the no BS podcast

Dawn Yeskulsky

This is the 2nd time that Dawn Yeskulsky has joined us on our podcast but the first as CEO & Founder of her own companies PMS Pros and Yes2vr Advisors.

With 28 years of experience in Vacation Rentals touching the majority of customer-facing verticals, Dawn brings her unique perspective and knowledge to helping short-term rental property managers and vendors navigate complex decisions.

A great listen!

Episode Highlights

  • Dawn reflects on Bob Ackerman pushing her into sales, initially resisting the shift but eventually embracing the challenge and giving RNS 14 years.
  • We share amusing anecdotes about the early days of technology, reminiscing about carrying large computer towers for demos.
  • John & Mateo discuss Dawn’s pioneering role as a woman in the vacation rental sales space. Dawn humbly acknowledges the challenges but expresses her deep connection and dedication to the industry.
  • John and Dawn discuss the intricacies of payment processing, its challenges, and the constant evolution of the industry.
  • Dawn shares her unique journey, highlighting her move from TRACK to Inhabit. John speculates on the California connection that made this transition possible.
  • The conversation shifts to industry trends, with John acknowledging the efforts of various companies like Travelnet Solutions, Guesty, and Hostaway in emulating Inhabit’s model through acquisitions.
  • Dawn emphasizes the significance of building long-standing relationships and earning the trust of property managers. She discusses the value of honesty in steering clients in the right direction and her desire to reconnect with them after spending years behind the scenes at various companies.
  • Dawn introduces PMS Pros as a response to the need for onboarding support consulting in the property management industry aiming to complement, not replace, existing PMS onboarding teams.
  • PMS Pros acts as a project manager for property managers, facilitating effective communication with onboarding teams.

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Show Transcript

[00:00:57] John: Good morning, Matea. How are you?

[00:00:59] Mateo: Morning, John. I’m good, man. Warm,

[00:01:03] Mateo: freezing my ass off in Portland. Dude. I got caught in that storm that was out there,

[00:01:07] John: oh yeah. Didn’t you lose

[00:01:09] Mateo: Three days with no power. Chopping wood. Living off a gas system, and a wood stove. Dude.

[00:01:15] John: can’t. I don’t know if I could see you chopping wood man.

[00:01:19] Mateo: I grew up in Oregon. Come on.

[00:01:20] John: Yeah. So we went through that cold chill and, I went down to Florida to escape it for work and it was literally, thirty-five degrees in Florida. So I didn’t really, I still, it was 40 degrees warmer there. Then it was,

[00:01:33] Mateo: Where was it? Thirty-five degrees in

[00:01:35] John: for one night it was thirty-five degrees.

[00:01:37] John: Man, it was cold. It was cold. It wasn’t I left Indiana. It was negative four so, yeah. Alright. But I’m home. Let’s push forward episode one 19. No, BS podcast. Great guest. Been on before, but in a different role, different environment, and we’re excited. I’ve, we’ve known her for a long time.

[00:01:59] John: I’ve known her for. Maybe forever. Seems like it. It’s been a long time.

[00:02:04] Dawn: That sounds reasonable.

[00:02:06] John: Dawn Yeskulsky, thank you so much. We’re super stoked to have you on the podcast.

[00:02:11] Dawn: Oh, I am thrilled to be here. This is fantastic. I love you guys. I’ve always supported what you’ve been doing, so it is all my pleasure to be able to be on here as me and not representing another company. So this is really exciting for me because I’m now Dawn what I’m trying to do.

[00:02:32] Dawn: So thank you.

[00:02:34] John: absolutely.

[00:02:35] Mateo: wanted, this is the interview we wanted the first time. So and I was disappointed. Loved having you on, we wanted to have you on in no BS fashion, so thanks for coming.

[00:02:44] Dawn: let’s do it.

[00:02:45] John: So we’ve known each other for you were my first role a superior. When I stumbled in. So those that listen, know that you and I came into the space at the same time. We met in Gatlinburg Tennessee at the first show I ever went to, and I was working with Ascent at the time.

[00:03:04] John: I had, and answered an ad on Indeed and stumbled into the vacation rental space and ascent. And that’s how we met. And so I’ve known, what is it, eight and a half years now? I think. Eight years or something like that. It’s been seven and a half. I don’t know. It’s been a long time.

[00:03:20] Dawn: Yeah. Yeah. I think it’s

[00:03:22] John: it was early 17. Late 16, early 17. Somewhere in there. You had been working with Ascent for a while, for quite a long time. Pre, prior to that and before that you had started, I think your first role, if I remember correctly. And I’m not looking at, normally I’m on LinkedIn and I’m looking at timelines, but I’m not today ’cause I don’t remember RNS in Florida.

[00:03:47] John: Let’s talk about how you came into this space.

[00:03:50] Dawn: Even before RNS, the reason I got into property management was completely by accident. I don’t think anybody ends up in vacation rentals intentionally. I. But I had just graduated college and I needed a job after college. And I had I was an IT person, so I was doing, server workstation setups.

[00:04:14] Dawn: And back then in the mid nineties, there weren’t a lot of women doing what I was doing. And I needed a job. So I thought, okay, let’s, let me find my IT job. And in the course of that, it was much more difficult than I had anticipated. And the apartment complex that I was living at that time said, Hey, listen, we need somebody to come in, to do all of our IT kind of stuff.

[00:04:40] Dawn: Would you be help willing to help us on a part-time basis? And I said, yeah, of course. That started that. Next thing I know, I’m actually working for them in reservations. They had a long-term division and they had a short-term division. Then I’m working at the corporate office and then now I’m in vacation rentals and I’m helping manage 200 properties.

[00:05:03] Dawn: And it was in the blink of an eye. And I was like, how did I get here? This is not what I intended on doing. This is not what I went to school to do, but you know what, it’s helping pay the bills now. So I did that for gosh I think almost two years. And my my ex-husband at that time, he was transferred, so we had to move for his new job.

[00:05:29] Dawn: And back in the day, there was no, indeed, there was no Monster. There wasn’t. So you went through headhunters. That’s what you did. You faxed your resume to a headhunter and then they looked and found opportunities for you. So I did that not thinking that the two would ever align. I’m like this is what I went to school for.

[00:05:50] Dawn: But the last few two years I’ve been working in property management. Yeah. There, there’s no connection here. The headhunter did call me and she said I hear so you’re moving to Bradenton, Florida? I said, yes. She said, there is a software company in Bradenton that is a property management software company, and they’re looking for someone I.

[00:06:09] Dawn: And I was like, what? Are you serious? This sounds like too good to be true. So make a long story short, I went, I interviewed and I was with RNS for 14 years. I.

[00:06:23] John: You were, and you were with RNS 14 years on the. On the sales side of things, right? I mean doing things or did you start off on sales or did you, where, how? Where did you start?

[00:06:32] Dawn: I started off back office doing support, doing, answering phones, doing support tickets, that kind of thing. And then about two years into that, Bob Ackerman pulled me kicking and screaming and said, you’re gonna sell. And I said, I don’t sell. That’s not me. No. I’m behind the phone.

[00:06:53] Dawn: That’s not me. And he said, Nope, you are going to sell. And he started making me go on demos with him. This is when you actually went on site and did a demo and you hauled your big old, tower in a set up, a monitor. This is, I am so dating myself right now.

[00:07:11] John: Hey I can date myself too. If I remember like Xbox days, like late nineties, when you’d go early two thousands, you’d go bring your whole Xbox and monitor to someone else’s house. So you can go ahead and connect the two together and you could play Halo. I don’t know. I’m

[00:07:27] Mateo: I’ll date you, I’ll date you even more. How about those actual, I know those towers that you had to bring, like I, I remember in our era you talk about the nineties computers, right? And all those other com

[00:07:40] Dawn: Yep.

[00:07:41] Mateo: That’s actually, it’s super interesting that’s where you started. So in, in your journey, did this feel like home? Like I, you transferred to sales, but you have, an IT mindset. You understand technology, looking at the state of what it was at that time. 14 years is a long time.

[00:07:58] Mateo: That’s a lot of experience, right?

[00:08:00] Dawn: It didn’t feel like home initially. Back in those days I was going up against the guys from FRS and Property Plus, and they were all men that I was selling against, and there it. It wasn’t the warmest welcome, I’ll tell you that right now. Here I am, five foot two blonde, in my early twenties, and they were like, who is this?

[00:08:30] Dawn: Nobody’s gonna take you seriously. Come on now. So I did have to, I had to prove my, chops, for lack of a better word with those guys. And many times I was like, this is not me. This is not me. But, Bob Ackerman kept me going and said no. You don’t understand. You’re gonna be really great at this.

[00:08:48] Dawn: So I kept plugging away at it and I. When I joined RNS, they had approximately 40 customers, and when I left in 2010, they were just under 400 customers. I. And I sold probably the majority of them. So that’s, that was my foundation in getting to know property managers, a lot of which are still in business these days.

[00:09:16] Dawn: So that, that really gave me the exposure that I needed in order to get my name out there.

[00:09:23] John: I think that a lot of people, looking back at your career, you’ve been doing this a long time and if you look back, you’re, 14 years at RNS, 10 years at ASCENT. X amount of years here, X amount of years there, you’ve had a career’s worth already in the vacation rental space.

[00:09:40] John: And then some. And I know it’s hard when you, for yourself to say call yourself a pioneer, right? It’s not really something that someone does. But if I were to look back, look at your career. As a woman in the late nineties, early two thousands that’s going in doors, sitting, doing sales calls with Bob, then solo and like you’re pioneer in the vacation rental sales space.

[00:10:06] John: Do you know that, do you, does that register in your mind? Is that something you’re like, oh, I’m a pioneer? Or is it, is that hard to say?

[00:10:13] Dawn: No it is hard to say. I don’t think I really did anything that anything truly outstanding. It was more just. I just wouldn’t quit. And for a fact, when you are in this industry, it takes a hold of you and it is very hard to leave to branch out just because you feel anchored to it almost immediately.

[00:10:40] Dawn: So. I didn’t think of it as, oh, I’m gonna be this trailblazer, this pioneer. I just wanted to continue in the industry that I had grown to love and wanted to help in a variety of different ways. Whether it be. At R&S or at Ascent or the companies that I was at after that. It’s just, yeah it did Mateo, just like you said, it became home and many times I wanted to quit, but I was like, no this is your home.

[00:11:10] Dawn: This is where you’re meant to be.

[00:11:12] John: You feel indebted to it, don’t you?

[00:11:14] Dawn: I do. I really do. It’s been amazing. I couldn’t picture myself in another industry. It. Seeing it evolve has just been the biggest trip going to these conferences that are now like VRMA last year. Oh my gosh. I can’t even tell you how many vendors were in that, that, trade show hall hundreds.

[00:11:39] Dawn: And I remember the days of going to VRMA when it was twenty-five booths in a small little trade show hall and Bob Ackerman. And I had our little toolboxes because our booth was this rector set and it would take us three hours to put up the booth and three hours to take down the booth. And. It’s just, it’s crazy to actually sit back and look and say, wow, this is really, this is mainstream now.

[00:12:11] Dawn: How did we get here?

