SkyRun Vacation Rentals - Kona Coast
Published
September 3, 2025
Location
Kailua-Kona, Hawaii
Category
Job Type
Salary
$50,000 base salary with on-track earnings (OTE) of $150,000

Description

COMPANY OVERVIEW:

SkyRun Vacation Rentals Kona Coast is an independently owned and operated branch of one of North America’s leading full-service vacation rental management organizations. We are a fast-growing company serving homeowners and guests on the Kona Coast and South Kohala.

When you join SkyRun Vacation Rentals, you join a passionate team of individuals who are guided by a dedication to their communities and a drive to delight their customers. Built on a foundation of innovation, technology, and honesty, SkyRun was named on the Inc. 5000 list as one of the nation's fastest-growing private companies and has experienced 70% year-over-year growth.

With SkyRun, associates enjoy the opportunity to flex their skills and grow their career within the vacation rental industry.

POSITION SUMMARY:

SkyRun is seeking a Business Development Associate to grow our portfolio of properties in West Hawaii. This sales role will focus on generating, qualifying, and closing a strong pipeline of leads by building and maintaining relationships with property owners, real estate agents, second homeowners, and the local community. Reporting directly to the CEO/Co-Founder/Owner of SkyRun Kona Coast, you will collaborate closely with both the local and national SkyRun teams to achieve growth goals.

This opportunity is ideal for an ambitious and independent sales professional who is confident, persuasive, and thrives in a fast-paced environment. The right candidate will be energized by challenges, motivated by opportunities to innovate, and skilled at making quick decisions with limited information. Strong networking abilities, creativity, and the ability to influence others will be key to success in this role.

RESPONSIBILITIES:

  • Developing a growth strategy focused both on financial gain and customer satisfaction
  • Conducting research to identify new clients in target market
  • Managing lead tracking and prioritization
  • Arranging and conducting business meetings (in person, online, via phone, etc.) with prospective clients and partners
  • Participating in scheduled caravans/open houses as networking opportunities
  • Attending other networking and industry events in Kona and South Kohala that may lead to new business opportunities
  • Preparing and delivering presentations about SkyRun to potential clients and partners
  • Preparing accurate revenue projections for properties
  • Preparing, negotiating and finalizing sales contracts
  • Coordinating property onboarding process
  • Building long-term relationships with new and existing clients and partners
  • Tracking and Reporting on Business Development KPIs
  • Staying informed on all state, county, and local regulatory requirements for Vacation Rentals in Hawaii County
  • Other duties, as appropriate

QUALIFICATIONS:

Required:

  • Active Hawaii Real Estate License
  • 5+ Years of proven sales experience
  • Experience with cold calling and prospecting leads
  • Comfortable delivering presentations
  • Strong communication (oral & written) and follow up
  • Proficiency using a CRM platform to manage leads
  • Proficiency in Excel and Google Drive
  • Ability to travel for client meetings
  • Self-motivated, proactive, forward thinker
  • High level of attention to detail
  • Proven time management skills and ability to prioritize tasks and problem-solve to meet deadlines

Preferred:

  • Active Hawaii Brokers License
  • Hospitality experience in the Vacation Rental industry

COMPENSATION & BENEFITS:

Compensation:

  • $50,000 base salary with on-track earnings (OTE) of $150,000

Job Type: 1099 Contractor

Job Location: Kailua-Kona, Hawaii