Finding Strength in Chaotic Scenarios with Bridget Winston
Pillar Talk: Building Sales Leadership with Rick Smolen · 2025-11-18 · 47 min
Substance score
53 / 100
Five dimensions, 20 points each
What our scoring noted
Our reviewer’s read on each dimension, with quotes from the episode.
Insight Density
The first ~15 minutes are almost entirely personal travelogue with minimal professional takeaway. The back half delivers a coherent turnaround playbook—segmentation before talent replacement, nine-box applied to accounts, LTV-to-CAC for segment exit, and retention-weighted comp—but none of these ideas are novel to a seasoned GTM operator.
the first thing that I saw was 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.
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.
Originality
The episode leans heavily on well-circulated reference points—Team of Teams, Five Dysfunctions, Challenger Sale, Switch—without meaningfully extending or challenging any of them. The 'inch pebbles' framing and applying a nine-box to account segments are the only fresh applications; everything else is standard leadership-book rehash.
one of my favorite ones is uh shockingly, Stanley McChrystal, General Stanley McChrystal's book called Team of Teams
The other thing I've read was Five Dysfunctions of a Team. That's one of my favorite books ever, too.
Guest Caliber
Winston is a genuine practitioner with verifiable CRO-level results at recognizable companies (Chief, Shutterstock) and speaks from direct operational experience rather than abstraction. She stops short of elite caliber because the companies are mid-market and the depth of strategic novelty in the transcript is moderate.
she helped grow membership in that community from 1,500 to over 20,000
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
Specificity & Evidence
The Shutterstock section is notably concrete: named company, before/after NPS scores, precise attrition percentages, quota attainment rate, account-size examples, specific sales methodology, named tools (SalesLoft), and the law firm churn vignette as a vivid ICP cautionary tale. This level of numerical specificity is above average for the genre.
the employee NPS score was a two out of 10. Uh, you know, the attrition rate was 35% uh when I was joining.
you could have one person who was managing an SMB account, but they also in their list had a$1.1 million organization
Conversational Craft
The host asks one genuinely sharp true/false framing question on talent and follows up with 'why wasn't that happening already?', and his playback synthesis usefully surfaces a replicable template. However, he spends the first quarter of the episode on travelogue without redirecting to business substance, never pushes back on any claim, and punctuates answers with 'Gosh, that was so well said'—classic softball validation.
Why do you think, in the example that you use, which is an excellent one with Shutterstock, why wasn't that happening already?
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
Conversation analysis
Computed from the transcript - who did the talking, and the verbal tics along the way.
Filler words
Episode notes
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
Full transcript
47 minTranscribed and scored by The B2B Podcast Index.
1 00:00:15,759 --> 00:00:19,120 SPEAKER_02: Hello, everyone, and welcome to another episode of 2 00:00:19,120 --> 00:00:20,160 Pillar Talk. 3 00:00:20,399 --> 00:00:24,239 This is where we build the foundations of sales leadership 4 00:00:24,239 --> 00:00:27,920 success and try to create clarity in terms of what good 5 00:00:28,079 --> 00:00:31,839 looks like for current and aspiring sales leaders. 6 00:00:32,079 --> 00:00:36,320 Today on Pillar Talk, I am joined by Bridget Winston. 7 00:00:36,880 --> 00:00:38,399 Thank you for being here, Bridget. 8 00:00:38,479 --> 00:00:41,439 She brings, before I let her speak, she brings over 20 years 9 00:00:41,439 --> 00:00:44,399 of experience in scaling go-to-market organizations 10 00:00:44,399 --> 00:00:48,719 across marketing, sales, customer success, the entire 11 00:00:48,719 --> 00:00:50,159 customer lifecycle. 12 00:00:50,399 --> 00:00:54,159 She was most recently the Chief Revenue Officer at Chief. 13 00:00:54,479 --> 00:00:57,280 This is where she helped grow membership in that community 14 00:00:57,280 --> 00:01:00,560 from 1,500 to over 20,000. 15 00:01:00,719 --> 00:01:03,600 Previously, beyond that, she was in many roles, including 16 00:01:03,600 --> 00:01:07,840 Shutterstock, where she led global sales through a pivotal 17 00:01:07,840 --> 00:01:09,359 transformation period. 18 00:01:09,599 --> 00:01:14,959 Bridget also advises CEOs, boards, investors on all things 19 00:01:14,959 --> 00:01:18,719 go-to-market strategy, growth, and customer experience. 20 00:01:18,959 --> 00:01:22,319 She's someone who blends ambition with reflection because 21 00:01:22,319 --> 00:01:28,560 between roles, she recently walked 75 miles of the Camino de 22 00:01:28,560 --> 00:01:32,879 Santiago, a sort of pilgrimage that offered lessons, and this 23 00:01:32,879 --> 00:01:38,000 is based on what I read, on slowing down presence, and 24 00:01:38,000 --> 00:01:39,760 rediscovering purpose. 25 00:01:39,920 --> 00:01:41,680 Bridget, welcome to Pillar Talk. 26 00:01:42,000 --> 00:01:44,000 SPEAKER_00: Oh, I'm so glad to be here with you, Rick. 27 00:01:44,319 --> 00:01:46,159 That is that's a lovely introduction. 28 00:01:46,239 --> 00:01:50,319 And what I will say to you is yes, it was meant to be a 29 00:01:50,319 --> 00:01:51,120 pilgrimage. 30 00:01:51,280 --> 00:01:54,000 A lot of people use it for a very religious pilgrimage. 31 00:01:54,159 --> 00:01:58,640 I was going to very much, you know, kind of accomplish a goal 32 00:01:58,640 --> 00:01:59,519 that I had. 33 00:02:00,480 --> 00:02:03,840 And it was it was really good though, because it ended up 34 00:02:03,840 --> 00:02:08,719 being much more of a reflective meditative jaunt for myself. 