Your Personal Short‑Term Vacation Rental Advisors

Dedicated one-on-one support for STR operators navigating PMS decisions, transitions, and ongoing operational success.

Your expert partner is here.

Testimonials

Meet Dawn Yeskulsky, Your Go-To STR Operations Expert

I started PMS Pros because I know how hard it is to find truly experienced, unbiased support in this industry. After years working across property management, tech, and fintech, I saw too many teams making big PMS and accounting decisions without someone in their corner — so I built a team that can be that partner.

We’re fully agnostic, never paid by vendors, and focused only on what’s right for your business. Whether you’re gearing up for a PMS switch,  trying to clean up accounting, or just need your systems and team running more smoothly, we’re here to bring clarity, structure, and a clear path forward.

At the end of the day, our goal is simple: help you run a stable, confident, scalable operation — without the stress.

What We Do

Choosing the Right PMS

If you’re overwhelmed by PMS options or worried about picking the wrong system, we’ll walk through your needs together and make sure any platform you consider actually fits the way your business runs.

PMS-Specific Pros

We match you with a Pro who truly knows your PMS — the workflows, the quirks, and the real-world challenges you’re dealing with. Our team includes experts in Guesty, Track, Streamline, and other platforms, so you’re paired with the right person from the start.

Optimize the PMS You Already Have

Not sure you’re getting everything you should out of your PMS? We take a close look at how you’re using your current system, identify what’s working (and what’s not), and show you exactly where you can improve to get more efficiency and fewer headaches.

Vendor Contract Assistance

We help you navigate contracts and pricing conversations with PMS and third-party vendors so you clearly understand the real costs, terms, and what you’re actually signing up for. Having a Pro in your corner makes all the difference.

third-party software recommendations

We help you sort through the noise and find third-party tools that actually make your PMS stronger. Our recommendations focus on what fits your workflow, fills the gaps, and creates a smoother, more connected tech stack.

payments evaluation & strategy

We review how payments run in your PMS and help make the process more efficient, secure, and cost-effective. We also build a plan for offering extra payment options—like Buy Now Pay Later, Pay By Group, or PayPal—so guests have more flexibility and you stay in control.

Here for Your Team. Focused on Your Success

It’s Not About the Software — It’s About Your Business

PMS Pros was created to make software transitions and day-to-day system management easier for property managers. Our mission is to support teams through onboarding, adoption, and optimization by offering cost-effective, PMS-specific services that take the stress out of the “dreaded software switch.” Today, we support Guesty, Track, Streamline, and several other platforms.
We’re committed to putting property managers first by offering personalized, one-on-one guidance through every stage of your PMS journey. Whether you’re preparing for a transition, navigating implementation, or settling into long-term use, our goal is to make sure you always have a knowledgeable partner who understands your operation and advocates for your needs. We envision a world where property managers feel supported, confident, and fully equipped to get the most out of their software — not just at go-live, but every day after.
We serve as your dedicated representative across every stage of your PMS journey — from choosing the right system, to onboarding, to long-term adoption and optimization. Our goal is to deliver a white-glove experience that minimizes disruption and keeps your operation running smoothly while the software evolves around you. Once your team is confident and fully equipped, we hand over the baton — and if you ever need us again, your Pro is only a message away.

904-821-PROS

Personal. Proactive. By Your Side.

Why Work With PMS Pros in Addition to Your PMS Provider?

Every PMS provider has its own approach to onboarding — videos, help articles, and scheduled calls designed to walk your team through the basics. These resources are important, and PMS Pros isn’t here to replace them. Instead, we’re here to elevate the experience for operators who need deeper, more personalized support than standard training can offer.
When you work with a PMS Pro, you’re not just getting extra help — you’re getting a partner who steps into the details with you. We’ll walk through your processes, help refine your workflows, verify your data, and make sure the right tasks land with the right people on your team. And when something comes up, you don’t have to wait for a ticket or a scheduled call. You can reach out directly to your Pro for real-time support. If your team needs deeper, hands-on guidance, we’re happy to come onsite and work alongside you to make the transition feel seamless.

Tailored Operational Expertise

Seamless Team Coordination

Pro-Level Strategic Insight