Associate Director of Sales

Position Overview

The Associate Director of Sales supports the overall sales strategy, owns a personal sales portfolio and assigned market segment, and serves as a senior leader who can act on behalf of the Director of Sales when needed. Success in this role requires strong prospecting, account development, collaboration across Catering, Revenue Management, Marketing, Reservations, and Operations, and the ability to convert opportunities into profitable group, corporate, association, leisure, and wedding business.

Essential Responsibilities

• Support the Director of Sales in developing and executing the resort’s overall sales strategy and achieving annual room night, revenue, and profitability goals.
• Maintain an assigned market segment and personal sales portfolio, with responsibility for developing, soliciting, and closing business to achieve established quarterly room night and revenue goals.
• Plan, direct, organize, and control departmental sales activities, including telemarketing, outside sales calls, client entertainment, walking tours, prospecting, lead development, and solicitation of new business.
• Develop and maintain a strong sales pipeline through targeted prospecting, account development, networking, client appointments, site visits, trade shows, and industry events.
• Prepare and present persuasive verbal and written sales proposals, contracts, and presentations to prospective and existing clients.
• Lead and coach assigned members of the sales team, providing direction, accountability, training, and performance feedback.
• Manage and grow key accounts and strategic relationships across priority market segments.
• Monitor sales pace, pipeline, production, conversion, and future business, identifying opportunities and strategies to close performance gaps.
• Collaborate closely with Catering, Revenue Management, Marketing, Reservations, and Operations to maximize revenue and ensure seamless execution of client business.
• Represent Hawks Cay Resort with key clients, meeting planners, industry partners, and community organizations to strengthen the resort’s market position.
• Support sales forecasting, budgeting, reporting, and strategic business planning.
• Assist with complex negotiations, high-value opportunities, and client escalations.
• Serve as a senior sales leader and act on behalf of the Director of Sales when needed, ensuring continuity of leadership and accountability.

Required Qualifications & Skills

• Minimum of 2 years of progressive sales experience with demonstrated leadership responsibilities.
• Strong knowledge of the designated geographic market and ability to travel throughout assigned markets as needed.
• Knowledge of the travel and hospitality industry, current market trends, and economic factors impacting hotel and resort business.
• Strong understanding of hotel operations and their relationship to sales, including budgeting, forecasting, business planning, quality assurance, personnel and labor relations, safety and security, hospitality law, and long-range planning.
• Strong computer skills, including Microsoft Word, Excel, and Delphi or comparable hotel sales and CRM systems.
• Strong analytical skills, including the ability to calculate room blocks, average rates, forecasts, and analyze budget and production information.
• Ability to organize and interpret detailed information and use data to make sound business decisions.
• Excellent verbal and written communication skills, with the ability to adapt communication style to effectively communicate with clients, colleagues, leadership, and business partners.
• Strong organizational skills with the ability to prioritize and manage multiple projects and deadlines in a fast-paced resort environment.
• Demonstrated ability to build relationships, negotiate effectively, and drive results.

Preferred Qualifications

• Bachelor’s degree in Hospitality Management, Business, Marketing, or a related field.
• Previous hotel or resort sales leadership experience, preferably within a full-service destination resort.
• Experience managing or mentoring sales professionals and leading team initiatives.
• Experience with group, corporate, association, leisure, wedding, or other resort-focused market segments.
• Experience with Delphi, Salesforce, Cvent, or other hospitality sales and CRM platforms.
• Established relationships within the Florida Keys, South Florida, Southeast, or other key feeder markets.
• Experience with destination resort sales, island destinations, or other complex resort environments.

What We Offer

EOS Hospitality and Hawks Cay Resort offer a competitive compensation and benefits package that may include:

• Medical, dental, and vision insurance
• 401(k) with company match
• Paid time off and holidays
• Employee discounts on resort accommodations, dining, and activities
• Professional development and career growth opportunities

Hawks Cay Resort is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other protected characteristic under applicable law.