35 00:02:08,800 --> 00:02:09,680 So that was lovely. 36 00:02:10,000 --> 00:02:12,319 SPEAKER_02: So I get excited when I see something interesting 37 00:02:12,319 --> 00:02:12,879 and different. 38 00:02:13,039 --> 00:02:15,599 And, you know, you just had a lot of responsibility in your 39 00:02:15,599 --> 00:02:19,199 last role, probably running around, handling huge amounts of 40 00:02:19,199 --> 00:02:22,560 initiatives, pressure, large scopes of organizational 41 00:02:22,560 --> 00:02:24,560 development, uh, strategy. 42 00:02:24,800 --> 00:02:29,039 And then you go from that to I'm gonna do something totally 43 00:02:29,039 --> 00:02:32,319 different, and I'm gonna go, you know, accomplish this, you know, 44 00:02:32,560 --> 00:02:33,520 personal goal. 45 00:02:33,680 --> 00:02:35,680 So I love to learn more about that. 46 00:02:35,840 --> 00:02:40,000 Can you share a little bit about what inspired that trip and what 47 00:02:40,000 --> 00:02:41,280 did you take away from it? 48 00:02:41,599 --> 00:02:42,560 SPEAKER_00: Yeah, absolutely. 49 00:02:42,719 --> 00:02:46,400 So uh, well, it was kind of a two-week adventure for me. 50 00:02:46,639 --> 00:02:49,840 So the first week I actually went to Tuscany and did an 51 00:02:49,840 --> 00:02:51,680 immersive cooking course. 52 00:02:51,840 --> 00:02:54,080 Um, but it was pretty difficult. 53 00:02:54,240 --> 00:02:58,159 It was not actually as meditative and as relaxing as I 54 00:02:58,159 --> 00:03:03,439 thought because we were cooking for five hours a day with an 55 00:03:03,439 --> 00:03:06,319 Italian chef who was very demanding. 56 00:03:06,800 --> 00:03:10,960 So it was me and a bunch of 60 and 70-year-old retirees going 57 00:03:10,960 --> 00:03:14,800 to this uh villa in Tuscany to do a cooking course. 58 00:03:14,879 --> 00:03:15,919 So that was fun. 59 00:03:16,080 --> 00:03:19,599 But I the good news is I was fueled up, I was carved up so 60 00:03:19,599 --> 00:03:24,159 that I could go on the next week to uh the Commune de Santiago. 61 00:03:24,240 --> 00:03:26,639 And both of these I chose to do do solo. 62 00:03:27,039 --> 00:03:30,240 Uh I have a great, amazing husband, but I really kind of 63 00:03:30,240 --> 00:03:32,319 wanted to do something for myself. 64 00:03:32,479 --> 00:03:35,840 I have, I'm 45 years old, so I felt like this was like that 65 00:03:35,840 --> 00:03:39,680 moment of, you know, prove me to me a little bit, go and do 66 00:03:39,680 --> 00:03:44,960 something uh that was a little, a little scary, a little, can I 67 00:03:44,960 --> 00:03:45,280 do it? 68 00:03:45,439 --> 00:03:47,039 These were things I'd always wanted to do. 69 00:03:47,199 --> 00:03:50,400 And so it was a little bit of prove me to me, particularly the 70 00:03:50,400 --> 00:03:53,840 Camino, because you know, you're strapping yourself into some day 71 00:03:53,840 --> 00:03:54,240 pack. 72 00:03:54,319 --> 00:03:56,879 I had to have, you know, water for the whole day. 73 00:03:57,039 --> 00:03:59,919 You're walking four to six hours a day. 74 00:04:00,080 --> 00:04:05,520 Um, and you know, going, I chose not to do the hostile route. 75 00:04:05,840 --> 00:04:09,840 I did stay in hotels, so I had it a little bit more uh of the 76 00:04:09,840 --> 00:04:10,400 high end. 77 00:04:10,479 --> 00:04:14,000 I wasn't doing the full pilgrimage, but it was a four, 78 00:04:14,400 --> 00:04:20,160 five-day jaunt that um was four to six hours a day. 79 00:04:20,240 --> 00:04:25,839 Uh, I think I walked at minimum 12 miles a day to 18 miles a 80 00:04:25,839 --> 00:04:26,240 day. 81 00:04:26,480 --> 00:04:31,439 Um, and I I'm pleased to say that it rained every single day, 82 00:04:31,759 --> 00:04:35,199 poured raining every single day, completely different than what I 83 00:04:35,199 --> 00:04:37,439 was expecting October in Spain to be like. 84 00:04:37,680 --> 00:04:40,480 I was expecting it to be this like beautifully, you know, 85 00:04:40,720 --> 00:04:41,839 wonderful moment. 86 00:04:42,000 --> 00:04:46,079 And it was, I mean, it was it was torrential downpours the 87 00:04:46,079 --> 00:04:46,959 entire time. 88 00:04:47,199 --> 00:04:50,480 Uh, you're walking with other pilgrims who are doing this. 89 00:04:50,560 --> 00:04:54,399 I did the Camino coastal route of Portugal. 90 00:04:54,639 --> 00:04:58,720 Um, and so you are walking this route with other people, 91 00:04:58,879 --> 00:05:01,680 sometimes seeing a lot of people, sometimes seeing few. 92 00:05:01,920 --> 00:05:05,920 Uh, and you're walking through little small towns in Portugal 93 00:05:05,920 --> 00:05:06,720 and Spain. 94 00:05:06,959 --> 00:05:10,959 And there were certain towns that I went to that didn't have 95 00:05:10,959 --> 00:05:12,720 any people and just cats. 96 00:05:12,959 --> 00:05:18,160 You're walking by chapels, you have to get your Camino passport 97 00:05:18,160 --> 00:05:18,720 stamped. 98 00:05:18,800 --> 00:05:21,519 Uh, so you have to stop every now and again to get your Camino 99 00:05:21,519 --> 00:05:23,680 passport stamped to prove that you did the walk. 100 00:05:23,839 --> 00:05:25,279 You walk next to certain people. 101 00:05:25,439 --> 00:05:28,000 Some people really want to talk to you, some people are, you 102 00:05:28,000 --> 00:05:29,680 know, kind of just walking in silence. 103 00:05:29,839 --> 00:05:33,519 I watched one lady doing the rosary the whole way, which was 104 00:05:33,519 --> 00:05:34,639 really sweet to see. 105 00:05:34,720 --> 00:05:38,160 But like the first couple of days, I will say, I was walking 106 00:05:38,160 --> 00:05:39,120 and I was on a mission. 107 00:05:39,199 --> 00:05:42,240 I was like, get this thing done because the rain, I was wringing 108 00:05:42,240 --> 00:05:45,279 out my socks three times, you know, I didn't stop for coffee, 109 00:05:45,360 --> 00:05:46,560 I didn't stop for lunch. 110 00:05:46,720 --> 00:05:47,920 I was just trying to get this done. 111 00:05:48,000 --> 00:05:50,879 And that is probably pretty standard about the kind of 112 00:05:50,879 --> 00:05:51,360 person I am. 113 00:05:51,519 --> 00:05:53,680 I'm I was a Division I college athlete. 114 00:05:53,839 --> 00:05:56,560 I was always like a person who likes to achieve a goal, 115 00:05:56,720 --> 00:05:58,879 relentless kind of pursuit of things. 116 00:05:59,120 --> 00:06:05,519 And but I will say by day three, I uh day three was the day that 117 00:06:05,519 --> 00:06:07,600 I was like, I don't feel like doing this. 118 00:06:07,839 --> 00:06:11,680 I am like annoyed that I have to get up and go walk this thing. 119 00:06:11,839 --> 00:06:15,199 Um, and so while it was enlightening and empowering, it 120 00:06:15,199 --> 00:06:19,680 was also really hard, both mentally and it grew to be hard 121 00:06:19,759 --> 00:06:22,160 physically, but like physically was less hard. 122 00:06:22,319 --> 00:06:25,439 It was mentally getting yourself to like do the thing. 123 00:06:25,680 --> 00:06:28,879 And so I had to honestly do the thing that was opposite my 124 00:06:28,879 --> 00:06:30,240 normal tendency. 125 00:06:30,399 --> 00:06:32,879 I had to actually give myself like little goals. 126 00:06:33,360 --> 00:06:37,680 And I had to like, you know, tease that hey, you can stop 127 00:06:37,680 --> 00:06:41,759 within two hours and rest your feet and take a coffee break. 128 00:06:42,000 --> 00:06:44,720 Um, you can talk to the people next to you. 129 00:06:44,959 --> 00:06:45,920 I wouldn't kill you. 130 00:06:46,079 --> 00:06:49,360 You know, this is not about this like relentless pursuit of like 131 00:06:49,519 --> 00:06:51,040 getting this thing done. 132 00:06:51,199 --> 00:06:53,839 It is meant to be really meditative. 133 00:06:53,920 --> 00:06:58,800 And I will say it culminated in some really like interesting 134 00:06:58,800 --> 00:07:00,879 discussions and and talks. 135 00:07:00,959 --> 00:07:05,199 And frankly, my blisters were better for it to stop a bit, but 136 00:07:05,199 --> 00:07:09,519 it culminated in the last day when I had two miles left to go. 137 00:07:10,000 --> 00:07:14,800 And I am almost to Santiago, which is this beautiful church 138 00:07:14,800 --> 00:07:15,920 in in Spain. 139 00:07:16,000 --> 00:07:17,360 Uh, and they say it's where St. 140 00:07:17,439 --> 00:07:18,319 James is buried. 141 00:07:18,480 --> 00:07:19,680 Who knows if this is true? 142 00:07:19,759 --> 00:07:25,600 But um, but I was two miles away from being done, and I come, I'm 143 00:07:25,600 --> 00:07:32,160 on it in a forest, and I come upon a man playing the piano in 144 00:07:32,160 --> 00:07:33,120 the forest. 145 00:07:33,439 --> 00:07:35,600 I mean, the most random thing. 146 00:07:35,839 --> 00:07:39,600 And I think what was most meaningful about this is my 147 00:07:39,600 --> 00:07:45,279 father, uh, who's passed away 17 years ago, was a big musician, 148 00:07:45,519 --> 00:07:50,480 and our home was always filled with music and the piano in 149 00:07:50,480 --> 00:07:50,959 particular. 150 00:07:51,199 --> 00:07:54,240 And so he used to play the piano, he used to play the piano 151 00:07:54,240 --> 00:07:55,920 at mass and all of these things. 152 00:07:56,000 --> 00:08:00,639 And I know that he would have been very proud of me for doing 153 00:08:00,639 --> 00:08:00,879 this. 154 00:08:01,120 --> 00:08:05,920 And I came upon this man in the forest playing the piano, and I 155 00:08:05,920 --> 00:08:10,800 stopped for 20 minutes and just cried because it was first off, 156 00:08:10,879 --> 00:08:13,600 he caught me at quite the time, two miles left to go. 157 00:08:13,759 --> 00:08:17,120 But also, it was just this like meaningful thing of being 158 00:08:17,120 --> 00:08:21,040 present and remembering why you do things and remembering the 159 00:08:21,040 --> 00:08:24,560 people who are really important in your lives, and um just 160 00:08:24,560 --> 00:08:26,480 taking that moment to pause. 161 00:08:26,560 --> 00:08:29,199 Um, and so it was just like one of the most meaningful things. 162 00:08:29,439 --> 00:08:31,040 I'll remember it for the rest of my life. 163 00:08:31,199 --> 00:08:34,960 Um, and it, you know, I passed countless cemeteries, right? 164 00:08:35,039 --> 00:08:37,840 And so I was already in this somewhat reflective mood of 165 00:08:37,919 --> 00:08:40,639 like, gosh, all of these people who came before us and who have 166 00:08:40,639 --> 00:08:44,639 lived here, but like to be there and to see in the middle of a 167 00:08:44,639 --> 00:08:48,720 forest a man playing the piano, um, it really made me feel like 168 00:08:48,720 --> 00:08:51,360 my dad was there and present with me in some ways. 169 00:08:51,600 --> 00:08:55,039 I don't know if I believe in all of that, but like it was it was 170 00:08:55,039 --> 00:08:59,840 just it was so poignant and and frankly just breathtaking to me, 171 00:08:59,919 --> 00:09:02,080 um, otherworldly in some ways. 172 00:09:02,399 --> 00:09:04,720 SPEAKER_02: Yeah, you had written about that in your post 173 00:09:04,720 --> 00:09:08,399 on LinkedIn, and that was certainly uh a moving and 174 00:09:08,399 --> 00:09:10,799 emotive uh aspect of that post. 175 00:09:10,960 --> 00:09:14,639 You could feel as the reader um you know a bit of what you were 176 00:09:14,639 --> 00:09:15,200 feeling there. 177 00:09:15,279 --> 00:09:16,879 So very powerful stuff. 178 00:09:17,279 --> 00:09:20,879 What what was you know when you're between roles and you 179 00:09:20,879 --> 00:09:23,840 have the opportunity to go do something different, there are 180 00:09:23,919 --> 00:09:26,639 many options, and there's no one right answer. 181 00:09:27,200 --> 00:09:31,440 What was the rationale behind these two journeys for you in 182 00:09:31,440 --> 00:09:36,399 immersive cooking in Italy and you know, the hiking um you know 183 00:09:36,799 --> 00:09:39,120 across the Camino de Santiago? 