Jetlago

Now hiring · Southeast Wisconsin

Open roles

Every role below is full time and W-2, based in Southeast Wisconsin. Reach out about any of them and we will set up a short screening call. No application portal to fight through.

CDL-A Driver

Open · Multiple openings

Regional line-haul middle-mile runs between customer facilities. No residential stops and no package handling — you move trailers between buildings, safely and on time, and you finish at home.

Type Full time · W-2
Based Southeast Wisconsin
Benefits Eligible

What you'll do

  • Complete assigned line-haul routes safely and on schedule
  • Perform disciplined pre-trip and post-trip inspections and report defects immediately
  • Operate within hours-of-service rules and keep logs current
  • Use in-cab telematics and safety systems as part of everyday driving
  • Stay in good standing on all required training and licensing

What we require

  • Valid Class A CDL
  • At least 21 years of age
  • Motor vehicle record and DOT compliance checks that meet our safety standard
  • Current DOT medical certification, or ability to obtain
  • Recent CDL graduates encouraged — we hire and develop new drivers deliberately
Reach out about this role

Driver Trainer

Open · 1 opening

An experienced driver who leads onboarding and behind-the-wheel coaching, certifies new hires, and carries our safety standard across the team. You still drive — you just also build the bench.

Type Full time · W-2
Based Southeast Wisconsin
Benefits Eligible

What you'll do

  • Lead onboarding and behind-the-wheel coaching for new hires
  • Certify new drivers against our standards before solo runs
  • Deliver defensive driving, load securement, and telematics training, including quarterly refreshers
  • Reinforce safety expectations daily and support incident reviews
  • Carry your own route assignments alongside training duties

What we require

  • Valid Class A CDL with a strong verifiable safety record
  • Substantial commercial driving experience
  • Demonstrated ability to coach and develop other drivers
  • Patience, professionalism, and genuine investment in other people's success
Reach out about this role

Operations Manager

Open · 1 opening

The operational heartbeat of the business, reporting directly to the General Manager. Our most important hire — the driver workforce reports to you.

Type Full time · W-2
Based Southeast Wisconsin
Benefits Eligible

What you'll do

  • Own day-to-day operations: driver scheduling and dispatch
  • Run daily driver check-ins and lead the daily safety discussion
  • Manage equipment reviews and keep assets road-ready and documented
  • Own scorecard performance and weekly KPI review
  • Maintain DOT compliance, audits, and the compliance calendar
  • Build four-week labor plans against volume forecasts

What we require

  • Experience leading frontline teams in transportation, logistics, warehousing, or a comparable operation
  • Working knowledge of DOT and hours-of-service compliance
  • Comfort with scheduling, scorecards, and operating from data
  • A safety-first instinct and the credibility to hold a standard consistently
  • CDL not required, but valued
Reach out about this role

Senior Driver

Filled from within

We do not hire Senior Drivers from outside. Proven performers who set the standard on the road and mentor newer drivers move up into it, and that bench feeds our Trainer and lead roles. If you join us as a Driver, this is the next rung — and the criteria are clear from your first day.

Filled by Internal promotion
Basis Safety record & reliability

Know a driver worth hiring?

Referrals from drivers we trust are our best long-term hiring channel, and we pay for them. If you know a CDL-A driver who belongs on a team like this, send them our way — mention the referral in your message and we will walk you through the bonus.

Equal Opportunity Employer. Jetlago is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, genetic information, marital status, or any other characteristic protected by federal, state, or local law. We are committed to providing reasonable accommodation to applicants with disabilities — if you need an accommodation at any point in the hiring process, tell us in your message and we will arrange it. All offers are contingent on motor vehicle record and DOT compliance checks, and on federally required pre-employment screening.

Open invitation

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We are growing, and we would rather meet a strong driver early than miss them entirely. Tell us what you are looking for.

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