to independently lead some of our most important implementations with limited oversight. Customers will view you as a credible partner who understands their business, and our internal teams will trust you to identify risks, make good implementation decisions, and bring in product or engineering resources only when necessary.
• Over time, we expect you to help us make implementations faster, more predictable, and more scalable while maintaining the high level of customer engagement required for complex fleets.

About Truckbase

Truckbase is a fast-growing vertical SaaS company building transportation management software for trucking companies. We focus particularly on specialized carriers whose operational complexity is poorly served by legacy transportation software.

We’re a small team, which means this role has meaningful ownership and direct exposure to customers, product decisions, and company leadership.

Compensation & benefits

• Competitive base salary + bonus opportunities
• Meaningful equity ownership
• Health benefits
• 401(k)
• Paid time off
• Remote-first culture
• Company-paid customer travel

This role requires regular customer travel, generally about once per month, with occasional additional travel depending on implementation needs.

Location: Anywhere USA
(Travel required approximately one customer trip per month; occasional additional travel depending on implementation needs.)