Head of Sales

The Role: You sell out the trips. Every departure has a date and a seat count, and your job is to fill it, on time, at price, and then do it again for the next one. Some of the pipeline is warm: past guests, their referrals, the founder's network, and inbound from our brand partners. The rest is net new: sophisticated, well-traveled people who need to be closed properly by someone who can hold the room. You will run both. You will text, call, Zoom, and sit across a dinner table. You will find the real objection (the spouse, the dates, the last trip that disappointed them) and you will get every prospect to a yes or a no. Nobody drifts. The founder has personally sold every trip to date. He will hand you the prospects, the story, and every objection he has heard. Then he will get out of the way. Your job is to sell so well that he never feels the need to step back in. You will build the system as you go: the HubSpot pipeline, the follow-up cadence, the reporting, the playbook. And when the volume justifies it, you will hire, train, and lead the salesperson who comes after you. You are not filling this seat. You are defining it. What You OwnThe trips. Each departure sold out, on time, at price. There is nowhere to hide in that number. The close. Discovery that surfaces the real objection, a next step on every conversation, and a firm yes or no from every prospect on the list. Price integrity. The date moves the price. The person never does. No one-off deals. You are paid on the price you achieve, not just the booking you log. The pipeline. Every prospect, every stage, every next step in HubSpot, with dashboards you built. If it is not in the system, it did not happen. The referral ask. After every deposit, without exception: who do you know who would make this trip better, and where do you still want to go. The next departure gets designed off those answers. Partner inbound. Leads from our hotel and coaching partners answered within the hour and closed by us, not by them. New channels. You open relationships with clubs, peer communities, and partner brands yourself, and you work them until they produce guests. On-trip and post-trip selling. The next departure converted while the excitement is highest. The next hire. When the volume calls for it, you write the job description, you interview, you train, and you set the bar. What You Have to BringFive or more years selling high-ticket, personal-purchase products or experiences to founders, executives, and wealthy families. Luxury real estate, yachts, aircraft, art, private club or residence memberships, private banking or wealth management, ultra-luxury travel, high-ticket CEO peer groups or coaching. Six-figure decisions made by the person paying. A closing record we can check. Personal-purchase decisions of $100,000 and up. How many, average ticket, close rate, and where the leads came from. Bring the numbers, not the narrative. Comfort with affluence and authority. You hold a peer-level conversation with a founder, a CEO, or the head of a family office without shrinking and without over-selling. You have been in their homes, their offices, and their group chats. Wisdom and hunger in the same person. You have built or run a sales function before, and you still want to make the first hundred calls yourself. Most people have one or the other. Follow-up discipline that does not need permission. You know the deal goes to the person who stays in touch, and you have a system for it. HubSpot fluency, or the ability to get there in a week. You will build the pipeline, the stages, the reporting, and the dashboards Discretion. Our guests' names, our economics, and how full a trip is never leave the building. Our guests are people whose names you know, and they expect that. Availability on the buyer's schedule. Evenings, weekends, time zones, and travel to meet prospects in person when it earns the sale. Coachable and self-critical. Every call is recorded. You want it reviewed. You treat a lost deal as data, not as a wound. What Would Put You At the FrontAny time in private aviation or ultra-luxury travel. Not required. Noticed. You have traveled the way our guests travel: private or charter flights, expeditions, safari, helicopters, small boats. You can sell the experience because you have lived it. You have sold experiences or memberships to couples, where two people have to say yes, not one. You have worked inside a luxury brand partnership or a white-label program and know how to close a lead that arrived trusting someone else's name. You have sold into founder and CEO peer communities and understand how a room of peers decides.

What Success Looks Like: We are direct about expectations. You should be too. Ninety days. Every prospect on the current departure has had a live conversation, not just a text, and carries a yes, a no, or a dated next step in HubSpot. The pace toward sold-out is ahead of plan. Your calls have been reviewed and the scripts are sharper because of it. Twelve months. The current departure sold out at price. The next two trips launched with a sales plan you wrote. The founder has not been on a sales call in six months. A documented playbook a second salesperson could run. Beyond that. A team underneath you, a profit share that means something, and the path to leading revenue across every trip we run. We would rather promote the person who proved it than hire a stranger to manage them. Compensation The best salespeople are not incrementally better than average ones. They are multiples better. We pay like we believe that, because we do. Base plus uncapped commission per seat closed, an accelerator on the price you achieve, and a profit share on every departure you sell out. No equity, and we will say so up front. We finalize the specific numbers with the right person. We are not looking for cheap. We are looking for the best. Here is the honest version. Do this well and you are the number one closer of private jet expeditions in the world, with earnings to match. But today, if you do not kill, you do not eat.

How To Apply: Do not send us a generic CV. Send proof to Your numbers. The last three years: what you sold, to whom, average ticket, close rate, and where the leads came from. One deal. The best six-figure personal-purchase decision you ever closed. How you found it, how you worked it, what almost killed it, and how you won it. One loss. A six-figure deal you lost and what you would do differently now. We learn more from this answer than from the first two. Five minutes of you selling. A recorded call or a mock close. Sell us a $300,000 trip to a couple who "need to think about it." Show us how you sell.