Head of Sales (Remote, Commission-Only) Full Time

Sales Executive – Commission Only | Fully Remote | Travel Media

The short version

Wayfinder is a bootstrapped travel media company, and I’m looking for a closer.

This is a commission-only, fully (and permanently) remote position — and I want that to be the first thing you read, not the fine print.

What we do

I’m Shea. I’m a travel content creator with a sixteen-year background in content strategy, production, and social media — including work with some of the biggest names in publishing and entrepreneurship. I left my client work behind to build Wayfinder full time, and I’m doing it right: slow, intentional, and on my own terms.

This is a young company. I’m not going to pretend otherwise. But the content machine is running, my production capacity is effectively unlimited, and what I’m missing is someone who can go out and sell it.

The role

You’ll be building a book of business from scratch — primarily selling User-Generated Content (UGC) deals to brands across a broad range of verticals, with brand partnerships as a secondary revenue stream.

There is no existing sales process. You’ll be building it. I’ll defer to your expertise on how we get there, and I’ll be the most responsive founder you’ve ever worked with while we do it.

What you keep: 50% of every deal you close. No ceiling.

What I’m looking for

A demonstrable track record of closing deals. That part is non-negotiable.

But just as important: the temperament of a builder. Someone who sees “starting from zero” as an opportunity, not a red flag. Someone who can experiment, iterate, and figure it out — because that’s exactly what we’ll be doing together.

What you should know about working with me

I’m not going to put you through a gauntlet of interviews and take-home assignments. If you’re the right person, we’ll both know it quickly — and I’d rather judge by results than by process.

You’ll be the top priority in my life from the moment you sign on until you close your first deal. Whatever you need to get there, I’ll provide it.

The upside

The 50% commission structure pays you now — not someday. But as Wayfinder grows into a multi-creator operation, there’s real opportunity to grow into a sales leadership role for the right person.

We’re at the ground floor. That’s the point.

Wayfinder is a fully remote company. This is a commission-only position.