Director of Business Development in Bradenton, Florida at Prime Vacations

Director of Business Development
Player-Coach, Sales Leader | Prime Vacations | Bradenton / Sarasota Barrier Islands, Florida

About Prime Vacations:
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 StayTerra, 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.

StayTerra 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.

Position Summary:
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 HubSpot, 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 StayTerra brands to share and leverage best practices that are applicable across the portfolio of brands.

What’s in It for You
• 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: HubSpot CRM, owner intelligence tools, revenue projection support, marketing/PR resources, and AI-enabled tooling
• Health insurance, paid time off, and paid holidays

Key Responsibilities:
Pipeline Development & New Owner Acquisition
• 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 multi-channel 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

Team Leadership & Operating Discipline
• 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 bi-weekly 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 leadership on compensation design aligned to outcomes (GRR quality and conversion) rather than unit count alone
Sales Process, Materials & Cross-Functional Partnership
• Implement and enforce a standardized owner acquisition playbook: stage criteria, proposal templates, revenue projection workflow, competitive positioning, and owner FAQs
• Partner with revenue management to build credible property performance projections and “why Prime” narratives grounded in Wheelhouse data and market benchmarks
• Collaborate with marketing/PR on campaigns, events, realtor roundtables, and top-of-funnel programs that feed the BD team qualified opportunities
• Work with CRM and operations leaders to ensure HubSpot is the system of record: mandated fields on closed-won deals, pipeline dashboards, lead-source tracking, and commission-ready reporting
• Coordinate process with onboarding and operations teams to create a consistent process for smooth handoff from signed contract to live property

Qualifications
Required:
• 7+ years of B2B sales experience, including at least 3 years in a sales leadership or team-lead role
• Demonstrated track record of meeting or exceeding revenue targets in a consultative, relationship-driven sale (vacation rental/property management, real estate services, hospitality asset management, or analogous high-touch B2B environments strongly preferred)
• Strong command of CRM-driven selling (HubSpot or comparable platform); disciplined about data entry, pipeline hygiene, and reporting
• Ability to sell on value using performance data, not discounting; comfortable presenting revenue projections and competitive comparisons to sophisticated homeowners
• Excellent communication, organizational, and executive presence; credible in owner-facing and realtor-facing settings
• Valid driver’s license and willingness to travel regularly across Prime’s Florida markets

Preferred:
• Existing relationships with Sarasota/Manatee/Pinellas real estate agents, brokers, or property owners
• Experience selling into HOAs, condo associations, or multi-unit ownership structures
• Familiarity with vacation rental economics: ADR, occupancy, RevPAR, channel mix, and owner contract structures
• Background using lead intelligence, outbound sequencing, or revenue analytics tools alongside CRM
• Experience implementing a CRM (HubSpot or otherwise)
• Bilingual (Spanish) a plus