Job Title: Assistant Roof Manager
Location: ROOF on theWit – Chicago, IL
Company Overview:
Located 27 stories above the city, ROOF on theWit is one of Chicago’s most sought-after rooftop destinations, known for its stunning skyline views, innovative cocktails, and vibrant nightlife. As part of theWit Hotel, a Hilton property, ROOF delivers a dynamic guest experience that blends luxury, entertainment, and exceptional service.
Position Summary:
The Assistant Roof Manager oversees the daily operations of ROOF on theWit, including food and beverage service, entertainment, guest experience, and team leadership. This role requires a highly motivated hospitality professional who can balance strategic management with hands-on service execution in a fast-paced, high-energy environment.
Responsibilities:
- Lead, develop, and motivate a diverse team of supervisors, servers, bartenders, and support staff to ensure a consistent, high-quality guest experience.
- Oversee nightly operations, ensuring adherence to service standards, health and safety regulations, and labor compliance.
- Monitor guest feedback and implement improvements to elevate the overall guest experience.
- Partner with marketing and event teams to support promotions, private functions, and entertainment programming.
- Conduct daily pre-shift meetings, staff training, and regular performance evaluations.
- Maintain a visible floor presence during peak periods, ensuring service excellence and prompt guest recovery when needed.
- Ensure compliance with all Hilton brand standards, local liquor laws, and city licensing requirements.
Qualifications:
- Minimum of 3 years of leadership experience in upscale, high-volume nightlife or rooftop venues, restaurants, or hospitality operations.
- High School Diploma or GED Required
- Strong understanding of mixology, bar operations, and beverage cost management.
- Proven ability to lead large teams with a focus on training, engagement, and accountability.
- Exceptional communication, organizational, and problem-solving skills.
- Availability to work evenings, weekends, and holidays as business demands.
- Knowledge of POS systems, inventory management, and Microsoft Office Suite.
- Hilton or luxury brand experience preferred.
- Must be 21 years of age or older.
Compensation:
$62,000 - $64,000 per year
Benefits:
We offer a comprehensive benefits package designed to support the health, well-being, and financial security of our employees. Our offerings include:
- 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
Please note that eligibility for certain benefits may vary depending on your employment status. Detailed information, including plan summaries and enrollment instructions, will be provided during onboarding or upon request. This summary complies with applicable state laws and is subject to change based on legislative updates or company policies.
E-Verify Participation:
theWit Hotel participates in the U.S. Department of Homeland Security E-Verify program to confirm the employment eligibility of all newly hired employees.
Equal Employment Opportunity:
theWit Hotel and ROOF on theWit are proud to be Equal Opportunity Employers. We celebrate diversity and are committed to creating an inclusive environment for all employees. Employment decisions are made without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, protected veteran status, or any other protected characteristic under applicable law.
About UsThis job posting is for a position at a hotel that is owned and operated by an independent franchisee. The franchisee controls all aspects of the hotel’s employment practices, including recruiting, hiring, salary, benefits and compensation decisions, and the collection and processing of the personal data that you provide on this website. If you accept this position, you will be employed by a franchisee and not by Hilton. You will not be eligible for compensation or benefits from Hilton. You will be eligible for compensation or benefits only as may be provided to you by the independent franchisee.Skills Required
- Minimum 3 years of leadership experience in upscale, high-volume nightlife, rooftop venues, restaurants, or hospitality operations
- High school diploma or GED
- Strong understanding of mixology, bar operations, and beverage cost management
- Proven ability to lead large teams with a focus on training, engagement, and accountability
- Exceptional communication, organizational, and problem-solving skills
- Availability to work evenings, weekends, and holidays as business demands
- Knowledge of POS systems, inventory management, and Microsoft Office Suite
- Hilton or luxury brand experience
- Must be 21 years of age or older
Hilton Compensation & Benefits Highlights
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Wellbeing & Lifestyle Benefits — The Go Hilton travel program offers up to 110 discounted nights per year, with employee room rates as low as $40 and additional friends-and-family and on‑property dining discounts. Select programs like Thrive Sabbatical and Thrive Reset provide paid time off with stipends for personal goals or recharge.
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Retirement Support — The U.S. 401(k) match is 100% on the first 3% of pay plus 50% on the next 2%, enabling up to a 4% employer match when contributing 5%. This delivers a clear, formula-based boost to long‑term savings.
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Parental & Family Support — New parents receive four weeks of fully paid parental leave, with birthing parents receiving an additional eight weeks for a total of 12 weeks. Adoption assistance and caregiving support resources are also available.
Hilton Insights
What We Do
Hilton (NYSE: HLT) is a leading global hospitality company with a portfolio of 28 world-class brands comprising more than 9,400 properties and nearly 1.4 million rooms, in 144 countries and territories. Dedicated to fulfilling its founding vision to fill the earth with the light and warmth of hospitality, Hilton has welcomed over 4 billion guests in its more than 100-year history. Named as the No. 1 World’s Best Workplace by Great Place to Work and Fortune, Hilton aims to create the best culture for its 500,000 team members around the world. Hilton has introduced industry-leading technology enhancements to improve the guest experience, including Digital Key Share, automated complimentary room upgrades and the ability to book confirmed connecting rooms. Through the award-winning guest loyalty program Hilton Honors, the more than 260 million Hilton Honors members who book directly with Hilton can earn Points for hotel stays and experiences money can't buy. With the free Hilton Honors app, guests can book their stay, select their room, check in, unlock their door with a Digital Key and check out, all from their smartphone.
Why Work With Us
Hilton is proud to be recognized as the World’s Best Workplace by Great Place to Work and Fortune. At Hilton, every job makes the stay. Team Members can make an impact, be themselves, build new skills, grow their careers, explore opportunities around the world, and enjoy people-first benefits like Go Hilton travel discounts.
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With more than 9,400 hotels and properties in 144 countries and territories, plus corporate offices and teams around the world, Hilton offers opportunities to build a career in destinations and communities worldwide.
