The CRO Spotlight Podcast

[00:00:00] Warren Zenna: Hello and welcome to this episode of the CRO Spotlight Podcast. I'm Warren Zenna. I'm the founder of the CRO Collective and I'm really excited today. I got a great guest [00:01:00] who I've been trying to get on this podcast for a while. I'm really lucky to have Bridget Winston here, who is the CRO of PatientNow, and the former CRO of Chief, the organization for Executive Women, which I use their space all the time for my events in New York. Bridget is a three-time CRO. It's a really great success story and you're gonna love this conversation. She's really smart and has some really great insights and hot takes on the CRO role. So stay tuned for this great conversation. So I'd like you to do, if you don't mind, first, why don't you introduce yourself, tell everybody who you are and a little background and what you're currently up to so people kind of get a sense of your incredible career.
[00:01:00] Bridget Winston: Oh yeah, absolutely. So Bridget Winston, I'm the chief revenue officer at a company called PatientNow. We do vertical SaaS and sell to med spas, plastic surgery centers, and cash-based aesthetics. Prior to that, this is now my [00:02:00] third time, I guess I should say, as a Chief Revenue Officer. My first time was at a company called Shutterstock, a publicly traded large organization that did both B2C e-commerce and enterprise. And then also I was the Chief Revenue Officer at Chief for five years. So built that from pretty much ground up all the way to our Series B, valued at $1.1 billion. So, pretty impressive. It was fun, it was a great ride there. Lots of learnings going on that journey from basically what was 1,500 members to 20,000 members. And really prior to that it was always in technology. So basically grew in my career, always came up through sales, and did a foray into customer success as well. And so I was always in technology. So whether that be cybersecurity, storage, [00:03:00] networking, unified communications. So I'm kind of going back to my background of being in technology again, and this time really focusing it on that SMB practice owner. 70% of whom are women. So it's a really great, let's call it marriage, between a good portion of my backgrounds where it's B2C, B2B technology, but also really focusing on that SMB buyer. We are truly giving them confidence in what they're buying for the entire journey. Not just the software, but the onboarding, the client success. That ongoing, there are no post-sales anymore, right? Every interaction someone has with you either says they will continue to be with you as a customer or not. So that true version of what a CRO should be, not just a glorified VP of sales.
[00:03:00] Warren Zenna: Yeah. Well, you know how I feel about that. So...
[00:03:00] Bridget Winston: I do.
[00:03:00] Warren Zenna: But you came up in sales. So walk me through how you made that jump. Like that's a really good story. I'm always interested in [00:04:00] hearing that because as you know, it's like a weird journey and everyone has a different story about it. So if you don't mind, I'd love to hear about that.
[00:04:00] Bridget Winston: Yeah, the company that I did that with was at ShoreTel, and that's actually where I really realized what was changing in the market. So ShoreTel was a unified communication platform. It was a premises-based platform. So we sold through channel partners in which, you know, you would make a capital expense, you would buy a very on-premises solution for your unified communications telephony needs. And there was certainly software to go along with it, but the market itself was migrating to unified communications as a service, so UCaaS. And so we ended up buying a company called M5. It was a cloud-based, unified communication service, and everything about us had to change. Because, you know, everything... it's almost, I always use the example of it's the difference between going, buying a membership to a gym versus buying a home gym and installing it in your house. You know, a customer has [00:05:00] to kind of take a look at the treadmill, take a look at the weights, do all of that themselves, and basically service anything that might be needed. You put out that big capital expense to buy it and then manage it yourself versus going to a gym where they're managing all of the equipment for you. And it's basically the service that you're getting. So everything about the capital expense, how you are as a company, how you incentivize your reps, how you incentivize your entire company, the cash flow that you are dealing with. So everything had to kind of change about the organization. And so we went from being very channel centric, focused on basically just big large capital expenses. You know, with $500,000 worth of an average deal size to a slow drip of MRR that was somewhere in the $2,000 range. So $2,000 range. And so it was a big change in transition for our company. And so we went to an org structure that had much more sales and [00:06:00] customer success. And this is when I started reading all sorts of books, becoming very familiar with Gain. And learning that, you know, they were using Salesforce as their model where they said, "Oh gosh, you know, we can sell all these customers, but what happens to the LTV? What happens with the lifetime value of a customer?" And in that, it was a real aha moment for me because it allowed me to go, "Oh gosh, sales is now becoming this sliver in this customer journey." The acquisition is a small part. I had already been feeling that marketing was encroaching on the sales journey, right? The whole, you know, people get 57% of the way through the buying cycle before they actually engage as a sales rep. So I'd already known that trend and now I went, "Oh gosh. The retention and upsell motion becomes so much more important in a unified communication as a service play or in the SaaS play." And so I purposely, after having this VP of sales and customer success role, [00:07:00] where I was managing that entire team, the MDRs, the sales, the CEEs, the onboarding, the support, the client success, it was a real foray. It was really my first shot at that. I purposely, when ShoreTel got acquired by Mitel, purposely made the move to go into a customer success role. So I became the VP of Global Customer Success when everyone else got acquired and they were thinking, "Okay, how do I get a sales job?" I purposely raised my hand and said, "I think I should actually round out my experience to really understand customer success." And boy does it tell you something. It shows you so much of how sales can absolutely be the engine to every great organization for sure. But boy, it could be the detriment too if you are selling to the wrong ICP and making promises that you can't necessarily deliver on. And it really showed me the real value of ICP as probably one of the most important things that [00:08:00] you are doing. And that product market fit is really never done.
[00:08:00] Warren Zenna: Yeah. You know, it's a great point. You know, I think that it's a weird dynamic that takes place with earlier stage organizations, which is, as you well know, they have to be sales focused from the beginning. They have to just get as many customers as possible. That's the way that they build a business. So they're essentially really for the first, I don't know, you and I can probably agree on this number, let's just say it's somewhere south of 25, 30 million. You're a sales organization essentially, right? And I get that. And you have to be, right? So you're building an entire sales motion and you need a lot of people with that competency. And it's all about getting customers. And part of it is either A, if you're a forward-thinking organization, you're thinking not about just getting new deals. You're also thinking about why are they buying and is it the right fit and what's the utilization model and what's the value and how long do they stick around? But sometimes it's not. Sometimes it's just how fast and how repeatedly can we get people to pay for what we have? And if we could build a machine that does that repeatedly enough, well then [00:09:00] we're onto something here. But it's not true because many times that sales organization figured out a way to cajole a segment of the population to buy their product, but in fact they're not a fit because they don't last. And so to make that shift when you've already been evaluated on the amount of sales that you make, and all of a sudden you realize, well, you know, we're not sticking around, which means we have to sell to different people. You know that if that different ICP is too far adrift from what you're selling to, it could take an entire few cycles before you can get that fit. And I think like, I don't know. I'm curious what your point of view on this is. Do you find now that's the same unfortunate sort of repeatable conundrum, or are companies being a bit more mindful now and thinking more about, well, you know, okay, we're getting deals, but what's the stickiness earlier? So that when they do get to a point where they need to focus much more on growth and retention, that they're closer to their ICP or everybody has to course correct. And I'm just curious if there's any changes or shifts going on there today.
[00:09:00] Bridget Winston: You know, I would say even for me, I actually thought that [00:10:00] product market fit was one of those things that was sort of like once you have it, you keep it. And it was a flawed hypothesis that I had that product market fit was something that you did once and then you kind of set it and forget it. And you could extend that to ICP and all of that. And so I would say I learned that probably the most at Chief where when we went out in 2019, we were only selling to Fortune 500 companies. We were brand new. We were the first one on the scene really to sell to that executive buyer. And so it was Fortune 500 corporate executives who we were targeting. But then a little thing called COVID happened, right? And so COVID happens, you know, a good portion of the world reevaluated their relationship with work, let's just say. And there were so many people who decided to leave that Fortune 500 job, or they got laid off from that Fortune 500 job. And so we've watched our member [00:11:00] base evolve and change. And this thing that was just this easy, 1,500 to 20,000 growth acquisition, it wasn't even that hard. It was also a tailwind market where DEI and the labor force had a good portion of the power during that time. And so people were doing anything to kind of cajole people to actually stay with them. And so paying for memberships was one of those things as well. And so we were in this tailwind market and then obviously COVID ends, our ICP changes. People want in-person. We had gone national and so everything about our organization had to change. And I will say that was probably the hardest, but gosh, I learned so much at that time of what do you have to do to quickly change your product market fit and to test and learn into different segments while you're still not losing potentially what made you so special? And what was that [00:12:00] initial brand cachet and that initial brand recognition that you had so much success with, but how do you actually evolve and test and learn? And so you'll see it even now within Chief's organization. You can segment in different ways so that you're approaching the different types of customers that you have in a different way. And so we had to evolve so much at Chief. So now we actually have a solopreneur track. You know, there's a Fortune 500 track. And so they've evolved very much to address the changing needs of their customers. And so that even if that growth at all costs at the beginning, or even growth at reasonable costs at the beginning was something that you could take full advantage of when time gets compressed or when the markets are filled with more headwinds than tailwinds, how do you still capture that different type of customer, even in an evolving and changing landscape?
[00:12:00] Warren Zenna: Hey everyone. I wanna thank you [00:13:00] again for listening. Get great comments across LinkedIn and other channels about the show, and it's really gratifying to see that we're having an impact on you. Another thing I wanted to let everybody know is that we also produce events. About two and a half years ago, we started the CRO round tables. Predicated on the idea that, well, two premises. One is that CROs are looking for other CROs to talk to, which is really true. It's a very lonely job. And how do we get a bunch of CROs in a room where they're not being, let's say, disintermediated by panel discussions and sponsorship events and demos and stuff, and really give them a chance to talk to each other. So we created a round table event. Essentially it's a three and a half, four hour discussion between 20 and 30 chief revenue officers. And these are amazing events. The format took off, people love them, and I get requests all the time as to when, when is your next CRO event. So, to that end, I just wanna let y'all know that we have a number of the roundtables coming up over the next year, over the next like 2026. And I wanna share 'em with you so you can, if they're in your market, you can come. So the next one we're having is gonna be in London, actually in February, February 24th in London. So if you happen to be a Chief Revenue Officer in the UK or even in Europe and you wanna come by, you'll be hearing about it more on my website and LinkedIn. But put it early on your calendar. And then following that, we're probably gonna be doing an event in San Francisco in March. There's gonna be one in New York in March. I'm gonna do another one in Chicago probably in April. And then I'm gonna do an event in Boston. I'll do an event in Atlanta. I'm gonna do an event in Salt Lake City. I'm gonna do an event in Austin and I'm gonna do an event in Los Angeles or the Southern California area. So [00:15:00] those dates are to be determined, but they'll be going across all next year. And these events are taking on huge momentum. They're the place to be if you're a chief revenue officer and you want to be in a room with no interruptions and have an opportunity to really share with each other in a sort of a private and confidential open discussion about everything that you wanted to talk about as a Chief Revenue Officer and collaborate with great people. So thank you and thanks for supporting the show and look forward to seeing you at the events.
[00:15:00] Warren Zenna: I'm curious to know what exactly you did do. I mean, it's cool. I get that. It's a really interesting situation, but it sounds to me like some of the obvious stuff is just having to widen the aperture a bit on who you bring in. But how do you do that without sort of in any way infringing on the value of this value proposition of it being somewhat exclusive. You know, that's why people wanna come to a place like that is because they're aspiring to be at a level that they want, and membership [00:16:00] indicates some kind of signifier of success, and now all of a sudden you're opening it up. You had to for the business. What was the way that you managed that? Walk me through that.
[00:16:00] Bridget Winston: Well, first it was very data driven. So what I would say is there is a great tool that I used called Good Work. So I will recommend that. I get no payment from this, but I've now used them at Chief and I'm now using them at PatientNow. First you need to evaluate who your customers are because we think we know, but we spend a lot of time not. And so this is an AI tool that goes in and measures all of our customers and then segments our customers. And so we thought we had, let's say, 80% Fortune 500 corporate executives. That's when we first learned, "Oh gosh, what we think we have in terms of solopreneurs," let's say it's 3% or independent consultants, we thought it was 3%, but you know, let's say it was upwards of a fourth of our customers...
[00:16:00] Warren Zenna: A quarter of...
[00:16:00] Bridget Winston: So that will tell you exactly. [00:17:00] Exactly. And so you've basically gotta start with the data. So first, be honest with yourself, right? First look inward and kind of go, okay. But none of this data was data that we were easily able to get because you're relying upon surveys or the customer should just tell you automatically. Now with AI, you can scrape for all of this information so that you are informed about who your customer is. And so that's what Good Work allows us to do. They also then help, and so that's their entire pitch, if we help you with ICP. And then also they allow you to enrich your data and do better targeting on your marketing side as well as enrich your data within your CRM platform. And so that, I will say, was actually very instrumental. But then it was secondarily, first understand who your customer base is now and how they have evolved. So that was probably the most critical element. The second thing I would say is evaluate who stays with you the longest within that. So understand your segments, but [00:18:00] then also look at your LTV. And so that's actually the little known secret that I always believe is that what separates someone who only cares about acquisition, let's say a VP of sales, a glorified VP of sales, from what a chief revenue officer is, is the Chief revenue officer should care about the LTV to CAC ratio that they're analyzing. So we have to look at who's staying with us the longest and how much does it cost for us to acquire them. And so that was actually the real enlightening moment too, was, okay, who stays with us the longest? Who is this most valuable for? What are the different segments? And then how do we then bifurcate the experience? To your point, people want to be with people, especially in a membership community, who are most similar to them. There are certainly moments of exchange and moments of collaboration between people who are very different from you. And in fact, sometimes that's the value of a diverse community for sure. [00:19:00] But a lot of times if you are dealing with a problem, you wanna talk to someone who's going through a very similar problem. And so you purposely actually have these different experiences so that you can in some ways make sure that everyone's getting the most value out of that experience. And then finding those points of intersection as well where you can bring the full community together too. And it's not about TAM, it's honestly just meeting the evolving member where they have gotten to. And so that was the real value that I saw. We're doing the same thing at PatientNow. We've seen a... we're a traditional kind of private equity, growth equity backed company where we acquired our way into the revenue that we are at. And so you've got tons of different types of customers. And so evaluating all of these different customers, salons, plastic surgery centers, cash-based aesthetics, med spas, dermatologists, you name it. And so [00:20:00] we've got a lot of different types of customers. We could spend all of our energy on serving everyone extremely well, or we get very crisp and specific and say, "Okay, these are the top segments that we are going after, and we can dip our toe in to see what that next horizon can be so that we can continue to grow." But we have to serve our ICP extremely well so that we are somewhat narrowed in who we serve and who we really dominate in terms and have designed our experience for. And then we can test and learn into some of those other adjacent verticals as well.
[00:20:00] Warren Zenna: Yeah, that's an interesting one, right? Because on your one hand, I hear this a lot, you sort of choose a... I have people tell me this, so as you can appreciate, right? I have a pretty narrow...