[00:12:13] Mateo: You got there through hard work and I think one of the things I’ve. Appreciated about you, Dawn, is you’re and this in the most positive way possible, understated, like you’re a force. Bob saw something in you and I got a question ’cause I wanna follow up with that too. But Bob saw something in you that was there and once that seed was sown, I mean look at what it’s grown into.

[00:12:36] Mateo: John asks people like, when did you think you were a pioneer? I. I don’t think a pioneer is a label that you give yourself. It’s your body of work. It’s what you’ve done like that. I’m John, I’ll tell you, know me all the time. I’m about verbs. It’s about what you do. And being able to sit back and look.

[00:12:53] Mateo: And I think it is important to point out like this is a male dominated industry, right? Like it’s been a male dominated industry and the level of rigor in, in fight that it takes and perseverance that it takes. To see success in this space in the time in which you came up is, you have to acknowledge that.

[00:13:13] Mateo: It’s a part of the story, right? Like again, it’s never an excuse. You could have quit a long time ago when things got tough. You could have quit a long time ago, but five foot you, and this is, and I think this is because I have a five foot tough mom, so like I know what that’s like. And we’re gonna get into that too, because through all of this.

[00:13:29] Mateo: OG thugging it out in corporate world. They’re also raising a fa a family. Two, two beautiful young daughters that we’re gonna talk about too. Out there. Buffalo ended up, out, out in Colorado. We’re gonna get to that. But when did it sink in on, like, when did you feel like, maybe Bob was right about what, when was, when did you feel like, all right, Bob was right?

[00:13:50] Mateo: I can do this. I will do this.

[00:13:53] Dawn: Probably. A year or two into it, um, where I was leading all of the sales from start to finish and I wasn’t pulling him for, in for different questions. He had sent me up to the Outer Banks. North Carolina and I was going up there for five days and he said, okay, here are the demos that I want you to do and the, these are the companies I want you to stop in and see.

[00:14:18] Dawn: And I remember doing a demo for Twiddy and here I am, I think I was probably twenty-five at the time, and demoing Twitty was probably the hardest thing I ever, I’ve ever done in my career up until that point. They put me in a room in the demo, lasted three days. And every day, every few hours a new group would cycle in.

[00:14:46] Dawn: And so we went through every department in the company, so accounting, housekeeping, maintenance, you name it. And we demoed a group for every single section I demoed. I was there by myself and. Literally, I felt at the end of every day I was like, how did I make it through that? Oh my gosh. And then the next day, how did I make it through that?

[00:15:10] Dawn: At the end of it, leaving that when it was done three days later, I was like, wow, I did that. Holy moly, I did that. I, of course I had to check back with the office on a few things ’cause I didn’t know everything about the software, but I knew enough to get through three days of being peppered by these, these incredible.

[00:15:34] Dawn: Yeah, these users that know what the heck they’re doing. And so that really gave me a few peacock feathers that I could say, and yes, they did buy

[00:15:44] John: Of course it did.

[00:15:46] Dawn: and they’re still using it to this day. And that was probably back in 1990

[00:15:52] John: That’s crazy, by the way. But we, we don’t need to get into that. That’s insane by the way. Talk talks. So 14 years there let’s continue this timeline. You had 10 years at Ascent, there’s what made you go, all I love this industry. I’m gonna stay in this industry, but I really think I can bring value to a payment processing front.

[00:16:14] John: Who at the, and I’m not sure. I know when I joined which was probably eight years into your tenure, seven or eight years into your tenure. That’s fun to say. At ascent, the, the players back then were VRP Lynnbrook at the, and Ascent were, , when you first came on were those the same players or was it just VRP and Ascent?

[00:16:38] John: I don’t know that timeline.

[00:16:39] Dawn: They were really, VRP was probably the the biggest competitor to Ascent from the Get-go and

[00:16:47] John: for those that are listening, that’s Vacation, Rent Payment.

[00:16:50] Dawn: Yep. Also known as Yapstone these days. So they were always there. And the reason I went from RNS to Ascent is, for one reason, Regina, Ebert, Regina,

[00:17:03] John: Shout out to Regina.

[00:17:05] Dawn: Shout out to Regina

[00:17:06] Dawn: she was a really great friend of mine and we were friends prior to me coming and working for Ascent and she was actually with me the night I met my husband.

[00:17:15] Dawn: True story. We were together. And I think I’ve told people this story before. I’m not gonna get into it, but she was with me the night I met my husband in San Diego and she was very protective of me. And to this day, my husband absolutely loves her for being such a great friend. But yeah.

[00:17:33] Mateo Bradford-Vazquez: hey, John. Let’s talk about one of the most frustrating challenges of hosting. Cleaning. Seriously. Hosting is hard enough. Why does cleaning have to be such a pain?

[00:17:43] John: SDR cleaning is not the same as residential, and you need someone who knows the difference. Plus cleaners have access to your property. You need to find people who are qualified and trustworthy.

[00:17:51] Mateo Bradford-Vazquez: Add to that, you need cleaners who don’t need to be micromanaged. Who has time to text schedules back and forth and try to confirm days and times? Especially when bookings change. And then, dealing with invoices, payments, and tax reporting.

[00:18:04] John: Turno has solved all of these challenges with this cleaning management software. Turno’s Cleaner Marketplace has over 55, 000 vetted short term rental cleaners, and they make finding a local cleaner super easy. You just enter some property and cleaning details, and cleaners start bidding.

[00:18:18] John: You can see things like competitive cleaner prices, business credentials, and reviews before you agree to work together. Plus, Marketplace cleaners are paid automatically once the job is completed. No more manual payment hassles.

[00:18:29] Mateo Bradford-Vazquez: When you sync Turno to your listing calendars, every turnover gets auto scheduled as bookings come in. And if anything changes, your cleaner is notified immediately. Plus, cleaners can see if it’s a same day turnover, so they know right away that time is critical.

[00:18:42] Mateo Bradford-Vazquez: And with tools like Photo Checklist, Inventory Management, Problem Reporting, and the Guest Checkout Review Prompt, Turno gives hosts real time eyes and ears on the ground, right from the cleaner to the host’s app.

[00:18:52] John: No BS. Listeners can get $150 Amazon gift card when they try Turno and its cleaner marketplace. New users can sign up at turno.com/noBS, search for a cleaner in your area, connect with one or more, and then complete a marketplace cleaning. Once you see how easy and simple cleaning management can be, you’ll love how much time and money you save, not to mention no more cleaning headaches. To learn more, go to turno.com/noBS and get started today.

 

[00:19:15] John: is your DJ husband, right? Remember, I know this story.

[00:19:19] Dawn: Yes. You know this story. So she was the one that said, listen, I need to expand Ascent and I need somebody to come in that will expand our footprint. Getting more merchant accounts with the PMS companies that, we have worked, we’re working with, and I think at that time, first Resort was the biggest PMS that Ascent was working with.

[00:19:45] Dawn: And then right at that same time, there was RNS, which I had already been referring customers from RNS to Ascend. There was Property Plus there was VRM. So she said, I need somebody. I can’t do it all. So I need somebody to come in and take over the sales side of the business. It was just an opportunity at that time after being with RNS for 14 years to do something different.

[00:20:11] Dawn: RNS was, it is a family owned business and I was not family. And so I had to recognize that at a certain point that, I was going to, I was as far up the ladder as I probably would, would’ve gotten. So Regina. Offered me a whole new way of looking at vacation rentals. I knew something, you knew a little bit about payment processing, but I had no clue.

[00:20:38] Dawn: And John, you can talk to this. Payment processing is like a different world.

[00:20:43] John: It’s definitely hard coming in and learning it, like all the pieces to it. Once you get it. And I could still talk to it and be, relatively smart on it and have decent conversations today. But it’s ever changing.

[00:20:57] John: It’s always evolving and it’s, yeah, it’s, and it’s, as far as sales go, it’s next to PMS sales. It is one of the hardest like sales cycles because it’s full like audit of your company. Today it’s a little different with some of these pay facts. It’s a little bit easier for certain services for that type of, for payment processing into onboard and stuff like that.

[00:21:23] John: But back in the day it was rigorous. And like it’s a hell of a sale. And I learned a lot in my what? Remember however many I was there like 18 months at Ascent. I learned so much or maybe two years, I don’t know, regardless. That was

[00:21:40] Dawn: Yeah, it

[00:21:40] John: and you were there 10 years.

[00:21:42] Dawn: 10 years. Yep. And then, at the end of those 10 years, it was, there were some changes within the structure of the company. We had new folks coming on board, and I had the opportunity at that point in time along with Regina to take a step back. And to really do other things.

[00:22:02] Dawn: So at that time I had I had sold my portion to the current CEO. And I then I. Had an opportunity to move over to TRACK. Ryan Bailey and I were on the board of the OPM a, the Onsite Property Managers Association at that time. And we were at a a planning meeting and. He and I just started talking and he said, have you thought about coming and working for us?

[00:22:31] Dawn: And it was not in violation of any of non competes that I had because

[00:22:36] John: We know the true reason why you came.

[00:22:39] John: You followed me there.

[00:22:40] Dawn: I followed you there. Yeah, you got it. You got it. This, yep. That’s exactly what it is. So John left a few months before I did and went to TRACK and so I, I called him up one day and I said, guess who’s gonna be working again together?

[00:22:58] John: It’s funny. That’s funny. Let, I wanna make sure that we get to your current timeline. And so a couple years how long were you at track?

[00:23:08] Dawn: About two years.

[00:23:09] John: Okay. Two years at track. I, I do wanna talk and you were one of the only that, that go from TRACK straight to Inhabit., I think it’s because you’re in a California girl which allowed that to happen.

[00:23:20] John: Because of the non-compete and it works out in California, throws that out the window. Um. I’m pretty deep. I’m a deep dude. The you spent a little bit of time at Inhabit. Tell us what you could tell us about that, and then let’s talk about why you let or leaving Inhabit in starting YesVR.

[00:23:40] Dawn: So Inhabit, both TRACK and Inhabit. Gave me alternative perspectives as to different ways that the industry is served. So RNS, legacy, property management software company, a lot of the features that are in that, that were then developed we’re really, I would go out and say, if we build it, will you buy it?

[00:24:06] Dawn: And coming back and saying, okay, we need to build this. Now going through Ascent and then coming back into the the software world, it really wasn’t like that anymore. And it had evolved considerably. So I was able to get back into it and really get a an understanding as to how all of these other software companies were were optimizing their software, what the new features were, what their ideal clients were.

[00:24:34] Dawn: And I saw that at TRACK. Then going to Inhabit, that was even more eye-opening because not, it wasn’t just only one PMS like track now it was three digital marketing companies payments, insurance, and five PMSs, and I spent. My first year at Inhabit I was over the three digital marketing companies, Blutent, Bizcore, and Q4 Launch.

[00:25:05] Dawn: And prior to that I didn’t have any digital marketing experience. I’d worked with those companies from integration standpoints. But what they truly did from, the web, the booking engines and all the digital marketing services that they did, that they provided, pay-per-click and SEO and card abandonment, and.

[00:25:25] Dawn: All these other things. I was like, wow, I didn’t know much about ’em, so I had to learn. And so that, that was really interesting and I loved doing that because I was learning as much as I was helping. And then about a year after that, I was promoted to the head of revenue and growth for the whole vacation brand division.

[00:25:49] Dawn: So that was. Digital marketing, PMS, revenue management and so forth, and that I was over sales client success and partnerships for those, all of those brands, and I’ll tell you, that was a, an extremely eye-opening position. It was, it challenged me probably the most out of any role I’ve ever had.

[00:26:16] Dawn: It taught me. A lot, it really did about how to look at these companies from a much larger perspective and not just what it’s like to work in the company, but how this ecosystem of companies really, attempted to work together to provide end-to-end solutions. Was it perfect? No. But if you really looked at what inhabit offered, there’s nothing like it out there.

[00:26:50] Dawn: They have essentially a one-stop shop. And that is what we were trying to really build over there is the ability to say there is no nothing, there isn’t anything else like this. So if you’re a new property manager, you can come to our marketplace and you can pick your PMS and you can pick your digital marketing and your website, and your revenue management, and your payments and your insurance and boom, there it is.

[00:27:17] John: It’s your bundle building with your, your best of class or your preferred brands, that are in-house. And it’s, it makes a ton of sense from a business standpoint. It makes a ton of sense. If I put myself in the shoes of, say, a consumer though, I’m like I could see both sides, I could see like, all right, yeah, I really like this piece, but, I want, if this is preferred, but I want to use this, but I get it.

[00:27:39] John: It makes I, it totally makes sense. And if that was, if Inhabit was my baby, that’s a hundred percent the direction I’d be driving it. And TRACK’s trying in doing this entity, Travelnet Solutions is trying to do the same. And Guesty is trying to do the same and Hostaway. Like they’re all trying to bring all, these different pieces in.

[00:27:55] John: Following suit from, how Inhabit led the way, it wasn’t, they didn’t build it from scratch. It was through acquisition, but. It still, and that’s the hard part about it. And I look at your position and everyone’s position. You acquired all these different pieces and now you, Hey, we have best of class.

[00:28:13] John: We got four PMSs, we got two insurance products, we’ve got three of these, we got two of these. Now I. This is, we talk about, unified code and clean APIs like all the time here on the show. And like how, you know the case for making single code structures for this. Now you’re trying to go ahead and make all these work well together and talk seamlessly together, and that’s the hardest part.

[00:28:37] Dawn: And it’s also tell you what was difficult. Is trying to create the ideal personas for each one of those companies because you’ve got everything from PMS that is. Really meant for companies under 50, seventy-five units, all the way up to, the large enterprise software clients. So there really is there, there is that whole gamut.

[00:29:06] Dawn: And how do you take a property manager and place them into the right software?

[00:29:14] Mateo: right.

[00:29:14] Dawn: Do you put them into the software that they need today? Do you put them into the software that they will need in two years that they’re going to grow into? So it wasn’t so much of how they compete with each other, but it, I think it was more putting the property manager in the right the right fit and then making sure that if they do outgrow it, then that there’s another option above that could, they could easily migrate to.

[00:29:40] John: With a seamless transition. List.

[00:29:43] Dawn: Seamless. Haha. I see where you’re going with that.

[00:29:47] Mateo: Yeah, it’s shameless plugs. It’s, but it’s interesting when you look at their ecosystem, right? Like they answered the call, right? The industry for so long wanted one, one place to go where they could get everything that they needed, right? Instead of having to go 18 different places and figure it all out.

[00:30:04] Mateo: But I think. The industry also evolved too, right? Like to what you just said, not, there’s not a homogenous group of property managers. And the tremendous growth that we’ve seen with new interest in new management and operators or whatever you wanna call in this space too. And it, it seems and I think you’re the best person to talk about it,

[00:30:25] Mateo: through all of this. We’ve never seen a time where there’s been also so much competition within the tech space in the tech operation space. And as that’s growing, so you know, you are on the front lines of it, you’re talking to the managers, you’re hearing and you’re getting their feedback right, about the products they use, that you’re selling about the wishlist products that they wish that they had. There always seems to be this disconnect of, I, I don’t think people think you can just snap your fingers and make it happen, but how do you communicate that these are the right tools? In, a climate that seems to be changing very quickly with everyone also and the room getting crowded with people saying, no, we’re the best solution for you.

[00:31:06] Mateo: Come and try it. You’re the best solution. Come and try it. And it’s not like you can just flip the switch and try it. These are arduous processes, like these are in-depth into your business. You have to get intimate to understand the right fit for their business. From a technology standpoint, how did you find success?

[00:31:22] Mateo: Because to me that’s number one. What I see John do a lot is relationship driven and trust.

[00:31:29] Dawn: It is. And I’ve, I’m lucky that through the course of my time in this industry, I’ve. Been able to build those long-standing relationships. And I have, customers that I consider them friends. I really don’t even consider them customers. They have trusted me to bring them with me along my journey.

[00:31:51] Dawn: I have people to this day that. I had sold RNs to that were my clients at Ascent that are now with one of the companies that I was previously at. So they’ve have that trust in me that I’m not going to, I. Steer them in the wrong direction intentionally, just because it’s where I am, I’m at that point in time that I’ll truly, I’ll be honest with them and say, listen, this might not be the best fit for you.

[00:32:20] Dawn: Or, Hey, listen, don’t you’re good where you’re at right now. The grass is not always greener. And I think being honest with a lot of those customers, they. They said, okay, she really does have her back.

[00:32:33] John: And this led to

[00:32:35] Dawn: It’s relationships. It is relationships and. That allowed me when I when I left Inhabit, I wanted to get back out there and reconnect with the property managers.

[00:32:48] Dawn: I had been behind a wall, a bubble for the last four years where I was only seeing things from the perspective of the brands or the companies that I worked for. And I said I wanted to get outside of that. So I went to VRMA. The very first time I went to VRMA without being associated with the company, and it felt.

[00:33:07] Dawn: Weird as hell. I’ll tell you that. It was bizarre walking into that trade show hall and not having a booth to call home. Not having that, that anchor point. And I said, okay, Dawn, here you go. Sink or swim. What are you gonna do? And I made it a point to speak to as many property managers as I could, and I asked them very simple questions.

[00:33:30] Dawn: I said, this is, I’m doing a research project, essentially. I said, I need you to tell me what you love about your PMS. What you don’t love about it, and don’t overthink it. Just tell me what, what comes to mind. And I was expecting things about, oh, this sec, this part of it, the revenue management doesn’t do this, or it doesn’t handle this way.

[00:33:55] Dawn: And I got some of that, but the majority of it was, which blew my mind. It does. It does, but it doesn’t, everybody said the software does. What it needs to do most of it, could it use a little something here and there? Yes. Do I have a wish list? Yes. But the onboarding and the ongoing support are lacking considerably and.

[00:34:25] Dawn: I would’ve been yeah, I get that. If it was just a few people saying this, but it was recurring theme, like I must have talked to seventy-five different companies and one of those, or both of those were probably in every single conversation and it was not me asking about it, it was them saying this. So I

[00:34:49] Dawn: was.

[00:34:50] John: this case study that you did, this impromptu case study would, I can’t remember. Had you already at that time, had you already started Yes2VR Advisors or was this impromptu case study, like what led you go, yeah, all right, this, we have to do this. I have to do this.

[00:35:06] Dawn: So I had yes to VR before this I actually started, yes to VR in between me working for TRACK and Inhabit. And then when I took the position at Inhabit, I could no longer do that just because, I couldn’t have a full-time job and also do consulting and, conflict of interest and all of that.

[00:35:25] Dawn: So when I left Inhabit, I just said I’m, I don’t want to jump back in to another role where. I didn’t have the control that I wanted to have and I wasn’t making the connections with the property managers that I lost essentially.

[00:35:48] Dawn: So I said, I’m gonna revise this, and it’s either sink or swim. If it works.

[00:35:54] Dawn: But I’m going to go down kicking or screaming because I think I’ve got enough. Acquired knowledge to provide insights to property managers and to other vendors in the industry that I could potentially create my next role out of this. And so that, that was why I. I revamped yes to VR, and I was lucky enough to get some clients right off the bat that wanted me to come in and do some work for them.

[00:36:24] Dawn: So I, I had that behind me and yeah the whole PMS Pros. Stemmed from that, those conversations, John, that around the what property managers need as far as onboarding assistance and support.

[00:36:42] John: So

[00:36:42] John: so when this goes live, this will be you on the twenty-fifth of January, you had a press release talking about PMS pros. So when this goes live, this will be a. About two weeks from your press release talk, talk to us about PMS Pros. What is it exactly, who is it for? Who’s your ideal your ideal client persona?

[00:37:03] John: Where are you taking this? And who are you gonna serve?

[00:37:06] Dawn: PMS Pros is a direct result of those conversations that I’ve had with property managers. The, there’s so much in our industry to pick from as far as technology companies and services. However, there was. There was no company that was providing property managers solutions to help with onboarding support consulting, and it was an aha moment.

[00:37:34] Dawn: I said, how can I fill this void? How can, and I knew I couldn’t do it alone because PMS is so specific, you have to know. A PMS, they all operate differently, so it’s not a one size fit all. So how could I gather talent from our industry that knows a PMS well enough to be able to go sit with a property manager and say, Hey, listen, this is.

[00:38:04] Dawn: I don’t think this is set up correctly. You might wanna look at adding this or using this portion of the software, or there might be some redundancy in what you’re doing here and sit down and act truly as a guide or a consultant for them. And my biggest fear in launching this was that. It was going to be perceived as I was trying to step into the onboarding process or replace the onboarding teams at the PMSs, and that is absolutely not what this is intended for.

[00:38:41] Dawn: Each PMS has an onboarding process and that process is created. To teach their clients how to best utilize the software and they know their software, so they’re the best ones to dictate what that process is. PMS Pros is meant to go to the property manager and act as their project manager essentially on their side.

[00:39:08] Dawn: So the property manager is hiring temporary help to come in on their side and work with them and their team alongside of the PMS onboarding team to really be that additional layer of help. Or to take the what is required by the onboarding team and translate that and apply it to how the property management team is going to do that in their office.

[00:39:38] Dawn: So if there’s a deadline coming up, and according to your onboarding team, your owners, your units, your rates need to be in for this call that they’re going to have, right? How are we gonna actually get that done? And the PMS Pro is the one that says, okay, this is how we’re gonna do it and this is the date that we’re gonna do it.

[00:39:57] Dawn: And takes that pressure away from the people that actually need to run the company

[00:40:05] John: The biggest win for me looking at this is that you have an onboarding. Team and you have the property manager team, the onboarding team has their best, cases like, hey, in this is how the majority of our users do this. Alright. But they don’t necessarily know or have the relationship with the property manager that say even the sales team has a proper onboarding experience and relationship.

[00:40:32] John: It, should have a solid kickoff between sales. Onboarding team as for the software side of things, but still the onboarding team doesn’t have the relationship with the the property manager that potentially they should, they don’t necessarily know their business. So when you bring in a PMS Pro who is acting as a project manager who knows the best interests for the PMC, better than anybody else, and they can fight for that PMC in a way, and I’m ex onboarding team from X property management software, and I’m saying, this is how we do it. This is the best way to do it. And they, the property manager’s no. That’s not how we, the business is run here. I think that it’s best to do it this way because if we architect it this way, we’re gonna check these boxes off that are really important to us and potentially the PMC wouldn’t. Might not speak up and say these things, and so you’re nipping things in the bud early, potential problems in there, so it’s, that project manager is super, super important. I love this idea.

[00:41:35] Dawn: If anyone has ever gone through a bad. Onboarding or even an onboarding to begin with, or a migration from one PMS to another. I’ve had people tell me they’d rather stick hot pokers in their eyes than do it again and. Not to say that adding a PMS Pro is gonna make everything sunshine and rainbows, but it is meant to for those companies that do not have the internal staff or the bandwidth to be able to give it the full attention that it deserves.

[00:42:08] Dawn: And I don’t want to I don’t want to. Seem like I am disparaging any of the PMS onboarding teams. Those folks work their butts off and

[00:42:20] Mateo: They’re under resourced, right? And so you have a small group of people that are carrying a ridiculous workload, right? Like at the end of the day, that’s what takes so much time

[00:42:29] John: and a lot of times these are junior people.

[00:42:31] Mateo: And and actually that’s my question, Dawn, like that we’re talking about one side of the coin is the, are you looking at helping the other side of the coin too?

[00:42:40] Mateo: Are you in your scope of services looking to help PMSs actually improve the process from their side as well? Because there, there can be improvements on that side, right? Like it’s not gonna say static. They have to get better at it with technology as they grow their company. There’s a strategy.

[00:42:57] Mateo: To be able to do that better. Is that something you do or

[00:43:01] Dawn: You know, I, we would love to do that. And during my time at the different my different companies, I’ve been able to sit down and work with those heads of onboarding and to talk about, okay, what would a truly. White glove onboarding look like and what do you add to what the standard format is to deliver that white glove assistance.

[00:43:24] Dawn: And it’s, they’re all like, yes, we would love to do this. It is just not the sheer volume of the amount of customers we have to have go live in a week, in a month doesn’t allow us to go that extra step, even though they want to, and they would love for their customers to have a wonderful experience and they’re handheld and they feel that when they go live that they’ve got a great knowledge of the software.

[00:43:51] Dawn: It’s just not, it’s not feasible and you have to standardize in order to be able to go through that, that sheer volume of clients you need to train. So this, the PMs pros is not gonna be for everybody. And I know people are gonna say why do, should I pay the PMs pros when I am paying for onboarding?

[00:44:15] Dawn: And I don’t have a good answer for that. My answer is, it is just another layer of service. If you need that additional layer of service, we are there to be that conduit or that advocate that helps you get through that time of getting your business transitioned from one PMS to another, and it can.

[00:44:41] Dawn: It can look very different from one company to another. One company might need help, 30 days before switching over all the way through to go live. And some companies might not just need very short term help in very specific areas of the software. So we’re able to step in and customize the type of help that we can provide depending on the individual needs of that property manager.

[00:45:08] Mateo: That’s an easy sell though. No, because it’s their time, it’s their energy and it’s ridding themselves of the headache. Avoid. This complicated structure and it makes sense. That’s valuable, right? Like to, to property managers who are busy property managers who are already dreading this process,

[00:45:25] John: Or understaffed.

[00:45:27] Mateo: right?

[00:45:27] Mateo: Or bogging your staff down like you or your staff. It’s freeing up time. It’s letting them work on other things. It’s actually getting this done in a sensible way that it’d be like, Hey if I can avoid this headache.

[00:45:39] Mateo: What does that cost you? Like at the end of the day, there’s value in that, right?

[00:45:43] Mateo: There’s a business value in that and it’s tangible. So I think it

[00:45:48] Dawn: what we used to hear, John, you can attest to this, is everybody said, I can’t do this during my busy season. I have to do this during my off season because I don’t have the staff, I don’t have the bandwidth, so I. PMS companies, when you look at their onboarding, you have that, that bell curve because you are trying to work with the staffing resources of the property manager and when their staff can actually dedicate time.

[00:46:14] Dawn: So it’s during their off season. So hopefully this will help to normalize the the, that flow. So when you have a pro, it doesn’t mean you have to do this only in your off season.

[00:46:28] John: A lot of what we’re doing at Direct is trying to go ahead. And make the onboarding as seamless of a transition as possible. It’s a huge priority for what we’re doing and how do you go ahead and make it so a company can onboard in their busy season? And which is interesting now because most.

[00:46:49] John: Property managers are seeing less be with shoulder seasons and everything are seeing less and less of an offseason with booking windows changing and everything that truly they’re busy year-round. The majority of location less you’re up in New England or someplace very seasonal. It’s different than it used to be, even say, three or four years ago.

[00:47:07] John: The, that doesn’t mean that, PMS pros wouldn’t be, something that would help. A company like Direct who is focusing on onboarding as a priority and making that, and bringing that time down and making it, because there’s still so much that needs that project manager standpoint is where the win is.

[00:47:27] John: I love this. I think it’s where you’re going is. There, there’s a huge runway for you. There’s gonna be so much changes that are already happening with more acquisitions and more people just getting tired of a stale solution or the same old in their software , depending on the length of term they signed everyone’s looking, no one’s necessarily, pulling the trigger right now. It’s a difficult year as far as sales because of the, the macro environment outside of it. But I’d, everyone’s kicking tires. And being able to come in as a solution and say, Hey, you know what? We’re gonna be able to make this transition easier for you.

[00:48:06] John: If you’re really thinking about pulling the trigger, Hey, let, let’s work together.

[00:48:11] Dawn: The way that I’m. Comparing this to other industries is think about Salesforce. So Salesforce, huge, large, utilized by millions and millions of people and companies on a yearly basis. Salesforce, you buy your license for Salesforce from Salesforce. Most of the time it’s not Salesforce that on board to you.

[00:48:35] Dawn: How many consulting companies or training companies out there are the ones that actually implement and train you and customize Salesforce for you? That is the kind of analogy that I use to explain this to other people in our industry that think the concept is, oh my gosh, you’re, you’re taking this away from the PMS.

[00:48:56] Dawn: No we’re not. We’re just acting as another. Option, another layer to, for you to get the best out of your software. And hopefully what this will do is lessen the load on the PMS companies for their onboarding teams and their support teams so they can then focus on developing the software and building new features and doing what really drives the evolution of their software.

[00:49:26] John: Who are you currently working with right now? What softwares

[00:49:29] Dawn: Our PMS pros have experience with Streamline, CiiRUS. TRACK, and Guesty,

[00:49:38] John: Okay.

[00:49:39] Dawn: and we are currently interviewing other pros that extend outside of those PMSs at the moment.

[00:49:48] John: And if people want to go ahead and utilize your services, how’s the best way to go ahead and do that?

[00:49:53] Dawn: Oh, go to ThePMSPros.com. We’re in the process of building a new website just bear with us by the time that this goes live. Hopefully everything will be nice and pretty up there. My contact information is up there. My email is dawn@thepmspros.com or through my consulting website, which is yes2vr.com, and we can do an interview with one of our pros and the PMs company and they can, you can say, Hey, listen, we’ve had the software for three years.

[00:50:29] Dawn: We don’t know if we’re getting the most out of it. We don’t know if we’re utilizing the housekeeping functionality to its best ability. Or, can you help us? Can you do a refresher training? On end of month reconciliation with our new bookkeeper, we’re able to not just help with the onboarding, but the ongoing optimization and consulting that goes along with it.

[00:50:52] Mateo: I love that.

[00:50:53] John: What do you wanna leave our audience with before we get outta here?

[00:50:56] Dawn: Thank you. Thank you to, to everyone that has. Supported this, the amount of support and encouragement I’ve received through, and I called a lot of people and I said, please talk me out of this. And these are folks that I’ve respected for many years that I know would tell me, yes, no, yes, Dawn this is a good idea.

[00:51:20] Dawn: No, don’t do this because of XYZ. So everyone that said you, you have to do this. I thank them and I hope that people help pass the word that this service is now available and we get to prove ourselves and prove how we can help property managers with their PMs needs while not, working in conjunction with the software companies.

[00:51:47] Dawn: Not as competition, but as an extension of them. I shouldn’t say extension that’s not the right word, because I have to make sure legal, legalize, legalese that I’m not saying the wrong thing, but really work as a in alignment with them.

[00:52:05] Mateo: They’re partnering. It’s a partner working together. It’s a good it’s a good model.

[00:52:09] Dawn: We wanna see them succeed.

[00:52:11] John: I have one thing to add. So I see a ton of people that when they get to the, they’ve been in an industry for a length of time and they get to a point where, alright, I’m done. I’m gonna do this on my own. And then they’re like, I’m gonna be a consultant. And it’s to me I’m, I’d say 90% of them that go into consulting, I’m like, oh, they’re done.

[00:52:30] John: I’ll see that. They’re get, they’re done. This is it. Like they, this is their. They’re riding off into the sunset. No one really takes that shit seriously. And when, I would be very transparent. I’m like, ah, when you came out with your yes to VR, I’m like, ah, I hope the fingers crossed that this isn’t like a.

[00:52:47] John: And of course I know with you that’s not the case, but still like anyone says, I’m a new, I’m a consultant to me, I’m like, oh, damn. My fingers crossed actually this is fucking awesome. I’m really stoked for you. This is gonna be everything that I’m, this PMS Pros is where it’s at.

[00:53:05] Mateo: I, I disagree with John. I thought it was because I usually feel that way, but I think, come on, you’re the OG, you’re the

[00:53:12] John: I, no, you’re not disagreeing with it. I said because Dawn, it’s a different

[00:53:15] Mateo: But again, like it,

[00:53:17] John: Ray, we’re

[00:53:17] John: gonna

[00:53:17] Mateo: But there’s a reason also ’cause like you came in, a lot of people. Automatically feel like they know what value they can provide, immediately, right?

[00:53:26] Mateo: Because of their experience or whatever. You came in asking questions and broadly asking questions, and really, that’s why I was like, all right, this is different. She’s not just gonna do the same. Consulting dance that a lot of people do, and shout out to the people that do it and do it well. I’m not knocking you at all.

[00:53:44] Mateo: But it, I remember when you came out I was like, all right, this is gonna be interesting. I’m, I wanna see where this goes. And it went in a direction I didn’t even, I didn’t even expect, but

[00:53:54] John: I am saying the majority of them, not Dawn, the majority of them, I’m like, fuck, they’re done.

[00:54:02] Dawn: I’m still doing, I’m still doing the consulting on the side and where I’ve found my niche. I always thought that I was gonna be really consulting for the vendor side of the industry and, but I do have companies that have hired me to help them pick their PMS. And just because I’ve seen the backside of them, of the majority of them, from that way, I kind, I’m able to take what they need.

[00:54:28] Dawn: Consolidate it into a needs assessment and then really narrow it down for them. So I’m trying to take that whole process and really shorten it and expedite it and say, okay, because of you need XYZ through Q over here, we can omit these companies. Here are the ones that I think we should focus on, and this is the way that we should evaluate them.

[00:54:55] Dawn: I’m still doing that and there are companies that I’m working with currently, but the PMS pros thing just, I couldn’t ignore it any longer and

[00:55:04] John: smart.

[00:55:05] Dawn: it’s going for it.

[00:55:08] John: Congratulations and until next time, Dawn,

[00:55:10] Dawn: thank you guys.

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