The Role

What You'll Do

• 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.

How Success Is Measured

Success in this role is measured by more than just revenue. High-performing Membership Directors consistently demonstrate excellence across several key areas, including:

• Club memberships sold
• Average membership value
• Travel attachment rate
• Territory development and pipeline health
• Forecast accuracy and Salesforce discipline
• Sales process execution
• Member experience and professionalism
• Collaboration with cross-functional partners

Our Best Membership Directors

• Build trust quickly with affluent buyers.
• Lead every conversation with thoughtful discovery.
• Sell value instead of relying on discounts.
• Maximize membership value on every opportunity.
• Follow a disciplined, repeatable sales process.
• Maintain exceptional CRM hygiene and forecasting accuracy.
• Embrace coaching and continuous improvement.
• Collaborate effectively across Sales, Member Care, Marketing, and Real Estate.
• Take ownership of their territory, pipeline, and business results.

What We're Looking For

Required

• 4+ 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.

Preferred

• 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.

Compensation

Why Inspirato