Short Term Rentals Jobs in Kissimmee, FL (NOW HIRING)

Blue Gems is hiring one exceptional Senior Account Executive to grow our portfolio of professionally managed vacation homes. This is a full-cycle, relationship-led sales role for a proven closer who can earn trust with homeowners, real estate professionals, investors, and referral partners - and turn that trust into signed management agreements.

This is not a junior SDR role or a purely transactional inside-sales position. We are looking for a mature sales leader who can build a durable local network, run a disciplined pipeline, navigate high-value decisions, and close consistently without being micromanaged.

• Build and deepen referral relationships with Orlando-area realtors, investors, homeowners, repeat clients, and other strategic partners.

• Own the full sales cycle from qualified opportunity through discovery, underwriting, proposal, negotiation, and signed management agreement.

• Lead consultative conversations that help property owners understand short-term-rental performance, projected gross rent, fees, risks, and the value of professional management.

• Create a systematic, high-value follow-up experience so prospects and partners always understand the next step.

• Maintain a clean, accurate CRM with clear opportunity stages, next actions, close dates, and forecasted revenue.

• Present a monthly business review covering market feedback, common objections, recent wins, all closed deals, the active pipeline, and your forecast for the month.

• Partner with marketing and outbound resources while building a relationship engine that produces repeatable referrals.

• Ensure a seamless handoff from Sales to Onboarding, preserving the trust and expectations established during the sales process.

• Share field insights that improve our target profile, messaging, underwriting assumptions, outreach strategy, and deal structures.

• Consistent growth in signed properties and gross rental revenue.

• A healthy, well-qualified pipeline with strong stage conversion and disciplined follow-up.

• Reliable forecasting: your monthly commitments are thoughtful, visible, and increasingly accurate.

• A growing network of productive realtor and referral relationships across the Orlando market.

• High homeowner confidence, clear expectations, and a clean transition into onboarding.

• Strong judgment about where to spend time, which opportunities to pursue, and how to move complex deals forward.

• 8+ years of successful sales or business-development experience, ideally in a full-cycle Account Executive role.

• A documented track record of closing high-value, consultative deals and building long-term client relationships.

• Executive-level communication skills with the ability to adapt to homeowners, realtors, investors, and high-net-worth clients.

• Strong local relationship-building instincts; an existing Orlando-area network is a meaningful advantage.

• Experience in short-term rentals, property management, real estate, hospitality, or another trust-based service business is strongly preferred.

• Comfort discussing financial projections, property performance, mortgages, taxes, insurance, market trends, and regulatory considerations.

• Excellent CRM discipline, pipeline management, follow-up, and forecasting habits.

• A high degree of ownership, urgency, resilience, and self-direction.

• You are looking for an entry-level SDR position or want success measured only by raw activity volume.

• You prefer one-call transactions over patient, long-term relationship building.

• You avoid direct accountability for pipeline quality, forecast accuracy, and closed revenue.

• You are uncomfortable with financial details, market data, or difficult homeowner conversations.

• You need constant direction to prioritize your week or advance your deals.

• You do not want to be active in the Orlando real estate and business community.

Compensation: Base Salary: $70-90k, OTE: $150-175k.

• A high-impact seat with meaningful ownership of portfolio growth.

• The autonomy to build relationships and close business in the way an experienced professional knows works.

• A simple compensation model directly tied to the value you create.

• The opportunity to help shape a more disciplined, accountable sales function.

1. Please send a Submit your résumé and a brief note describing the most relevant high-value sales role you have held, the results you produced, and any experience you have building referral relationships in the Orlando market.

2.  Please submit a 1-minute introductory Loom video briefly talking about your experience and highlighting any relevant or valuable experience you have for this position. Please make sure your Loom video is set to public so we can access and watch it.

Please send the video link via email to gabriela@stayd.co, including your full name and the position you are applying for in the email subject line.