[Hiring] Head of Sales @Entrepreneur Cooperative

Role Description

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 and will hand you the buyers, the story, and every objection he has heard.
• You will also build the sales system as you go (the HubSpot pipeline, follow-up cadence, reporting, and playbook).
• When volume justifies it, you will hire, train, and lead the next salesperson.
• This seat starts hands-on and 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.

Qualifications

• 5+ years selling high-ticket, personal-purchase products or experiences to founders, executives, and wealthy families.
• A closing record that can be checked: many personal-purchase decisions of $100,000 and up.
• Comfort holding peer-level conversations with founders, CEOs, and heads of family offices.
• 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.

Requirements

• 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.

Benefits

• 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.