Obsidian is more than a hospitality company — it’s a team of passionate people redefining what group travel can be. If you believe in quality, authenticity, and making people feel at home, you belong here.
At Obsidian, you’re not a cog in a machine. You’re part of a small, intentional team where every person has real impact. Our flat structure means your ideas are heard, your contributions are valued, and your growth is prioritized.
We’re building something that didn’t exist before: a hospitality brand that puts groups first, that treats every guest like family, and that proves you can run a premium business without losing your soul. That takes a special kind of team.
We’re looking for people who: care deeply about quality, thrive in autonomous environments, and believe that the best work happens when you genuinely love what you do.
Benefits & Perks
We invest in our people because we believe great hospitality starts with happy employees.
Above-market salaries, performance bonuses, and profit-sharing for senior roles. We believe great work deserves great pay.
Comprehensive health insurance, dental, vision, and mental health support. Your wellbeing is our priority — in and out of work.
Flexible hours, remote work options where applicable, and generous PTO. We trust you to manage your time and deliver results.
Based in Sint Maarten? Enjoy island living as part of your daily routine. Beach days, stunning sunsets, and a community that feels like home.
Annual learning budget, mentorship programs, and clear career pathways. We invest in your growth because your growth is our growth.
Quarterly team retreats, annual company trips, and regular social events. We work hard together and play hard together.
That’s what our team says. And it’s not a marketing line — it’s the truth. When you love what you do and who you do it with, work doesn’t feel like work.
Our Values
These values guide every decision we make, every hire we make, and every experience we create.
We never compromise on quality — in our properties, our service, or our team. If it's not good enough for our guests, it's not good enough for us.
Our guests, our team, our partners — people come before profits. When we take care of people, the business takes care of itself.
We're real. No corporate speak, no fake smiles. We show up as ourselves — flawed, passionate, and genuinely committed to what we do.
We're always learning, always improving. We embrace feedback, challenge assumptions, and never settle for "good enough."
Every team member thinks like an owner. We take responsibility, make decisions, and act with the understanding that this is our company too.
We're part of this island's story. We support local businesses, employ local talent, and give back to the community that makes Obsidian possible.
Everything you need to know about applying and working at Obsidian.
Our process is designed to be thorough but respectful of your time. It typically includes: (1) Application review, (2) Phone or video screening with our people team, (3) Interview with the hiring manager, (4) Team interview or skills assessment, and (5) Final conversation with leadership. The entire process usually takes 2–3 weeks.
Yes! Many of our roles offer remote or hybrid options. Technology, marketing, and some operations roles can be done remotely. Concierge and property-based roles require presence in Sint Maarten. Each job listing specifies the work arrangement.
Not necessarily. For on-site roles, we can assist with relocation and visa processes. For remote roles, you can work from anywhere. We have team members in Sint Maarten, the United States, Canada, and Europe. What matters most is your commitment to the work and our team.
We’re always interested in talented people. Select “Other / General Application” in the position dropdown and tell us about yourself, your skills, and what kind of role you’re looking for. We’ll keep your information on file and reach out when something aligns.
We’re a small, close-knit team that values authenticity, quality, and people. We work hard but also know how to have fun. There’s no corporate bureaucracy — just passionate people doing meaningful work together. If you read our team testimonials, you’ll get a genuine sense of what it’s like here.
We occasionally offer internships and entry-level positions, particularly in concierge, marketing, and operations. These are typically seasonal or project-based. Follow us on social media or check this page regularly for updates on entry-level opportunities.
Obsidian isn’t just a company — it’s a team of people who believe in what they’re building. If that sounds like the kind of place you want to be, we’d love to hear from you.