[00:20:00] Bridget Winston: You can...
[00:20:00] Warren Zenna: I have a very narrow profile, the person I'm going after, right? So it's pretty self-evident. I really have two people, it's CROs and CEOs, but they have to be, it's pretty specific, the thing. And so a lot of people come to me, "You know, [00:21:00] you should probably start targeting salespeople, you know, they probably need this too. Or maybe you should do sales training." And say, "Look, it's not what we do." And the temptation is like, "Well, I know, but..."
[00:21:00] Bridget Winston: It's so tempting.
[00:21:00] Warren Zenna: Right. There's a market there and they'd buy from you and you'd make a lot more money. And so there's this battle between... I could see if there was someone who had invested in my organization, they'd probably be pressuring us to do that. They'd say, "Look, you're leaving money on the table. There's other segments outside of yours." And you know, there is the pure play, which is, "Nope, this is what we do and this is all we do, and we have to maintain our brand guardrails." And the other one is, "Well, you know, we can expand, we can bring our offers to other people." And both are legitimate. I tend to be more of a purist. I tend to... and I think people do too. When you buy a product, I think there's probably a number of reasons why you're buying a service or a product or anything. One is its usefulness. It solves a problem for me and they do it really well. The other one is too, this sort of a sense that they've got a [00:22:00] specificity and they've got an expertise of depth and that makes me trust them. And when I start to see them start doing a lot of other things, it makes the offer seem less integrous. Like, "Oh wait a minute, all of a sudden..." And what happens most often is the original segment gets ignored. Right. They're just not important anymore because now we've got this bigger world to deal with. And I think the growth metastasizes and turns a company into something that it's not. And over time, a brand that you sort of felt an affinity toward no longer seems to have an affinity for you anymore. And I think that that's interesting. But in your situation, your situation was really cool in that you had to, because your market disappeared through an act of God. Right. And...
[00:22:00] Bridget Winston: Yes. Our customers told us. Yeah, exactly. And you can still, and I will say, I can't tell you how many HBS case studies I actually started looking about how do you have a brand that has [00:23:00] multiple layers to it, that doesn't still lose its brand cachet, but can serve each of those audience. It is a delicate balance. I am not saying that we nailed it. I'm not saying that it is even the easiest thing to...
[00:23:00] Warren Zenna: Well, sure. But it wasn't in your...
[00:23:00] Bridget Winston: You are listening to your customers. Yeah.
[00:23:00] Warren Zenna: You were put in a situation you had to respond to, and that was what makes it interesting is that it wasn't like you guys made some strategic businesses and it was... you had to respond to reality and you made it work. And that's an interesting situation. Because that's like what I think if I'm a CRO at a company and I'm in this situation, we'll get into in a second, like what the CRO does and all that stuff. But, okay, so I'm in the role, much like you. I'm sure at this stage you're probably given a great deal of authority over that particular part of the business. And they wanna make a decision like this. You're involved. I mean, you probably could say, "No, we're not doing that." Right. You have a voice. But in this case you don't. The market's saying, "We don't have a choice. Our market went away." You know, if [00:24:00] you're an in-house gym, if you're a gym and no one's going to the gym anymore, well, we're gonna have to build gym equipment now. You know?
[00:24:00] Bridget Winston: Totally. Like you go back, you go from that opposite side of the story that I was talking...
[00:24:00] Warren Zenna: Exactly. I mean, we were involved in that because we were... I have a marketing agency and we were Equinox's agency of record for a long period of time. And they went through COVID. They started creating their own business that was similar to Peloton. They started creating like...
[00:24:00] Bridget Winston: Mm.
[00:24:00] Warren Zenna: ...sort of, you know, business. And it was interesting to see how they... now, they could have done a better job, but my point of making is they were day two were faced with a very difficult decision and they had to figure out what to do about it. But anyway, I think it's interesting. I think the other thing I wanted to ask you about this is, because you mentioned this before, it's a cool topic. So you have someone who's a VP of sales...
[00:24:00] Bridget Winston: Mm-hmm.
[00:24:00] Warren Zenna: ...used to running sales organizations, which, you know, they've been trained and they've been developed in a way that makes them really good at gaining new customers and closing deals and creating playbooks and velocity around that particular motion. And the ones that are really good at it are very [00:25:00] focused on it. And you can count on them to do that. And if you build an organization around them, that'll feed it right. But a lot of it is also, as you know, it's also incentives. I mean, the reason why VPs of sales do this is because they're incentivized to, right? That's how they win. They take the job because they know if they make a lot of sales, they make a lot of money, and they're rewarded that way, and they get promoted that way, and they get better jobs that way. So if I went to a really good VP of sales, this was a hypothetical, and I went to that person who showed good business acumen and was a very talented leader, and I said, "Alright, we wanna promote you, but we're gonna change your incentives."
[00:25:00] Bridget Winston: Yeah.
[00:25:00] Warren Zenna: "You're no longer gonna make money on the growth of your portfolios and your pipeline. You're gonna make money on the profitability of the company now."
[00:25:00] Bridget Winston: Oh.
[00:25:00] Warren Zenna: How many VPs of sales on average do you think would be able to make that switch? Or would they just certainly not be able to? In other words, my question sort of is not about them, it's more about how much do [00:26:00] incentives play a role in the way that people operate as opposed to their more innate nature? Like where's the balance between the two? I do think that if people are told to do things and they're being managed against a certain outcome, then they manage against that outcome now. Because that's the way they're being managed. Not everyone can make that shift, but I would venture to guess a lot of people are. I think that's what makes a CRO different is that you're being measured on, you know, customer acquisition costs and NRR and GRR and all that stuff, right? And that lifetime value is ACV and that those are different incentives. It's not the same. So you spoke about it as someone who, and it's probably true, you sort of saw the bigger picture. And you recognized how sales was just a piece of a larger pie that was about really customer retention, and that expanded your thinking around how you approach the job as opposed to someone coming to you and saying, "Alright, Bridget, [00:27:00] we're now elevating you to a different level. We want you to focus on this now." How much of it is just an innate thing and how much of it is a response to new incentives? I'm just curious what you think about that.
[00:27:00] Bridget Winston: Well, I think the... look, I'm still a... look, I was a D1 college athlete. I was a soccer player, so I responded well to goals and incentives and things like that. So it didn't...
[00:27:00] Warren Zenna: Driven. You like to win.
[00:27:00] Bridget Winston: Yes, exactly. So I love to win, but winning for me was helping that company, ShoreTel at the time, grow from being a premises based organization into a cloud-based organization, winning in the market, making the company succeed. And so to me, what I realized was, "Oh my gosh, the rules I was playing by before are not going to make us successful in the world of tomorrow." So I've got to, I've...
[00:27:00] Warren Zenna: The market.
[00:27:00] Bridget Winston: Change. Yes, exactly.
[00:27:00] Warren Zenna: You too sort of responded again to the marketplace and you adapted.
[00:27:00] Bridget Winston: Didn't even think [00:28:00] about all of that. Yes, that's good. I do think one of the things I love is like a "what got us here won't get us there." I love companies with that inflection point. That is my number one thing I test for at any organization is what pivot are we trying to make? What next horizon are we trying to get to? But to your question though, Warren, the incentives. We didn't just incentivize me differently. I incentivized my entire team of 150 people. So no longer was the MDR, the sales rep, the SE, the channel team, the onboarding, the support and client success team only incentivized on the one metric they owned. So the sales reps were no longer only incentivized on their bookings number. They also had 25% of their comp based on billings or a total revenue number. Same thing for my marketing team, same thing for my onboarding team. So it was time to live plus their bookings number we share, or plus their billings number. The overall revenue number we shared. 25% of [00:29:00] our compensation was all shared. That could basically be correlated to LTV, GRR number, retention rate, number of customers who were staying with us. So it made conversations really easy when I could say, "Hey guys, look, we did all of this work to sign a legal company or a law firm for a unified communication solution. We did all this work. Marketing generated the lead. The MDR qualified it, the sales rep went in and sold it. It took, you know, three months, 80 million red lines as you could imagine. Then it took two months to actually get them live. Then the first time they have a support ticket, they churn, right? Because something in the contract allowed them to get out. What a nightmare, right?" For us to look at that, that hit everyone's compensation. That hit everyone's compensation when they churned. So it was very easy for me to say to the organization in this one team mentality, "Look, that hurt all of us. So you know what? We are no longer selling to [00:30:00] law firms," as an example was a decision we started making, that was no longer our ICP. So it's what allowed me to start with ICP and end at the end in mind and to then get the entire organization doing things right. I read a book, General Stanley McChrystal wrote this book and he has this concept of talking about doing your thing right versus doing the right thing. And that was the concept that I brought to the team. It's not just about you doing your thing right. Sales, you sold it great, you make your commission. Onboarding, you onboarded them. But if the ultimate thing, which is doing the right thing, is keeping this customer as a long term invested customer who's using this product, then we all haven't done our thing. Then we haven't done the right thing. And so it made it easy. Incentives are an easy way, an easy carrot to reinforce that. But there's ways to kind of do that, even just as you're inspiring a team, even as you are showcasing what visible [00:31:00] you're giving visibility to across the organization. But I will say incentivizing the entire company in that way really made a difference. And so these were people who were also not traditionally on comp plans, right? But these were people who, whether it was the company bonus or our comp plan or more traditional sales comp plan, that it really did make a difference. And it really unified everyone on the most important metric is total revenue that we kind of keep going with every year.
[00:31:00] Warren Zenna: Thanks again for listening to the CRO Spotlight Podcast. We're excited about all the great guests we have, and more importantly, we're excited mostly about you for being avid listeners and supporting the work that we do here. Feel free, please, to share, like the podcast with any of your colleagues. We just think there's a great wealth of information here and we wanna get the word out to as many people as possible and your support of the show is really appreciated. I wanted to share information about a program that we offer called the [00:32:00] CRO Masters Council. The CRO Masters Council is a bi-monthly group of six seasoned chief revenue officers who are looking for a chief revenue officer board of directors, so to speak, so that they could share what's going on with them. Collaborate with ideas, get some feedback on what's going on in their current role. And these are great conversations. I facilitate them. The CRO Masters councils, again, they're twice a month and they last for at least six months to a year. So if you're interested in having your own CRO suite, your own board of directors of Chief Revenue Officers, it's a private, confidential conversation that we have. It's infinitely useful. Imagine having a room full of other Chief Revenue officers you can talk to and say, "Hey, I'm working on this, or Have you guys figured that out? Or I'm having this issue right now with my business or my results." These are just invaluable conversations with Chief Revenue officers. Chief Revenue Officers have a very, very unique role. It's a very lonely job, and only other CROs understand what you're going through. So that's why we created this program. [00:33:00] So if you're interested in being a member of the next CRO Master's Council, which we have a number of them being put together right now, just go to my LinkedIn and DM me "masters" or "Master's council" and I'll follow up with you and set up a call or send you some more information about it. Looking forward to seeing you there and thank you.
[00:33:00] Warren Zenna: Yeah, I hear this one. It's great. And it sounds like you, in this particular situation, had the authority to sort of make those decisions and change the whole focus of your business. Right. And this is one of the issues I wanna talk about, which is the constraints on chief revenue officers who may frequently, and they usually, they come to us at the point at which this stuff happens, which is, you know, they know what to do, but they're not given the tools, the resources, the authority to do it. And this is not their fault. It's like they probably have the competencies and the instincts to do things that they need to, but the organization, the system that they've inherited is not designed for them to do it. So I don't know, but you tell me. I mean, have all the situations you've been in been environments where you've been given that latitude and that authority, [00:34:00] or did you have to earn it? And what are some situations where that sort of evolved for you as you obviously developed a track record and you were able to come in and be a bit more forceful on the content way you wanted to be operated? When you got into your organization, you came in with some gravitas and said, "Look, you wanna hire me, this is how I need things to be." But when you're first starting out, you sort of gotta take the pie they give you. Where do you see the change in there? Like how in your career did that play out in terms of you battling the environment that you're in and the system that you're building?
[00:34:00] Bridget Winston: Yeah, I think I'll give a couple of examples here, and maybe a couple of pitfalls that I have seen too. So maybe one of the first ones, and maybe I'll give a couple. The first one is, it is always flawed whenever you are interviewing. You will always hear this and you need to inspect it. You will always hear that talent sucks. You will always hear that. They will always say that. And then another flaw that [00:35:00] comes up a lot is that typically your investors will tell you that if you need to grow sales, you need to add headcount. Another flaw. So both of these, and I can say this now as a three time CRO coming in, and these are traps that I think we fall into. And so I think the way that you make sure that you get out of this trap is that you are very aligned with your CEO about the most important metrics for you to measure. So that is how I have overcome that within interviews or within an operating role, is to make sure that me and the CEO as well as, and hopefully the CEO is aligned with the board in terms of the most important metric to measure against. I always say to them, "One of the metrics you should grade me against is not just total revenue, but how efficient I am at getting that revenue." And people shy away from that. They shy away from unit economics. They shy away from those traditional sales leaders do. And so it's one that I always make sure I bring [00:36:00] back is, "Measure me against LTV to CAC," especially if I'm also managing marketing, which, depending on the CRO role, sometimes I do, sometimes I don't. Sometimes I partner with an amazing CMO, like I am at PatientNow right now. But we are always aligned on LTV to CAC on that. So first look inward on the talent side. So what I will say is everyone always blames the talent for being the problem. And I always find that it is the system usually. There's definitely some talent problems. I'm not, I won't lie and say that there's not certain upleveling that needs...
[00:36:00] Warren Zenna: Yeah. I would say good talent is hard to find and it's hard to keep. There's no question about...
[00:36:00] Bridget Winston: It is, which is what makes the system so much more important. And so for example, I was at Shutterstock, a publicly traded company. And when I got there, I was definitely told, "Hey, the talent could maybe use a... and we could take a look at that." And what became very clear [00:37:00] though was that there was no rhyme or reason to how many people we had on the team. There had never been a capacity model that had been built upon how many leads, what are the conversions, what is average productivity, what's an average rep do in a day, a time study of like, how long does all of that take. So even from the sales and capacity modeling, like there was work to be done. So if you were just looking at are they achieving quota or not, it was kind of a false flag because the ones who were achieving it were doing it through potentially heroics or because maybe even not because of something that was so great about what they were doing. But there was definitely a system that needed to be approached first in terms of capacity planning, productivity modeling. The second thing I would say is the incentives were also off. We were, you know, triple comping the same thing. We weren't using the incentive plan to the best of our ability, [00:38:00] overpaying for certain things, underpaying for the things that drove consistent, predictable revenue, forecasting accuracy. And so there were a couple of things just with the system alone. And then there's obviously just even the upleveling and commitment to coaching. There was commitment to role playing and practicing what we wanted to do, implementing a sales methodology, which we did there, the challenger sales methodology too. So there were things that we could be doing, and I always say that first look inward on the structure and the system that you have created. And you always talk about this Warren of, you know, revenue is actually a system. And then absolutely look at the people and see, "Alright, is this person getting on board? We've now aligned their territory. We've now given them a very clear direction. We've shown them what good looks like. We've practiced with them. We've given them what the incentives should be doing to motivate them." And then if you still do have a [00:39:00] people problem, then you know that you've actually done what you needed to do to actually weed out the thing that could be really attributed to the organization. This second element I would say is the, "You should just hire. We need to acquire new customers. And so let's just hire people." That is the most expensive way to not hit your goals that I could imagine. And so I am always, and I always tell our investors, our sponsors, "Why don't we maximize productivity in our rep? Look at the time studies. Look at how long..." I would rather a rep be overloaded and hitting 120% of quota because they have more opportunities they know what to do with, so that we've reached a breaking point, and that's what tells us when we actually need to hire. And then you're planning for the ramp. And of course you're not ridiculous with this. You're obviously very judicious with it. But I would rather that, and I would rather give the money to marketing or client success so that we can be building those other revenue levers in a [00:40:00] more predictable way than just expecting the most expensive person on our team to cold call, you know, to create a pipeline for themselves. And so that's sometimes a controversial hot take, but it's really a spreadsheet exercise filled with a little bit of art that I see so many people fall into in terms of that.
[00:40:00] Warren Zenna: Yeah. We had a number of clients who we knew. They were like looking at an IPO, who intentionally just hired a whole bunch of people just because it made them look like they were doing better. It's a very weird signal. It sends in the marketplace that when you have a lot of employees, it says something about, and it's a very strange thing, but you know that some of this incentives, like I was saying [00:41:00] before, are driven by a lot of weird economic factors that have nothing to do with the customer. And you're working in this company, it's bewildering to me like with wireless, but you know what, there are other people who are looking at the market a lot differently than you are, right? If you're in the seat. And you do have, like, you obviously do a very conscientious understanding and empathy for the customer. Someone who paid money and you wanna make sure that person gets the value outta what they paid for. And you feel somewhat part of the machine, you're responsible for that. All of a sudden you see the company making these really strange decisions coming from the board that for them, you could talk to them and they'd probably give you good reason as to why they're doing it. But it also seems sort of so off kilter with what you're really trying to accomplish. And I again, I would say that the companies I see that have the fortitude and the individual strength to kind of stick to their principles and always make it customer first tend to be the ones that last the longest. It's a very difficult, difficult thing to do because there's so much pressure for you not to, you know. So I think, look, if you're in a chief revenue officer role, you're at the center [00:42:00] of those decisions. I mean, you're the ultimate customer advocate. I mean, if you're doing the job in the way you're describing, which I'm sure you're very conscientious of, you really have a strong customer success foundation, and you're looking at that stuff and you protect that part of the business. You know, it's almost like your baby in a way. You know? And when you see it being screwed around with these weird decisions, it sort of makes you feel a little cynical about things. But then again, it is a business and that's the way it goes, you know?
[00:42:00] Bridget Winston: Yeah. That's when you know when there's gymnastics happening. And I will say I, that whole, "Hire before there's demand, hire because it makes you look bigger." All of those things, look, we get it, like there's a bit of a game that you're playing too, but in this world of AI, I can't imagine that...
[00:42:00] Warren Zenna: No, we've reached a point now where there is a good case to be made, and I don't know if it's fully there, but it's pretty close that there's certainly a lot of things that we can get done without having to hire [00:43:00] people. I don't know about salespeople yet. I don't know yet. But we're gonna talk about AI in a sec, but I think it's an interesting topic, and I wanna ask you this though. You mentioned before something you've just offhandedly mentioned about having a good partner as a CMO. So I wanna talk a bit about marketing because you're a CRO, right? And I have a pretty strong opinion about this. Even someone who owns a marketing agency. You know, I think it's a very important thing, and that is that, you know, on one hand, because I'm the strong advocate for the CRO and the role and how it's most, I would say in the, let's say, vacuum, optimal state. Okay. If I were to have full control, I was the board members and I had full operational control over the hierarchy, I would say at a certain stage, when you're gonna bring on the CRO, CRO should come in and oversee all revenue functions and everyone should report into that CRO and CRO should have a direct line to the CEO and the board. And that's the cleanest, no signal free, no interference sort of way to run it. And if you have the right person operating that role, you're gonna have a much leaner, better [00:44:00] organization for reasons I think you and I probably agree on, but it doesn't always work that way. You know, sometimes you end up in a situation with like, "Eh, you know, Marilyn's been with us for a really long time and she's a really great marketing person and we just wanna keep her in that position because she'll really be upset to report to..."
[00:44:00] Bridget Winston: Good old Marilyn. Yeah.
[00:44:00] Warren Zenna: Just get along with each other. Okay. Figure it out. You guys can collaborate. She's very collaborative and you know, sometimes it works out, right? Like you just said, you have a good... but I would say though it's still not optimal. I would like to know your thoughts on this. You know, what's the general philosophy you have? Like here, look at it this way. Be more, let's say, consultative. So people listening to this conversation are looking at chief revenue officer roles. They're gonna be faced with this situation. What's the way that you'd approach the way which a CRO should approach marketing as a part of their system?
[00:44:00] Bridget Winston: Yeah. So I actually, as you're, as you were talking about this, I was thinking about this. So in a world where, okay, so I've worked at companies where it's both consumer and B2B, right. Chief...
[00:44:00] Warren Zenna: Different, [00:45:00] those are different animals. I would say that's a big distinction. I agree with that part. Yes. Very...
[00:45:00] Bridget Winston: So that is where I would...
[00:45:00] Warren Zenna: I think from a B2B state almost only because, and frankly, and I'm sorry to interrupt. I wanna make sure, this is really interesting you just said this because I don't work with any B2C companies. Only CROs I work with are at B2B companies, and I agree. I personally wonder if I would be so bold...
[00:45:00] Bridget Winston: Mm-hmm.
[00:45:00] Warren Zenna: Because I've worked with a lot of B2C organizations in my...
[00:45:00] Bridget Winston: Oh, yes.
[00:45:00] Warren Zenna: It's a marketing driven enterprise. That thing. I mean, if you're selling to single customers, marketing should be the most important thing that you have. And it should be the most competent because it's all marketing. You know, if P&G taught us anything, you can build a trillion dollar business just by marketing and packaging alone and well, distribution and product availability. But those are infrastructure. But at the end of the day, the reason why people buy the product in that model is because they recognize it from all the marketing they [00:46:00] see. They have a recognition and trust in the brand and the label and the packaging, and they go to the stores first and they pick them up. Right. So this is like the classic thing. But in a B2B space, this is where it gets interesting. So I'm curious to know from a B2B perspective, what's your thought on this?
[00:46:00] Bridget Winston: Well, here's what I'm gonna say though. I believe my biggest, maybe this is my second biggest hot take. I think that the common wisdom is usually that in consumer markets you care so much about the brand, the emotional play, very much tied to the consumer. And in B2B we think much more about that rational approach. Like how does my product help a company make money, save money. My hot take is that I believe the B2B and B2C worlds in marketing very much are converging because of LLMs. Because the thing that gets you noticed and gets you surfaced in LLMs are very much consumer methods, if you will. It's earned by the media. It's YouTube, it's Wikipedia, it's some founder stories. All of those [00:47:00] emotional resonance of your brand are actually now the thing that are surfacing you. And so my take is I typically like to partner with a marketer, a CMO, who is much more of a brand CMO. I'm not good at that. That's not like me, that's not what I rock...
[00:47:00] Warren Zenna: I...
[00:47:00] Bridget Winston: That their VP of marketing, that VP of marketing, who is more of the demand gen lifecycle, could either sit with me or sit with that CMO. And it depends on how, let's say numbers based, focused that CMO is. And if we are at least aligned on that, let's call it CAC, LTV, bookings and upsell opportunities. So I have seen it, so depending, so because obviously Chief, both consumer and B2B. At PatientNow, very much a vertical SaaS company where it has, like, it's still because SMB can be sort of consumery...
[00:47:00] Warren Zenna: It is consumery.
[00:47:00] Bridget Winston: And there's word of mouth. [00:48:00] Yeah.
[00:48:00] Warren Zenna: Yeah. Small... almost like a consumer. They do. It's a very consumer-like niche. I have a lot of friends who own health spas and I'm very familiar with this business and we also work with some, and it has a strong, very consumer feel to it. Even though it's a B2B motion, it has more of like a, if I would say heavy touch, emotional type of a way in which it goes out to the market.
[00:48:00] Bridget Winston: Instagram. Instagram is the, you know, Instagram and TikTok. Now, I will say if I had owned our marketing approach here. The best I can bring to that is LinkedIn, right? LinkedIn knowledge, okay. Should we do paid LinkedIn? Should we do these things? But because the way that we will acquire customers in this, in even this SMB focused area is much more word of mouth, much more consultant led, much more vibes. [00:49:00] Like some of that. I actually need that partner who is so strong in...
[00:49:00] Warren Zenna: Yeah. Yeah.
[00:49:00] Bridget Winston: ...to be actually the tip of the spear for me on that. But if I were selling at my enterprise B2B play, give it to me all day long because it's much more numbers focused, probably even client success focused, expansion motion, all of those. And so, to me it depends on which organization I'm the CRO of.
[00:49:00] Warren Zenna: I totally makes sense and I could see now, like, now your answer makes a lot of sense to me because at PatientNow, and their focus and their ICP, you'd want a brand heavy lead in that seat because of the value that that's gonna bring to the offering that you're ultimately enabling, whereas you're selling cybersecurity, not so much.
[00:49:00] Bridget Winston: Right.
[00:49:00] Warren Zenna: But, but I...
[00:49:00] Bridget Winston: Although I will say. There is a community. So I will tell you about one of my best friends, he's the CEO of a [00:50:00] cybersecurity company. And one of the things I shared with him was, "Hey, you've got a community play here that you don't even know." Something he would've never traditionally thought of as a way of acquiring customers. He was gonna go the traditional LinkedIn paid media route, the pay-per-click, all of the traditional B2B tactics. And I said, "Actually, cybersecurity, you are selling to CISOs who are scared every minute of every day that they are going to end up in the headlines and basically lose their job. You have a population of folks who are potentially lonely and craving community in some way." So what he changed, and again, this is not a traditional B2B play, but to add community into his strategy has actually now become his second biggest lead gen engine was this community play where word of mouth between each of these customers, and again, customer testimonials have always been a thing, but now you [00:51:00] can actually activate a community who brings 'em all together in Napa, they do an event, all of the great stuff that we both know very well, that can actually generate business for you. And that's a more traditional B2B play that no one does, no one thinks of. And because potentially if you've just done the traditional B2B playbook, that's the way, and those are the people who also talk about it on Instagram, talk about being there. You know, kind of even maybe even give a testimonial in a press piece. All those things that then get surfaced in some ways in an LLM. So it's why I think this consumer and B2B approach is actually starting to converge a little bit. And so it's great when people have some ideas across the two and know when to frankly deploy them.
[00:51:00] Warren Zenna: Yeah, it's a great point. I see in my world, they're gonna ask this question because it's a very provocative [00:52:00] topic. There's a, as you know, right? It's huge, it is a great one, and because I sit on both sides of it, I'm in both worlds. I'm more of a salesperson than I am a marketing person, only because I made more of my living as a salesperson. And, but they're both communication mediums. Selling and marketing are both communication mediums, right? It's a different form of persuasion. You're persuading people in a different way. And that's why you tend to find people who are really good salespeople and are also really, really good at writing sales copy. Because they sort of understand how to articulate things in a way that a marketer wouldn't know what it's like to be in a sales context. And so they're not looking at it that way. And I think that's where that collaboration comes in. Like a really good marketer will say, "How do you talk to your customers about this? What do they say about it?" As opposed to, "This is what you should say to your customers." Like, "No, no, you're not listening to my customers. I am all day long." And I think that's the breakdown too. And the other part too...
[00:52:00] Bridget Winston: Well, and that's why I love the marketers who [00:53:00] come with me. And we are doing that consumer approach where they have a finger on the pulse of what our customers are knowing. And my first thing that I did at PatientNow was learn from my CMO, because he has his finger on the pulse of that. He knows the word of mouth, he knows the testimonials, he's listening to the customers constantly. And so I felt very lucky that I had someone who was as customer centric. And I think that's the key is when no matter what, as long as the executive team is super cut, CFO to CTO, you name it, should all care.
[00:53:00] Warren Zenna: Yeah. It comes down to incentives. Again, it's the word I use a lot because it really does drive a lot of behavior. So if I'm a CRO, I am thinking about this context almost all the time. I'm thinking, "Okay, how does the decision that we're about to make impact our customer from two perspectives: is it gonna negatively impact the value we give them? Or is it gonna result in them having to make [00:54:00] choices based on our needs as opposed to theirs?" It's, you see this all the time. You go to a website and the way the website's built is inconvenient for you, but they tell you, "Well, we have to because we have these issues." Like, "I know, but that's not my problem. It's your problem. You're passing your problem onto the customer." This is a very common thing. And I think like, if you can protect the customer, and I mean not just protect it, but also advocate for it, listen to it, understand it, empathize with it, and everyone in the entire food chain and the go-to-market team is thinking that way, you're likely all gonna be, it's easier for you to come to a similar conclusion about what the right thing to do is. Whereas from thinking about things as a marketer, from thinking about this as a salesperson, it's not the right context. Because those people have different incentives within that context. Marketing people are generally being asked to bring as many SQLs and MQLs to the table as possible so they can justify their salary. And salespeople look at just building pipelines so they can close more deals. [00:55:00] When you put those two things in the same room together without a customer-centric thinking in there, they're gonna be fighting with each other all the time. It's not gonna make the same thing. And I think this is again, why it goes back to my earlier point, which is if you have a chief revenue officer who oversees all this stuff and who's framing it that way, you're gonna have a system that's focused on the right things all the time. Because that model is always gonna ladder up to that conversation all the time. And I think that that's the thing, no matter what kind of business you're in, that the old model of a suite of C-executives who all are kind of aspirationally being promoted to have seats at the table is a very self-indulgent way to run a business. It's really more about my employees than about my customers. And the pushback I hear a lot when I talk about this, when I speak to CMO groups is they get really upset because they're like, "I want a seat at the table," and say, "Well, what table, what's this table you're talking about?" You know, and I know what they mean. I'm being somewhat cute. [00:56:00] But what I mean is, what's really more important is, here's a thing I'll sort of go on this rant for a sec. The one thing that I find happening in these jobs is both the CRO and the CMO suffer from the same degrading issue, which is that their jobs are always sort of like, they're always on their last month in a way until they kind of do more, you know? And not all of 'em, but you know, it is sort of like a degrading thing. Like after your first year, you're sort of on call or notice, you know? And it doesn't have to be that way. And I think that if I'm a marketer, I think the marketing organizations have always had a very similar and legitimate complaint, which is that their budgets are always the first to get taken away, which is true. I get it. It shouldn't be. But as is the case, the irony is the model that we're proposing here, the one that I think you likely philosophically agree with, is this makes the marketer far more secure because now you're baked into the whole marketing and sales and customer... it's, you're actually like a revenue [00:57:00] center as opposed to a cost center. And I think that giving up the illusion of authority and control for more of an integrated opportunity gives you a better opportunity to participate in the whole ecosystem. And I think that's the shift I'm hoping happens. And I think CROs need to sort of advocate for that because I think that's the way ultimately it's gonna probably manifest over time. So, I wanna talk about AI. So how are you using it and what's the way that you view it, and how would you rate yourself in terms of your own AI, individual AI capabilities, like when you play around with these things and how do you operationalize them across the people in your organization today?
