Pineapple Hospitality Company Front Desk Supervisor in Chicago, Illinois

Pineapple Hospitality is a rapidly expanding boutique hotel management company. We are looking for team members who are all about providing outstanding guest service—this is hospitality after all. We’re fun, a little quirky, and always striving to get better (that’s where you come in). Currently we have nine hotels in five states, with plans to continue growing. If you want to be part of a far-from-stuffy company with lots of opportunities, this may be the place for you.

Who We’re Looking For:


Around here, we have a reputation for being ridiculously friendly, helpful and accommodating—and nothing will tank that faster than lousy front desk service. That’s where you come in. As Front Desk Supervisor you are responsible for making sure the front desk staff is providing service consistent with impeccable Pineapple Hospitality standards.

What You Bring:

We do not set a low bar—it’s our goal to make each and every stay the very best one a traveler has ever had. And that starts with the front desk. You will be the captain of this ship, serving as team lead for the front desk staff ensuring smooth team operations and effective collaboration. Oh but that’s not all. Here are a few of the other tasks that will keep you busy on a daily basis:

  1. Proving training and guidance for front desk staff on hotel standard operating procedures and departmental standards.

  2. Occasionally stepping in to complete daily hotel front desk tasks.

  3. Assisting Front Desk Manager with monitoring performance and attendance.

  4. Balancing daily paperwork: Cash drawer, deposits, reconciling credit cards and submitting batches.

Where You’ve Been:

We’re looking for someone with a High School diploma (or equivalent) and six to 12 months of related experience. No wallflowers wanted—you must be able to contribute to a collaborative and diverse team dynamic while quickly assessing situations and creating effective resolutions to problems. This probably goes without saying, but a passion for customer service is an absolute must. A working knowledge of Microsoft Windows and Office is preferred.

When You’re Here:

Sometimes you’ll be behind a desk—but also be prepared to move around because more than half of the time you will be standing/sitting, carrying/lifting up to 50 pounds, walking, bending/twisting, climbing stairs and more. You also must be able to accommodate varying schedules including nights, weekends and holidays. But wait, there’s a great upside: in exchange for your flexibility we offer excellent pay, hotel discounts, F&B; discounts and the opportunity to be part of an anything-but-standard growing hotel company.

Department: Front Desk

Location: Chicago, IL