184 00:09:40,240 --> 00:09:45,759 SPEAKER_00: Yeah, I mean I think what was drawing me to do both 185 00:09:45,759 --> 00:09:50,080 of these is something a little bit more either in nature or 186 00:09:50,080 --> 00:09:51,360 with my hands, right? 187 00:09:51,600 --> 00:09:55,519 We sell SaaS and cloud, and I always think about I've got all 188 00:09:55,519 --> 00:09:58,480 of these relatives who live in Ireland, and whenever I go 189 00:09:58,480 --> 00:10:02,000 there, I'm always explaining what my job is to them. 190 00:10:02,159 --> 00:10:05,679 And the a good portion of these people are teachers, they are 191 00:10:06,000 --> 00:10:12,080 builders, they are people who um or chefs, and whenever I tell 192 00:10:12,080 --> 00:10:15,279 them what I do, I mean I feel like I'm in some way selling 193 00:10:15,279 --> 00:10:16,399 vaporware, right? 194 00:10:16,480 --> 00:10:20,639 That we are just selling this thing that is, you know, 195 00:10:20,960 --> 00:10:26,799 fulfilling a um certainly a utility, and it it's important, 196 00:10:26,879 --> 00:10:30,320 and there are things that we are doing, but I feel like you lose 197 00:10:30,320 --> 00:10:37,600 a little bit of the one-on-one connection with others, um, and 198 00:10:37,919 --> 00:10:43,600 the the meaning in life and like the visibility of seeing what 199 00:10:43,600 --> 00:10:44,399 you create. 200 00:10:44,879 --> 00:10:49,679 Um, and so there was something in this around the cooking, 201 00:10:49,759 --> 00:10:53,039 although I think I I I may have come back a worse chef after 202 00:10:53,039 --> 00:10:53,200 that. 203 00:10:53,759 --> 00:10:55,039 unknown: I've got to be honest. 204 00:10:55,840 --> 00:10:58,399 SPEAKER_00: Like I'm even thinking of like, what is my 205 00:10:58,399 --> 00:10:59,200 LinkedIn post? 206 00:10:59,279 --> 00:11:03,120 And I really think like the lesson I learned was this did 207 00:11:03,120 --> 00:11:04,240 not teach me anything. 208 00:11:04,399 --> 00:11:06,879 It taught me just to like just enjoy it. 209 00:11:06,960 --> 00:11:09,600 Like someone's gonna make something good and just eat it, 210 00:11:09,679 --> 00:11:11,840 you know, like even if you're a terrible chef. 211 00:11:12,080 --> 00:11:14,879 Um, so but it was it was one of those things. 212 00:11:14,960 --> 00:11:18,240 And then the Camino was seriously like the feet on the 213 00:11:18,240 --> 00:11:23,200 ground of just meditatively walking through towns that 214 00:11:23,279 --> 00:11:26,960 honestly I just watched old people, you know, harvesting 215 00:11:26,960 --> 00:11:35,440 pumpkins and picking apples and you know uh walking amongst 216 00:11:35,440 --> 00:11:36,320 their cats. 217 00:11:36,559 --> 00:11:40,320 It was, it was just, and I I sit there and think, do these people 218 00:11:40,320 --> 00:11:43,200 understand what I, you know, like are they gonna understand 219 00:11:43,200 --> 00:11:45,519 the SaaS software solution I'm selling? 220 00:11:45,600 --> 00:11:48,159 You know, it's probably never entered their mind. 221 00:11:48,320 --> 00:11:50,000 But God, there were laughter. 222 00:11:50,159 --> 00:11:53,519 There was people who were, you know, you could hear kids, you 223 00:11:53,519 --> 00:11:58,000 could hear um, you know, you watch generations of people be 224 00:11:58,000 --> 00:11:58,639 all together. 225 00:11:58,720 --> 00:12:02,879 And so there was just something very moving about like what 226 00:12:02,879 --> 00:12:05,360 really makes a difference in the world, you know, and it is 227 00:12:05,440 --> 00:12:07,919 sometimes it's just the food and the connections that we have. 228 00:12:08,240 --> 00:12:10,720 SPEAKER_02: In your post, you mentioned you you use this 229 00:12:10,720 --> 00:12:15,200 phrase, a superpower overused becomes a weakness. 230 00:12:15,519 --> 00:12:16,000 SPEAKER_00: Yes. 231 00:12:16,240 --> 00:12:18,080 SPEAKER_02: Um tell me a little bit about that. 232 00:12:18,240 --> 00:12:19,840 That's an interesting quote. 233 00:12:20,559 --> 00:12:24,639 SPEAKER_00: Well, it was born out of one of my favorite things 234 00:12:24,639 --> 00:12:25,519 is strengthfinders. 235 00:12:25,759 --> 00:12:28,559 Have you ever read uh or have you ever done Strength Finders 236 00:12:28,559 --> 00:12:31,679 as a um as one of those personality tests or anything? 237 00:12:31,919 --> 00:12:33,759 I believe I did that once, yes. 238 00:12:34,080 --> 00:12:38,559 Yeah, and so um, and it's also born out of, you know, whenever 239 00:12:38,559 --> 00:12:40,320 anyone's like, what's your biggest weakness? 240 00:12:40,399 --> 00:12:43,279 You know, what you usually what I always do is I always throw in 241 00:12:43,279 --> 00:12:45,039 a superpower for use becomes a reason. 242 00:12:45,120 --> 00:12:46,000 Yeah, yeah, yeah, exactly. 243 00:12:46,240 --> 00:12:47,039 Well, yeah, exactly. 244 00:12:47,279 --> 00:12:50,480 Like, I'm just such a hard worker, it's a workaholic. 245 00:12:50,720 --> 00:12:57,440 Um, and so um, but I do think that generally speaking, um it 246 00:12:57,440 --> 00:13:00,720 is the things we are best at that sometimes we over-rely upon 247 00:13:00,720 --> 00:13:06,000 or over-index on that become the thing that probably is our 248 00:13:06,000 --> 00:13:07,759 shadow side, if you will. 249 00:13:08,000 --> 00:13:11,200 Um and so, and that's what I've seen. 250 00:13:11,360 --> 00:13:16,159 Like my relentless pursuit, my driven, my ambitious, my, you 251 00:13:16,159 --> 00:13:20,879 know, probably, you know, sometimes command and control is 252 00:13:20,879 --> 00:13:25,039 the thing that prohibits me from being the leader I should be, 253 00:13:25,200 --> 00:13:28,080 and to get even better at being a leader. 254 00:13:28,240 --> 00:13:32,559 And so sometimes us doing the opposite, or at least being open 255 00:13:32,559 --> 00:13:33,519 to doing the opposite. 