Assistant General Manager in Chicago | Steer a Premier Hotel’s Success

Are you a seasoned hospitality leader ready to elevate your career? The Grand Oak Hotel, a cornerstone of Chicago’s vibrant downtown scene, seeks a strategic and passionate Assistant General Manager. This is your opportunity to be the operational engine behind a beloved landmark, directly influencing daily excellence, team morale, and unforgettable guest journeys.

About The Role: The Operational Architect

As the right hand to our General Manager, you are the linchpin of our hotel’s seamless operation. This role transcends traditional management; it’s about being the chief problem-solver, the culture champion, and the driver of financial performance. You will oversee the intricate dance of front desk, housekeeping, food & beverage, and guest services, ensuring every department aligns with our brand’s gold standard. Your days will be a dynamic blend of floor presence, data analysis, staff coaching, and strategic planning. You will be entrusted with P&L oversight, budget management, and the implementation of systems that boost efficiency and profitability. Most importantly, you will foster an environment where your team feels empowered and guests feel genuinely welcomed, directly contributing to our reputation and revenue growth.

Key Responsibilities

Operational & Financial Leadership

• Directly oversee daily operations across all hotel departments, ensuring compliance with brand standards and local regulations.
• Manage departmental budgets, control labor and supply costs, and analyze weekly/monthly financial reports to identify opportunities and address variances.
• Implement and refine operational policies, procedures, and training programs to maximize efficiency and service quality.
• Lead inventory control, asset management, and vendor relations to optimize cost and quality.

Team Development & Culture

• Recruit, onboard, train, and mentor department heads and supervisors, building a strong, cohesive leadership pipeline.
• Champion a positive, inclusive, and service-oriented workplace culture. Conduct regular team meetings, performance reviews, and recognition initiatives.
• Address employee relations issues promptly and fairly, ensuring compliance with employment laws.
• Lead by example—be visible on the floor, demonstrating the highest level of customer service and professional conduct.

Guest Experience & Quality Assurance

• Own the resolution of major guest concerns and complex service recovery situations, turning challenges into loyalty-building moments.
• Conduct regular quality inspections of public areas, guest rooms, and back-of-house to uphold impeccable standards.
• Analyze guest feedback (surveys, online reviews) and drive departmental action plans to continuously enhance the guest journey.
• Collaborate with sales and marketing to support group bookings and local partnerships.

What You Bring: The Ideal Candidate

Must-Have Qualifications

• Bachelor’s degree in Hospitality Management, Business Administration, or a related field preferred; equivalent progressive experience will be considered.
• Minimum 5 years of management experience in a full-service hotel, with at least 2 years in a supervisory or assistant management role (e.g., Front Office Manager, Housekeeping Manager).
• Proven ability to manage a P&L, create budgets, and interpret financial data to make sound business decisions.
• Exceptional interpersonal and communication skills; adept at motivating diverse teams and negotiating with vendors.
• Strong proficiency with MS Office Suite and hotel management systems (e.g., Opera, Cloudbeds).
• In-depth knowledge of hospitality industry regulations, safety protocols (OSHA), and ADA compliance.

Preferred Attributes

• Experience in an upscale or boutique hotel environment.
• Certifications such as CHAM (Certified Hotel Asset Manager) or similar.
• A track record of successfully implementing process improvements that increased efficiency or guest satisfaction scores.
• A calm, decisive demeanor under pressure and a passion for creating “wow” moments.

Compensation & Benefits

We believe in rewarding exceptional leadership. The salary range for this critical role is $65,000 – $85,000 USD annually, commensurate with experience and qualifications. This is complemented by a robust benefits package designed for your total well-being and long-term security:

• Performance Incentives: Eligibility for a substantial annual bonus tied to hotel profitability and individual performance metrics.
• Health & Wellness: Comprehensive medical, dental, and vision insurance plans with generous employer contributions.
• Financial Security: 401(k) plan with company match, life insurance, and short/long-term disability coverage.
• Time Off: Generous paid time off (PTO) accrual, including vacation, sick days, and holidays.
• Travel Perks: Significant discount on room rates at The Grand Oak Hotel and sister properties for you and your immediate family.
• Growth Fund: An annual professional development stipend for conferences, certifications, or courses.
• Additional Perks: Complimentary meals during shifts, parking allowance, and a dynamic, supportive work culture.

Join a Legacy in the Making

The Grand Oak Hotel isn’t just a place to work; it’s a community dedicated to the art of hospitality. Here, your leadership will have a tangible impact on our guests’ cherished memories and your colleagues’ career trajectories. If you are driven by operational mastery, inspired by team development, and committed to the relentless pursuit of excellence, we want to hear from you.

To apply for this Assistant General Manager position, please submit your resume and a cover letter detailing your most significant operational achievement and your leadership philosophy to careers@grandoakchicago.com. We review every application with care and will contact qualified candidates for the next steps.