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Assistant Director of Sales

Four Seasons

Chicago, IL · HybridFull-time$100–112K/yrPosted 1 day agoStill listed today

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At a glance

Compensation
$100–112K/yr
Location
Chicago, ILHybrid
Schedule
Full-time
Work Authorization
Not specified

Olive lists jobs from US employers, including remote roles you can work from the United States.

Job overview

The Assistant Director of Sales works with the Director of Sales and Commercial Director to achieve group sales team goals and individual territory targets. The role focuses on prospecting and soliciting group business, qualifying leads, negotiating contracts, and representing the hotel in site inspections and client relationships. It also supports budgeting, marketing plans, presentations, and team engagement at Four Seasons Hotel Chicago.

Skills & qualifications

RequiredNice to have

Skills

Independent Decision-MakingMentoringInterpersonal SkillsSalesDelphi/Golden S&CCRM Data ManagementSales ReportingAnalytical SkillsOrganizational SkillsStrategic PlanningAttention to DetailMicrosoft Office SuiteSales SystemsWritten CommunicationVerbal CommunicationPrioritization

Qualifications

5+ Years Group Sales Manager Experience

Benefits

Medical Insurance
Dental Insurance
Vision Insurance
401(k) Match
Paid Time Off

Full job description

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 & solicit new & repeat business for assigned territory, focus on Entertainment & Production, Middle East, and Citywide markets

  • 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 inspections. 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

How this job compares

Set against the 2,122 open Sales Management jobs on Olive Jobs, counted November 4, 2026.

Pay
  • This posting$100–112K/yr
  • Illinois median$125–155K/yr53 salary ranges
  • US median$120–161K/yr1,315 salary ranges

This range's midpoint, $106K, is 24% below the Illinois median midpoint ($140K) — in the middle half of Sales Management salary ranges in Illinois.

Openings
Olive Jobs lists 67 open Sales Management jobs in Illinois and 2,122 across the US. 9% of them nationwide are listed as remote or flexible.
Hiring the most in Illinois
Experience
This posting asks for at least 5 years of experience; Sales Management postings that state a minimum ask for 5 years at the median (1,615 postings).
Education
371 of the 2,122 open Sales Management jobs (17%) ask for a bachelor's degree or higher.

Counted across the open, public US postings on Olive Jobs on November 4, 2026. Pay medians are the middle values of the low ends and of the high ends of postings that list both ends of a range in the same cadence (a yearly salary or an hourly rate); a range's midpoint is halfway between its ends. Pay and experience figures resting on fewer than 20 postings are left out.

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