Housekeeping Training Lead - Vacation Rental Cleaning Company (Saturday Only)

You know what guest-ready looks like, and you know how to get other people there.

Squeaky Duck provides cleaning services to premium vacation rentals on Anna Maria Island. Our reputation is built on consistency, and consistency doesn't happen by accident. It happens because someone is in the field, working alongside teams, reinforcing standards, and helping people get better every single Saturday.

That someone is our Education & Training Lead.

This is a hands-on field coaching role. You'll be assigned a rotation of cleaning teams to follow throughout our busiest day. You'll observe their work in real time, reinforce our standards, demonstrate the right way to do things, and jump in when a team needs an extra set of hands on a tight turn. The goal isn't to catch mistakes. It's to build teams that don't make them.

What You'll Be Doing:

• Shadow cleaning teams during turnovers. Observe technique, pace, and attention to detail. When something needs to change, step in and show them, not just tell them. Make sure the "why" behind the standard is understood, not just the "what."
• Use Squeaky Duck's checklists and brand standards as your teaching framework. Your job is to make sure every team internalizes them, not just follows them when someone's watching.
• Roll up your sleeves when needed. Whether it's demonstrating technique or helping a team through a tight turnaround, you lead from the front.
• Track each team's progress, recurring issues, and wins. Document feedback through our apps with photos and clear notes so leadership can see who's leveling up, who needs more support, and where the gaps are.
• Set the energy. Our teams are diverse, with different backgrounds, experience levels, and personalities. The right person makes people feel supported, not surveilled. You motivate through respect and lead by example.

Who We're Looking For:

Someone who has supervised, trained, or led teams in a standards-driven environment. That might mean housekeeping leadership in hotels or vacation rentals, but we're also open to candidates from restaurants, healthcare, or other industries where cleanliness standards are non-negotiable and attention to detail is everything.

• Sharp eye for detail. You catch what others walk past.
• Ability to coach, not just critique
• Experience motivating and developing a diverse team
• Strong communication skills, both in person and through written documentation
• Comfortable with smartphone apps for task tracking, reporting, and communication
• Genuine understanding of professional cleaning standards

Requirements:

• Saturday availability is non-negotiable. This is a Saturday-only position on our highest-volume turnover day. If you can't commit to every Saturday, this isn't the right fit.
• Reliable transportation for travel between properties on Anna Maria Island
• Active role. You're on your feet all day, moving between properties, bending, and occasionally lifting up to 25 lbs.
• Valid Driver's License, clean background, and eligibility to work in the U.S.

Ready?

If you've got the eye, the leadership skills, and the kind of personality that makes people want to do better (not just tells them to), apply now. We want to talk to you!

Job Type: Part-time

Pay: $28.00 - $30.00 per hour

Application Question(s):

• Have you ever been convicted of a crime?
• Do you have reliable transportation to travel to and from assigned locations? Public transportation, motorcycles, or bikes are not acceptable for this role.
• What interests you most about this job?
• Do you have previous supervisory and/or training experience in standards-driven environment like housekeeping, hotel/vacation rental operations, restaurants, healthcare or similar?

Language:

• English (Preferred)
• Spanish (Preferred)

License/Certification:

• Driver's License (Required)

Ability to Commute:

• Anna Maria, FL 34216 (Required)

Work Location: In person

Salary : $28 - $30