256 00:13:33,679 --> 00:13:36,559 Now, there's the other side of me that's also like embrace your 257 00:13:36,559 --> 00:13:39,919 strengths because like one ounce of energy tied towards something 258 00:13:39,919 --> 00:13:43,120 you're already naturally good at is probably gonna deliver more 259 00:13:43,120 --> 00:13:43,679 for you. 260 00:13:44,000 --> 00:13:47,759 But wouldn't we all be better, more reflective people if at 261 00:13:47,759 --> 00:13:50,159 some point we also said, and what's my opposite? 262 00:13:50,399 --> 00:13:54,639 Or how do I supplement myself with either people on my team 263 00:13:54,639 --> 00:14:00,320 who think differently than I do, or um, or inviting debate, and 264 00:14:00,639 --> 00:14:02,639 you know, like argue this from the other side. 265 00:14:02,799 --> 00:14:06,159 I do that sometimes with my team when we're all in agreement, you 266 00:14:06,159 --> 00:14:06,399 know? 267 00:14:06,720 --> 00:14:07,679 SPEAKER_02: Yeah, yeah. 268 00:14:07,919 --> 00:14:11,600 Well, I I certainly think um this idea of doing something 269 00:14:11,600 --> 00:14:14,559 completely different than your norm, when your norm is a lot of 270 00:14:14,559 --> 00:14:18,320 Zoom calls and zeros and ones, which is the world we live in, 271 00:14:18,399 --> 00:14:21,679 and we're very lucky to be here, you know, trudging through the 272 00:14:21,679 --> 00:14:25,919 mud in sort of like spiritual, truly powerful, you know, 273 00:14:26,159 --> 00:14:29,440 historic areas, um, you know, definitely scratches that itch, 274 00:14:29,519 --> 00:14:30,000 doesn't it? 275 00:14:30,320 --> 00:14:31,279 SPEAKER_00: Yeah, absolutely. 276 00:14:31,440 --> 00:14:33,120 I mean, and there was just funny things. 277 00:14:33,200 --> 00:14:37,120 I mean, the things that you just see on the way. 278 00:14:37,279 --> 00:14:40,720 I mean, the there was a chapel I passed that had like Mary 279 00:14:40,720 --> 00:14:45,120 Magdalene laid out like she was a French, you know, you know, 280 00:14:45,360 --> 00:14:46,639 French painting. 281 00:14:46,799 --> 00:14:47,679 It was so funny. 282 00:14:47,759 --> 00:14:50,080 I mean, there were just things that I would just snicker to 283 00:14:50,080 --> 00:14:51,679 myself and just laugh. 284 00:14:51,759 --> 00:14:54,879 And I didn't use headphones the entire time, which I was like, 285 00:14:55,039 --> 00:14:56,799 all right, you are gonna be present, girl. 286 00:14:56,960 --> 00:15:00,080 You are going to get through this, you're gonna talk to 287 00:15:00,080 --> 00:15:02,720 people, you're gonna experience this, you're gonna hear the 288 00:15:02,720 --> 00:15:04,639 roosters crowing. 289 00:15:04,799 --> 00:15:06,320 And they they woke up late. 290 00:15:06,480 --> 00:15:08,399 They woke up late at least 9 a.m. 291 00:15:08,799 --> 00:15:11,919 I was like, there's no more Spanish rooster thing than 292 00:15:11,919 --> 00:15:14,399 waking up at 9 a.m., you know? 293 00:15:15,759 --> 00:15:17,919 SPEAKER_02: Well, Bridget, welcome back, and I know you're 294 00:15:17,919 --> 00:15:20,960 gonna be getting back into engaging all types of companies. 295 00:15:21,120 --> 00:15:26,159 We're in a time of you know, uncertainty within the business 296 00:15:26,159 --> 00:15:28,720 landscape, especially in SaaS and tech. 297 00:15:29,120 --> 00:15:32,080 Um, you're gonna walk into situations whether you're in 298 00:15:32,080 --> 00:15:36,240 advisory capacity or full-time capacity or anything in between, 299 00:15:36,399 --> 00:15:39,919 and you're gonna see situations where organizations are 300 00:15:39,919 --> 00:15:41,360 struggling with growth. 301 00:15:41,519 --> 00:15:44,720 You're gonna see organizations struggling with the uncertainty 302 00:15:44,720 --> 00:15:45,759 of where to go. 303 00:15:46,000 --> 00:15:48,879 And one of the things you're gonna hear a lot about is we 304 00:15:48,879 --> 00:15:51,120 have the wrong talent in the organization. 305 00:15:51,279 --> 00:15:54,799 So when you approach a situation where an organization is 306 00:15:54,799 --> 00:15:58,639 struggling or not performing to goals, true or false, it's a 307 00:15:58,639 --> 00:15:59,200 talent issue. 308 00:15:59,360 --> 00:16:01,279 Just replace the people and you're good. 309 00:16:01,840 --> 00:16:04,799 SPEAKER_00: Oh, I can't tell you how many times I've heard that. 310 00:16:05,039 --> 00:16:09,200 So when interviewing for Chief Revenue Officer Jobs coming in, 311 00:16:09,519 --> 00:16:12,799 uh, and I always hear, especially if they're struggling 312 00:16:12,799 --> 00:16:16,879 with growth goals or uh they've done a lot of acquisitions and 313 00:16:16,879 --> 00:16:21,759 the culture and the team morale isn't there, um, you always hear 314 00:16:21,759 --> 00:16:24,240 when you ask, you know, any of the folks that you're 315 00:16:24,240 --> 00:16:26,960 interviewing with, well, what's what's the what's the main 316 00:16:26,960 --> 00:16:27,279 challenge? 317 00:16:27,360 --> 00:16:29,600 And the number one thing you hear is talent. 318 00:16:29,759 --> 00:16:33,440 And what I would say is I'm going to dispel that myth right 319 00:16:33,440 --> 00:16:34,399 now, Rick. 320 00:16:34,559 --> 00:16:40,240 Not fully, but at least start with first look inward, first 321 00:16:40,559 --> 00:16:44,639 look inward organization, uh, and investigate have you 322 00:16:44,639 --> 00:16:47,120 actually set the team up for success. 323 00:16:47,360 --> 00:16:49,440 It's not that it's never the talent. 324 00:16:49,600 --> 00:16:52,159 Um, so there's always talent improvements. 325 00:16:52,320 --> 00:16:55,279 And uh in certain organizations that I've been in, there was 326 00:16:55,279 --> 00:16:57,759 definitely a time for us to address the talent. 327 00:16:58,080 --> 00:17:01,440 But um in some of the organizations that I've seen, 328 00:17:01,759 --> 00:17:05,839 the first thing that I saw was that there was no plan for the 329 00:17:05,839 --> 00:17:06,160 plan. 330 00:17:06,400 --> 00:17:09,519 Uh, and there were there were no operating rhythms that were 331 00:17:09,519 --> 00:17:13,359 actually ensuring that the team was going to be successful. 332 00:17:13,519 --> 00:17:15,519 So I always look at organizations and say, first 333 00:17:15,680 --> 00:17:16,319 look inward. 334 00:17:16,480 --> 00:17:20,000 How are you ensuring that this talent that you have is 335 00:17:20,000 --> 00:17:20,720 successful? 336 00:17:21,039 --> 00:17:22,079 SPEAKER_02: So let's talk about that. 337 00:17:22,160 --> 00:17:23,680 What does it mean to look inward? 338 00:17:24,079 --> 00:17:24,720 Yeah. 339 00:17:25,039 --> 00:17:27,680 SPEAKER_00: Well, um, I'll even use an example. 340 00:17:27,839 --> 00:17:29,839 Um, personal level looking inward, but that's the one. 341 00:17:30,000 --> 00:17:30,559 Yeah, yeah, yeah. 342 00:17:30,720 --> 00:17:31,839 Yeah, first look inward. 343 00:17:32,160 --> 00:17:34,480 And then you're gonna go on a Camino de Santiago. 344 00:17:34,640 --> 00:17:35,519 I hate to say it, Rick. 345 00:17:35,680 --> 00:17:39,599 Then you'll go and maybe you'll go to this uh go to this villa 346 00:17:39,599 --> 00:17:40,640 in Tuscany. 347 00:17:40,960 --> 00:17:45,759 Uh so yeah, so when you first look inward, uh, the biggest 348 00:17:45,759 --> 00:17:48,319 thing I always like to see is is there an operating rhythm? 349 00:17:48,480 --> 00:17:50,640 Is there a plan for the plan? 350 00:17:50,880 --> 00:17:54,720 Um, so for example, um, I went into an organization, 351 00:17:54,880 --> 00:17:59,119 Shutterstock, as an example, and what we found was that no one 352 00:17:59,119 --> 00:18:01,039 was hitting their goals. 353 00:18:01,279 --> 00:18:06,000 Um the employee NPS score was a two out of 10. 354 00:18:06,400 --> 00:18:11,680 Uh, you know, the attrition rate was 35% uh when I was joining. 355 00:18:11,759 --> 00:18:13,759 And so obviously something was going on. 356 00:18:13,920 --> 00:18:16,880 And despite all of these acquisitions that Shutterstock 357 00:18:17,039 --> 00:18:21,599 had made, um, no one was selling any of the new products uh that 358 00:18:21,599 --> 00:18:22,000 they had. 359 00:18:22,079 --> 00:18:23,039 And so it was really interesting. 360 00:18:23,200 --> 00:18:25,519 So therefore they weren't hitting their goals and growth 361 00:18:25,519 --> 00:18:27,200 had really stalled uh and slowed. 362 00:18:27,279 --> 00:18:31,119 And so what became really interesting to me was, and of 363 00:18:31,119 --> 00:18:34,000 course, as I was interviewing, it was the talent's terrible. 364 00:18:34,079 --> 00:18:35,359 It's the talent, it's the talent. 365 00:18:35,519 --> 00:18:37,519 And it wasn't that the talent was terrible. 366 00:18:37,599 --> 00:18:40,160 I mean, a good portion of them had been there for eight years. 367 00:18:40,319 --> 00:18:44,160 They may needed to be retrained and retooled a little bit, of 368 00:18:44,160 --> 00:18:44,640 course. 369 00:18:44,799 --> 00:18:49,359 Um, but the first thing that I saw was there was no plan for 370 00:18:49,359 --> 00:18:49,680 the plan. 371 00:18:49,759 --> 00:18:52,799 There was no rhyme or reason to why there were the number of 372 00:18:52,799 --> 00:18:56,000 sales reps that they had, sales and customer success reps that 373 00:18:56,000 --> 00:18:56,480 they had. 374 00:18:56,720 --> 00:19:01,039 Anyone that they had within the organization did not have any 375 00:19:01,039 --> 00:19:02,079 kind of segmentation. 376 00:19:02,240 --> 00:19:05,680 So, like you could have one person who was managing an SMB 377 00:19:05,680 --> 00:19:08,640 account, but they also in their list had a$1.1 million 378 00:19:09,119 --> 00:19:09,759 organization. 379 00:19:09,839 --> 00:19:12,400 Um, they were in completely different industries, completely 380 00:19:12,400 --> 00:19:13,359 different verticals. 381 00:19:13,440 --> 00:19:16,480 Uh, the person who and so, and there was just a mishmash of 382 00:19:16,480 --> 00:19:16,799 accounts. 383 00:19:16,960 --> 00:19:20,000 So, one of the first things that I looked at was all right, if we 384 00:19:20,000 --> 00:19:24,799 were no names and boxes, no people, uh, you know, at all, 385 00:19:25,039 --> 00:19:26,160 what do we look at? 386 00:19:26,240 --> 00:19:27,920 Like, what should this organization look like? 387 00:19:28,079 --> 00:19:31,680 How would we organize this organization if we were thinking 388 00:19:31,680 --> 00:19:35,200 about vertical expertise, if we were thinking about segmentation 389 00:19:35,359 --> 00:19:39,200 and the way that an SMB account needs to be serviced versus a 390 00:19:39,200 --> 00:19:40,960 large enterprise customer? 391 00:19:41,119 --> 00:19:44,640 Um, you know, certain what was the sales cycle and velocity of 392 00:19:44,640 --> 00:19:48,000 a sale for an SMB customer versus someone who needed a lot 393 00:19:48,000 --> 00:19:52,880 more high attention and probably concierge-like support. 394 00:19:53,039 --> 00:19:56,640 And so we began to design the organizational structure to 395 00:19:56,640 --> 00:20:00,319 support the multifaceted way we were going about doing business. 396 00:20:00,480 --> 00:20:02,960 Then we started looking at, okay, we'd have these different 397 00:20:03,039 --> 00:20:04,559 eight different product types. 398 00:20:04,720 --> 00:20:08,559 Um, how and which accounts are our biggest high potential 399 00:20:08,559 --> 00:20:10,880 accounts versus also high performing. 400 00:20:10,960 --> 00:20:14,720 So, you know how there's the nine box that you do for talent 401 00:20:14,720 --> 00:20:16,799 assessment, you know, is this high potential and high 402 00:20:16,880 --> 00:20:17,359 performing? 403 00:20:17,440 --> 00:20:19,039 You can do the same thing with accounts. 404 00:20:19,119 --> 00:20:22,720 Um, and that's in fact how we how we looked at our customer 405 00:20:22,720 --> 00:20:25,519 success modeling was high performance and high high 406 00:20:25,519 --> 00:20:26,319 potential. 407 00:20:26,480 --> 00:20:30,720 Um, and started to assess, okay, what is the sales motion and the 408 00:20:30,720 --> 00:20:31,920 support motion for those? 409 00:20:32,000 --> 00:20:34,960 And then also what is the potential for those? 410 00:20:35,119 --> 00:20:39,119 So uh where can we actually, you know, expect to see all eight 411 00:20:39,440 --> 00:20:42,720 all eight of our product lines being sold versus someone who's 412 00:20:42,720 --> 00:20:46,400 literally just doing something very high velocity and a little 413 00:20:46,400 --> 00:20:47,599 bit more transactional. 414 00:20:47,759 --> 00:20:50,079 And so then we started to look at our talent. 415 00:20:50,240 --> 00:20:52,640 That's when we started looking at our talent and started to 416 00:20:52,640 --> 00:20:54,720 assess where do we have some bright spots? 417 00:20:54,799 --> 00:20:58,480 Where do we have folks who are really killing it and can teach 418 00:20:58,480 --> 00:20:58,880 others? 419 00:20:59,119 --> 00:21:02,000 So I didn't start by letting go of the team. 420 00:21:02,240 --> 00:21:05,839 I started by looking at the team and saying, okay, where do we 421 00:21:05,839 --> 00:21:07,119 have really good performers? 422 00:21:07,279 --> 00:21:08,559 Where can they teach others? 423 00:21:08,720 --> 00:21:12,799 And so we brought in challenger sales methodology into the 424 00:21:12,799 --> 00:21:16,799 organization because a lot of them, even themselves, needed to 425 00:21:16,799 --> 00:21:20,079 be challenged to think differently a little bit. 426 00:21:20,240 --> 00:21:22,880 So we brought in challenger sales methodology to the 427 00:21:22,880 --> 00:21:23,440 organization. 428 00:21:23,599 --> 00:21:26,799 And then there were certain folks that honestly we uh after 429 00:21:26,799 --> 00:21:30,960 doing different role plays and and um and listening to calls 430 00:21:31,119 --> 00:21:34,480 and doing coaching, where we did have to part ways with them or 431 00:21:34,480 --> 00:21:36,319 reallocate them to other parts of the business. 432 00:21:36,400 --> 00:21:39,200 We had an entire support organization that was that was a 433 00:21:39,200 --> 00:21:41,279 really good um fit for some of the people. 434 00:21:41,440 --> 00:21:45,039 And then some of the people just didn't like the new approach and 435 00:21:45,039 --> 00:21:47,440 so decided to self-select out. 436 00:21:47,599 --> 00:21:50,319 Um, but it was really interesting because it was um 437 00:21:50,319 --> 00:21:54,000 such a great way for us to, you know, kind of leverage the 438 00:21:54,000 --> 00:21:56,480 existing talent to help us hire the new talent. 439 00:21:56,640 --> 00:21:59,200 And they became people who we added on the panels. 440 00:21:59,359 --> 00:22:01,759 They became the people that we did recognition for. 441 00:22:01,920 --> 00:22:06,160 And so every month we did fun videos and kept the change alive 442 00:22:06,160 --> 00:22:08,799 by showcasing, look, see, there's success. 443 00:22:08,960 --> 00:22:11,359 We have people who are having success doing this. 444 00:22:11,519 --> 00:22:13,680 And so we would give out awards every month. 445 00:22:13,839 --> 00:22:17,200 There were global awards, we would do fun videos where we 446 00:22:17,200 --> 00:22:18,640 would show all of the different offices. 447 00:22:18,720 --> 00:22:22,000 We had offices in Brazil, Mexico, you know, Germany, uh, 448 00:22:22,160 --> 00:22:24,799 Italy, all over the world, um, Singapore. 449 00:22:25,359 --> 00:22:28,240 And everyone would send in videos once a month of, you 450 00:22:28,240 --> 00:22:32,000 know, kind of their spotlighted customer and also like just fun 451 00:22:32,000 --> 00:22:34,480 things that they'd been doing, whether it was like a plank 452 00:22:34,480 --> 00:22:35,519 contest or something. 453 00:22:35,680 --> 00:22:38,079 So there were just ways that we were trying to keep the culture. 454 00:22:38,240 --> 00:22:42,559 So in the end, we ended up with at least an employee MPS score 455 00:22:42,559 --> 00:22:44,000 of like seven out of 10. 456 00:22:44,240 --> 00:22:49,839 The attrition had switched from a high 35% down to a 2% 457 00:22:50,480 --> 00:22:51,599 attrition rate. 458 00:22:51,759 --> 00:22:56,079 And we had 67% of the team start to pay quota, so a little bit 459 00:22:56,079 --> 00:22:57,279 more of that best practice. 460 00:22:57,440 --> 00:23:01,920 So um, because we'd organized appropriately and reassessed the 461 00:23:01,920 --> 00:23:05,279 talent, but it was secondary, not the primary thing that we 462 00:23:05,279 --> 00:23:07,279 did was just come in and fire everybody. 463 00:23:07,680 --> 00:23:10,720 SPEAKER_02: So let me play back to you the sequence of the 464 00:23:10,720 --> 00:23:15,440 things that I heard and see how much of that can be a template 465 00:23:15,440 --> 00:23:19,359 for you and others when they sort of enter an organization 466 00:23:19,359 --> 00:23:23,039 and things aren't going the way you know we'd hoped uh they'd 467 00:23:23,039 --> 00:23:23,279 be. 468 00:23:23,599 --> 00:23:25,759 So one of the first things you mentioned was just like, well, 469 00:23:25,920 --> 00:23:29,200 take a step back and put a clean slate against the business and 470 00:23:29,200 --> 00:23:31,680 say, hey, if I was going to build a go-to-market motion for 471 00:23:31,680 --> 00:23:34,960 this business as it is today, what would that look like rather 472 00:23:34,960 --> 00:23:38,160 than how do I make the best use of whatever's going on here 473 00:23:38,160 --> 00:23:38,559 today? 474 00:23:38,799 --> 00:23:41,519 And the example that you gave within that was segmentation. 475 00:23:41,680 --> 00:23:44,640 So if I look at the types of deals that are being done by 476 00:23:44,640 --> 00:23:47,920 this business, what is the where is their variety? 