Assistant Director of Sales
Four Seasons Hotels and Resorts
Chicago, IL · Posted November 3, 2026
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Where Chicago, IL ranks
Where Chicago, IL placed in our monthly rankings, month by month. Each month stays online at its own address.
November 2026
- #1Best cities for government pay after cost of living$146k · of 18
- #1Cities with the most jobs that do not need a four-year degree in the Midwest684 jobs · of 51
- #1Cities with the most jobs that do not need a four-year degree in the Great Lakes684 jobs · of 36
- #1Best cities for software and engineering jobs in the Midwest1,140 openings · of 59
- #1Best cities for software and engineering jobs in the Great Lakes1,140 openings · of 48
- #1Best all-round cities for mid-career professionals in the Midwest80 / 100 · of 20
Rankings about sales jobs
- Best cities for sales jobs #1 New York (2,774 openings)
- Best cities for sales pay after cost of living #1 Santa Clara ($175k)
- Most requested AI skills in sales jobs #1 AI tools in daily work (4.1%)
- AI tools named most often in sales jobs #1 Gong (0.93%)
- Employers with the most sales jobs #1 Charter Communications (389 roles)
How AI is used in this kind of work
AI use among sales managers is little observed so far. Measured exposure for sales managers: 4% (little observed).
Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.
Skills this job asks for
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About the job
About Four Seasons:
Four Seasons is powered by our people. We are a collective of individuals who crave to become better, to push ourselves to new heights and to treat each other as we wish to be treated in return. Our team members around the world create amazing experiences for our guests, residents, and partners through a commitment to luxury with genuine heart. We know that the best way to enable our people to deliver these exceptional guest experiences is through a world-class employee experience and company culture.
At Four Seasons, we believe in recognizing a familiar face, welcoming a new one and treating everyone we meet the way we would want to be treated ourselves. Whether you work with us, stay with us, live with us or discover with us, we believe our purpose is to create impressions that will stay with you for a lifetime. It comes from our belief that life is richer when we truly connect to the people and the world around us.
About the location: Our property is a vibrant hub of culture, style and energy and includes our newly transformed restaurant which embodies iconic luxury boldly reimagined to capture the essence of Chicago through inspired food, drink, art and music. Four Seasons Hotel Chicago is honored to be ranked as one of Conde Nast Traveler Reader's Choice Top 50 Hotels in the World. We offer 345 elegant guest rooms and suites: and a luxury spa. We are located steps away from the famed Magnificent Mile, glamorous North Michigan Avenue shopping and minutes from the city’s business and financial center. Adorn Restaurant features globally inspired cuisine starring the bounty of the Midwest. Adorn Bar showcases craft cocktails and a wine list that sparks conversation, all with a lively, convivial vibe beckoning to be discovered.
About the role Assistant Director of Sales - works closely with Director of Sales & Commercial Director in achieving group sales team goals, while responsible for achieving individual sales targets based on assigned territory.
What you will do
Prospect & s olicit new & repeat business for assigned territory , focus on Entertainment & Production , Middle East, and C itywide market s
Respond promptly to business inquiries and qualify leads to maximize group room nights, catering revenue, and overall RevPAR performance
Negotiate, prepare, and finalize group contracts that support the Hotel’s revenue objectives and commercial strategy
Serve as the on-site representative for remote Sales Managers by conducting all in-person site inspection s . Assist DOS & CD on team dynamics, engagement, and drive for group team achievement
Business Travel as needed to develop client relationships, representing the hotel in a professional manner
Assist with budget setting, marketing plan, presentations, strategies, and overall department representation internally
What you bring
Minimum 5 years as Group Sales Manager in previous role
Ability to work and make decisions independently in the best interest of the hotel
Ability to mentor team members to make highest level of achievement
Exceptional interpersonal dynamics to create relationships externally & internally
Driven, competitive, & focused sales person
Proficiency with Delphi/Golden S&C and a commitment to maintaining high-quality CRM data and sales reporting
Strong analytical, organizational, and strategic planning abilities with exceptional attention to detail
Strong knowledge of Microsoft Office Suite and relevant sales systems
Excellent written and verbal communication skills
Ability to prioritize multiple responsibilities and thrive in a fast-paced luxury hospitality environment
What we offer:
Compensation: $100,000 - $112,000
Energizing Employee Culture where you are encouraged to be your true self!
Comprehensive learning and development programs to help you elevate your craft.
Competitive wages and benefits (Medical, Dental, Vision and Retirement Plan) as well as Paid Time Off & Holiday Pay
401(k) Retirement Plan including Employer Matching Program
Inclusive and diverse employee engagement & recognition events all year-round .
Exclusive discount and travel programs with Four Seasons
Complimentary Dry Cleaning for Employee Uniforms & Employee Meals
And so much more!
Schedule & Hours:
Full Time - some weekends/evenings if needed & Business Travel
Hybrid role with on property days required weekly
Four Seasons is an Equal Opportunity, Affirmative Action employer. Minorities, women, veterans, and individuals with disabilities are encouraged to apply. To access the 'EEOC is The Law' Information poster please visit this website - https://www.eeoc.gov/know-your-rights-workplace-discrimination-illegal