Senior Account Executive — Orlando Property Management

Stayd Collective; Orlando (FL); On-site; USD 70,000 - 175,000; Full time

Job summary

Blue Gems is seeking a Senior Account Executive in Orlando to own the full sales cycle, nurture relationships with homeowners, realtors, and investors, and close management agreements for vacation homes.

You will lead consultative discussions on rental performance, forecast revenue, and build a robust referral network while maintaining a tight CRM and dependable pipeline. This is a senior, relationship-driven role in a dynamic market.

Qualifications

• 8+ years in sales or business development, ideally full-cycle Account Executive.
• Track record of closing high-value, consultative deals and building long-term relationships.
• Executive-level communication with homeowners, realtors, investors, and high-net-worth clients.
• Strong local relationship-building instincts; existing Orlando-area network is advantageous.
• Experience in short-term rentals, property management, real estate, hospitality, or related trust-based services.
• Comfort discussing financial projections, property performance, mortgages, taxes, insurance, market trends, and regulatory considerations.
• Excellent CRM discipline, pipeline management, follow-up, and forecasting habits.
• High ownership, urgency, resilience, and self-direction.

Responsibilities

• 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.

Skills

Closing high-value deals

Executive communication

CRM discipline

Pipeline management

Relationship building

Forecasting

Industry knowledge

Strategic mindset

Tools

CRM systems

Job description

Blue Gems is seeking a Senior Account Executive in Orlando to own the full sales cycle, nurture relationships with homeowners, realtors, and investors, and close management agreements for vacation homes.

You will lead consultative discussions on rental performance, forecast revenue, and build a robust referral network while maintaining a tight CRM and dependable pipeline. This is a senior, relationship-driven role in a dynamic market.