[00:57:00] Bridget Winston: Yeah. So I would say, I always like to, and maybe, yeah, I'd, okay, so one to 10, I'd give myself a seven.
[00:57:00] Warren Zenna: Okay.
[00:57:00] Bridget Winston: I'm, I've done a, I create my little, [00:58:00] my own apps using Lovable. I'm playing around with Claude, Cowork. I have let's say deployed at least two that are in production already. Very integrated tools, whether it's Good Work or Pro Short, which is our AI coaching tool that we use to...
[00:58:00] Warren Zenna: So in other words, you took third party platforms and you've pushed 'em through your organization, right?
[00:58:00] Bridget Winston: Pushed them through my organization. So Good Work, as I mentioned before, to help us with ICP segmentation. We're using it now to actually do a round two with them and looking at product usage data and how that correlates to LTV. Therefore, using all of that now in our marketing and our sales pitch and our onboarding to understand which parts of our product... We have a very robust product, a very broad product. And so I wanna see which parts of the product adoption actually leads to highest LTV and upsell potential. So that's kind of our round two with Good Work. So Pro [00:59:00] Short allows us to do AI coaching, so in listening to calls, basically highlight what good looks like in a sales call and measure our reps against that. We can compare them against any rubric that we have. You could compare it to MEDDPICC, you could compare it to any kind of sales...
[00:59:00] Warren Zenna: You've created a standard and you utilize it. I understand. Mm-hmm.
[00:59:00] Bridget Winston: And what is great about it too is that automatically for a leader gives them kind of a stack rank of their team, understanding where to go in and coach. And so we've been doing many more coaching sessions because we now know what was good, what needs to be improved. It also for the reps, allows them to have a follow-up email that's automatically created based upon some of the notes within the call as well as the follow ups. And even better yet, any of these one call closes that we have, it automatically generates our new customer memo that we send to onboarding, so to our onboarding team. So making those handoffs more seamless. I [01:00:00] always joke about how this is a relay race between let's say marketing, sales, onboarding, customer success, and sometimes it feels like you just take that baton and you're throwing it, you know, like, "Not my problem anymore." This is meant to be a way that these really do feel like that customer handoff feels very smooth. And is not reliant upon adherence by the rep, but rather something that is automatically just naturally occurring and naturally being documented based upon the natural steps that they're taking. I've built ROI calculators using Lovable as I mentioned. And we are also investigating using Claude, Cowork to do some of the work based upon the automatic triggers that we learn from product adoption. Like how might we automate emails, automate intervention tactics with our client success team. We're using tools in onboarding the same thing, as well as support. So we're investigating a couple of different [01:01:00] tools, whether it's Intercom Fin, HubSpot, Agentforce, or another cool one called Pylon for an AI chat so that we can enhance our support experience and extend our hours. So a lot of cool things that we are either underway with or investigating. I kind of call it I'm, and maybe this is not a popular statement to make, but PatientNow is gonna keep growing. We are going to go to the moon, like I believe in this business, and I believe in what we are creating for our company, for our customers. I would love for our headcount to not have to grow at the same rate as our organization is. And so what I would love to do is supplement using these tools to both enhance the experience, as I mentioned on the support side. So enhance our hours, enhance the experience, enhance the customer's ability to get questions answered quickly, and then leverage humans for the things that are most impactful for them. These are small to medium business owners. They are not experts in [01:02:00] vertical SaaS solutions. And so they are naturally going to have questions that they want a US-based support team member to be helping them with. I want to dedicate humans to that. But if you have a quick, "Can you reset my password?" Let's leverage AI for something like that, that's very quick and let's call it low technical skill. So I would give myself a seven and only because I think, I always feel like I'm not doing enough. And so I always wanna do more.
[01:02:00] Warren Zenna: Uh-huh. So you guys are all in basically. I mean, it's great. Do you think that they'll, I don't think so. But do you think there will be AI driven salespeople, do you think they're gonna have people replace first conversations with humans? You know, where's this gonna go in your view? Is it gonna always be just more like an operational kind of administrative function, or are we gonna find it sort of encroaching upon some human interactions? And to what degree [01:03:00] do you think...
[01:03:00] Bridget Winston: I think it will encroach upon human interactions. So my hot take is, yes, I think it will, I think it will be the stuff that had a human in it that never needed a human. I mean, there are examples I have from my past where I was like, "That's a very low consideration purchase and doesn't have a lot of questions." Anything that you could probably, if you could think of a way to either PLG it or e-commerce it, I think that could actually be enhanced by having an AI agent who's helping you. I think it'll be a long time before we get to an enterprise level sale that is using or basically frankly using an agent instead of a seller. But as a copilot, someone who can pull up the demo better than a human could or go to the pricing page and deal with some objections in the chat, I absolutely think that it could be a ride along. [01:04:00] And always behind the scenes, I think behind the scenes making us better. As I mentioned using Pro Short, any of those things that allow for seamless handoffs, I think that's a given.
[01:04:00] Warren Zenna: Yeah. I guess, yeah, I agree. I mean, I certainly, I'm already using these tools to interact with... I weirdly, I'm text messaging robots a lot all day right now, you know, and asking them questions and I'm saying "please" and "thank you" to them like any other moron is, you know.
[01:04:00] Bridget Winston: Well, it'll be good when they come for us, when they come for us, they'll remember your sweetness.
[01:04:00] Warren Zenna: The polite ones. Yeah, sure.
[01:04:00] Bridget Winston: Yeah, yeah, exactly.
[01:04:00] Warren Zenna: Mm-hmm. Yeah. "You were always nice to me, you know, we're gonna let you..."
[01:04:00] Bridget Winston: Yeah.
[01:04:00] Warren Zenna: But, but you know, I think the other thing too is I'm talking about more, and I know you know what I mean, but more independently, like where people literally know no other humans involved in the conversation. So... because I...
[01:04:00] Bridget Winston: Right. Like agent, agent, buyer agent, seller agent.
[01:04:00] Warren Zenna: That'll happen. I think that makes [01:05:00] sense because you're saying, like, for example, right now, there's no reason, and I think it already is kind of happening in a way. I'm just probably not using it, is look at all my Amazon purchases and Amazon could easily, I don't know why they haven't done this yet, just roll up to me like an interface one day, it says, "Look, look at your buying habits and you buy this stuff on average these many times. We're just going to buy it for you from now on. Like, just, we'll buy it from you. Don't even have to do anything. Just give us a budget." Right. I think there...
[01:05:00] Bridget Winston: Cowork can do it. You can create an agent for it. It'll do it for you.
[01:05:00] Warren Zenna: So I think that's fine. But like he said, like shampoo and toothpaste and dog food and stuff like that. But what I mean, I'm talking about like you are not around and your phone or your company phone or your email gets an email and independently an agent answers and takes that call or that question pretty far into the funnel before you're brought into it. You know, I don't doubt that it's completely doable and in fact, I know there are companies that are doing it right now. Maybe more experimentally, but [01:06:00] I think it's gonna, the comfort level... I see the same thing. Almost like, I remember, remember that, you probably remember this when people were like, "You mean you buy things online, you mean you put your credit card into the computer and you let the com... it's gonna get stolen." Right now it's like, right, you press a button every two seconds in your life, right? But there...
