Head of Sales - Luxury Travel

★ PLEASE SUBMIT YOUR CV IN ENGLISH ★

Head of Sales (Luxury Travel)

Location: Remote - LATAM
Work Arrangement: Fully remote. No travel required.
Employment Type: Full-time
Industry: Luxury Travel / Private Jet Expeditions
Compensation: Commission-heavy package. Competitive base salary according to the candidate's market, plus $500-$1,000 USD commission per seat sold, tiered accelerators, and a $5,000-$15,000 USD bonus for every sold-out trip.
Reports To: The President
Schedule: U.S. Eastern Time (Miami) business hours
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.

The company provides leads: inbound inquiries, past guests and their referrals, and partner leads. You will also drive outbound through partner organizations such as CEO groups, where leadership makes the introduction and you deliver the pitch and close. Event budgets are lean, so we need someone ROI-minded who chooses where to invest time and money based on results. You will text, call, and run video calls, 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.
• Commission-heavy pay: $500-$1,000 USD per seat sold, tiered accelerators, and a $5,000-$15,000 USD bonus for every sold-out trip, on top of a competitive base.
• Company-provided leads from past guests, referrals, and luxury brand partners, plus warm introductions into CEO groups and other partner organizations.
• 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.
• Fully remote role, 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

• Work the leads the company provides and 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.
• Drive outbound through partner organizations such as CEO groups: follow up on introductions, pitch, and convert members into guests.
• Measure the return on every channel and event, and put time and budget where the results are.
• Ask for referrals after every deposit, and convert past guests into the next departure 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.
• An ROI mindset: you track what each lead source and event returns and invest accordingly.
• 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.
• Full availability during U.S. Eastern Time (Miami) business hours.
• Coachable and self-critical: comfortable with every call being recorded and reviewed.
• Excellent spoken and written English, plus Spanish or Portuguese.

Preferred Qualifications

• A valid U.S. visa.
• 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, sold-out bonuses on every trip, and a path to leading revenue across every trip the company runs.

Why Join Us

• Commission-heavy compensation with real upside: per-seat commission, tiered accelerators, and sold-out trip bonuses, on top of a competitive base.
• 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.
• Fully remote work, with 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. Compensation is commission-heavy, so most of your earnings will come from the seats and trips you sell.

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 to work U.S. Eastern Time (Miami) business hours.
• 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 fully remote position for candidates based in Latin America.