Dear Guests,

It has been an absolute pleasure hosting you and so many others over the years at StayWithJay. Managing our properties in Cleveland has been an incredible journey, and I want to personally thank you for being part of it.

I’m deeply grateful for our host team—Shymeika, and Erica especially—who have worked tirelessly to ensure a safe, comfortable, and reliable stay for our commuter guests, gig workers, and those traveling from cities like Atlanta and beyond. Alongside our tourist guests who visit for events, we’ve built a vibrant community that makes Cleveland feel like a second home for so many.

This journey has been rewarding beyond words. The conversations, connections, and shared experiences have made every moment worthwhile. However, as our business continues to grow, so do the demands of maintaining and improving our residences. Providing great guest experiences isn’t just about responding to messages or handling logistics—it also requires ensuring that our spaces are well-maintained and continually improving.

What’s Staying the Same?

Your local StayWithJay team isn’t going anywhere—Shymeika and the crew will still be here, ensuring your stay is smooth. Our team will continue handling:
✔ Cleaning & turnovers
✔ Restocking essentials
✔ On-site maintenance & upkeep

What’s Changing?

With that in mind, we’ve made the decision to transition the back-office operations to a highly reputable Cleveland-based company specializing in short-term rental management. You may have already noticed some changes, including interactions with new support staff. These professionals are now our digital team, handling check-ins, check-outs, and making sure all the essential information is available to you seamlessly.

This shift allows us to focus on long-term improvements while maintaining the same level of care and hospitality you’ve come to expect, and increasing the consistency by which we deliver this great service.

The Bigger Picture

StayWithJay is more than just a hosting operation—it’s a brand, and we’re growing. We’re also part of launching Studio Haus, an exciting Airbnb franchise designed for serious investors looking to scale their short-term rental businesses.

Personally, I’ll be dedicating more time to my work as a realtor and developer, helping other Airbnb investors grow and optimize their businesses through my consulting work. We’ve got some exciting things in the pipeline, and this transition gives us the bandwidth to expand, improve, and bring even more value to our guests and partners.

I appreciate your continued support, and I’m excited for you to experience the upgrades we’re rolling out in 2025. Whether you’re a commuter, a returning guest, or a first-time visitor, we’re committed to making StayWithJay the best place to stay in Cleveland.

Looking forward to seeing you again soon!

Jay & Team