Head of Sales

Head of Sales

Private jet expeditions | You personally sell out the trips | Remote, U.S. NOT REQUIRED, with travel | Base plus uncapped commission plus profit share on sold-out departures

Scroll down the page to see all associated job requirements, and any responsibilities successful candidates can expect.

You Should Not Apply for This Job If

• You have never sold something expensive to someone spending their own money. Luxury real estate, yachts, aircraft, art, private club or residence memberships, wealth management, ultra-luxury travel, high-ticket CEO peer groups or coaching. A corporate sales background counts if you have also closed six-figure decisions with the person paying. If every deal you have closed ran through a company budget, this is a different buyer and a different conversation, and our pipeline is not where you learn it.
• You have never personally closed a six-figure decision with a wealthy founder, executive, or family. One person, or one couple, deciding on a call with you to spend roughly $300,000 of their own money. Many deals like that, not one. If you have to wonder whether your deals count, they do not.
• Your best numbers came from a brand doing the selling for you. Some of our buyers arrive trusting a hotel logo or a friend. Most of the ones you will work have never heard of us. You have to earn the yes from a stranger, at full price.
• You are too senior to pick up the phone. This seat starts at the bottom. You will personally text, call, follow up, and close every prospect until the trip is full. If your first instinct is to hire a team so you can manage it, do not apply. We have made that hire before.
• You flinch at the number. If the silence after you say three hundred thousand makes you uncomfortable, this will be miserable for you.
• You are looking for a seat, not a stake. This seat exists to take the founder out of the sales conversation for good and to build the team that comes after you. If your plan is to coast at quota, do not take the interview.

We want winners. We are not for everybody, and we do not want to be. We would rather you self-select out now than discover it in month two. No hard feelings either way.

Still here? Good. Here is what this actually is.

Who You Would Be Selling For

Bucketlist Xperiences runs route-based, invitation-only expeditions around the world aboard a fully custom private jet. A typical departure takes about 25 couples across several countries over 16 to 20 days, with the entire aircraft reconfigured to lie-flat. Our guests do things almost nobody else on earth gets to do: dinner with a royal family, a military helicopter to hike with gorillas, a private audience with a head of state.

Eighty percent of our guests come back. We are now growing past our referral base. We are building white-label expeditions with one of the most recognized luxury hotel brands in the world, a departure built with a national CEO coaching organization, and Private Expeditions: fully custom trips for a single family or a group of four to six couples, starting at seven figures. Buyers on those trips arrive trusting a brand or a peer. They do not yet know us.

We have the product, the guests, the referrals, and the partners. What we do not have is the person who owns the moment between "this sounds incredible" and a signed deposit. That is the whole job. It is open because it matters.

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 Own

• The 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 Bring

• Five 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 Front

• Any 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. xuwmhxw Sell us a $300,000 trip to a couple who "need to think about it." Show us how you sell.