Director of Sales and Marketing - theWit

DREAMWEAVER HOTELS LLCChicago, IL
$150,000 - $160,000Onsite

About The Position

theWit Hotel is seeking a Director of Sales & Marketing to lead its Sales Department and bring its 6 Xs Hotter Service Philosophy to life. theWit is more than a hotel—it’s an experience, and they are searching for someone who can elevate their culture of wit, humor, artistry, and world-class service. As the Director of Sales & Marketing, you’ll oversee the entire Sales Department and set the tone for passion, professionalism, and playfulness across the property. You’ll be responsible for driving revenue generation, leading innovative marketing efforts, and positioning theWit as a top choice for travelers, dining guests, groups, and events. Working closely with the General Manager, Executive Chef, and other department heads, you’ll guide a talented team of sales and catering professionals, build strong client relationships, and ensure service and revenue goals consistently exceed expectations.

Requirements

  • A proven track record of success in hotel sales, marketing, and leadership.
  • Previous Director of Sales experience with luxury hotels is required.
  • Strategic thinker with a bold, imaginative approach to sales and marketing.
  • Strong leadership abilities with a passion for coaching and team development.
  • An innovative mindset and ability to foster a motivating, high-energy work environment.
  • Passion for delivering personalized, Four Diamond guest experiences.
  • Strong knowledge of revenue management strategies, sales reports, and competitive benchmarking.

Nice To Haves

  • Hilton Experience is a strong plus
  • Embody wit, creativity, humor, and sophistication.
  • Thrive in environments that value individuality, teamwork, and culture.
  • Not afraid to push boundaries, bring fresh ideas, and deliver results with flair.

Responsibilities

  • Lead, inspire, and motivate the Sales Department to deliver an exceptional Four Diamond experience for every guest.
  • Direct all sales, revenue management, catering, and marketing efforts to maximize room and food & beverage revenues.
  • Develop fresh, innovative strategies to position theWit above the competition.
  • Partner with the Executive Chef and General Manager to promote unique dining outlets, private events, and the renowned rooftop lounge.
  • Build strong community and business relationships to attract groups, retain loyal partners, and drive profitability.
  • Work with PR and creative agencies to lead high-impact advertising and marketing campaigns.
  • Host client events, engage in networking functions, and represent theWit passionately in the market.
  • Lead, develop, and coach a results-driven sales team through training, accountability, and collaboration.
  • Monitor department performance, budgets, and revenue targets to consistently achieve and exceed hotel goals.

Benefits

  • Medical Plans: Choice of three plans to meet your healthcare needs.
  • Dental Plans: Two options for dental coverage.
  • Vision Insurance: Coverage for routine eye care and eyewear.
  • Paid Time Off (PTO): To support work-life balance.
  • Accident/Hospital Indemnity/Critical Illness plans (new for 2026).
  • 401(k) Retirement Plan: Plan for your future with employer contributions.
  • Flexible Spending Account (FSA): Pre-tax savings for healthcare and dependent care expenses.
  • Life and AD&D Insurance: Employer-provided coverage with additional voluntary options.
  • Short-Term Disability (STD): Employer-provided coverage to support you during temporary disability.
  • Voluntary Long-Term Disability (LTD): Additional protection for extended disability.
  • Commuter Benefits: Save on transit and parking expenses.
  • Pet Insurance: Options to support your furry family members.
  • Hilton travel discounts and employee room rates worldwide
  • Career growth and training opportunities
  • Access to wellness programs and employee appreciation events
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