Pillar Talk: Building Sales Leadership with Rick Smolen
Join Rick Smolen and other seasoned B2B sales leaders on the quest for defining great sales leadership. Learn the pillars of successful leadership, hear stories about what works and what doesn’t, lessons learned, and come away with specific tactics you can apply to your job or career right now.
Pillar Talk: Building Sales Leadership with Rick Smolen
Finding Strength in Chaotic Scenarios with Bridget Winston
We explore how a solo Camino de Santiago pilgrimage reset attention, then translate those lessons into a pragmatic playbook for fixing stalled revenue. We walk through segmentation, ICP, LTV:CAC, methodology, enablement, culture, and the myth that “it’s all talent.”
• solo travel as a reset for presence and purpose
• inch pebbles as a tactic for motivation and change
• myth-busting the talent-first diagnosis for missed targets
• clean-slate org design with segmentation by motion and support
• ICP as an executive alignment tool across GTM, product, and finance
• first-team mindset and Team of Teams principles
• aligning compensation with retention to stop silo optimization
• culture mechanics: recognition, repetition, and making progress fun
Find Bridget on LinkedIn. “My DMs are open. Feel free.”
Music by Ben Cina & Ayler Young
Hello, everyone, and welcome to another episode of Pillar Talk. This is where we build the foundations of sales leadership success and try to create clarity in terms of what good looks like for current and aspiring sales leaders. Today on Pillar Talk, I am joined by Bridget Winston. Thank you for being here, Bridget. She brings, before I let her speak, she brings over 20 years of experience in scaling go-to-market organizations across marketing, sales, customer success, the entire customer lifecycle. She was most recently the Chief Revenue Officer at Chief. This is where she helped grow membership in that community from 1,500 to over 20,000. Previously, beyond that, she was in many roles, including Shutterstock, where she led global sales through a pivotal transformation period. Bridget also advises CEOs, boards, investors on all things go-to-market strategy, growth, and customer experience. She's someone who blends ambition with reflection because between roles, she recently walked 75 miles of the Camino de Santiago, a sort of pilgrimage that offered lessons, and this is based on what I read, on slowing down presence, and rediscovering purpose. Bridget, welcome to Pillar Talk.
SPEAKER_00:Oh, I'm so glad to be here with you, Rick. That is that's a lovely introduction. And what I will say to you is yes, it was meant to be a pilgrimage. A lot of people use it for a very religious pilgrimage. I was going to very much, you know, kind of accomplish a goal that I had. And it was it was really good though, because it ended up being much more of a reflective meditative jaunt for myself. So that was lovely.
SPEAKER_02:So I get excited when I see something interesting and different. And, you know, you just had a lot of responsibility in your last role, probably running around, handling huge amounts of initiatives, pressure, large scopes of organizational development, uh, strategy. And then you go from that to I'm gonna do something totally different, and I'm gonna go, you know, accomplish this, you know, personal goal. So I love to learn more about that. Can you share a little bit about what inspired that trip and what did you take away from it?
SPEAKER_00:Yeah, absolutely. So uh, well, it was kind of a two-week adventure for me. So the first week I actually went to Tuscany and did an immersive cooking course. Um, but it was pretty difficult. It was not actually as meditative and as relaxing as I thought because we were cooking for five hours a day with an Italian chef who was very demanding. So it was me and a bunch of 60 and 70-year-old retirees going to this uh villa in Tuscany to do a cooking course. So that was fun. But I the good news is I was fueled up, I was carved up so that I could go on the next week to uh the Commune de Santiago. And both of these I chose to do do solo. Uh I have a great, amazing husband, but I really kind of wanted to do something for myself. I have, I'm 45 years old, so I felt like this was like that moment of, you know, prove me to me a little bit, go and do something uh that was a little, a little scary, a little, can I do it? These were things I'd always wanted to do. And so it was a little bit of prove me to me, particularly the Camino, because you know, you're strapping yourself into some day pack. I had to have, you know, water for the whole day. You're walking four to six hours a day. Um, and you know, going, I chose not to do the hostile route. I did stay in hotels, so I had it a little bit more uh of the high end. I wasn't doing the full pilgrimage, but it was a four, five-day jaunt that um was four to six hours a day. Uh, I think I walked at minimum 12 miles a day to 18 miles a day. Um, and I I'm pleased to say that it rained every single day, poured raining every single day, completely different than what I was expecting October in Spain to be like. I was expecting it to be this like beautifully, you know, wonderful moment. And it was, I mean, it was it was torrential downpours the entire time. Uh, you're walking with other pilgrims who are doing this. I did the Camino coastal route of Portugal. Um, and so you are walking this route with other people, sometimes seeing a lot of people, sometimes seeing few. Uh, and you're walking through little small towns in Portugal and Spain. And there were certain towns that I went to that didn't have any people and just cats. You're walking by chapels, you have to get your Camino passport stamped. Uh, so you have to stop every now and again to get your Camino passport stamped to prove that you did the walk. You walk next to certain people. Some people really want to talk to you, some people are, you know, kind of just walking in silence. I watched one lady doing the rosary the whole way, which was really sweet to see. But like the first couple of days, I will say, I was walking and I was on a mission. I was like, get this thing done because the rain, I was wringing out my socks three times, you know, I didn't stop for coffee, I didn't stop for lunch. I was just trying to get this done. And that is probably pretty standard about the kind of person I am. I'm I was a Division I college athlete. I was always like a person who likes to achieve a goal, relentless kind of pursuit of things. And but I will say by day three, I uh day three was the day that I was like, I don't feel like doing this. I am like annoyed that I have to get up and go walk this thing. Um, and so while it was enlightening and empowering, it was also really hard, both mentally and it grew to be hard physically, but like physically was less hard. It was mentally getting yourself to like do the thing. And so I had to honestly do the thing that was opposite my normal tendency. I had to actually give myself like little goals. And I had to like, you know, tease that hey, you can stop within two hours and rest your feet and take a coffee break. Um, you can talk to the people next to you. I wouldn't kill you. You know, this is not about this like relentless pursuit of like getting this thing done. It is meant to be really meditative. And I will say it culminated in some really like interesting discussions and and talks. And frankly, my blisters were better for it to stop a bit, but it culminated in the last day when I had two miles left to go. And I am almost to Santiago, which is this beautiful church in in Spain. Uh, and they say it's where St. James is buried. Who knows if this is true? But um, but I was two miles away from being done, and I come, I'm on it in a forest, and I come upon a man playing the piano in the forest. I mean, the most random thing. And I think what was most meaningful about this is my father, uh, who's passed away 17 years ago, was a big musician, and our home was always filled with music and the piano in particular. And so he used to play the piano, he used to play the piano at mass and all of these things. And I know that he would have been very proud of me for doing this. And I came upon this man in the forest playing the piano, and I stopped for 20 minutes and just cried because it was first off, he caught me at quite the time, two miles left to go. But also, it was just this like meaningful thing of being present and remembering why you do things and remembering the people who are really important in your lives, and um just taking that moment to pause. Um, and so it was just like one of the most meaningful things. I'll remember it for the rest of my life. Um, and it, you know, I passed countless cemeteries, right? And so I was already in this somewhat reflective mood of like, gosh, all of these people who came before us and who have lived here, but like to be there and to see in the middle of a forest a man playing the piano, um, it really made me feel like my dad was there and present with me in some ways. I don't know if I believe in all of that, but like it was it was just it was so poignant and and frankly just breathtaking to me, um, otherworldly in some ways.
SPEAKER_02:Yeah, you had written about that in your post on LinkedIn, and that was certainly uh a moving and emotive uh aspect of that post. You could feel as the reader um you know a bit of what you were feeling there. So very powerful stuff. What what was you know when you're between roles and you have the opportunity to go do something different, there are many options, and there's no one right answer. What was the rationale behind these two journeys for you in immersive cooking in Italy and you know, the hiking um you know across the Camino de Santiago?
SPEAKER_00:Yeah, I mean I think what was drawing me to do both of these is something a little bit more either in nature or with my hands, right? We sell SaaS and cloud, and I always think about I've got all of these relatives who live in Ireland, and whenever I go there, I'm always explaining what my job is to them. And the a good portion of these people are teachers, they are builders, they are people who um or chefs, and whenever I tell them what I do, I mean I feel like I'm in some way selling vaporware, right? That we are just selling this thing that is, you know, fulfilling a um certainly a utility, and it it's important, and there are things that we are doing, but I feel like you lose a little bit of the one-on-one connection with others, um, and the the meaning in life and like the visibility of seeing what you create. Um, and so there was something in this around the cooking, although I think I I I may have come back a worse chef after that.
unknown:I've got to be honest.
SPEAKER_00:Like I'm even thinking of like, what is my LinkedIn post? And I really think like the lesson I learned was this did not teach me anything. It taught me just to like just enjoy it. Like someone's gonna make something good and just eat it, you know, like even if you're a terrible chef. Um, so but it was it was one of those things. And then the Camino was seriously like the feet on the ground of just meditatively walking through towns that honestly I just watched old people, you know, harvesting pumpkins and picking apples and you know uh walking amongst their cats. It was, it was just, and I I sit there and think, do these people understand what I, you know, like are they gonna understand the SaaS software solution I'm selling? You know, it's probably never entered their mind. But God, there were laughter. There was people who were, you know, you could hear kids, you could hear um, you know, you watch generations of people be all together. And so there was just something very moving about like what really makes a difference in the world, you know, and it is sometimes it's just the food and the connections that we have.
SPEAKER_02:In your post, you mentioned you you use this phrase, a superpower overused becomes a weakness.
SPEAKER_00:Yes.
SPEAKER_02:Um tell me a little bit about that. That's an interesting quote.
SPEAKER_00:Well, it was born out of one of my favorite things is strengthfinders. Have you ever read uh or have you ever done Strength Finders as a um as one of those personality tests or anything? I believe I did that once, yes. Yeah, and so um, and it's also born out of, you know, whenever anyone's like, what's your biggest weakness? You know, what you usually what I always do is I always throw in a superpower for use becomes a reason. Yeah, yeah, yeah, exactly. Well, yeah, exactly. Like, I'm just such a hard worker, it's a workaholic. Um, and so um, but I do think that generally speaking, um it is the things we are best at that sometimes we over-rely upon or over-index on that become the thing that probably is our shadow side, if you will. Um and so, and that's what I've seen. Like my relentless pursuit, my driven, my ambitious, my, you know, probably, you know, sometimes command and control is the thing that prohibits me from being the leader I should be, and to get even better at being a leader. And so sometimes us doing the opposite, or at least being open to doing the opposite. Now, there's the other side of me that's also like embrace your strengths because like one ounce of energy tied towards something you're already naturally good at is probably gonna deliver more for you. But wouldn't we all be better, more reflective people if at some point we also said, and what's my opposite? Or how do I supplement myself with either people on my team who think differently than I do, or um, or inviting debate, and you know, like argue this from the other side. I do that sometimes with my team when we're all in agreement, you know?
SPEAKER_02:Yeah, yeah. Well, I I certainly think um this idea of doing something completely different than your norm, when your norm is a lot of Zoom calls and zeros and ones, which is the world we live in, and we're very lucky to be here, you know, trudging through the mud in sort of like spiritual, truly powerful, you know, historic areas, um, you know, definitely scratches that itch, doesn't it?
SPEAKER_00:Yeah, absolutely. I mean, and there was just funny things. I mean, the things that you just see on the way. I mean, the there was a chapel I passed that had like Mary Magdalene laid out like she was a French, you know, you know, French painting. It was so funny. I mean, there were just things that I would just snicker to myself and just laugh. And I didn't use headphones the entire time, which I was like, all right, you are gonna be present, girl. You are going to get through this, you're gonna talk to people, you're gonna experience this, you're gonna hear the roosters crowing. And they they woke up late. They woke up late at least 9 a.m. I was like, there's no more Spanish rooster thing than waking up at 9 a.m., you know?
SPEAKER_02:Well, Bridget, welcome back, and I know you're gonna be getting back into engaging all types of companies. We're in a time of you know, uncertainty within the business landscape, especially in SaaS and tech. Um, you're gonna walk into situations whether you're in advisory capacity or full-time capacity or anything in between, and you're gonna see situations where organizations are struggling with growth. You're gonna see organizations struggling with the uncertainty of where to go. And one of the things you're gonna hear a lot about is we have the wrong talent in the organization. So when you approach a situation where an organization is struggling or not performing to goals, true or false, it's a talent issue. Just replace the people and you're good.
SPEAKER_00:Oh, I can't tell you how many times I've heard that. So when interviewing for Chief Revenue Officer Jobs coming in, uh, and I always hear, especially if they're struggling with growth goals or uh they've done a lot of acquisitions and the culture and the team morale isn't there, um, you always hear when you ask, you know, any of the folks that you're interviewing with, well, what's what's the what's the main challenge? And the number one thing you hear is talent. And what I would say is I'm going to dispel that myth right now, Rick. Not fully, but at least start with first look inward, first look inward organization, uh, and investigate have you actually set the team up for success. It's not that it's never the talent. Um, so there's always talent improvements. And uh in certain organizations that I've been in, there was definitely a time for us to address the talent. But um in some of the organizations that I've seen, the first thing that I saw was that there was no plan for the plan. Uh, and there were there were no operating rhythms that were actually ensuring that the team was going to be successful. So I always look at organizations and say, first look inward. How are you ensuring that this talent that you have is successful?
SPEAKER_02:So let's talk about that. What does it mean to look inward? Yeah.
SPEAKER_00:Well, um, I'll even use an example. Um, personal level looking inward, but that's the one. Yeah, yeah, yeah. Yeah, first look inward. And then you're gonna go on a Camino de Santiago. I hate to say it, Rick. Then you'll go and maybe you'll go to this uh go to this villa in Tuscany. Uh so yeah, so when you first look inward, uh, the biggest thing I always like to see is is there an operating rhythm? Is there a plan for the plan? Um, so for example, um, I went into an organization, Shutterstock, as an example, and what we found was that no one was hitting their goals. Um the employee NPS score was a two out of 10. Uh, you know, the attrition rate was 35% uh when I was joining. And so obviously something was going on. And despite all of these acquisitions that Shutterstock had made, um, no one was selling any of the new products uh that they had. And so it was really interesting. So therefore they weren't hitting their goals and growth had really stalled uh and slowed. And so what became really interesting to me was, and of course, as I was interviewing, it was the talent's terrible. It's the talent, it's the talent. And it wasn't that the talent was terrible. I mean, a good portion of them had been there for eight years. They may needed to be retrained and retooled a little bit, of course. Um, but the first thing that I saw was there was no plan for the plan. There was no rhyme or reason to why there were the number of sales reps that they had, sales and customer success reps that they had. Anyone that they had within the organization did not have any kind of segmentation. So, like you could have one person who was managing an SMB account, but they also in their list had a$1.1 million organization. Um, they were in completely different industries, completely different verticals. Uh, the person who and so, and there was just a mishmash of accounts. So, one of the first things that I looked at was all right, if we were no names and boxes, no people, uh, you know, at all, what do we look at? Like, what should this organization look like? How would we organize this organization if we were thinking about vertical expertise, if we were thinking about segmentation and the way that an SMB account needs to be serviced versus a large enterprise customer? Um, you know, certain what was the sales cycle and velocity of a sale for an SMB customer versus someone who needed a lot more high attention and probably concierge-like support. And so we began to design the organizational structure to support the multifaceted way we were going about doing business. Then we started looking at, okay, we'd have these different eight different product types. Um, how and which accounts are our biggest high potential accounts versus also high performing. So, you know how there's the nine box that you do for talent assessment, you know, is this high potential and high performing? You can do the same thing with accounts. Um, and that's in fact how we how we looked at our customer success modeling was high performance and high high potential. Um, and started to assess, okay, what is the sales motion and the support motion for those? And then also what is the potential for those? So uh where can we actually, you know, expect to see all eight all eight of our product lines being sold versus someone who's literally just doing something very high velocity and a little bit more transactional. And so then we started to look at our talent. That's when we started looking at our talent and started to assess where do we have some bright spots? Where do we have folks who are really killing it and can teach others? So I didn't start by letting go of the team. I started by looking at the team and saying, okay, where do we have really good performers? Where can they teach others? And so we brought in challenger sales methodology into the organization because a lot of them, even themselves, needed to be challenged to think differently a little bit. So we brought in challenger sales methodology to the organization. And then there were certain folks that honestly we uh after doing different role plays and and um and listening to calls and doing coaching, where we did have to part ways with them or reallocate them to other parts of the business. We had an entire support organization that was that was a really good um fit for some of the people. And then some of the people just didn't like the new approach and so decided to self-select out. Um, but it was really interesting because it was um such a great way for us to, you know, kind of leverage the existing talent to help us hire the new talent. And they became people who we added on the panels. They became the people that we did recognition for. And so every month we did fun videos and kept the change alive by showcasing, look, see, there's success. We have people who are having success doing this. And so we would give out awards every month. There were global awards, we would do fun videos where we would show all of the different offices. We had offices in Brazil, Mexico, you know, Germany, uh, Italy, all over the world, um, Singapore. And everyone would send in videos once a month of, you know, kind of their spotlighted customer and also like just fun things that they'd been doing, whether it was like a plank contest or something. So there were just ways that we were trying to keep the culture. So in the end, we ended up with at least an employee MPS score of like seven out of 10. The attrition had switched from a high 35% down to a 2% attrition rate. And we had 67% of the team start to pay quota, so a little bit more of that best practice. So um, because we'd organized appropriately and reassessed the talent, but it was secondary, not the primary thing that we did was just come in and fire everybody.
SPEAKER_02:So let me play back to you the sequence of the things that I heard and see how much of that can be a template for you and others when they sort of enter an organization and things aren't going the way you know we'd hoped uh they'd be. So one of the first things you mentioned was just like, well, take a step back and put a clean slate against the business and say, hey, if I was going to build a go-to-market motion for this business as it is today, what would that look like rather than how do I make the best use of whatever's going on here today? And the example that you gave within that was segmentation. So if I look at the types of deals that are being done by this business, what is the where is their variety? So in a classic segmentation model, you have SMB, min-market, and enterprise, if I see that there's a very different sales motion that's happening, and yet I'm asking the team to do one minute sell to the Fortune 100 and the next minute sell to a mom and pop, that there might be challenges associated with scaling. And so segmentation might be the first thing. And then if we know we're going to segment, the second thing is then around okay, what is the profile of talent that I would need for those types of roles, depending on how many of each that I require? Another thing that you mentioned was around looking at, if you have a multi-product portfolio, looking at the product types individually and saying, okay, which of these is both performing really well right now, and which of these has the potential to perform with some added investment, and then be making decisions around, again, with the clean slate, how do you bring additional products outside of maybe the core to market? And then maybe two other things that you mentioned within there. One, I heard a lot on communication of change. So communication of what's going on as you try to move an org, and then communication in its forms, whether they're videos and highlighting folks and making people feel a part of that change, that alone, communication is probably a big driver of MPS. Like feeling like you're on the team and not just like people making decisions in the ivory tower alone is probably pretty possible.
SPEAKER_01:Yeah.
SPEAKER_02:And then to the extent you get that all going, okay, how do I institute a methodology to get consistent execution? You selected the challenger sale. And it's like, man, if you can just do these things that you're gonna help. I mean, anybody would want to achieve the results of going from zero quota performance to two-thirds or from um 35% attrition to two. So uh that's just like what I'm hearing. I'm wondering how much of that is the sort of playbook, if you will, of entering other difficult situations.
SPEAKER_00:Well, I love that. Gosh, that was so well said. The um the other thing I think that we did that I think is really relevant too was we outfitted the team with tools as well so that they could sell a multi-product solution. Part of what happened was obviously like the uh the same, or I'm sorry, the challenger sales methodology was really helpful for sure. But also it was the mechanism for them to be able to sell new products to their solution to their to their customers was one of those things that they didn't know necessarily how to bring it up always. And so we had outfitted them with sales loft at the time. Um, but now I think of all of the different AI tools that you could be leveraging to either um uncover who has the most potential. Uh you know, not obviously you've got your performance already with the revenue, uh, revenue that folks are doing, but you can look with any of these AI tools to start to go, okay, who might be have the propensity to be able to use it? And then obviously, then how do I do any outreach with marketing tools and all that? And so we had used sales off at the time, but now I think that there's all sorts of other ways to uncover intent uh and propensity to buy too. The other thing I would say is in that performance and potential uh on the performance side, one of the other elements that was really interesting and required partnership with our finance team in particular was evaluating the LTV to CAC for each of these. And so there were also segments that we decided to exit and say, this is actually not a profitable segment for us to for us to sell to anymore because they don't stay with us, or because the CAC is not worth it. Um so you could evaluate all of those elements. And so when we started to look at, you know, all of the different segmentation, you started to almost see, okay, here's where we're going to organize, here's how we're going to organize, here's how we're going to support it, and then here are ones that we're just going to exit. Um so it was a really interesting kind of RevOps finance product and sales marketing and customer success, um, you know, kind of cross-functional initiative that made us stronger and got us growing again.
SPEAKER_02:Why do you think, in the example that you use, which is an excellent one with Shutterstock, why wasn't that happening already?
SPEAKER_00:I think they had just had so much chaos. There had been so much chaos in adding all of these companies. And they had been on a growing spree, you know, they had been on an acquisition spree, frankly. And so they were bringing all of these people together. And so if you had been there for eight years, which as I mentioned was the average tenure, you could just kind of keep doing your thing and not add all of these. And then it it only, you know, it only became apparent once you weren't hitting your number. Why you weren't hitting your number was because you were selling the thing you had eight years ago, as opposed to all of the new stuff that you had to sell.
SPEAKER_02:Did you come in after all those acquisitions?
SPEAKER_00:Yeah. So I came in after all the acquisitions.
SPEAKER_02:What an interesting dimension. And I think we're starting to see consolidation and acquisitions happening. Acquisitions are um so difficult to execute because of all the examples that you just gave. It's like fun to get the deal done, but then making it work afterwards is like way harder. Oh, and so I mean, I had to multiple times over, it does just naturally create a high state of unsettledness, and that's being you know optimistic.
SPEAKER_00:Absolutely. Well, and I've had to do that short held before that. We were a premises-based unified communication solution, and we bought a cloud company. Everything about us was different, right? Uh, it was monthly recurring revenue versus upfront CapEx investment, making all of your money through partners uh and through that upfront investment, in fact, selling against each other a lot of the times. Um, and so it was really interesting to watch that happen. And that was the first place that I became, frankly, uh it was a VP of sales and customer success where I saw the impact across marketing, sales, onboarding, customer success, support. I saw the impact of selling to the wrong type of customer. Um, we had an example of we used to sell to law firms as an example in our cloud solution. And you You would do so much work to market to them, to then go through the months of red lines with this law firm, right? Then it would take months and months to onboard them. Um, and then the second that you got them live and there was any disruption in service at all, they churned. And so it turned into, it was actually very fascinating. This was my entire career, had just been in sales. And so here I am thinking, well, we did our thing right. We got that, we got that deal closed, right? Um, we got our commission. And it turned into this was the first time where I really went, oh my gosh, it's not about doing your thing right, it's about doing the right thing. And so we evolved and changed our entire 150-person team to where no longer was anyone able to sell to law firms or market to law firms or keep a law firm because we now went, who is the longest, who's the LTV, who has the longest tenure, retention, et cetera, with us? Who is the right ICP for us to be selling to? And so not only did we change who our ICP was and like all get aligned to it, but then I also changed the compensation model for everyone. So everyone had the compensation that they were entitled, you know, that they were responsible for. So sellers, it was new ARR for the support team, it was their, you know, uh their uh first call resolution, uh, was their primary way of getting paid, right? Either for their bonus or their commission. But 25% of everyone's variable compensation had a retention element to it. So that you were not just doing your thing right, but you were doing the right thing holistically for the organization to succeed, which was all about retention and long-term value of the customers.
SPEAKER_02:Bridget, you know, just in this conversation, it's clear you've walked into some tumultuous situations. Walk into acquisition-based tumult. That's probably like on the degree of difficulty scale as high as it gets. And if you can successfully navigate the change management or transformation in that context, imagine what you can do when you don't have the one hand, the one arm tied behind your back in terms of doing that. I wouldn't underestimate the um the skills that one acquires to be able to effectively um manage growth. Um, but if you think about coming into a situation in a you know more favorable starting point, so to speak, um, you know, that the idea of accelerating growth might be really compelling and exciting based on what because you've already seen the harder uh you know, sort of picture. Another thing that kind of comes to mind for me is in order to effectively transform an organization in any way, I imagine you you talked about this cross-functional dynamic working with finance and working with RevOps and looking at LTB and cat to cat and making the tough decisions that you can't make on your own about what are we not going to do anymore? Law firms, in your example, being the perfect thing. We're able to close deals there, but it's not good business. It takes a village, so to speak, to come to agreement that we can't do this anymore. Can you talk a little bit about um you know how you pursue now cross-functional relationships at the executive level and maybe the learnings that have gotten you to your worldview today?
SPEAKER_00:Yeah, I mean, I'm a big, let's say, management book reader. I love books on leadership. So one of my favorite ones is uh shockingly, Stanley McChrystal, General Stanley McChrystal's book called Team of Teams, where he talks about how they were able to defeat Al-Qaeda in Iraq. And he uh he managed the joint operations special forces, and it was all of these individual branches of the government, right? And so they were all in Iraq trying to, you know, kind of defeat this very nimble enemy. And he found that this, you know, we're the US had the strongest military in the world, and we're getting beat every day by a more nimble, flexible, you know, adversary. And it was because of the things they were doing internally to make things harder. So one branch of the military had like an informant and someone who was, you know, kind of their their go-to guy. Another branch of the military was like targeting that person. So, you know, they it everything was misaligned. And so I think of that book a lot, and that's where I got that whole, you know, do the right thing versus doing your thing right, um, because he basically changed it to where he said, now we are a team of teams, we are doing missions together, we are aligned on what our missions are, and the ultimate goal is the, is like, is the is to defeat al-Qaeda and Iraq. Uh, in the same sense, I think of, you know, the ultimate goal is the organization's goal, not just your sales goal or not just your product team's goal. The other thing I've read was Five Dysfunctions of a Team. That's one of my favorite books ever, too. And they always highlight that the team that you are on is your most senior team that you are on cross-functionally, not the team you lead. And so, again, my team is not my sales or my customer success or my marketing team. My team is me and my chief product officer, my chief financial officer. We are solving the CEO's problems, uh, not necessarily just the problems of our team, um, or only answering that. And so, and I think there's no better, you know, kind of definition of that than aligning on, let's say, an ideal customer profile. That I would be, you know, that is like one of the perfect examples of you think that maybe that's just a go-to-market challenge. Absolutely not. Your CFO, your chief product officer, your CEO, um, everyone within your organization needs to be aligned on who your ICP is and what that means if you are only selling to that or if you are choosing to go beyond it. Um, so even something like the ICP work that I think is probably the most important thing, allows you to know where are we, where are we targeting and and what are we willing to spend to get that customer and what are we doing, you know, to service and support and keep that customer. Uh, and I think there there's there's no more kind of example of something where it aligns the entire executive team more than something like ICP.
SPEAKER_02:Yeah, I mean, that's a great example. Um, you know, Lencioni's five dysfunctions of a team. Um, I've heard a lot about this, that the idea that your team is your peers and not the folks that roll up to you. And I think everybody nods and you know vigorously agrees, yeah, sure. But the actual like application of that in the real world is much tougher than it sounds. It's very easy to live within your um your silo of responsibility. Uh, first of all, those folks report up to you, and so if you call, they answer, and you understand the deep context of the things that A, that they should be doing, B, the things they are doing, and C the struggles or challenges or objectives or obstacles that they might be facing. And so the inertia is pushing you at all times to work within that silo. Yeah. Like, for example, you might not be the head of engineering, you might not have any idea how to write code. So, like, what are you gonna talk to the head of engineering about? It's like you don't want to tell him about or her about the quality of the engineers because that's not your role. So you don't want to be coming across like you're infringing, or the head of product, or finance, or whatever the area of specialization is. So I think the idea that, like, hey, your first team is your peers and not just like the folks that report up into your org is much harder to actually apply because all the inertia is also pushing them to focus on the things they need to do day to day and so on and so forth. So I think a challenge for leaders is a the recognition of what you described, but then B, how do I put that into practice? How have you done so?
SPEAKER_00:Oh, yeah. Well, it's aligned compensation, number one. So, you know, the salesperson in me dies hard because I think aligned compensation always is a way to reinforce the the goals that you have. So, um, and I mean that company wide. Um, I think there's also um I think what is it, people have to hear something nine times before it actually sticks. Um so I think it's also every single I think yeah, exactly. Yeah, yeah. It was nine. I think it's nine. I don't know. It's either seven or nine, and I can never remember. Yeah. And I'm like, I clearly I need to hear it more often. So the um, but I think at every uh, you know, all team meeting that you hold, every organizational meeting that you have, every time you kick off a meeting, as a reminder, our goal is that we are getting to this revenue target or retention rate should be this, or ICP is this, and we are looking at our ICP penetration rate. Like whatever that one thing is, and I always usually, if it can be one thing, it's ideal. Uh, if it is one thing that you can find is the ruthless priority of the organization that you are galvanizing the team around, then it is it's the one thing that you are always talking about. It's the one thing you are paying them on, whether it's their bonuses for uh usually the non-commission carrying folks or the uh or the commission carrying folks having a component of it to be uh to be um uh you know something that they are incentivized to. And then the third element I would say, so it's you know, aligned compensation, number two would be the you know, relentless discussion about it. The third would be find some way to make it fun. Find some way to make it fun. Um, and that they care about it because I have done, I can't even tell you the amount of embarrassing things that I've done where like if we hit a certain goal, there's pie in the face. If we hit a certain goal, I'm doing chapel roan karaoke, which you don't have to ask me too much. I will, I will raise my hand to do. But the there's so many things that are, you know, ways to like make that fun, or you know, the whole company gets um, you know, I don't know, a what have we done? We've done like yoga class together. Um, uh the entire company gets to have a half day off or something. You know, like there were there were things like that that we would do, and there were always little small milestones. And I've also heard this is what they do. Um, that, you know, as you were in pursuit of a goal, you don't do milestones, you do inch pebbles. Love that term. Um, I stole that from my favorite book, Switch, How to Change When Change is Hard. That's another one of my books that I love. Um, and they basically are like, this is the this the way that you create success is to show that success can be uh can can happen. And so, for example, if you're showing a timeline, you never show yourself at the beginning of this. You show yourself, see, we've already started. We're about 25% of the way there. So you already show, look, success is is already begetting success. People would rather be in part way through a longer journey than at the beginning of a shorter one. That is one of the invaluable lessons uh that Switch teaches you. And so that's where these little inch pebbles of shrinking the change that you were trying to get to work. And I will tell you, on that third day, on that Camino de Santiago, when I did not want to do this, I was using inch pebbles to motivate myself on this journey. I was doing, I was like, just get to that place so that you can have a coffee. Just get to that place so you can wring out your socks. It was small little change, or and I was like, you know, giving myself, uh giving myself little treats. Oh, then you can get your protein bar. You know, I was doing little things to like motivate myself because I couldn't talk to her, you know, I wasn't really talking to anybody. Um, and so all of those things are, you know, all of these change management tactics that you use are things that you can use on yourself too.
