Work directly with a proven founder.
Eric has built and exited multiple companies and leads Zillow Home Loans. You'll get real mentorship — direct access, real decisions, real feedback. No middle-manager buffer. LinkedIn →
Careers at Drift
We're looking for builders who move fast, think in systems, and want to shape how AI-native companies actually work.
Open Role
Drift is an AI-powered luxury yacht charter concierge. We connect travelers with the world's best charter providers through a conversational AI experience — think Kayak meets a really knowledgeable friend who's sailed everywhere.
We're pre-launch, moving fast, and building something genuinely new: a business designed from day one to be run by AI agents, with humans steering strategy and creative direction.
Our founder, Eric Wilson, is a tech executive who leads Zillow Home Loans and has multiple startup exits. Our AI general manager, Trevor, is already live — an autonomous agent that manages operations, writes code, creates content, designs product, and runs 24/7 across every function of the business.
As our Orchestrator in Residence, you'll work directly with Eric and Trevor to take Drift from beta to market. You'll build product, create content, design systems, and — critically — architect the agentic automation that makes the business self-sustaining.
This isn't a "learn by watching" role. You'll ship real product to real users from week one. The AI does the heavy lifting on execution; your job is to direct it, QA it, improve it, and push the boundaries of what's possible.
Daily progress is expected. That doesn't mean you need to be working around the clock — it means you need the foresight to set Trevor up with the right tasks so work keeps moving, even on nights and weekends.
Eric has built and exited multiple companies and leads Zillow Home Loans. You'll get real mentorship — direct access, real decisions, real feedback. No middle-manager buffer. LinkedIn →
Trevor is not a chatbot or a demo. He's an autonomous AI agent already running the business — writing code, creating content, managing deployments, and coordinating tools 24/7. You'll learn to orchestrate AI at a level most people won't touch for years.
Everything you build goes live immediately. Real users, real stakes, real portfolio pieces. In 3 months, you'll have more shipped work than most people accumulate in 3 years.
The intersection of AI agents and business operations is brand new territory. You'll help write the rules for how AI-native companies actually run.
No set hours. No time tracking. No busywork. We care about outcomes. If you can get the job done in 4 focused hours a day plus smart delegation to Trevor, that's a win.
Eric is a tech founder and executive with 15+ years building and scaling companies. He leads Zillow Home Loans and has multiple successful exits. He and his wife Cathy own a 46-foot Lagoon catamaran (WAGMI) in the British Virgin Islands — and he's building Drift to modernize the $5B+ yacht charter industry. This is a rare opportunity to work 1:1 with a senior tech leader on a ground-floor venture. Connect on LinkedIn →
Send a short note to hello@driftyacht.com with the subject:
"OIR — [Your Name]"
Include a link to something you've built, your take on how AI should run a business (2-3 sentences), and your resume or LinkedIn.
Bonus: 60-second Loom video introducing yourself.
Apply Now