Senior Account Executive - Homeowner Acquisition

The Opportunity

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.