[Hiring] Director, Fleet Solutions @Waabi

Role Description

You will...

• Solidify yourself as a truck purchasing/selling SME.
• Meet with customers evaluating fleet purchases and talk shop from a position of real experience with the nuances of the buying process.
• Own customer value cases.
• Build value propositions grounded in the customer's actual network and freight data (lane economics, fleet sizing, utilization) and present them to VP/C-level audiences at carriers, shippers, and private fleets.
• Speak TCO at the line-item level.
• Tractor lifecycle, depreciation and residuals, driver cost structures, fuel, insurance, maintenance, empty miles, cost-per-mile vs. cost-of-ownership — and clearly articulate the cost impact of autonomy against the customer's current operating reality.
• Hold your own in operational discussions.
• Responsible for quickly comprehending customer's supply chains, pain points and areas of opportunity. Propose solutions that fit within their desired operating model.
• Support customer hosting.
• Partner with your Commercial sales counterpart to run demos, on-sites, and multi-day working sessions as the face of the solutions engagement, owning both the room and the agenda.
• Shape the commercial constructs behind a pilot.
• Work with Sales, Product, and Finance on the structures behind a signed pilot, and with Operations on what can actually be committed and when.
• Build with AI tooling.
• Use Claude Code / Codex daily to build and extend analysis pipelines, models, and customer deliverables in a shared codebase.
• Scale the playbook.
• Turn one-off analyses into repeatable frameworks so each new customer engagement is faster than the last. As the team grows, help shape it — mentoring future hires and building out the function.

Qualifications

• 10+ years in trucking or logistics, with deep exposure to fleet operations or truck OEMs — carrier network and pricing leadership, fleet management, or OEM vocational/TCO sales engineering (or a comparable path).
• Direct experience in the Class 8 equipment lifecycle — buying, selling, or leasing.
• A demonstrated record of building and presenting quantitative value propositions and business cases to senior executives.
• Strong quantitative modeling skills, with the ability to apply them inside an agentic coding environment.
• Autonomous vehicle or fleet-tech exposure strongly preferred.
• Executive presence — sharp storytelling, strong deck craft, and the judgment to know what belongs on a slide and what doesn't.
• Integrity under commercial pressure — holds the line on what the technology and the timeline can and cannot support.
• Comfort operating in ambiguity — early-commercial-stage motion, evolving pricing, no established playbook.

Requirements

• Experience with freight data — TMS extracts, rate benchmarks (e.g., DAT), network optimization.
• Working, current fluency with AI coding agents (Claude Code, Codex, or equivalent).
• Prior experience in consulting or solutions engineering.

Benefits

• Competitive compensation and equity awards.
• Health and Wellness benefits encompassing Medical, Dental and Vision coverage (for full-time employees only).
• Unlimited Vacation.
• Flexible hours and Work from Home support.
• Daily drinks, snacks and catered meals (when in office).
• Regularly scheduled team building activities and social events both on-site, off-site & virtually.
• As we grow, this list continues to evolve!