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Assistant Director of Property Operations - The Drake Hotel

$90k - $100k

Hilton Chicago

Job Identification: 208257

Job Category: Engineering, Maintenance and Facilities

Job Schedule: Full time

Salary $90,000-$100,000/USD/Yearly

Equal Opportunity Employer EOE, including disability/vets

Exceptional Hospitality Starts with You

Picture yourself brightening someone’s day. When you join our Hotels team, that’s exactly what you’ll do every time you come to work! As an Assistant Director of Property Operations , you’re not just assisting the Director in overseeing the safety and functionality of the property – you’re spreading the light and warmth of hospitality by delivering memorable experiences that make the stay for every guest.

Here's what you'll do during a typical day:

  • Partner in leading facility operations: Assist in directing the functionality, safety, and compliance of buildings, mechanical systems, electrical systems, HVAC, life safety systems, and grounds in accordance with federal, state, and local regulations

  • Oversee facility maintenance: Perform facility inspections and supervise construction, installation, maintenance, and repairs of electrical, mechanical, and architectural systems

  • Support property improvement projects: Assist in directing capital projects and property rehabilitations – including scheduling, budgeting, contractor bidding, and licensing/permitting – while ensuring regulatory compliance

  • Oversee work order fulfillment: Ensure routine maintenance and repairs are assigned, verified, and documented in the property maintenance management system

  • Ensure regulatory compliance: Communicate with government officials to maintain permits, coordinate inspections, and uphold safety and code standards

  • Cultivate a high-performing team: Drive engagement and retention through performance management, professional development, and recognition programs

What It Takes to Make the Stay

At Hilton, our core values define what it takes to succeed here and guide the qualities we look for in every team member:

A passion for spreading the light and warmth of Hospitality . Acting with Integrity and always doing the right thing. Inspiring others through Leadership . A belief that Teamwork drives the best outcomes. A sense of Ownership and accountability. And a focus on the Now , bringing urgency and discipline to every moment, knowing it can make a lasting impact.

In addition, this role requires the following minimum qualifications:

  • High School Diploma/University Degree (list highest required level only)

  • X years of experience in Y (e.g., hotel management)

  • License or Certification

  • Languages

How We'll Help You Thrive

At Hilton, the hospitality we’re known for doesn’t end with our guests. We proudly invest in our Team Members’ wellbeing, supporting you through all of life’s moments. When you join Hilton, our exceptional care extends to you with unmatched perks and benefits, including*:

  • Incredible travel perks – Enjoy 110 nights of deeply discounted travel, with room rates as low as $40/night at our world-class hotels through our Go Hilton travel program

  • Own a piece of Hilton – Through our employee stock purchase program (ESPP), you can invest in Hilton shares at a 15% discount to help build your financial future

  • Paid parental leave – Because family matters. We offer paid leave for eligible Team Members, including partners and adoptive parents

  • Personalized caregiving support – Access dedicated caregiving concierge services to help navigate caregiving for yourself and your loved ones

  • Crisis concierge – In times of loss, our Crisis Concierge offers a single, compassionate point of contact for both practical support and emotional care

  • Mental health resources – Your wellbeing comes first. Eligible Team Members can access free counseling and support through our best-in-class Employee Assistance Program (EAP)

  • Generous paid time off (PTO) – Recharge, relax, and take time for what matters most

  • Health & welfare benefits – From checkups to dental cleanings to new glasses, we offer a variety of health plans that keep you and your family covered

  • Financial security for your future – Our retirement plans make it easier to save for what’s next

*Benefits availability may vary depending on Team Member’s location as well as terms and conditions of employment and are subject to the terms and conditions of each specific program/plan.

Join an Award-Winning Workplace Culture

At Hilton, we don’t just deliver exceptional experiences for our guests—we build an exceptional workplace for the Team Members who make it all possible. As a global leader in hospitality, we’ve welcomed more than 3 billion guests worldwide, all while staying true to our founding vision: to fill the earth with the light and warmth of hospitality.

Our award-winning culture has earned us repeated recognition on the World’s Best Workplaces list by Great Place to Work and Fortune. With our suite of world-class brands ( , and a company-wide commitment to providing the best stay for every guest, we’re setting new standards for the future of travel.

Whether you’re starting your career or exploring something new, Hilton supports your journey every step of the way. Come for the job, stay for the career—and help us make every stay a little more magical.

Curious about life at Hilton? Explore our Careers Blog ( to see why we’re more than a great place to stay—we’re a great place to work.

Vacancy posted 1 day ago
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