Complex Director of Sales & Marketing

Pyramid Global Hospitality • Chicago, IL

1d • $180,000 - $200,000

About The Position

The Complex 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.

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.

Responsibilities

• 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.

Benefits

• comprehensive health insurance
• retirement plans
• paid time off
• on-site wellness programs
• local discounts
• employee rates on hotel stays
• medical insurance with employer contribution and 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 our portfolio of hotels

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed