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Paula Rivera: 

Welcome to The AI Factor. The podcast where we explore how AI and emerging tech are transforming customer experiences, one conversation at a time. I’m your host, Paula Rivera, and today’s CX explained episode is all about demand generation in the dental space, and how technology is helping DSOs scale smarter, faster, and more profitably. 

Joining me is Jill Nesbitt, CEO of Optimized Dental Consulting, a leader in helping dental organizations streamline their tech stack and workflows. Jill’s been on the front lines of innovation and today she’s sharing insights from the Dykema Tech Summit, her philosophy on software strategy, and what’s really driving success in 2025. Jill, welcome. 

Jill Nesbitt: 

Why, thank you, Paula. 

Paula Rivera: 

I’m so excited to have you here. I always enjoy speaking with you. Before we jump into the heart of the discussion, I’d like to start things off with something a little bit softer, although the topic I chose wasn’t really soft, it actually sounds like it comes straight out of science fiction, but it’s actually very real. 

So research is in Japan. I thought this is absolutely fascinating. They’ve announced a clinical trial for a medication that could allow humans to regrow a third set of teeth. No more dentures, no more implants, a third set, grown all on your own. If all goes well, this could actually be available by 2030. The science behind this involves blocking a protein that limits tooth growth, and early trials in mice have shown promising results. For dental professionals this could be a game changer. For the rest of us, it’s a reason to rethink flossing. From someone who just came back from the dentist this morning, I couldn’t agree more. 

So Jill, if you could grow a third set of teeth, what would you eat first to celebrate? Something crunchy, chewy, or just plain fun? 

Jill Nesbitt: 

Oh my goodness. The last thing I need is a reason to continue to eat more, but I think if I could continue to expand my palate, I would continue to enjoy key lime pie as one of my favorite things. So yeah, more is better. 

Paula Rivera: 

Ooh, I think I would be right next to you enjoying a slice of that pie as well. So on a more serious note, how do you think breakthroughs like this, regenerative medicine in dentistry might impact the way DSOs think about long-term patient care, and their technology investment? 

Jill Nesbitt: 

Oh, I completely agree. In fact, I think forward-thinking DSOs are going to be watching just for these kinds of jumps. I was actually on a call just the other day with a very large DSO and they were talking about how AI is really, everyone’s focused on process improvement, but they specifically called out and said, “But we have to be scanning for those blue ocean moments where there’s some new technology that is actually a game changer.” It’s not going to come from, “Oh, I’m looking to solve this problem in the logical way,” that I will definitely talk about later on in our conversation, but it’ll just be like we didn’t ask for the iPod situation, and yet now we can’t live without it. So yeah, I think it’s going to be really, really exciting to see what really fun things come into our world, and then we have available to take care of our patients. 

Paula Rivera: 

I love it. And I like that thought process of the blue ocean moments because I think those are the moments, we’re always looking to improve processes, even when you think you’ve improved it, there’s still room for improvement. But it’s those critical moments that really are like the flash pan moment that sets the stage for really unique discoveries and unique advancements. 

So Jill, you’ve built a career helping dental organizations optimize operations and scale with confidence. I’d like to talk a little bit about your journey. So tell us about your path to founding Optimized Dental Consulting. What inspired you to focus on tech strategy for DSOs? 

Jill Nesbitt: 

I found early on it’s what actually works. So I’ve got 15 years or so of working as an administrator, so effectively operations for a multi-specialty dental group. We had three general practitioners and every specialty. And that was my foundation in dentistry. And then I had an incredible opportunity to work for a DSO. I had the incredible opportunity past that to work for an early stage cloud-based software, and get a foot in the door to most of the DSOs across the country who wanted to test out what does it look like to actually move our software and our processes over to the cloud? But what I found was sometimes it just doesn’t matter how great the software is, it only matters that you implement it well. And so when I wanted to start, it’s been this fall, it will be three years that I founded Optimize. And I did that simply because, well, two things. 

