Head of Sales (Luxury Travel)

★ PLEASE SUBMIT YOUR CV IN ENGLISH ★

Head of Sales (Luxury Travel)

Location: Remote - Mexico, with travel to meet clients in person
Work Arrangement: Remote position with travel when it earns the sale.
Employment Type: Full-time
Industry: Luxury Travel / Private Jet Expeditions
Compensation: $8,000-$10,000 USD/month, plus uncapped commission, an accelerator on the price achieved, and profit share on every sold-out departure. No equity.
Reports To: The President
Schedule: On the buyer's schedule, including evenings, weekends, and multiple time zones
Start Date: To be confirmed
Experience: 5+ years selling high-ticket, personal-purchase products or experiences to founders, executives, and wealthy families
Languages: Excellent spoken and written English, plus Spanish or Portuguese (required for Latin American markets)

About the Company

Our client is an invitation-only luxury travel company that runs route-based 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 configured with lie-flat seats. Guests do things almost nobody else gets to do, from a dinner with a royal family to a private audience with a head of state.

Its guests are founders, CEOs, and families who have already flown first class everywhere. Eighty percent of guests come back, the company reports a Net Promoter Score of 100, and trips have sold out in minutes and oversubscribed into back-to-back departures.

The company is now growing past its referral base: white-label expeditions with one of the world's most recognized luxury hotel brands, a departure built with a national CEO coaching organization, and fully custom Private Expeditions for a single family or a small group of couples, starting at seven figures.

About the Role

Our client is seeking a Head of Sales who will personally sell out its private jet expeditions. Every departure has a date and a seat count. The job is to fill it on time and at full price, then do it again for the next one.

Part of the pipeline is warm: past guests, their referrals, the founder's network, and inbound from brand partners. The rest is net new, made up of sophisticated, well-traveled buyers who need to be closed by someone who can hold the room. You will text, call, run video calls, and sit across a dinner table, and you will get every prospect to a clear yes or no.

The founder has sold every trip to date. He will hand you the buyers, the story, and every objection he has heard, and then step back. You will also build the sales system as you go (the HubSpot pipeline, follow-up cadence, reporting, and playbook), and when volume justifies it, you will hire, train, and lead the next salesperson.

This seat starts hands-on. It is a strong fit for someone who has built or run a sales function before and still wants to make the first hundred calls personally.

Why This Opportunity?

• Sell a product with an 80% repeat rate and a Net Promoter Score of 100.
• Typical decisions of about $300,000 per couple, with custom expeditions starting at seven figures.
• $8,000-$10,000 USD/month, plus uncapped commission, an accelerator, and profit share on sold-out departures.
• Warm flow from past guests, referrals, and luxury brand partners, plus direct coaching from a founder who has sold every departure.
• A clear path to leading revenue across every trip the company runs, including hiring the next salesperson.
• Remote role with travel, working with some of the most influential travelers in the world.

What You'll Do

Sell Out Every Departure

• Fill each departure on time and at full price.
• Run discovery that surfaces the real objection (the spouse, the dates, the last trip that disappointed them) and secure a next step on every conversation.
• Get a firm yes or no from every prospect on the list. Nobody drifts.
• Hold price integrity: the date can move the price, the person never does. No one-off deals.

Pipeline, Follow-Up & Partner Leads

• Follow up relentlessly: every other day until they answer, then daily, then by phone.
• Answer leads from hotel and coaching partners within the hour, and close them.
• Ask for referrals after every deposit, and convert the next departure on-trip and post-trip while excitement is highest.

Build the Sales System

• Track every prospect, stage, and next step in HubSpot, with dashboards you build yourself.
• Record and review every call, using the company's AI coaching system to get measurably better each week.
• Write the sales plans and the playbook a second salesperson could run.

Build the Team

• When volume calls for it, write the job description, interview, train, and set the bar for the next salesperson.

Qualifications

Required Qualifications

• 5+ 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, or high-ticket CEO peer groups or coaching).
• A closing record that can be checked: many personal-purchase decisions of $100,000 and up, with numbers on volume, average ticket, close rate, and lead sources.
• Comfort holding peer-level conversations with founders, CEOs, and heads of family offices, without shrinking or over-selling.
• Follow-up discipline that does not need a manager.
• HubSpot fluency, or the ability to get there within a week.
• Discretion with client names, economics, and trip details.
• Availability on the buyer's schedule, including evenings, weekends, other time zones, and travel to meet prospects in person.
• Coachable and self-critical: comfortable with every call being recorded and reviewed.
• Excellent spoken and written English, plus Spanish or Portuguese.

Preferred Qualifications

• Experience in private aviation or ultra-luxury travel (a plus, not required).
• A book of wealthy clients who would take your call about where they should travel next.
• Experience selling experiences or memberships to couples, where two people have to say yes.
• Experience closing leads from a luxury brand partnership or white-label program.
• Experience selling into founder and CEO peer communities.
• Experience taking a sales function from a spreadsheet to a system: CRM, cadence, reporting, and the next hire.

Tools You Will Use

HubSpot CRM, call recording with AI coaching, phone, text, and video calls.

How Success Is Measured

• First 90 days: every prospect on the current departure has had a live conversation and carries a yes, a no, or a dated next step in HubSpot. The pace toward a sold-out trip is ahead of plan, and your scripts are sharper because your calls were reviewed.
• First 12 months: the current departure is sold out at price, the next two trips have launched with a sales plan you wrote, the founder has not been on a sales call in six months, and there is a documented playbook a second salesperson could run.
• Beyond that: a team underneath you, a profit share that means something, and a path to leading revenue across every trip the company runs.

Why Join Us

• Competitive compensation: $8,000-$10,000 USD/month, plus uncapped commission, an accelerator, and profit share.
• A world-class product with an 80% repeat rate and a Net Promoter Score of 100.
• Direct access to a founder who has sold every departure and will teach you the buyer.
• Recorded calls and AI coaching on every conversation.
• A seat built to grow into leading revenue for the company.
• Remote work with travel, and a client base of some of the most influential people in the world.

Important Notes

This seat starts hands-on. You will personally text, call, follow up, and close every prospect until each trip is full. There is no equity.

Applications may not be considered if candidates:

• Have never personally closed a six-figure decision with the person actually paying.
• Have mainly sold to budget owners inside companies (B2B) rather than to individuals spending their own money.
• Need a team underneath them before picking up the phone.
• Are not available evenings, weekends, across time zones, or for travel.
• Do not have excellent English plus Spanish or Portuguese.

Please submit your CV in English, highlighting your high-ticket, personal-purchase sales experience. If possible, include (in your CV or cover letter) your numbers for the last three years: what you sold, to whom, average ticket, close rate, and where your leads came from. Shortlisted candidates will be asked to walk through their best six-figure close, a six-figure deal they lost and what they would do differently, and five minutes of selling (a recorded call or a mock close of a $300,000 trip to a couple who "need to think about it").

This is a remote position with travel.