Paradise (aka Puerto Rico) Based Position

Hi there. We are a family run business that operates boutique hotels in Puerto Rico. We have properties in Condado & Vieques with Culebra coming soon. 

We are growing rapidly and want the right person to help us design & train an amazing team of players who like to create amazing experiences for our guests. 

more text here. 

If you’re interested, then please carefully read this entire page and follow the instructions for next steps…

You, In a Nutshell:

This position will work in Puerto Rico, both San Juan & the island of Vieques. You are a well grounded leader who is an organized “get shit done” person who is practical yet dynamic. You are a kind soul but not naive. You have a disciplined mind and can smile when confronted with uncertainty. You are a problem solver that creates solutions and trains the team. You know in your hear service is a blessing and giving is the greatest opportunity for learning and receiving. 

Salary is negotiable (perhaps relative to experience) and hours can be flexible, but would be about 40 hours/week. XXXX experience not required. XXXXX is a requirement.

Us, In a Nutshell:

We’re a fun family who loves to travel and experience the world. We create hotels so we can give back to the world what we love.  We know what people want when they book a vacation or business trip. We love exceeding their expectations. 

We know that creating this comes down to the right people and training. 


Are You and This Position a Perfect Match?

Hmmmm, could be. Depends, does this sound like you?…

  • You agree – It’s cool to work with a fun group of people, and be involved in helping plan and execute all things fun, safe, experiential, and  educational with our the little ones. We like these things too. 

  • You’re self-reliant – You follow instructions well, but can also think for yourself and don’t always have to be told every little thing to do in detail.
  • You’re conscientious – Naturally mindful & thoughtful about the details of a thing, and really need for things to be “done right”.
  • You’re maybe even a little nutty or weird – Our family has a unique culture. We’ve kinda mastered the art of not taking ourselves too seriously, and just enjoying life as it comes our way. “Characters welcome.”

If this sounds like you, then keep reading and read carefully

What Does a “Family Kid Hero” Even Do?

Our Hero will work alongside the Dennis Family to make sure our kids are in a safe, fun loved, having fun & safe. From picking them up at pre-school, taking them to the park, reading them their favorite books, dancing with them, coloring, playing games, making tasty, healthy snacks with them.

We are raising well mannered, kind, independent children and want you being part of that. Our goal is to “teach them to fish” and be kind to others. 

Basically this person will be a front-line kid champion, not just “babysitting” but going the extra mile to ensure our kiddos have a safe environment full of love and kindness where they are set up to excel in the world today.



Yes! I already listed a bunch up top, but additionally to those already mentioned the right person for this will…

⟶ Know your way around kids, understand they are unpredictable.
⟶ Have super-high integrity, and a track record of being honest, dedicated and loyal.
⟶ Be extremely organized, with special attention to detail.
⟶ Be able to adapt and adjust to things quickly, thoroughly, and in detail.
⟶ Be respectful and comfortable with all cultures, cause we will be traveling the world.
⟶ Have solid interpersonal skills, so extremely comfortable talking to and dealing with our family.

Hours and Pay…

As mentioned, our Kid Hero’s salary is negotiable (perhaps relative to experience), and it is a full time position. Specific hours may be flexible, but should be able to be consistent and reliable.

We are willing to work with a “live-in” or local who loves to travel. 

How to Apply

If you think this job is peanut butter and you’re jelly, then please submit the application form below:

The Dennis Family looks forward to hearing from you!

– The Dennis Family

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