First is I found that, like I said, we all work based on our software workflow. So if I figured if I could implement that process well, that gives a guide for our teens to follow, and now we can really take care of our patients well because we have consistent excellence in the process. But then the second part of it is really maybe a little personal that, boy, I love helping patients and I love working in healthcare, and boy, I faint at needles. So if I’m going to get involved and do something helpful, it’s not going to be anywhere near clinical. 

Paula Rivera: 

Well, I think that was a smart move. 

Jill Nesbitt: 

Right. Right. Let’s just keep me out of the operatory from a clinical perspective. But yeah, no, I love it. It’s been such a ball to get to do this work, and I found it to be really incredibly meaningful. And who knew it would end up really deep, and leading me deep into this technology strategy role? 

Paula Rivera: 

Excellent. I love it. That’s a great path. That’s a great journey to have been on. I love it. So what’s one lesson you’ve learned from working with multi-location dental groups that you wish more people understood? 

Jill Nesbitt: 

I think the lesson is it’s not just a collection of solo practices. Sometimes people think, oh, well it’s just the same thing. I’m going to do the same thing if I have a multi-location group as if I have 10 separate locations. And that’s just not true. It is very, very different. Anyone that’s really worked with the solo or small group market compared to the DSO space, they’re very different animals. And they make decisions differently, they’re often thinking about centralization, there’s often an investor that’s involved. It’s just a very different segment. 

And so I think that’s something that’s really important. Whether you’re a tech vendor wanting to sell into dentistry, or you’re trying to make decisions from a dental practice perspective, which direction makes more sense to you and what’s a better fit? These are very different models. It feels very different. 

Paula Rivera: 

That’s really interesting and not a dot that I personally would’ve connected myself. Obviously I’m not steeped in the industry like you are, but I just would’ve assumed it’s the same across the board. So that’s a really interesting observation. So Jill, you recently participated in a Dykema Tech Summit, which our team was at as well. You facilitated a benchmarking session where DSOs were able to compare their tech stack with others in the room. So I’m sure this was actually a really interesting session to run, and there was probably a lot of interesting discussion that took place as people were looking at what’s in their tech stack, what are the successful companies doing? From what you saw with the attendees during your session, how is the overall maturity of these tech stacks, and where is there room for improvement? 

Jill Nesbitt: 

So let me give you a little lay of the land there. First of all, yeah, I am so fortunate to, this was my third year running this Dykema Tech workshop to not just give a presentation but actually give a space for our DSOs to have a conversation in the room. And there were no vendors there, so I did not have any technology vendors for this part of the conversation, which allows our DSOs to speak freely, and share what’s working and what’s not. 

So to give you a sense, I had about 40 or so DSOs in the room and it was actually a beautiful cross section. I had about 10 DSOs in the one to five location, 10 in the six to 20, 10 in the 21 to 50, and then I had five in the 51 to 100 location segment, and four that were larger than 100 locations or more. So I felt like now we have a really fantastic cross section of the DSO marketplace based on the number of locations. It was fun because this year I got to introduce polling because we were going to be in a much larger room, and I wanted to make sure that even if not every single DSO in the room had a chance to speak up, that we would be able to capture, share data through the polling, and then capture new insights because the polling was live. 

Paula Rivera: 

So let me jump in and ask a quick question. That’s a pretty, was that happenstance, that breakdown of the different organizations? 

Jill Nesbitt: 

We literally just got lucky. That DSO, in fact, this gave me such a kick. So it’s open to any DSO that wants to register. It’s always been on the Wednesday afternoon right before the reception. I had one solo practitioner in the room. And I had, I will name-drop a bit because he’s been there every year. I had a couple of friends from Heartland. And at one point I watched a solo practice woman ask the Heartland folks, “Hey, can you speak up? I couldn’t quite hear you.” How many times do you get to be in the room with enterprise class organizations to hear about their technology successes, and strategy, and what they’re working on, to be part of that conversation? 

So I love it so much. And the people that I talk to after the conference, when walking down the hall, they said, “This is my favorite part of it because I get to learn from everyone else.” And that can sometimes be hard to find the real discussion that is guided enough to not end up down a rabbit trail. 

