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Careers · Engineering

Chief Technology Officer

Own the platform the business runs on, from the booking site and operator portal to the apps, and build the engineering team around it.
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

The product is built and in production: an instant all-in price, deposits and balance collection, an operator portal, a staff console, matching with live FMCSA checks, a chat assistant, and a pricing service the founder wrote. It was built fast, by the founder with AI coding tools, and it needs a technical owner who will keep it honest, keep it up and decide what comes next.

You’d be our first technical leader: own the stack, the roadmap and the standards, ship with your own hands for a good while, and hire the engineers after you. The stack is modern and boring on purpose: TypeScript, Next.js, Postgres, Stripe, Vercel.

What you’d do

  • Own the whole platform: the booking site, the operator portal, the ops console, the pricing service and the integrations behind them, from payments and maps to FMCSA, email and telephony.
  • Ship. For a good while you’re the engineer, AI tools and all.
  • Keep customer and operator data safe. Money moves here, and we hold personal information, driver details and payment flows. Security and access control are yours.
  • Decide with the founder what gets built next and what doesn’t, from what customers, operators and the ops team actually hit.
  • Set the engineering standards: tests, reviews, migrations, on-call, and how we use AI in the codebase without losing the plot.
  • Hire and lead the engineering team when the business earns it, and know the difference between then and now.
  • Be the technical voice with partners: operators’ telematics platforms, payment providers, enterprise clients’ IT and procurement.

Your first 90 days

  1. 01Days 1 to 30: read the codebase, run a trip end to end in production, and write down what worries you.
  2. 02Days 31 to 60: own deploys, incidents and the security posture, and fix the things that worried you most.
  3. 03Days 61 to 90: a 12-month technical roadmap agreed with the founder, and a hiring plan with the first role defined.

You might be a fit if

  • You’ve been the senior or lead engineer on a product that took real money from real customers, and you’ve been paged for it.
  • You’re fluent in TypeScript and at home across the stack: React, Node, Postgres, a cloud platform, payments.
  • You’ve worked on a product with customers on one side and suppliers on the other, or in logistics or travel, or you want to learn how buses, operators and FMCSA rules fit together.
  • You use AI coding tools well, and you can tell when they’re wrong.
  • You’d rather delete code than add a service.
  • You’ve hired engineers, or you’ve been the person who should have been doing the hiring.

Probably not for you if

  • You want to architect and delegate. There’s nobody to delegate to yet.
  • You need a big team or a big budget to do good work.
  • Rewriting it in your favorite framework is the first thing you’d do.

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 “Chief Technology Officer” 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.