This is a unique opportunity to lead sales efforts for a dynamic portfolio of three hotels situated in the strategic Chicago Midway Airport market. The cluster includes one full-service property and two select-service hotels, each positioned to capture a diverse mix of business and leisure demand. Our properties are committed to delivering exceptional guest experiences and are poised for significant market share growth under the right sales leadership.

Role Summary

We are seeking a results-oriented and experienced Cluster Director of Sales to provide strategic revenue leadership across our three-hotel portfolio. The ideal candidate will be a market expert with a proven track record of driving RevPar growth and developing high-performing sales teams. This role is responsible for creating and executing a cohesive sales strategy that maximizes revenue across all segments, including airline crew, corporate negotiated, transient, and group business. You will be the primary driver of new business acquisition and key account retention, leveraging deep knowledge of the Chicago Midway submarket to outperform the competition and exceed budget goals. This position will oversee 2 Sales Managers and 1 EMM.

What You’ll Do

• Develop and implement a comprehensive, portfolio-wide sales strategy to achieve revenue and market share objectives.
• Partner closely with the revenue management team on pricing, segmentation, and channel mix strategies to optimize profitability.
• Lead, coach, and mentor on-property Directors of Sales and Sales Managers, fostering a culture of accountability, pipeline discipline, and proactive selling.
• Personally manage and cultivate relationships with top-producing accounts, with a focus on acquisition and retention of key airline, corporate, and group clients.
• Oversee and direct the entire airline/crew contracting process, from negotiation to execution.
• Manage the annual RFP process for GDS, consortia, and corporate negotiated accounts, ensuring high win rates and optimal positioning.
• Build and maintain strong partnerships with local community stakeholders, including Choose Chicago, local Chambers of Commerce, and other CVBs.
• Collaborate effectively with hotel operations teams to ensure seamless service delivery and client satisfaction for all sold business.
• Conduct targeted sales travel to key feeder markets to drive new business opportunities.

What You’ll Bring

• Experience: 5-7+ years of progressive hotel sales leadership experience, with a strong preference for multi-property oversight.
• Market Expertise: Verifiable, in-depth knowledge of the Chicago Midway Airport market. This includes understanding feeder cities, airline schedules and irregular operations, crew layover patterns, seasonal demand shifts, compression from McCormick Place, and the impact of schedules for the United Center, Bulls, and White Sox. A firm grasp of local construction, industrial, and government demand generators is essential.
• Technical Skills: Proficiency with RFP management systems, Opera Cloud, PEP, Fosse, Delphi and CI/TY software.
• Leadership: Demonstrated ability to lead, inspire, and develop a team of sales professionals to achieve ambitious goals.
• Negotiation: Superior contract negotiation and analytical skills with a history of securing profitable, long-term agreements.
• Relationships: An established network of client and industry relationships within the Chicago South/Southwest corridor is highly desirable.

Preferred Qualifications:

• Experience with major brand systems (e.g., Marriott, Hilton, IHG, Hyatt and Choice).
• Direct experience negotiating and managing airline crew contracts.
• Bilingual proficiency in Spanish or Polish is a plus.

How We Measure Success

Your performance will be evaluated based on a clear set of key performance indicators (KPIs) that directly reflect your impact on the portfolio's success:

• RevPAR Index Growth
• Market Share Attainment
• Pace vs. Budget and Forecast
• Key Account Production & Growth
• RFP Win Rate
• Lead-to-Booking Conversion & Response Time
• Sales Activity & Pipeline Metrics

Compensation & Benefits

We offer a competitive compensation package designed to reward top performance.

• Competitive base salary - $100K - $120K + 25% Annual Bonus
• Comprehensive benefits package including medical, dental, and vision insurance
• Paid time off and holiday pay
• 401(k) retirement plan
• Travel and expense reimbursement

If interested please send a copy of your resume to jay@geckohospitality.com