Executive Assistant at Freewyld

About Freewyld & Freewyld Foundry:

Freewyld Foundry is a high-performance revenue management service for short-term rental operators generating $1M+ in annual revenue. We manage $40M+ in revenue across 1,000 listings, helping operators maximize profitability through data-driven pricing, automation, and expert strategy.

We are not a company for people who want easy work. We believe in hard work, high performance, and continuous personal growth. If you seek challenges, thrive in dynamic environments, and are passionate about hospitality, travel, and revenue optimization, this is the perfect role for you.

We built Freewyld Foundry because we live and breathe this industry. In addition to our revenue management services, we also own and operate Freewyld, a collection of beautifully designed cabins in nature-driven destinations. This operator-first mindset shapes everything we do.

If you’re looking for a place to grow, push limits, and make an impact in hospitality, Freewyld Foundry is where you belong.

Who We’re Looking For:

We are searching for an elite-level Executive Assistant to work directly with our CEO, supporting him in managing and scaling Freewyld and Freewyld Foundry. This person must be incredibly organized, proactive, highly skilled, and capable of managing complex workflows with precision and efficiency.

This is not a role for someone who needs constant direction—it is for a driven self-starter who can anticipate needs, handle tasks before they arise, and make our CEO’s life as seamless as possible.

This is a long-term position with significant growth opportunities for high performers who want to develop deep expertise in revenue management and short-term rental operations.

Key Responsibilities:

Executive Support & Operations

• Manage CEO’s email inbox, prioritizing, responding, and organizing messages
• Handle complex calendar scheduling, coordinating internal and external meetings
• Organize, manage, and streamline communication between the CEO, team, and clients
• Coordinate travel arrangements, including flights, accommodations, and itineraries
• Maintain confidential documents, agreements, and reports
• Assist in high-level decision-making by organizing and presenting key information

Client & Team Coordination

• Act as the first point of contact between CEO and clients, ensuring smooth communication
• Coordinate meetings, follow-ups, and ensure deliverables are met
• Support in project management, ensuring key priorities are executed efficiently
• Assist in onboarding and communicating with Freewyld guests, handling high-level bookings, requests, and VIP guest experiences
• Help plan and coordinate company retreats, events, and team offsites

Process Optimization & Strategic Assistance

• Identify inefficiencies and implement systems to streamline operations
• Proactively take tasks off the CEO’s plate to maximize productivity
• Handle personal tasks related to business, including bills, subscriptions, and logistics
• Support CEO in managing key hiring processes, performance tracking, and culture development

Top 5 Key Performance Indicators (KPIs)

1. Inbox & Communication Management
   • Maintain 90%+ inbox-zero rate daily.
   • Respond to all priority emails within 12 hours.
   • Reduce CEO’s time spent on emails by 50%.
2. Calendar & Scheduling Accuracy
   • 100% accuracy in CEO’s calendar (no conflicts, missed meetings).
   • Weekly agenda prepared and reviewed in advance.
   • All scheduling adjustments made within 24 hours.
3. Guest & Customer Support
   • 100% of guest inquiries answered within 2 hours during working hours.
   • All vendor and product orders placed without CEO intervention.
   • Monthly guest issue report with trends and solutions.
4. Task & Project Execution
   • 90%+ of assigned tasks completed ahead of deadlines.
   • CEO action items updated daily in ClickUp.
   • All meeting follow-ups completed within 24 hours.
5. Travel & Event Coordination
   • 100% accuracy in flights, hotels, and itinerary planning.
   • Team retreats and events planned and executed on schedule.
   • CEO travel logistics handled seamlessly.

This is an incredible opportunity for a highly motivated individual who wants to work with a growing hospitality company, develop deep expertise in revenue management, and be part of a team that values growth, challenge, and high performance.

Reach out to us today, and let’s grow together.

Compensation & Benefits: 

• Salary: $3,000+/month (based on experience and results).
• Performance-based raises and bonuses for high performers.
• Small company benefits after six months.
• Remote position with flexible work hours, but must be available during PST/EST business hours.
• Opportunities for career growth within Freewyld.
• Full-time position