Paula Rivera: 

Yeah, and I appreciate someone will probably call me up and say, “Why didn’t you say that?” But I actually appreciate the no vendors in the room. It definitely leads to a different conversation, and one that is probably more meaningful for the attendees. 

Jill Nesbitt: 

Yeah, they appreciate it. So going back though, like you were asking like, okay, what are we seeing? I asked a couple different questions. So I have some data, which is fun. So I wanted to know of all the different technology, what have they rolled out? And I mean full rollout. Not what are they piloting, what are they thinking about? Well, what’s the most common technology that they have done a full rollout? And what I heard in the room was the most common one was AI imaging. However, only five people in the room said that more than 75% of their doctors are using it. So even something as almost ubiquitous as AI imaging, it’s on the tip of everyone’s tongue. Even that is not fully rolled out. 

Paula Rivera: 

Repeat that stat. How many are using it? 

Jill Nesbitt: 

So the most common tech that was rolled out in the room was AI imaging of one brand or another. 

Paula Rivera: 

Yeah. 

Jill Nesbitt: 

But only five people in that room, only five answers on the poll said that 75% or more of their doctors are using it. 

Paula Rivera: 

Interesting. 

Jill Nesbitt: 

I know. In that same slide, and again, I think there were 10 answers on that polling question that had 0%, zero doctors using it. I was just talking to actually a private equity group before this call, and they were talking about interest in investments both on the DSO side as well on the technology side. And what we discussed was that there is so much impact on how you implement the technology that you have to really be thoughtful about what you’re going to invest in, and you have to make sure you implement it well because that seems to be the factor. It was super interesting. 

Paula Rivera: 

Yeah, I know I have a few in our little script here, I have a few implementation questions, but one of the things we found, and we’re working closely with our customers across the board with this is the technical implementation may be fine and everything should be where it is. But then there’s the education and the training of the employees who are supposed to be using the technology. 

Jill Nesbitt: 

Yes, yes. 

Paula Rivera: 

And that’s, yep, that’s an area where we’ve started spending a lot of time with our customers of, okay, let’s help you roll this out to your, whether it’s the front office staff, whether it’s the clinicians in the back of the office, let’s make sure that we’re providing them that educational level, so that the technology is used, which I think is pretty powerful. So that’s interesting that’s what you were seeing live in that room. 

Jill Nesbitt: 

Yeah. You’re smart to really focus on that. The change management piece of this, and I’m sure we’ll talk about it later, but this change management piece is hard. It’s just hard work. And so the more that you can provide content and support the practices and the DSOs to make this transition, massively impactful. 

Paula Rivera: 

Yeah, I concur. 

Jill Nesbitt: 

I’ll tell you another stat that I found was super interesting. 44% of the people in the room, the DSOs in the room, are still operating with more than four practice management software systems. And so when I asked at the beginning of the presentation, “What would you like to walk away with?” Most of the comments related to PMS integration in one way shape or another, and then the conversation in the room really highlighted a lot of the planned sunset of Dentrix Enterprise or, okay, what is everyone doing if they’re on 5, 10, 13 or more practice management software solutions? And I’m sure that impacts the world that you guys live in as well, that the more standardized some of those solutions are, the easier it is to integrate with your solution or with others as well. 

Paula Rivera: 

But that’s actually me. I thought the four was a lot, but there are dental organizations that have 10 to 15 different PMS systems. 

Jill Nesbitt: 

Oh, yeah. Oh, yeah. 

Paula Rivera: 

That’s a little crazy. 

Jill Nesbitt: 

It’s a lot crazy. It’s a lot crazy. 

Paula Rivera: 

This is why everybody needs a Jill in their life. 

Jill Nesbitt: 

Hey, I definitely am feeling like we’re in the right place at the right time. There’s a lot of good work that can be done in this space. 

Paula Rivera: 

Yep. I concur completely. Were there any standout moments for you or themes from the summit that really resonated? 

