Your Personal PMS Experts

PMS Pros is redefining short term rental expectations by offering property management teams with one-on-one expert assistance with the evaluation, selection, onboarding, and ongoing optimization of today’s leading PMS brands.

Your expert help is here!


Project Management


PMS Experienced Pro


Confident Handover


Get the Most Out of Software

“I was at my wit’s end when I found PMS Pros! My PMS provided onboarding; however, I spent most of my onboarding sessions just trying to get our footing. After onboarding was complete, I realized we needed additional assistance. I saw PMS Pros online, reached out to Dawn and she connected me with an onboarding specialist who is an expert in my PMS, and he is excellent! This service is well worth the investment, and I highly recommend it. Five stars and two thumbs up!!”

Janice Hollaway

What We Do.

software optimization

Are you getting the most out of your PMS? Beyond implementation assistance, our optimization services include a thorough analysis of the your existing software usage. PMS Pro’s identify areas for improvement and provide tailored solutions to optimize workflows, increase efficiency, and maximize software benefits.

Accounting only? Housekeeping and Maintenance? Rates and Fees? Automations, OTA setup? etc. we can customize a solution to give you what you need.

Unleash the Power of Your PMS

PMS specific pros

Our meticulous process of matching pros with clients is the hallmark of PMS Pro’s. We currently have Pro help for Track, Guesty, Ciirus, Hostaway and *Streamline clients. We prioritize understanding client needs, software specifications, and goals to ensure a tailored match. Our pros are not meant to replace a PMS onboarding team, they act as a client-side project manager that will help manage, prioritize, and facilitate all of the details that are required.

*Disclaimer: PMS Pros are NOT employees, partners or affiliated in any way.

Smarter Experience

third-party software recommendations

We can provide recommendations for third-party software that complements and enhances the functionality of your PMS, creating a cohesive and efficient software ecosystem.

Cut Through the Noise

PMS needs evaluation

For Property Managers considering a new PMS platform, we will conduct a confidential preliminary needs evaluation ensuring that potential new software aligns with their business objectives. This cuts down on vetting and demo time spent. We can take it to the next level by transforming your evaluation into a detailed RFP (Request for Proposal) to ensure you find the PMS that best fits your needs.

Get It Right the First Time

payments evaluation & strategy

Assess and optimize the payment processing systems integrated into your PMS, ensuring efficiency, security, and cost savings. Develop tailored strategies for additional payment options (BuyNowPayLater, Pay By Group, PayPal etc.), balancing convenience for guests and financial stability for your company. “I love chargebacks”, said no one ever.

Payments Outside of the Box

contract assistance

We support PMCs through contracts and pricing discussions with PMS and third-party companies to help you understand true costs and contract requirements. A pro in your corner, never hurts.

A Pro by Your Side

Passionate – Dedicated – Professional

its’ not about software,
it’s about ‘YOU’!


+1 (800) 555 555

Dawn Yeskulsky
CEO and Founder

Since 1996, I’ve had the privilege of working in various capacities with some of the largest and most influential tech companies within this industry. I began as a property manager, a role I consider the cornerstone of my career. Subsequently, I spent a combined 17 years working in technology and software roles, followed by a fulfilling decade in fintech and payment processing for VR managers. Over the years, I’ve had the opportunity to witness and contribute to the remarkable growth and transformation of the vacation rental industry, from its early days as a relatively unknown alternative to traditional lodging to its current status as a mainstream travel option. It has been an incredible journey, and I feel fortunate to continue to be a part of it

Fun Fact: I am a beekeeper

Chantal Winters
PMS Pro – *Streamline

I have 8 years of SASS software onboarding and training experience. I worked for Streamline VRS for 3 years. I have extensive experience in onboarding, training and troubleshooting questions within Streamline. My specialty in *Streamline is the Accounting part of the system. As a passionate pro I have accumulated experience first had helping clients set up, utilize and successfully use/ onboard with *Streamline. My passion is helping my clients reach their goals and exceed expectations as start with Streamline and grow their business.

*Disclaimer: PMS Pros are NOT employees, partners or affiliated in any way

Fun Fact:

Jason Conway
PMS Pro – Guesty, Track

With over two decades in leisure hospitality, I excel in leveraging technology to maximize revenue for vacation rentals and resorts. From founding BookedVR to leading teams at Bluegreen Vacations and Vacation Resorts Internationals, I’ve optimized operations through strategic tech integration. My expertise spans property management systems like Guesty and Track, channel management solutions, and revenue management tools. I excel in navigating and integrating various systems for portfolios of 30 – 14,000 properties. With strong industry relationships and analytical skills, I’m poised to drive success in any hospitality tech team.

