Careers
SendSites is a lean, founder-led company. We don't post formal job listings. When we hire, we look for a specific kind of person — and we'd rather find them through a good conversation than a résumé stack.
If what you read here resonates, we'd like to hear from you.
Who thrives here
You enjoy making people's work easier. That's not a job requirement — it's how you're wired.
Your standards come from inside. Mediocre work bothers you — not because someone is watching.
You thrive remotely. You hold yourself accountable without needing external structure.
The people who do their best work at SendSites share a few things in common.
They are genuinely service-oriented — not in a performative way, but in the sense that making someone's day easier or their results better is its own reward. They bring high standards to everything they touch, not because they're managed to, but because doing something poorly simply doesn't sit right with them. And they work well independently — they're self-directed, remote-capable, and comfortable holding themselves to a high bar without external structure or oversight.
If that sounds obvious, it isn't. Those traits are rarer than they seem, and they're what make someone genuinely effective here.
The world we work in
Hospitality is a genuinely interesting industry to work in.
The people are warm, service-oriented, and passionate about what they do. The properties are remarkable — grand resort collections, remote mountain retreats, iconic cruise lines, destination cities that people plan trips around for years. And the work gives you a front-row view into how these places present themselves, tell their stories, and compete for the business that keeps them running.
You won't be staying at The Broadmoor or sailing on Windstar. But you'll know them well — their spaces, their sales teams, their challenges, and what makes them exceptional. For someone who finds that world interesting, it's a genuinely enjoyable place to spend your working hours.
Areas of interest
No formal postings — but two areas where we're consistently open to the right people.
Customer success at SendSites isn't a support function — it's the core of how we retain and grow. Our CS team maintains direct, personal relationships with every account. They onboard new customers, ensure the platform is being used effectively, and are often the reason a renewal conversation is a formality rather than a negotiation.
We're interested in people who find genuine satisfaction in a customer who launches confidently, figures something out, or closes a deal they're proud of. People who listen well, communicate clearly, and bring warmth and competence to every interaction. Hospitality industry experience is a plus — but not required. The right instincts matter more than the right résumé.
We're not looking for a specific number of years of experience or a particular stack. We're looking for someone who thinks of code as craft — who finds satisfaction in an elegant solution and frustration in one that merely works.
We're especially interested in people who have been genuinely curious about AI — not because it's fashionable, but because they see it as a capable collaborator and have spent time figuring out what that actually means in practice. Someone who has experimented widely, thought carefully about what it actually makes possible — and is as interested in the new problems it introduces as the ones it solves.
The work here is meaningful and the surface area is wide. A small team means your fingerprints are on everything. If you find that energizing rather than overwhelming, we should talk.
What to expect
SendSites is a founder-led company. We're lean, remote, and deliberate about how we grow. We don't move fast and break things. We move carefully and build things that last — because our customers depend on us and our reputation depends on them staying.
Working here means real ownership of your work, direct access to decision-makers, and the satisfaction of seeing the impact of what you build or do. It also means operating without the infrastructure of a larger company — you won't have a dedicated team for every function, and you'll need to be comfortable with that ambiguity.
We think that's a fair trade for the right person. We hope you do too.
We don't post formal job listings. If what you've read here resonates — if you recognize yourself in the kind of person we've described — we'd like to hear from you. Tell us a little about yourself, what you're interested in, and what you've been working on. We read everything and respond to everyone who takes the time to reach out thoughtfully.