Complex Assistant Director of Sales and Marketing

About Our Property

The Midland Hotel, located in the bustling heart of Chicago, Illinois, offers 403 stylish guest rooms, 12,589 sq ft of versatile meeting space, and a dynamic environment for guests and employees. The hotel prides itself on outstanding service and memorable experiences. The property provides diverse positions across various departments and offers comprehensive training programs to ensure team members develop their skills.

Employees receive a comprehensive benefits package, including medical insurance with employer contributions, vision, dental, life, pet, and accident insurance options, a 401(k) program with an employer match and immediate full vesting, paid time off, and exclusive discounts across the portfolio of hotels. On‑site wellness programs and local discounts are also available.

The Complex Assistant Director of Sales & Marketing supports the overall sales, marketing, and revenue‑generating efforts for multiple properties. This position works directly under the guidance of the Complex Director of Sales & Marketing and plays a key role in driving hotel revenue through proactive sales activities, relationship development, client engagement, marketing initiatives, and operational collaboration.

The position requires a dynamic hospitality professional with strong relationship‑building skills, a passion for customer service, and the ability to identify and secure new business opportunities while maintaining and growing existing accounts. This role requires a high level of professionalism, creativity, organization, and responsiveness in a fast‑paced hotel environment.

• Support the execution of strategic sales plans to achieve and exceed revenue goals for guestrooms, meetings, catering, and hotel services.
• Actively solicit new business through prospecting, networking, cold calls, site tours, outside sales calls, and community involvement.
• Maintain and grow relationships with corporate, group, entertainment, social, and travel industry accounts.
• Assist in identifying market trends, competitor activity, and emerging business opportunities within the hospitality market.
• Conduct hotel site inspections, client presentations, and sales appointments for prospective and existing clients.
• Collaborate with operational departments to ensure successful execution of group and client expectations.

• Assist with implementation of marketing campaigns, promotional initiatives, social media coordination, and brand visibility efforts.
• Support hotel positioning within the local market while maintaining brand standards.
• Participate in community networking events, industry organizations, trade shows, and client events to promote both hotels.
• Assist with development of sales collateral, presentations, and promotional materials.

• Respond promptly to inquiries, RFPs, and client communications.
• Maintain accurate account, activity, and pipeline information within designated sales systems.
• Support contract negotiation and account follow‑up activities.
• Foster long‑term client relationships through exceptional communication and personalized service.

• Prepare reports, forecasts, and sales activity updates for leadership review.
• Participate in weekly sales strategy meetings and revenue discussions.
• Assist with budgeting, market analysis, and performance tracking initiatives.
• Maintain knowledge of brand and corporate systems, brand standards, and company policies.

• Bachelor’s degree in Hospitality Management, Business, Marketing, or related field preferred.
• Minimum of 5 years of leadership roles in hotel sales & marketing, preferred.
• Brand experience preferred.
• Strong verbal and written communication skills.
• Excellent interpersonal, organizational, and presentation skills.
• Ability to multitask and prioritize in a fast‑paced environment.
• Proficiency in Microsoft Office and hotel sales systems.
• Knowledge of the hospitality market preferred.

• Ability to sit or stand for extended periods of time.
• Frequent walking throughout hotel properties,…