Fun Fact: My Favorite Show is Street Outlaws

Matt Hamlett
PMS Pro – Guesty

I am a previous CEO & Founder of Yosemite Vacation Homes which I sold to Vacasa in 2021. Since that time I have been a Market Manager for Guesty and currently the owner of a 6 room boutique hotel call the Four Daughters. I have extensive knowledge of Vacation Rental Operations with expertise in Guesty PMS as well as *Streamline.

Fun Fact: I have 4 daughters

Francois Greffard
PMS Pro – IQWare, Vacation Rental Operations Expert

Since 1992, I’ve navigated the hospitality world, from hotels to vacation rentals, mastering both front and back-office roles before transitioning into technology and software roles. With 24 years in tech, including leadership roles like President and CEO at IQware, I’ve worked closely with key players in the industry, driving tech adoption and innovation. My approach is characterized by dynamism and analytical rigor, underpinned by a proven track record of delivering impactful solutions. I am passionate about sharing my industry knowledge and technological expertise to drive continued innovation and growth and offer continuous process improvement.

Sebastian Yepes
PMS Pro – Hostaway

I’m Sebastian Yepes, an experienced Hostaway Onboarding Specialist dedicated to ensuring smooth transitions and exceptional experiences for clients. With a background rooted in customer service, I bring a wealth of expertise and a passion for delivering top-notch support to every interaction. As a Hostaway Onboarding Specialist, I leverage my diverse skill set to streamline processes and guide clients through the implementation journey with ease. Whether it’s troubleshooting technical issues or providing personalized support, I am committed to exceeding expectations and fostering long-lasting relationships.

Abby Matlin
PMS Pro – Guesty

I have over five years of experience in the property management software industry. Throughout my time at Guesty, I helped hundreds of property managers and owners onboard successfully to the software. I have extensive knowledge and experience when it comes to training and troubleshooting and personalizing software to a client’s needs. By leveraging efficient workflow strategies and proactive problem solving techniques, I will be able to help you and your team in a timely and efficient manner!

Robert Ehrhart
PMS Pro – Springer-Miller

With over 25 years in Hospitality, I specialize in Custom Reporting for Hotels, Resorts and National Parks utilizing R&R Report Writer (Visual FoxPRO and SQL) and Crystal Reports (SQL), using the Springer-Miller PMS. With my vast knowledge of PMS database structure, I’m committed to exceeding my clients’ expectations with their reporting needs and creating lasting relationships.

Jennifer Ray
PMS Pro – Track

I am a seasoned project manager with over a decade of experience across many industries including college athletics, private university higher education, vacation and tourism, small business, and SaaS software. I am an out of the box creative who enjoys customizing project plans to meet unique and varied needs and building long lasting relationships. I also enjoy fundraising for the ASPCA and serving on several advancement and strategy committees for my local chapter of Cub Scouts.

Fun Fact: I am an avid pool and poker player.

Utilize your PMS Knowledge

Are yOU a Pro?

Do you know your way around a particular PMS platform? Maybe you were a previous employee or a power user? Is Trust Accounting your superpower? Do you geek out over OTAs and Automations ? Is setting up a new property your idea of a good time? You see where we are going with this. If so, then we would love to speak with you. We are looking to bring on Pros of all levels for full time, part time and project work. Give us a call or shoot us an email at dawn@thepmspros.comu a


+1 (800) 555 555

Passionate – Dedicated – Professional

Why should I hire the PMS Pros when I pay my PMS provider for this?

Each PMS provider follows distinct outlines and methodologies for training their customers through instructional videos, how-to documents, and periodic scheduled calls between you and the onboarding team. These steps are essential in the onboarding process, and the PMS Pros are not intended to replace this process. However, the PMS Pros are here to provide an elevated level of assistance for those seeking additional or advanced services beyond what is provided through training and support.

This includes guidance on operational best practices, process recommendations, data verification, internal task delegation and verification within your team, and crucial live assistance from your dedicated PMS Pro as needed (i.e. You can pick up the phone and call them). We can even come onsite and spend a few days with your team if that works best for you.

Consulting 85%
Management 76%
Brainstorming 92%