Senior Account Executive - Homeowner Acquisition at Stayd Collective in Orlando, Florida, United States

Job description

• About the job Senior Account Executive - Homeowner Acquisition
• Apply on Stayd to complete your application for this role.
• Complete the official application on stayd.co: www.stayd.co/careers/blue-gems/senior-account-executive-homeowner-acquisition
• Please use this direct link for your introduction and role questions. A resume submitted through a job board or Manatal is only the first step.
• Blue Gems
• Own consultative homeowner sales and build productive Orlando-area referral relationships.
• 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.
• 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.

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.

Requirements

• 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.

Skills

Required

• Consultative sales
• Full-cycle sales
• Relationship building
• Pipeline management
• CRM discipline
• Forecasting
• Financial discussions
• Communication
• Negotiation
• Self-direction

Preferred

• Short-term rentals
• Property management
• Real estate
• Hospitality
• Trust-based service business

Benefits

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