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Fleet Owner / Transportation Company Manager

Transportation

You went from driving one car to owning twenty. You're a small business owner in the transportation space — managing vehicles, hiring drivers, negotiating insurance, handling compliance, and trying to turn a profit in an industry where Uber and Lyft are constantly undercutting you. The overhead is real, the margins are thin, and every fender bender costs you money. But you're your own boss, you built something from nothing, and nobody can deactivate your account with an algorithm.

Salary Range

Low

$55k

Median

$65k

High

$90k

10-Year Growth

5%

US Workers

30K

Education

7+ years industry experience + business license + fleet insurance + vehicle maintenance management

Environment

indoor

Tools & Technical Skills

  • Business licensing & compliance
  • Fleet insurance management
  • Vehicle procurement & maintenance
  • Revenue management & P&L
  • Driver hiring & onboarding
  • Regulatory compliance (TLC/PUC)

People & Mindset Skills

  • Entrepreneurial drive
  • Financial discipline
  • Personnel management
  • Negotiation
  • Risk tolerance
  • Adaptability
  • Competitive strategy

What you'll actually do

  • 01Manage vehicle maintenance schedules and pray the transmission holds out one more month
  • 02Hire, train, and occasionally fire drivers — the hardest part of the job
  • 03Negotiate insurance rates that somehow go up every year regardless of your safety record
  • 04Handle regulatory compliance, licensing, and permit renewals
  • 05Review daily revenue reports and calculate whether you're actually making money
  • 06Deal with the constant pressure of rideshare apps eating into your business