Job Description

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.

This 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.