[01:06:00] Bridget Winston: It was great. I was in cybersecurity at that time. Yeah. So it was perfect. I could say, "Don't worry, I can help."
[01:06:00] Warren Zenna: Right, right. So I think that that's similar, right? I think it's gonna be like...
[01:06:00] Bridget Winston: Yeah.
[01:06:00] Warren Zenna: ...let that happen, but as you know, it'll happen sort of under the boiled frog, you know, we'll get to the point where all of a sudden...
[01:06:00] Bridget Winston: I, yeah.
[01:06:00] Warren Zenna: ...I'm having some person talk to some robot, talk to people all the time, and it's become normal. And it happens with a high degree of success enough that, "You know what, this is actually better." I mean, we already have people letting their cars drive for themselves. That's pretty amazing. So, I, you know, I'm sort of, I think that we're gonna push this as far as possible, and I think it's gonna be fascinating. We're living in this crazy time [01:07:00] and I'm kind of excited about it, but I wanted to ask you a little bit more about PatientNow. So you can just talk a bit about the business that you're excited about, you know, who are your customers, what do you do for them, and tell me a little bit more about what's up for that organization and what's going on for you there.
[01:07:00] Bridget Winston: Yeah, absolutely. So PatientNow obviously does the patient management software for cash-based aesthetics and plastic surgery centers. Everything from anything that can help make you money or save you money, that's how I always like to talk about it. We can do everything from the charting that all of the providers need, inventory management, scheduling. Even all the way down to employee scheduling and even your marketing and scheduling from an AI receptionist. It can do that marketing engine too, where it's automatically calling on your behalf so that if you are a small to medium business owner where you don't [01:08:00] have the time or energy or ability to necessarily always answer every single phone call, it can answer on behalf, schedule on your behalf so that you're making money even when you're not there. And also call back out and make sure that it's following up on any of the leads that maybe you weren't able to get to. Or if someone came to your chat and was communicating with you and wanted to know, "How much is your Botox," and then all of a sudden went dark, you can actually proactively reach back out to them and follow up in a cadence. So I will say I am selling what I'm talking about in some ways here and helping our small to medium business owners who potentially don't wanna invest in that, or actually wanna prioritize their front desk's time, their front desk time with the people who are in front of them so that some of that other stuff that ends up either getting missed that really could generate a lot of revenue for the practice actually can get done. And that you're having some oversight and seeing that it is getting done. Even [01:09:00] whether you are there to be able to, whether you're alive to be able to do it or not. So we're seeing that...
[01:09:00] Warren Zenna: What's the size of the market? How many of these centers are there in the country right now on average? What are we talking about?
[01:09:00] Bridget Winston: So the med spa practice is basically, as you know, it's growing. It sounds like you've got some familiarity.
[01:09:00] Warren Zenna: Yeah, I do. I have a...
[01:09:00] Bridget Winston: ...industry. Yeah. $20 billion industry growing at 15% annually. And so, and there's no shortage, and that's just the med spas, that's not even plastic surgery centers. And then as you start to think about adjacent verticals, whether it's cosmetic dentistry, dermatology, all of the other types of, types of, you know, adjacent verticals, it just...
[01:09:00] Warren Zenna: How about mental health therapy groups, practice groups? Is that, would it fall into that or is it outside of that for you?
[01:09:00] Bridget Winston: Yeah. It's a little outside of it. What you see is wellness clinics very much like GLP-1 clinics that [01:10:00] you're seeing, IV therapy, drip, facialists...
[01:10:00] Warren Zenna: Not mentally, like giving out prescription medications for depression or ADHD, like, that's not really in your world, or it is, or not?
[01:10:00] Bridget Winston: I mean we could, but I would say a good portion of those are more on the cash-based aesthetic side. And so the ones who are doing insurance, I would say are a little bit different than, and require different...
[01:10:00] Warren Zenna: Ah.
[01:10:00] Bridget Winston: ...are definitely very much designed for beauty, built for growth. Yeah. So you see the cash base versus insurance.
[01:10:00] Warren Zenna: That's an important distinction. Okay. I get it. Interesting. I ask because we happen to have a client who's in that space.
[01:10:00] Bridget Winston: I love it. I love it. Hey, Warren, you know, salesperson to salesperson. I love...
[01:10:00] Warren Zenna: Exactly. We can talk about it. So, okay. Well, look, I really appreciate... I have a really strange follow-up question for you, and that is, what is it that the people whom you will work for have to tolerate about [01:11:00] you?
[01:11:00] Bridget Winston: Oh, what a great question. I expect a lot of myself, and so I expect a lot of them. I always expect myself to be ahead of my CEO...
[01:11:00] Warren Zenna: Can't you be like, like...
[01:11:00] Bridget Winston: ...what she would say. And so I am always expecting, and this is the thing that I always say to them, "I need you ahead of me so that when I ask something, it's actually already, it was already a consideration point." So I am, I expect a lot of us, and I expect us to move faster than I did earlier in my career, and maybe it's because now I've got the pattern recognition and so I expect us to actually move faster. So I'm hoping and looking for folks who are... like for example, right now I'm hiring someone a VP on my team and within my case study I said, "How would I know that by the first week, day five, [01:12:00] that you'd made an impact?" I want, I don't want a traditional 30, 60, 90, the same thing that you've shared from org to org. And you just, you know, first I'm gonna listen, then I'm gonna audit, and then I'm... I don't want... I am looking for someone who, the case was part of that, the case that we are putting you through. You've asked a lot of questions. You've asked for data so that literally on day one, you are at least directionally informed on some of the motions that you're gonna put underway. And so I would say maybe it's that I want them ahead of me and I want them moving fast. And that's hard. That can be hard. And I think the biggest mistakes I've made in my past have been when I moved too slow on certain things, certain decisions that I knew were probably right. And so what I would say is when in doubt, it's the rugby analogy that I had a CEO once tell me. He said, "Look, an object in motion [01:13:00] can actually continue to move." So he uses the rugby analogy that he got the ball. He said that his coach told him, "Just start running. It doesn't matter, you come out of the scrum, you don't know what direction is which." And the advice that he said was, "Just start running. Because if you are running, you can course correct. And maybe you're running towards your goal, maybe you're running towards the other one, but at least you can course correct. But if you stall and you stop and you think about it and you're in analysis paralysis, then you're gonna get tackled." So I would say that that's actually, if I have to err on one side, it's how do we move quickly, at least with a directional sense of purpose and sense of intention.
[01:13:00] Warren Zenna: That's great. Got it. Good. Well, they probably all learn a hell of a lot from you in that process, so cool. It was good having...
[01:13:00] Bridget Winston: Well, I've loved...
[01:13:00] Warren Zenna: ...is great. Yeah, it was great. It was a great conversation and I really appreciate it. So thank you. And you know, we'll talk offline [01:14:00] about some other stuff. I have some thoughts which I'd like to get your thoughts on. And I'll see you, I guess we're having like a number of round tables over the next year and hopefully you'll be able to make a couple of them. You're always good to have.
[01:14:00] Bridget Winston: There.
[01:14:00] Warren Zenna: Great. And thank you so much for being here.
[01:14:00] Bridget Winston: Thank you, Warren. I've loved it. And always happy to see you and to hear from you, and to learn from you.
[01:14:00] Warren Zenna: Well, thank you. [01:15:00]