VP of Transportation & Fleet Operations $200,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Not accepting applications on crossover.com at this time.
Description
You’ve built the transportation playbook before — not just run it. You created the audits, wrote the checklists, set the SLAs, and held the vendors to them. When something breaks, you fix the root, not the symptom.
At 2 Hour Learning, we compress an entire school day into just two focused hours, unlocking time for students to build life skills, explore passions, and grow into exceptional humans. Our academic model is new, but our families’ expectations are not. They demand precision, polish, and professionalism in every part of the experience. Transportation included.
In this role, you’ll design how transportation works across the country. Not just today — but at scale. You’ll build the systems that campuses use to run flawless daily pickups, multi-leg trips, and everything in between. You’ll define what “ready” means, how vendors are selected and scored, and when something should be escalated to you. You’ll start hands-on — walking the lot, running dispatch, answering the 6 a.m. call — and then you’ll build the structure that means you don’t have to. You’re not here to manage the chaos. You’re here to eliminate it.
What you will be doing
- Designing the national transportation playbook: systems, standards, escalation paths, and contingency plans
- Building scalable processes that campuses can run independently — with you stepping in only for edge cases or critical failures
- Creating tools and infrastructure: vendor scorecards, audit checklists, standard contracts, and readiness dashboards
- Leading initial operations where needed, then sourcing, training, or automating your way out of them
- Establishing visibility across campuses to catch issues before they reach families
What you will NOT be doing
- Running routes forever. You're expected to build systems that replace yourself in day-to-day logistics.
- Accepting inconsistency across campuses. You’ll define what “good” looks like and make it stick.
- Relying on others to escalate problems. Your systems will surface risks before they break trust.
- Managing from behind a screen. This is a field-based, real-world role with a 50–75% on-site expectation.
- Delivering commodity transportation. Every ride reflects the standards of a premium brand.
Key responsibilities
Architect and implement a national transportation model that any campus can run — ensuring safe, seamless, high-trust travel for families at scale.
Candidate requirements
- 3+ years leading transportation, fleet, or logistics operations in high-accountability settings
- Demonstrated experience building systems across multiple jurisdictions or regions
- Strong communication skills with both field teams and family-facing stakeholders
- Proven track record of owning outcomes, not just managing processes
- Based in the US, eligible to work without sponsorship, and able to travel frequently (50–75%)
Nice to have
- Background in private education, charter networks, mobility startups, or other premium service fields
- Experience designing operational systems from scratch (vs inheriting legacy tools)
- Familiarity with vehicle compliance and transportation regulations in multiple states
- Leadership experience across distributed or multi-site environments
Applying for a role? Here’s what to expect.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
Chat-style screening interview.
Cognitive aptitude test.
Prove real-world job skills.
Interview with the hiring manager.
Accept job offer.
Pass proctored test.
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