Director of Business Development

Player-Coach, Sales Leader | Prime Vacations | Bradenton / Sarasota Barrier Islands, Florida

Prime Vacations is a leading vacation rental management company on Florida’s Gulf Coast, managing over 1,000 premier vacation rental homes across Anna Maria Island, Siesta Key, and adjacent markets. As part of Stay Terra, a collection of premier vacation rental brands across America, Prime delivers full-service property management and has built its success on revenue optimization, owner partnership, and exceptional guest experience.

We are hiring this role to lead our business development function to drive sustainable portfolio growth and expand into new markets with discipline and accountability.

Stay Terra is a collection of premier vacation rental brands committed to providing best-in-class property management for owners and seamless, elevated experiences for guests in top destinations across America.

The Director of Business Development is Prime’s sales team leader and the lead owner‑acquisition engine — and a true player‑coach. You will personally source, pitch, and close owner agreements while building and managing a high-performing BD team and standing up a professional, data-driven sales process. This is a hands‑on leadership role in a competitive and highly sought-after vacation rental market, where real estate brokerages, local property managers, and national platforms all compete for the same homeowners.

The ideal candidate is a self‑starter with an entrepreneurial, builder-oriented approach.

Success in this role means more than signing units. You will be accountable for gross rental revenue (GRR) quality, leading the analytical work to segment the market and strategize how and where the business should grow, ensuring pipeline visibility in Hub Spot, and developing a repeatable, data-driven playbook to compound learnings into repeatable growth. You report to Prime’s COO and partner closely with local revenue management, operations, and marketing teams.

You will also be committed to collaboration with other Stay Terra brands to share and leverage best practices that are applicable across the portfolio of brands.

• Competitive base salary + performance‑based incentive
• Leadership seat on a high‑priority function rebuild with executive sponsorship and clear 90‑day milestones
• Direct impact on a ~$100M portfolio and the opportunity to professionalize BD at scale
• Ability to leverage a modern sales stack:
  Hub Spot CRM, owner intelligence tools, revenue projection support, marketing/PR resources, and AI‑enabled tooling
• Health insurance, paid time off, and paid holidays

• Own Prime’s new owner pipeline end to end: lead generation, qualification, pitch, proposal, negotiation, and contract signing
• Build and maintain a consistent qualified pipeline with clear stage definitions, aging discipline, and reliable forecasts
• Prospect and develop opportunities across core markets (Anna Maria Island, Siesta Key) and prioritized expansion markets (e.g., St. Pete Beach, Longboat Key)
• Lead multichannel sourcing: real estate agent and brokerage relationships, owner referrals, competitive takeaways, inbound/web leads, developer relationships, and targeted outbound campaigns (email, phone, events)
• Conduct property/site visits and owner meetings; use data-driven revenue projections and competitive calendar analysis to support a consultative, value-based pitch
• Close agreements that meet portfolio quality standards (based on target GRR per new home) while protecting economics and contract terms
• Represent Prime professionally with homeowners, realtors, HOAs, and condo associations

• Recruit, coach, and hold accountable a lean BD team (including field closers and pipeline support)
• Set weekly activity standards, pipeline SLAs, and individual KPIs (calls, meetings, proposals, GRR signed)
• Run weekly pipeline reviews; maintain a biweekly operating rhythm with senior leadership
• Model the behavior expected of the team: CRM hygiene, follow‑up speed, and data-backed selling
• Partner with HR and…