Complex Director of Sales & Marketing

Welcome to The Midland Hotel, a distinguished property in the Pyramid Global Hospitality portfolio. Located in the bustling heart of Chicago, Illinois, our hotel features 403 stylish guest rooms and 12,589 sq ft of versatile meeting space, creating an exceptional environment for both guests and employees. At The Midland Hotel, we pride ourselves on delivering outstanding service and creating memorable experiences. As a member of our team, you'll work in a dynamic and supportive setting, surrounded by the vibrant energy and iconic architecture of Chicago. We offer diverse positions across various departments, including guest services, food and beverage, housekeeping, spa and wellness, sales and marketing, and more. Joining our team means becoming part of a close-knit community that values teamwork, professionalism, and a passion for excellence. We provide comprehensive training programs to ensure our employees have the skills and knowledge needed to excel in their roles. If you are a dedicated and enthusiastic individual with a passion for hospitality, we invite you to explore the exciting career opportunities available at The MIdland Hotel. Take the first step towards a rewarding career by applying today. At Pyramid Global Hospitality, we are committed to caring for our team members by offering a comprehensive benefits package for full-time employees. Our benefits include medical insurance with employer contribution and vision, dental, life, pet, and accident insurance options. We also provide a 401(k) program with an employer match and immediate full vesting. In addition, employees enjoy paid time off and exclusive discounts across our portfolio of hotels. Join our team and experience the support, flexibility, and benefits that help you thrive both professionally and personally.

What you will have an opportunity to do:

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.

Key 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.

What are we looking for?

• 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.

Compensation:

$180,000

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$200,000