SPEAKER_02:Totally. Bridget, you're back here in New York. What's next for you?
SPEAKER_00:Um I'll be uh the chief revenue officer at a company called Patient Now. Uh it is the back-end practice management uh for med spas and aesthetic practices, uh, an amazing vertical SaaS company that is in the hyper-growth$20 billion uh market and growing at 15% every year. So extremely great space and uh allows for Patient Now to be the market leader in that. So I'm excited for that.
SPEAKER_02:Fantastic, Bridget. I feel like we just got started here talking, but we have run out of time. Best wishes, and I'm sure you're gonna do an amazing job in the new role. It was fun talking about your personal experience and your personal reasons, about your experience with revamping process and incorporating talent into the bigger picture and how you sort of cross-functionally bring the org along with you. Um, it's been awesome. So, Bridget, thank you very much for joining. Where should people find you? LinkedIn the place to go?
SPEAKER_00:Yes, LinkedIn is the place. My DMs are open. Feel free. Awesome. Thank you very much. Thank you so much, Rick. This was so fun.
SPEAKER_02:Reflecting on the conversation we just had with Bridget Winston, so many little tidbits of wisdom that were shared, it's hard to sort of compile it down to three big themes, but I'm gonna attempt to do that. And the first thing that stands out to me, so much of this show, is about tactics to help us be better sales leaders, better leaders, better professionals. And there's a whole nother side to us beyond our professional selves that in our personal journeys outside of just work, and Bridget's sharing her story and her personal journey between roles, taking a trip on the other side of the world, stories of adversity, stories of loss, stories of meaning, stories of spirituality, it gives us an opportunity to reflect and think about what is our own journey? What is the meaning we are finding beyond the work that we do? And when you hear another leader, a successful leader, share a story with some vulnerability in it, with some, you know, unconventional or not, you know, not your typical trip that folks would take, it helps form thoughts about our own search for meaning in our humanity beyond our ambition and our professional careers. So thank you, Bridget, for that uh storytelling. The second thing, the difficulty in when you have a company that grows through acquisition. And I'm not saying just one acquisition, I'm talking multiple acquisitions. And Bridget told stories that reflect the challenges associated with digesting and consuming and moving forward successfully when you've been in an acquisition-heavy environment. She told stories of having to like take a step back and get to the fundamentals of how would we run this business if we were to start it today and having to do basic things that weren't being done in an environment that you know might be described as chaotic. Um, and so that you know, I want to tip my hat to all of the sales leaders out there that are leading businesses that have been acquisition heavy, and I want to acknowledge the difficulty it is. And now I kind of understand at a greater level why such a large percentage of deals that get done don't translate into the value creation that was sold as part of that acquisition effort. Now, if you have a leader like Bridget, you have a better chance of being able to take a step back and then execute accordingly. But boy, her stories uh showed the difficulty in doing that. And so it's like almost operating with one arm tied behind your back. And so um, for me, it's like, okay, uh acquisitions sound fun, and when you see them happen on LinkedIn, people are celebrating them, but the there is hard work that has to happen on the other side of that. Um, the last reflection I have from the episode is when Bridget was talking about cross-functional leadership. And she made the point of making it fun. And I think it's a super important point. We all are trying to make the biggest impact we can on our organizations and develop the right relationships. And it's difficult when we are in a large group of humans working together towards a common goal. And it is important that the journey doesn't just have to be hard. It can be hard and fun. And it can be fun to be in a challenging environment. And I loved Bridget uh emphasizing the importance of that. I think we all need to be having fun along the way while we do the hard work of being great leaders, of learning how to be positive impacts across the areas of responsibility that we are working through. So thank you, Bridget, for a great discussion. Really appreciate it. Thank you to Ari Smolin for producing. Thank you to Sons of Summer for the tunes. Thank you, listener, for being here today. We will see you next time on Pillow Talks.