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Pyramid Global Hospitality Logo Pyramid Global Hospitality · Sales

Director of Sales & Marketing

United States, Chicago 180000.00 - 200000.00 USD / Year · Job Posted February 20, 2026
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Job Description

The Director of Sales & Marketing (DOSM) is responsible for the strategic leadership, execution, and performance of all sales, marketing, and revenue-generation efforts for The Midland and The Wade Hotels, two distinct yet complementary hospitality assets in the Chicago market. This role requires a sophisticated commercial leader with the ability to balance independent brand positioning, maximize market share penetration, and drive profitable top-line growth across transient, group, corporate, and lifestyle segments.

Job Responsibility

  • Develop and execute integrated, property-specific and portfolio-aligned sales and marketing strategies that drive sustained revenue growth and market share gains
  • Lead annual and long-range Sales & Marketing Plans, including segmentation strategies, channel mix optimization, and brand positioning for both hotels
  • Analyze market trends, competitive intelligence, and demand drivers to proactively adjust strategies in a dynamic Chicago hospitality landscape
  • Serve as the primary commercial liaison to ownership and asset management, presenting performance updates, forecasts, and strategic recommendations
  • Partner closely with Revenue Management to align pricing, inventory controls, and demand strategies with sales initiatives
  • Drive profitable mix across group, transient, corporate negotiated, entertainment, social, and lifestyle segments
  • Ensure disciplined management of sales costs, ROI tracking, and marketing spend effectiveness
  • Directly lead and mentor a multi-disciplinary sales team, including Group Sales, Catering/Event Sales, Business Transient, and Sales Support
  • Establish clear performance expectations, accountability metrics, and incentive structures
  • Foster a high-performance, collaborative sales culture grounded in data-driven decision-making and relationship excellence
  • Recruit, train, and retain top commercial talent in a competitive labor market
  • Oversee all branding, marketing, PR, and digital initiatives for both properties, ensuring each hotel’s identity is clearly defined and differentiated
  • Collaborate with creative agencies, PR firms, and digital partners to execute campaigns across web, social, email, and experiential platforms
  • Ensure consistency in storytelling, visual identity, and guest messaging while tailoring campaigns to distinct audiences
  • Lead initiatives to enhance brand awareness, reputation management, and community engagement in Chicago
  • Personally manage and cultivate high-value corporate, group, and entertainment accounts
  • Lead strategic RFP responses, contract negotiations, and complex group business opportunities
  • Strengthening relationships with local businesses, associations, sports, entertainment, and destination partners
  • Represent both hotels at industry events, trade shows, and community functions
  • Work closely with Hotel Operations, Finance, Events, and Food & Beverage teams to ensure seamless execution of sold business
  • Support operational leaders with demand forecasting, staffing alignment, and guest experience considerations tied to sales strategy
  • Ensure compliance with all brand standards, ownership expectations, and reporting requirements

Requirements

  • Minimum 5–10 years of progressive hotel sales & marketing leadership experience, preferably in upper-upscale or lifestyle hotels. (Marriott brands preferred)
  • Proven success leading dual-property or multi-hotel commercial strategies in a major urban market (Chicago experience strongly preferred)
  • Strong background in group, corporate, transient, and lifestyle segments
  • Demonstrated ability to partner effectively with ownership, asset managers, and brand stakeholders
  • Advanced knowledge of sales systems and tools (CI/TY, CRM platforms, STR, business intelligence tools)
  • Financial acumen with experience managing budgets, forecasts, and ROI-driven marketing investments
  • Exceptional leadership, communication, negotiation, and presentation skills

What we offer

  • comprehensive health insurance with employer contribution
  • vision, dental, life, pet, and accident insurance options
  • 401(k) program with an employer match and immediate full vesting
  • paid time off
  • exclusive discounts across portfolio of hotels
  • on-site wellness programs
  • local discounts
  • employee rates on hotel stays
  • ongoing training and development opportunities
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