Business Development Executive - Siesta Key, FL

COMPANY OVERVIEW: · The Cottages on the Key is a luxury vacation rental management company based in Siesta Key, Florida. We deliver exceptional hospitality experiences for guests from around the world while providing white-glove, performance-driven property management for vacatio ...

Job description

COMPANY OVERVIEW:

The Cottages on the Key is a luxury vacation rental management company based in Siesta Key, Florida. We deliver exceptional hospitality experiences for guests from around the world while providing white-glove, performance-driven property management for vacation rental owners.

Our success is built on personalized service, thoughtful revenue strategy, and a culture rooted in collaboration, accountability, and growth. We believe great results come from great people—and we are intentional about building a team that supports one another while operating at a high level.

POSITION SUMMARY:

The Business Development Executive (Luxury Properties) is a full-time, outbound-focused business development role designed for high-energy professionals who thrive on the phone, love building relationships, and want to grow within the luxury vacation rental industry.

This role is lead-generation and lead-qualification focused, not a closing role. Business Development Executives engage property owners, investors, and real estate professionals through heavy outbound activity—including calling, SMS, email, and personalized video outreach—to establish interest and qualify opportunities.

Our Business Development E work closely with our Luxury Property Executives (LPEs), who serve as the closing experts. Once a qualified opportunity is established, the LPC hands the account off to the LPE and continues supporting the deal through enrollment.

In addition, Business Development Executives collaborate directly with our Data Team to help evolve our data stack—providing frontline feedback on lead quality, participating in data refinement, and contributing to improvements in targeting, segmentation, and outbound performance.

This role offers a clear growth path into senior business development and executive sales roles. You'll be joining a leadership team with 40+ years of combined vacation rental experience and a fast-growing organization that continues to create downstream opportunities across sales, marketing, and operations.

RESPONSIBILITIES:

• Execute heavy outbound outreach (calling, SMS, email, loom video production) with minimal downtime

• Spend 7+ hours per day on the phone engaging prospective property owners and partners

• Work company-generated and self-sourced leads across residential homes, multi-unit owners, boutique motels, inns, and real estate influencers

• Establish interest, credibility, and trust through consultative conversations

• Qualify opportunities and progress them to a Proposal Presented stage

• Maintain a clean, accurate pipeline and consistent follow-up cadence in HubSpot

• Collaborate closely with Luxury Property Executives (LPEs) to ensure strong handoffs and successful enrollments

• Work directly with the Data Team to refine lead quality, improve data accuracy, and enhance outbound targeting

• Provide feedback on data performance to help evolve the company's data stack, enrichment strategies, and output

• Enroll and activate referral partners and Ambassadors to expand the portfolio network

• Participate in team meetings, trainings, and performance reviews to continuously improve execution

QUALIFICATIONS:

• Proven experience in outbound sales, business development, or marketing

• 2+ years in real estate OR 4+ years in hospitality, sales, or marketing

• Extremely comfortable with high-volume phone outreach and rejection

• Strong communicator with the ability to build rapport quickly

• Organized, disciplined, and capable of managing a large pipeline

• Self-motivated and performance-driven with a competitive edge

• Background in luxury real estate, vacation rentals, or luxury goods is a plus

• Comfortable working remotely in a fast-paced, metric-driven environment

COMPENSATION & BENEFITS:

• $50,000 base salary

• Front-of-funnel commissions tied to qualified opportunities and successful handoff at the Proposal Presented stage

• Commission paid per enrollment, allowing LPCs to earn before and at close

• On-Target Earnings (OTE):

  • Year 1: $60,000 – $80,000

  • Year 2: $80,000 – $100,000+

• Company-provided leads with upside from self-sourced opportunities

• Clear, merit-based growth path into Luxury Property Executive (LPE), senior business development, or leadership roles

• Ongoing training, coaching, and performance support from a seasoned leadership team

• Opportunity to work with a highly respected luxury brand and expanding national footprint

TO APPLY:
If you're a motivated, entrepreneurial professional who thrives on meaningful conversations and helping clients unlock the full potential of their luxury properties, we'd love to meet you. Apply today and take the next step in building a flexible, fulfilling career with The Cottages on the Key.