Membership Director

Inspirato • Quinte West, ON

5d • $50,000 - $120,000 • Remote

About The Position

Inspirato is looking for a driven, resourceful Membership Director to join our consumer sales team. This is a consultative, full-cycle sales role responsible for guiding affluent consumers through a high-consideration purchase while delivering an exceptional buying experience. Our Membership Directors serve as trusted advisors, helping prospective members determine whether Inspirato is the right long-term travel solution for their family. Success in this role comes from conducting exceptional discovery, creating urgency, maximizing membership value, and delivering an outstanding member experience from first conversation through close. Our best Membership Directors combine strong business acumen, consultative selling skills, and a passion for luxury travel with the competitive drive to win while operating with integrity, accountability, and care in every interaction.

Requirements

• 5+ years in a quota-carrying sales role with revenue-based performance metrics, preferably in a consultative B2C environment.
• Demonstrated success selling premium, luxury, or other high-consideration products or services.
• Consistent history of meeting or exceeding sales goals.
• Expertise in consultative selling, including discovery, objection handling, negotiation, and closing.
• Ability to confidently discuss investment, budget, and value with affluent consumers.
• Strong executive-level communication skills with the ability to build credibility and trust quickly.
• Demonstrated discipline maintaining CRM accuracy, pipeline hygiene, activity tracking, and forecasting integrity.
• Excellent organizational and time management skills with the ability to manage multiple opportunities simultaneously.
• Proficiency with Salesforce.com and Microsoft Teams.
• Passion for travel and enthusiasm for representing the Inspirato brand.
• Growth mindset with a commitment to coaching, accountability, and continuous improvement.
• Flexibility to accommodate customer schedules outside traditional business hours when necessary.

Nice To Haves

• Experience selling luxury hospitality, private clubs, luxury real estate, financial services, automotive, or other premium consumer offerings.
• Experience managing longer sales cycles involving affluent or executive-level buyers.
• Experience building and managing a geographic territory.

Responsibilities

• Manage the full sales cycle, including prospecting, qualifying, discovery, proposal development, objection handling, negotiation, and close.
• Build and grow a defined sales territory while developing strong relationships with prospective members.
• Articulate the Inspirato value proposition with confidence, centering conversations around Certainty, Care, and Value.
• Conduct deep discovery to understand each prospect's travel habits, lifestyle, and motivations while creating urgency around a discretionary purchase.
• Maximize the value of every membership opportunity by confidently selling the appropriate membership level and minimizing unnecessary discounting.
• Introduce and position Inspirato travel experiences as a natural extension of membership to increase member engagement and long-term value.
• Maintain disciplined pipeline management, ensuring Salesforce data, opportunity stages, and forecasts remain accurate and current.
• Build pipeline through virtual appointments, events, referrals, LinkedIn, outbound prospecting, and territory development activities.
• Collaborate closely with Member Care, Marketing, Real Estate, and other internal partners to deliver a seamless member experience.
• Participate in ongoing coaching, role-play, training, and professional development programs to continuously improve selling effectiveness.
• Operate with both high activity levels and high-quality execution while consistently delivering an exceptional customer experience.

Benefits

• Competitive base salary plus uncapped commissions
• Compensation designed to reward both the quality and quantity of sales, including individual Club sales, travel sales, and quarterly production accelerators.
• Compensation structures that reflect comparable market rates for companies of similar size, revenue, and geography, while recognizing individual experience, performance, and demonstrated capability.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed