November 19, 2021

Meet the Women of the Vacation Rental Industry: Dawn Yeskulsky

Meet Dawn Yeskulsky, CEO of yes2vr

Leading up to the Vacation Rental Women’s Summit, we’re catching up with the women in our industry to learn more about their journey and passion for the vacation rental space, let’s learn more about Dawn!

All About yes2vr from Dawn…

My career within the vacation rental industry started immediately after college with Paragon Group Properties in Tampa, FL.  I was an IT major in college but, needing a job right after graduation, decided to take a job with Paragon Properties Group until I found my “real” IT job. Who knew that one temporary job would set me on a much different career path straight into the world of vacation rentals. Since 1996, I’ve been fortunate to work in this industry as a property manager (most important), then a short combined 16 years on the technology/software side, and finally ten years in fintech/payment processing. I was lucky enough to have gotten a front-row seat to the growth and explosion of that once pre-mainstream vacation alternative.  What a ride it has been! 

I am utilizing my 25 years of experience to provide professional consulting services to the industry I love. From strategic planning to innovative solutions, my focus is always on building an efficient and results-driven relationship. I’ll work with you to create a customized plan of action for yourself or your organization. I work with both property management teams as well as the supplier business that support the industry.  Get in touch to learn more about my vision and consulting approach.

yes2vr provides consulting and project work for the professionally managed vacation rental industry and the businesses that serve it.

yes2vr vacation rental consulting

Let’s Learn More about Dawn!

How did you begin your career in the vacation rental industry?

My career within the vacation rental industry started immediately after college with Paragon Group Properties in Tampa, FL. I was an IT major in college but needing a job right after graduation, decided to take a job with Paragon Group until I found my “real” IT job. Who knew then that one temporary job would take me on a much different career path, eventually managing over 200 units in the Tampa Bay, FL area. In 1996, I left Paragon Group and spent the next 14 years as Director of Sales and Marketing for the vacation rental software provider, Rental Network Software Corp.  

What was your experience as a female-identifying person (FIP) then vs now?

When I started with RNS in 1996, I was the only female VR software sales rep in the industry, which continued for a number of years. Legacy companies like FRS, RDP, and Instant Software all had male reps. In the beginning, I was not taken seriously. Let’s face it, I was 23 years old, five-foot-three, and blonde. I had a few occasions where I went to do an onsite software demonstration only to be told that they were expecting a “Don,” not a “Dawn”. On one specific occasion, a gentleman that owned the VR company said to me in his very sweet southern accent, “ Oh honey, my business is very complicated, not sure you would understand, why don’t you just have Bob call me.”  I am happy to see how much the industry has evolved since that time. Women now hold some of the highest positions within both the VR space as well as vendor partner companies. I don’t believe that the discrimination is completely gone, but it is a different game for sure.

Who mentored you and your career? Were there FIP’s in leadership roles around you?

My very first mentor is hands down Bob Ackerman from RNS. Bob pushed me, screaming and kicking, from a back-office young geeky girl into my very first sales role. He gave me my educational foundation in the VR world. After Bob, I would have to say my friend and eventual partner, Regina Ebert. Regina mentored me in the payment processing industry which only furthered my understanding of the VR world, but from a different perspective. She was a role model as a female business owner and I was proud to have helped her build Ascent Processing. 

What is your advice for FIP’s looking to grow their career in the VRM industry? 

Work hard and don’t take crap from anyone.  If someone tells you there are no biases left in our industry, don’t buy it. And that is okay! Being underestimated is a valuable tactic.  

Don’t let anyone put doubt in your head. Self-doubt is paralyzing and has the ability to eat away at your self-value. I myself have fallen prey to this and am amazed looking back to those times and realizing just how wrong I was.  

Find those strong, empowering, supportive friends and colleagues that are always there to hold you up, help pick you back up when you are down, give advice when it’s needed (and even when it is not). They are your sounding board and probably understand your work-specific challenges better than your spouse. You will need them.  

And lastly, never burn a bridge. There will be times when you want to give someone a dissertation on how you feel followed enthusiastically by a not so lady-like hand gesture.  It may feel good at that time, but it could come back to haunt you. Who knows, in our ever-evolving world of mergers, acquisitions, reshuffling etc, you just might find that same person in the box to your right on your next Zoom call.


Rented is proud to sponsor the Vacation Rental Women’s Summit this December 2-3 in New Orleans. There’s still time to register here, and join us for an amazing conference different from any other!

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