Short Term Rental Secrets
November 10, 2023
Beverly, Massachusetts
Job Type
Annual Salary: $50,000 to $60,000 based on experience and achievement



How it began

It all started in 2016 when our visionary CEO and his wife welcomed their first child who was born with a rare lung disease. Months in the hospital and mounting medical bills pushed our CEO to his limits. With depleted vacation time, he had to reluctantly leave his wife and child behind to return to his corporate accounting job, where he traded time for money. Determined to provide for his family without sacrificing precious moments, he made a promise to his wife before leaving the hospital – to build a business that would never require them to trade time for money again.

Enter the world of short term rentals. In just 15 months, our CEO and his wife built a business managing a portfolio of 15 properties across 5 states working less than 4 hours/week, allowing them to leave their corporate jobs behind and embrace financial freedom. Today, their incredible journey has expanded to include 102 rentals, including 3 boutique hotels.

Short Term Rental Secrets was founded in 2019 to help others break free from the rat race and live life on their own terms. As a real estate investing, coaching, and mentorship program, we empower individuals to achieve financial freedom through short-term rentals and boutique hotels. With our proven mindset, strategy, and tactical coaching, we have already assisted thousands of people worldwide in launching, automating, and scaling their portfolios.

By joining our family team, you not only gain the opportunity for financial success but also a sustainable work-life balance that truly transforms lives. Come be a part of our mission to become the #1 real estate investing mentorship program in the world.


Are you a master of organization, ready to step in and use your skills to optimize the life of a CEO?

We’re seeking a meticulous Executive Assistant (EA) with an eye for detail and a passion for systems. As our EA, you’ll ensure that our CEO’s personal, business, and household tasks work together efficiently. Your keen precision, forward-thinking approach, and commitment to refining day-to-day operations will be instrumental in fostering a balanced work-life rhythm - especially as the business continues to grow.

You’ll be our ideal candidate if you’re always ten steps ahead, view challenges as puzzles waiting to be solved and thrive supporting visionary leaders.


Apply today and become part of the journey to help others achieve success in real estate investing.


  • Manage household services and contractors for all aspects of the CEO’s life, including business and personal appointments, visitors, and entertainment
  • Correspond and communicate with various external parties on behalf of the CEO
  • Calendar & travel management, including planning, scheduling, coordinating, and other logistics
  • Keep the office and documents organized.
  • Create documents, briefings, reports, and presentations as directed and ad hoc data entry projects.
  • Liaise with bookkeepers to ensure books are completed and reconciled every month.
  • Assist in replacing batteries & supplies at rental properties.


  • Able to thrive in a fast-paced, innovative environment while remaining flexible, proactive, resourceful, and efficient
  • Emotionally self-regulate even during times of pressure and stress to be present for the CEO & teams they lead
  • Strong organizational skills
  • Proficient in using a computer and work-related apps.
  • Excellent interpersonal skills with the ability to develop important relationships with key stakeholders
  • Driver’s license and reliable transportation


Annual Salary: $50,000 to $60,000 based on experience and achievement


  • Commuting/travel assistance
  • Workplace perks such as recreation activities, food and coffee, and flexible work schedules

Schedule: We are a 7-day-per-week company. This position will require some weekend hours at different seasonal times throughout the year.