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Careers · Operations

Director of Operations

Run the operator network and every trip on it: vetting, matching, backup when an operator falls through, and the playbook for doing it in all 50 states.
Send your resumeRemote, US · Full time
Location
Remote, US
Reports to
Reports to the founder
Type
Full time

About SimpleShuttles

SimpleShuttles books group charter buses in all 50 states: one all-in price in seconds, a vetted independent operator, and the legwork handled from booking to drop-off.

We’re an early-stage startup. The product is built and live, the company is founder-run today, and the next few hires will shape what it becomes. We exist to serve our customers and to serve our operators, and we win on transparency: no hidden fees, no fine print, no surprises for either side.

The role

Every trip we book runs on an independent, licensed operator. Our promise is that the bus still shows up: the operator is vetted before they ever see a trip, the driver is confirmed the day before, and if an operator falls through we replace them at the booked price. Today the founder keeps that promise by hand. This role owns it, and makes it hold as we grow.

You’d run the supply side of the business: recruiting operators into the network, keeping the vetting gate honest, matching trips to the right operator, and writing the playbook for doing all of it in all 50 states. The console, the operator portal and the live FMCSA checks exist. You’d decide how the operation runs on top of them.

What you’d do

  • Recruit operators into the network, state by state, starting where our trips are: the pitch, the paperwork, the portal, the first trip.
  • Own the vetting gate: active authority, insurance on file, a safety record that passes. No exceptions for a better rate.
  • Make sure every booked trip is covered: send the offers, work the phones when nobody accepts, split a big trip across operators when that’s the right call.
  • Run the day before and the day of: driver confirmations, problems reported, the backup when someone falls through.
  • Hold up our end with operators: every trip detail up front, pay on the terms we published, straight answers when something goes wrong.
  • Write the playbook: checklists, escalation paths, and the ops roles that come after you.
  • Tell the engineers what the console and the operator portal should do next, with the evidence.

Your first 90 days

  1. 01Days 1 to 30: run trips beside the founder. Learn the console, the operator portal, the vetting gate and the FMCSA checks.
  2. 02Days 31 to 60: own trip coverage and the day-before check-ins end to end.
  3. 03Days 61 to 90: an operator recruiting plan for our busiest states, the first version of the ops playbook, and a hiring plan for your team.

You might be a fit if

  • You’ve run operations where the product is other people showing up on time: charter or motorcoach, transit, logistics, field service, events or travel.
  • You know, or will learn fast, how operating authority, insurance certificates and safety ratings work, and why we check them live.
  • Operators like working with you. You negotiate fairly and you pay attention to their side of the trip.
  • You’re calm at 5 a.m. when a bus is late and clear at 5 p.m. writing up why.
  • You build systems, so the second time is easier than the first.
  • You’ve hired and run a small team, or you’re ready to.

Probably not for you if

  • You want a mature team and a playbook already written. You’re writing it.
  • You see operators as vendors to squeeze. We exist to serve them too.
  • You’d rather manage from a dashboard than get on the phone.

What you get

A founding seatYou’d be one of the first people here, working directly with the founder, with real say over how your function gets built.
EquityEarly hires own a piece of what they build.
Remote-firstWork where you live. Our trips run in all 50 states, and so do our operators.
A product that already worksA live booking site, an operator portal and an ops console, all in production. You’re not waiting on a build.
The stage, said plainlyWe’re small and pre-scale, and we say so. You’ll always know where the business stands.

How hiring works

  1. 01Send your resume with the role in the subject line. A few lines on why you want this one beat a cover letter.
  2. 02A person reads it and replies. Every resume gets an answer from someone, not a system.
  3. 03A 30-minute call with the founder: the role, where the business stands, your questions.
  4. 04A working session on a real problem from the job. A couple of hours, not a take-home project.
  5. 05References, then a written offer with everything spelled out.

Interested?

Send your resume and a few lines on why this role. A person reads it and replies.

Send your resume

Or email careers@simpleshuttles.com with “Director of Operations” in the subject line.

The other roles we’re hiring first

SimpleShuttles is an equal opportunity employer. We hire on what you can do and how you treat people, without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability or veteran status. If you need an accommodation at any step, say so in your email and we’ll sort it out.