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 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.
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
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Competitive base salary + performancebased incentive
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Leadership seat on a highpriority function rebuild with executive sponsorship and clear 90day milestones
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Direct impact on a ~$100M portfolio and the opportunity to professionalize BD at scale
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Ability to leverage a modern sales stack: HubSpot CRM, owner intelligence tools, revenue projection support, marketing/PR resources, and AIenabled tooling
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Health insurance, paid time off, and paid holidays
Pipeline Development & New Owner Acquisition
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Own Prime’s newowner pipeline end to end: lead generation, qualification, pitch, proposal, negotiation, and contract signing
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Build and maintain a consistent qualified pipeline with clear stage definitions, aging discipline, and reliable forecasts
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Prospect and develop opportunities across core markets (Anna Maria Island, Siesta Key) and prioritized expansion markets (e.g., St. Pete Beach, Longboat Key)
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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)
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Conduct property/site visits and owner meetings; use datadriven revenue projections and competitive calendar analysis to support a consultative, valuebased pitch
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Close agreements that meet portfolio quality standards (based on target GRR per new home) while protecting economics and contract terms
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Represent Prime professionally with homeowners, realtors, HOAs, and condo associations
Team Leadership & Operating Discipline
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Recruit, coach, and hold accountable a lean BD team (including field closers and pipeline support)
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Set weekly activity standards, pipeline SLAs, and individual KPIs (calls, meetings, proposals, GRR signed)
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Run weekly pipeline reviews; maintain a biweekly operating rhythm with senior leadership
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Model the behavior expected of the team: CRM hygiene, followup speed, and databacked selling
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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
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Implement and enforce a standardized owner acquisition playbook: stage criteria, proposal templates, revenue projection workflow, competitive positioning, and owner FAQs
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Partner with revenue management to build credible property performance projections and “why Prime” narratives grounded in Wheelhouse data and market benchmarks
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Collaborate with marketing/PR on campaigns, events, realtor roundtables, and topoffunnel programs that feed the BD team qualified opportunities
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Work with CRM and operations leaders to ensure HubSpot is the system of record: mandated fields on closedwon deals, pipeline dashboards, leadsource tracking, and commissionready reporting
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Coordinate process with onboarding and operations teams to create a consistent process for smooth handoff from signed contract to live property
Qualifications
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7+ years of B2B sales experience, including at least 3 years in a sales leadership or teamlead role
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Demonstrated track record of meeting or exceeding revenue targets in a consultative, relationshipdriven sale (vacation rental/property management, real estate services, hospitality asset management, or analogous hightouch B2B environments strongly preferred)
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Strong command of CRMdriven selling (HubSpot or comparable platform); disciplined about data entry, pipeline hygiene, and reporting
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Ability to sell on value using performance data, not discounting; comfortable presenting revenue projections and competitive comparisons to sophisticated homeowners
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Excellent communication, organizational, and executive presence; credible in ownerfacing and realtorfacing settings
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Valid driver’s license and willingness to travel regularly across Prime’s Florida markets
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Existing relationships with Sarasota/Manatee/Pinellas real estate agents, brokers, or property owners
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Experience selling into HOAs, condo associations, or multiunit ownership structures
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Familiarity with vacation rental economics: ADR, occupancy, RevPAR, channel mix, and owner contract structures
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Background using lead intelligence, outbound sequencing, or revenue analytics tools alongside CRM
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Experience implementing a CRM (HubSpot or otherwise)
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Bilingual (Spanish) a plus
PRIME VACATIONS provides premium unforgettable vacation experiences throughout coastal Florida. We offer our property owners comprehensive services for managing their homes and deliver exceptional guest experiences at our boutique hotels, restaurants, marinas, and rental properties. Creating a workplace environment for team members to thrive is paramount. PRIME VACATIONS is committed to our communities and strives to make them a better place for locals and visitors. Passion – 24/7, we work with a passion for serving our guests the best we can. We are local experts and share the same love for vacations that you do.
