Head of Sales (Luxury Travel)

About the role

A remote, full-time Head of Sales position for an invitation-only luxury travel company that runs route-based expeditions aboard a fully custom private jet. The company sells to founders, CEOs and wealthy families; the role fills each departure on time and at full price, then repeats for the next one. The founder hands over the buyers and objections and steps back, while the candidate builds the sales system and, when volume grows, hires, trains and leads the next salesperson.

Key responsibilities

• Sell out every departure: run discovery, get a clear yes or no from every prospect, and hold price integrity
• Follow up leads every other day until answered, then daily, and close leads from hotel and coaching partners within an hour
• Ask for referrals after every deposit and convert the next departure on-trip and post-trip
• Track prospects and stages in HubSpot, record and review every call with the company's AI coaching system, and write the sales plans and playbook
• When needed, write the job description, interview, train and set the bar for the next salesperson

Required profile

• 5+ years selling high-ticket, personal-purchase products or experiences to founders, executives and wealthy families
• Proven closing record of personal purchases of $100,000 and up, with numbers on volume, average ticket, close rate and lead sources
• Comfortable holding peer-level conversations with founders, CEOs and heads of family offices
• Excellent spoken and written English, plus Spanish or Portuguese (required for Latin American markets)
• Available evenings, weekends, across time zones and willing to travel to meet prospects; discretion with client names and trip details

Required skills

• HubSpot fluency, or the ability to reach it within a week
• Text, phone and video communication
• Preferred: experience in private aviation or ultra-luxury travel, building a sales function from a spreadsheet to a system, and closing leads from luxury brand partnerships

What we offer

• $8,000-$10,000 USD per month, plus uncapped commission, an accelerator on the price achieved and profit share on every sold-out departure (no equity)
• Direct coaching from a founder who has sold every departure
• Remote work with travel, working with some of the most influential travelers in the world

Applications are submitted via the recruiter's platform in English, with numbers from the last three years and a short walk-through of a big deal. Candidates who have never closed a six-figure personal purchase, who mainly sell to corporate budget owners, or who need a team before making calls are not considered.