Jill Nesbitt: 

Yeah, actually. I really am feeling new technology and AI is just everywhere. And I definitely have the sense of how it can feel a little overwhelming for DSOs to navigate that. I will tell you a standout moment for me was to realize how unique the team I’ve built with Optimized Dental is, because we are independent and product agnostic. So definitely at Dykema where everyone, the DSOs were feeling like everyone is trying to sell us something. I felt like our team is really playing an important role by helping to guide strategy, and then support them with those implementation services. But I definitely, that was the feeling that I had really from this conference, and what I was being told a lot from the different DSOs that I spoke with. 

Paula Rivera: 

You recently wrote on LinkedIn a post that emphasized the importance of meaningful implementation over early adoption, what we were just talking about. You said that getting the software right, and I love it when you say this because you’re so passionate about it. It’s about intention, clarity, and time. Can you unpack that for us? 

Jill Nesbitt: 

Absolutely. I’m a huge believer that software implementation actually starts with business strategy. And I would say the only caveat is from what you and I talked about 95% of the time, this is how it really should, the tech strategy should follow your business strategy outside of this blue ocean event like we discussed earlier. But I’m a huge fan of a DSO starting with analyzing their numbers and identifying what is the problem they want to solve? That will help also identify success metrics. How will you even know that this is successful? And you do all of that before you even start shopping for software. So what I believe in is establishing this kind of change management approach, so that you can explore the needs, you can understand your numbers, hear what the pain points are, and then you start looking for solutions. 

Frankly, when you take your time in that part of the process, you’re building buy-in, and you’re setting the stage for a successful implementation no matter what software you end up selecting. So that I think is a huge piece of the puzzle that a tech vendor sometimes is so excited about what all great stuff their software can do. It’s really up to the DSO to take that first step and think what is the problem I’m trying to solve? 

Paula Rivera: 

I think that cannot be stated enough. And I’ve had a few guests on who basically say almost the same thing, maybe not as eloquent as yourself. But it’s amazing that, and for me, this is a little bit of my German coming out, but I’d like to believe I’m very thoughtful, and you really need to understand what you’re trying to accomplish, and you need to have some KPI set up. It amazes me that organizations don’t do that, and that you could have so many loose projects that perhaps don’t turn out to be very productive or very fruitful for an organization because they just didn’t take time to do that step. 

Jill Nesbitt: 

Well. And they need good partners to help them remember. It is so easy to get in this frenzy, and feel like all I need to do is find this silver bullet solution, and all my problems are going to go away. And I actually just posted this on LinkedIn just the other day, because I was in a conversation with someone who said, “Hey, I know you had this technology workshop. Can you just tell me the top few RCM solutions so that I can pass those along to my clients?” And I said, “I can, but let’s talk about that. What are you actually, if you see yourself as a strategic advisor to your clients, how does just tossing out a few IT company names, how does that actually help them?” 

And then we had a deeper conversation around this entire concept. What is the numbers? What is the pain point? What is the strategy? What is the model? What is the long-term goal? If you know all those things for the DSO you are working with, then it’s not just throwing a couple of silver bullet potentials over the fence, it’s actually then thoughtfully helping them understand the tech strategy follows the business strategy. And then you could be a really good partner to move them or even introduce them to me if that’s helpful. But I think it was really, I felt really good about helping even, not even another DSO, but another vendor partner to realize they have such an incredible impact on their clients, and that they even need to remember to pause and to think about how we can best really guide our DSOs and our multi-location groups. 

Paula Rivera: 

Yeah, I love it. What is your advice to DSOs who feel overwhelmed by the pace of AI and tech innovation in general? 

Jill Nesbitt: 

It’s not been that long ago I read a great Harvard Business Review article, I think I posted that on LinkedIn, but it really helped me realize like any other hyped up item, the smart thing to do is to tackle this with the same thoughtfulness you put into designing your DSO model in the first place. Take your time, learn, maybe even find a good consultant or partner who can guide you. That was actually one of the things we talked about in the workshop is that’s one of the things Optimize does. But heck, I’ve learned some great things. I really like the Economist Podcast that Mike Huffaker puts on from Planet DDS. I listened to that and learned about a new book that I read, and now I’ve signed up for Jeff Woods purpose or AI leadership, emails. There’s a ton of good resources out there to get lay of the land. 

But I think just then thinking about I’m in information gathering, and then talking to other people and understanding, and then deciding where you’re going to get those inputs. Although I would also suggest curate that a little bit right now, and you probably see this a ton, Paula. Everyone wants to stand up and say, “I’m an AI strategy expert.” You guys have been doing this. You know what you’re doing. You can speak to the overall industry, you can speak to the technology. I think really trying to make sure you learn from people who are somewhat trustworthy. And maybe again, you have to be thoughtful about who your partners are as you move down this path. 

Paula Rivera: 

Yeah, I really like that. And it’s funny that lends itself so nicely to my next question, which is how do you help DSO stay away from the shiny objects? And it sounds like it all goes back to this, we need to start thoughtfully. 

Jill Nesbitt: 

That’s exactly right. And specifically when I think about, okay, how do I engage with a client? My step one is let’s get to know you. I like starting with an onsite assessment. I want to get to know finance and marketing, operations, clinical leadership, RCM, every single part of the business. I want to visit a practice. I want to understand who you are. What is your model? What is your payer mix? Are you special? I want to understand all of those things and where you’re trying to go. And then I want to benchmark that against your preferred software. 

And because I’ve worked in dentistry for so long, I know how to talk to team members as does my team. And so people will tell us, “We love this, we hate this part,” or, “This is such a waste of time,” or, “This makes me crazy.” So now we can identify what are the findings and what are the recommendations? And from that, now we can move forward. And whether that’s moving forward from a software selection perspective, or it’s moving forward from a now we’re going to go ahead and implement successfully. We don’t jump straight to the software. We want to first understand who are you as the client, as the DSO, or the multi-location private practice, so that we can identify what is the right fit? That’s my favorite part. 

Paula Rivera: 

I love it. I wish I could hire you. I don’t have a need to hire you, but I would like to hire you because I’m sure whatever project I’d hire you for, it would come out really well. 

Jill Nesbitt: 

That’s the goal, right? Branding up helps you go. 

Paula Rivera: 

Exactly. So you recently contributed to a Becker’s article. And it was basically about tech strategy is now, your comments were along the lines of how tech strategy is now a non-negotiable for DSOs looking to grow. And you mentioned that private equity is all in on PMS standardization. Why is this such a game changer? 

Jill Nesbitt: 

I’m actually saying that investors are the ones encouraging their DSO executive teams to move forward with this standardization. They’re willing to put up with the disruption, and they’re even willing to put up with some short-term production dip during the migration, so that they can gain the long-term benefits of trusted data and just massive efficiencies. 

Paula Rivera: 

As you were speaking, it’s funny that you ended up there. That’s what, as you were talking, I was like, oh yeah, once everything’s standardized, then you have a nice data set that is trusted. I wasn’t using the word trusted, but I think I was, in my head, I was thinking, oh, that would lead to a clean data set. 

Jill Nesbitt: 

Well, I’ll tell you too, at the Dykema Tech Workshop, I always have my friend Tom Cregan, who’s an investment banker with Raymond James, and he always does the mic drop moment at the end, because I can talk all this interesting stuff about tech and facilitate a conversation, but he can help us understand from the money in the room, from the investment and the private equity, and the money if they’re not going to back it, what are we doing anyway? 

Paula Rivera: 

Right. 

Jill Nesbitt: 

But he has said to me from this PMS standardization perspective, there was one group I was talking with and I said, “Yeah, they just decided they’re just not quite ready. They want to make this change.” And they’re 65 locations or something. But I said, “They’ve worked with their private equity company for I think more than seven years or something that in private equity investment that’s dog years forever. And what they’re trying to decide is do they have to switch the software to a standard? Do they have to be the ones to do it, or can they just kick the can down the road, hopefully have a transaction and make that the next company’s problem?” And I said, “My understanding of that would just be, well, they’ll just get a lower multiple.” And Tom specifically said, he is like, “Nope, that is not right.” And I’m like, “Oh, tell me all about it.” He said, “If they don’t standardize their practice management software, there probably won’t be a transaction. It’s really, really difficult to have the right story.” 

It’s like buying a house when you’re like, well, I have to put in all new everything. I have to gut it and start over. So anyway, I think that’s the part where, and I’m learning that from him. That isn’t something that I live and breathe. That is something, but I’m starting to see it more and more because when I’m having these conversations with the DSOs, the private equity is in the room and they’re saying those very things. 

Paula Rivera: 

That’s absolutely fascinating. I’m going to have to have you back on, and we could do maybe an end of year check in on that because that is fascinating. What are the biggest gains you are seeing from DSOs that invest in tech and optimization? 

Jill Nesbitt: 

I see a lot of interest in RCM. And if you’re an RCM leader in a DSO that has 10 different practice management systems, you’re doing the best you can, but you’re generally stuck with having to maybe outsource or just leave work at the office level. But I’ve seen RCM leads who have narrowed down to one or maybe two systems, they’ve really been able to design just beautiful automation, specific guides that are consistent across the organization, and they can just keep dialing in on more and more specific improvements. 

Paula Rivera: 

Wow, okay. So that’s great. So I know I mentioned that I’ll have you back at the end of the year if you would be so kind, but let’s talk about the beginning of the year. We’re a little bit more than halfway through 2025. Earlier this year, back in January, you made a bunch of the typical new year predictions that we all see that come out in December and January. There was talk back then, I believe you mentioned this about a wave of PMS transitions. Are we seeing that play out? 

Jill Nesbitt: 

That’s so good. I love this question about, all right, you said X. now we’re standing here and it’s end of August. 

Paula Rivera: 

Just very quickly, I’ve been in PR my entire life and it always amazes me that journalists never double back and ask you, “Well, you said X. It’s now a year later, did that come true?” It amazes me that people don’t follow up on that. 

Jill Nesbitt: 

No, it’s a fantastic question. I love it. And it’s really good because it makes you think, take a step back and think, oh, that’s a good question. So I will tell you some yes and some no. So I worked with a client that they said, “We’re just going to do a few offices, that’s all.” And they just kept going. I give full credit to their tech director or their IT lead because he was like, “We’re going to keep going.” Because he knew this. He understood all the benefits we’ve been talking about standardization. 

But I also know that I talked with a handful of 50 plus location DSOs that were planning a transition off of Dentrix Enterprise come Q4 of last year and Q1 of this year. But then we watched, I think just the economic volatility of our world just go crazy bonkers in the last several months. And I think people just said, “Pause.” So I think a lot of people that were pretty excited about making a plan, I think they hit pause to see, “Wait a minute, what’s actually happening in our country right now?” And now I actually think we’ll see that play out the rest of the year. 

Paula Rivera: 

Interesting. Interesting. So that answered my next question about what surprised you most about the first half of the year? 

Jill Nesbitt: 

Yeah, I think so. The only other sad thing that surprised me that I did hear some stories of is I heard a few horror stories, and I feel like I’m deep into this piano standardization, which is obviously a lot of where I live, but I do lots of other things in that. So please do have me back. I talk about lots of other technology I promise next time. But I tell you, I heard some horror stories of three different DSOs who changed software to try and standardize, but they missed critical pieces, and then the projects stopped in their tracks. 

So they didn’t design a clear workflow for how they were actually going to use the software. They didn’t end up communicating it effectively on the change management, and they didn’t document custom SOPs to make sure everyone was on the same page. And I felt, I was just really surprised because those three items are part of the work that my team does every single time. So again, it just goes back to you need a plan, not just for the data conversion because you’re right, people think it’s just a conversion, it’s just data, it’s just tech. That is not the story. And that’s where again, I’ll give you guys full credit for the way you’re thinking about communication and the why behind the move, and how to communicate with the individual doctors, and those teams in a one-on-one conversation. 

Paula Rivera: 

Yes. And the other thing that we’re encouraging is they’re communicating to their patients. So you need in-office folks to be on board, but then there is a degree of education that then you need to do with your patients, especially some that might be a little bit tech adverse, and maybe those who grew up in the era of bad chat box who might have that resistance to technology. We’re implementing this technology, but you could still always talk to us type of thing. 

Jill Nesbitt: 

Agreed. 

Paula Rivera: 

To give everybody the comfort level. So this is a nice segue into one of the last serious topics I want to go through with you. You had recently led a rollout for an emerging DSO in Nashville, and you worked with the custom tech stack and a private equity partner. Can you walk us through this project and maybe give us some insight as to what made it unique? 

Jill Nesbitt: 

Yeah, thanks for asking on that one. So yeah, that project I had the opportunity to roll out a practice management software, an integrated engagement platform, and an analytics solution. I’ve been super impressed with the leadership at this group because they are fully committed to investing in the best experience for their doctors. And so I was really excited to get to be a part of that to lead the project. And then we’ve designed a training program, and those custom SOPs that extends the support, so that it’s not just let’s get you started, but it’s after go live that you have a really clear support plan. 

I think one unique aspect that I have found really interesting is they’ve also then expanded. They have a handful of offices in Nashville, which continues to grow. They’ve also expanded into Florida. I was just down there literally the week after Dykema, we got to meet these two fantastic offices, and they are on paper charts, so you don’t get to see that many paper charts practices anymore. And again, you walk in the front door and there’s just giant bookcases of paper charts. So that would probably be the more unique piece of this project so far. 

Paula Rivera: 

Which is so funny. I literally, I think earlier I said it was today, it was actually yesterday. I literally was at my dental office. And there’s bookcases and bookcases, but there’s only two or three actual sections of the bookcase that actually has charts in it. And I was looking at it and I’m like, they’re either going through the transition because there is an awful lot of tech throughout their office or I don’t know, for some reason they just haven’t gotten rid of these files. But it’s funny, I was literally staring at that and I’m like, in this day and age, I’m like, why are they using paper files? 

Jill Nesbitt: 

Yeah. Yeah. Well, and I think again, it speaks to you have to really be ready for the project, right? 

Paula Rivera: 

Yeah. 

Jill Nesbitt: 

You just have to be ready. 

Paula Rivera: 

Yeah. So what lessons from this rollout could help other DSOs in planning a tech transition? 

Jill Nesbitt: 

I think a good lesson is we really started out by designing their workflow first, and then we documented the full patient journey with every step by software and the function. Again, you’ve heard me say we created these custom SOPs. I think that is really valuable. And just writing out. There’s always going to be something when you do a full rollout like this where maybe something doesn’t integrate. And so writing step by step, what do you do in one software? What do you do in the next software? How does that exactly work? And getting that all documented. 

I think the other lesson learned is just what we’ve been talking about. This is a lot of work. And so understanding what is the job to do? That is step one. And then next is identifying who’s going to tackle this work, and are they qualified? Who’s going to be your resource, whether it’s IT or revenue cycle, or project leadership for the overall lead, or training. Really making sure you have the right resources pulled together. 

I think the other interesting thing, Paula, is really thinking about how software like yours can be used actually as part of this PMS migration process. One of the biggest challenges that I see is what are we going to do about legacy AR? We got a lot of money sitting in our old system. And the reality is my team doesn’t want to look at the old system, and then at the new, and how quickly do they forget to look at the old when they’re so focused on training, and getting it right in the new software. 

So I know you guys have done some really cool stuff with outbound calling for collections. I think there could be a really interesting application of, hey, when you’re getting ready for a PMS migration, maybe you want to really, and in fact, I’m a huge fan of planning that in advance. Not only thinking about your resources, but when you talk about revenue cycle resources, what if you could take the time that you’re preparing for change management, and you’re talking with your teams, and you’re gaining buy-in, but you’re also implementing perhaps some technology that’s helping you to collect this money, and not leave it outstanding, then we don’t have to worry about what that migration looks like from the old system. 

I don’t know if you’re starting to see that as a use case that’s becoming more and more popular from your customers, but to me that could be a really fantastic approach. 

Paula Rivera: 

I love your thinking. And I’m not sure if we’re approaching it from that perspective, but the more we talk about collections, it’s like everyone’s ears perk up. They’re like the worst job in the world and we can automate it? 

Jill Nesbitt: 

Exactly. 

Paula Rivera: 

Yeah. Jill, this has been fabulous. What I like to do is I wrap things up just like I started with a few fun questions just to get you, to know you a little bit better beyond today’s discussion. So I’m going to ask you three questions. You can provide one word answers, you can expound upon your answers as much as you would like. I’m here for all the goodness you bring to the table. So the three questions, what’s one AI myth you wish would disappear? If you could use AI to predict one thing in business, what would it be? And one word to describe the future of dental tech myth? 

Jill Nesbitt: 

Okay. The one AI myth that there is a silver bullet out there, you just have to find it. I think that’s a myth. I would like that to go away. 

Paula Rivera: 

I think I’ve fallen into that trap a few times. 

Jill Nesbitt: 

And who knows? Like we talked about, maybe there’ll be a blue ocean thing and there will be something that will solve all of our problems, and cook dinner, and walk the dog, and all the things too. I guess we’ll keep waiting on that. Oh, okay. The next one. What was that? Predict? I could use it to predict? 

Paula Rivera: 

Yeah, one thing in business or personal. 

Jill Nesbitt: 

Okay. Timing. If I can predict the timing. I’ve been having such fun conversations over the last few months with some really large groups about, “Yep, we’re making this plan, we’re going to do this great work, we’re going to do this transition.” And then some of them are like, “Okay, we need to start yesterday.” And then others are like, “Yeah, we haven’t decided.” So I think if I could use AI to really predict that, I would predict the timing, so that I could make sure when do you want to actually get started so that again, I have the right team at the right time. So timing would be my answer to that one. 

Paula Rivera: 

Nice. And then the future of dental tech, one word to describe? 

Jill Nesbitt: 

I picked the word catalyst. So here’s why. It’s funny, it’s been a few years ago. I actually had a very big birthday coming up, and I gave myself the gift of an executive coach or a life coach thing. And they get to know you at first or whatever, and they give you three or four words that are who you are. And one of my words was catalyst. And so I was thinking about there’s so much fun with this word catalyst because there’s so much excitement around dental technology that could really solve problems, make things happen, just be that catalyst to really take action. And I feel like that’s a little bit what I, like my personality, that I like making things happen and being that spark to make things move forward. And I think dental technology is exactly the same way. So I will stick with the word catalyst on that one. 

Paula Rivera: 

Well, that’s a very positive way to wrap up the segment. I like that. So Jill, thank you so much for joining us. I really appreciate your coming on. It’s always great to talk to you. You’re fun and interesting to speak with, but you’re also a wealth of information, so you’re like a double-edged sword. So thank you, Jill. I really appreciate your being on. 

Jill Nesbitt: 

Oh, Paula. Flattery will get you everywhere. 

Paula Rivera: 

Excellent. Jill Nesbitt has shown us that the future of DSO success isn’t just about adopting technology, it’s about optimizing it with purpose. From PMS standardization to AI powered workflows, the smartest dental organizations are using this moment to scale with confidence. Thanks again to Jill for joining us, and to you, our listeners. If you enjoyed today’s episode, be sure to follow The AI Factor wherever you get your podcasts. Until next time, keep scaling smarter. 

About this episode

Discover how dental organizations are scaling smarter in 2025. In this episode of The AI Factor: CX ExplAIned, host Paula Rivera sits down with Jill Nesbitt, CEO of Optimize Dental Consulting, to explore how DSOs are leveraging AI, tech strategy, and operational optimization to scale smarter in 2025. From insights at the Dykema Tech Summit to a behind-the-scenes look at a multi-location rollout, Jill shares how private equity is driving PMS standardization and why aligning your tech stack is now essential for growth, valuation, and long-term success. Whether you’re in healthcare, tech, or investment, this episode delivers bold predictions and practical takeaways for the future of dental innovation.

For those looking to understand how AI is shaping the future of CX. 

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