477 00:23:48,079 --> 00:23:51,039 So in a classic segmentation model, you have SMB, min-market, 478 00:23:51,279 --> 00:23:54,240 and enterprise, if I see that there's a very different sales 479 00:23:54,240 --> 00:23:57,920 motion that's happening, and yet I'm asking the team to do one 480 00:23:57,920 --> 00:24:00,640 minute sell to the Fortune 100 and the next minute sell to a 481 00:24:00,640 --> 00:24:03,200 mom and pop, that there might be challenges associated with 482 00:24:03,200 --> 00:24:03,599 scaling. 483 00:24:03,680 --> 00:24:06,000 And so segmentation might be the first thing. 484 00:24:06,160 --> 00:24:08,960 And then if we know we're going to segment, the second thing is 485 00:24:08,960 --> 00:24:12,319 then around okay, what is the profile of talent that I would 486 00:24:12,319 --> 00:24:15,680 need for those types of roles, depending on how many of each 487 00:24:15,680 --> 00:24:16,640 that I require? 488 00:24:16,880 --> 00:24:20,000 Another thing that you mentioned was around looking at, if you 489 00:24:20,000 --> 00:24:23,440 have a multi-product portfolio, looking at the product types 490 00:24:23,440 --> 00:24:26,799 individually and saying, okay, which of these is both 491 00:24:26,799 --> 00:24:29,599 performing really well right now, and which of these has the 492 00:24:29,599 --> 00:24:32,640 potential to perform with some added investment, and then be 493 00:24:32,640 --> 00:24:36,079 making decisions around, again, with the clean slate, how do you 494 00:24:36,079 --> 00:24:40,240 bring additional products outside of maybe the core to 495 00:24:40,240 --> 00:24:40,559 market? 496 00:24:41,119 --> 00:24:43,680 And then maybe two other things that you mentioned within there. 497 00:24:43,839 --> 00:24:46,400 One, I heard a lot on communication of change. 498 00:24:46,559 --> 00:24:51,440 So communication of what's going on as you try to move an org, 499 00:24:51,680 --> 00:24:55,039 and then communication in its forms, whether they're videos 500 00:24:55,039 --> 00:24:58,240 and highlighting folks and making people feel a part of 501 00:24:58,240 --> 00:25:01,839 that change, that alone, communication is probably a big 502 00:25:01,839 --> 00:25:02,960 driver of MPS. 503 00:25:03,039 --> 00:25:06,079 Like feeling like you're on the team and not just like people 504 00:25:06,079 --> 00:25:09,599 making decisions in the ivory tower alone is probably pretty 505 00:25:10,240 --> 00:25:10,640 possible. 506 00:25:10,799 --> 00:25:11,119 SPEAKER_01: Yeah. 507 00:25:11,440 --> 00:25:14,480 SPEAKER_02: And then to the extent you get that all going, 508 00:25:14,559 --> 00:25:17,440 okay, how do I institute a methodology to get consistent 509 00:25:17,440 --> 00:25:17,920 execution? 510 00:25:18,000 --> 00:25:20,000 You selected the challenger sale. 511 00:25:20,160 --> 00:25:24,240 And it's like, man, if you can just do these things that you're 512 00:25:24,240 --> 00:25:24,960 gonna help. 513 00:25:25,039 --> 00:25:27,519 I mean, anybody would want to achieve the results of going 514 00:25:27,519 --> 00:25:31,920 from zero quota performance to two-thirds or from um 35% 515 00:25:32,319 --> 00:25:33,200 attrition to two. 516 00:25:33,519 --> 00:25:35,680 So uh that's just like what I'm hearing. 517 00:25:35,759 --> 00:25:40,319 I'm wondering how much of that is the sort of playbook, if you 518 00:25:40,319 --> 00:25:42,799 will, of entering other difficult situations. 519 00:25:43,200 --> 00:25:43,920 SPEAKER_00: Well, I love that. 520 00:25:44,079 --> 00:25:45,519 Gosh, that was so well said. 521 00:25:45,680 --> 00:25:49,039 The um the other thing I think that we did that I think is 522 00:25:49,039 --> 00:25:52,960 really relevant too was we outfitted the team with tools as 523 00:25:52,960 --> 00:25:56,000 well so that they could sell a multi-product solution. 524 00:25:56,240 --> 00:26:00,319 Part of what happened was obviously like the uh the same, 525 00:26:00,559 --> 00:26:03,119 or I'm sorry, the challenger sales methodology was really 526 00:26:03,119 --> 00:26:04,799 helpful for sure. 527 00:26:04,960 --> 00:26:10,000 But also it was the mechanism for them to be able to sell new 528 00:26:10,000 --> 00:26:13,440 products to their solution to their to their customers was one 529 00:26:13,440 --> 00:26:15,680 of those things that they didn't know necessarily how to bring it 530 00:26:15,680 --> 00:26:16,160 up always. 531 00:26:16,240 --> 00:26:19,359 And so we had outfitted them with sales loft at the time. 532 00:26:19,519 --> 00:26:22,799 Um, but now I think of all of the different AI tools that you 533 00:26:22,799 --> 00:26:28,160 could be leveraging to either um uncover who has the most 534 00:26:28,160 --> 00:26:29,119 potential. 535 00:26:29,519 --> 00:26:32,480 Uh you know, not obviously you've got your performance 536 00:26:32,480 --> 00:26:35,839 already with the revenue, uh, revenue that folks are doing, 537 00:26:36,079 --> 00:26:39,359 but you can look with any of these AI tools to start to go, 538 00:26:39,440 --> 00:26:42,559 okay, who might be have the propensity to be able to use it? 539 00:26:42,720 --> 00:26:46,880 And then obviously, then how do I do any outreach with marketing 540 00:26:46,880 --> 00:26:49,359 tools and all that? 541 00:26:49,440 --> 00:26:52,480 And so we had used sales off at the time, but now I think that 542 00:26:52,480 --> 00:26:56,319 there's all sorts of other ways to uncover intent uh and 543 00:26:56,319 --> 00:26:58,000 propensity to buy too. 544 00:26:58,160 --> 00:27:01,119 The other thing I would say is in that performance and 545 00:27:01,119 --> 00:27:04,960 potential uh on the performance side, one of the other elements 546 00:27:04,960 --> 00:27:07,839 that was really interesting and required partnership with our 547 00:27:07,839 --> 00:27:12,240 finance team in particular was evaluating the LTV to CAC for 548 00:27:12,240 --> 00:27:12,960 each of these. 549 00:27:13,039 --> 00:27:18,799 And so there were also segments that we decided to exit and say, 550 00:27:18,960 --> 00:27:21,839 this is actually not a profitable segment for us to for 551 00:27:21,839 --> 00:27:25,359 us to sell to anymore because they don't stay with us, or 552 00:27:25,359 --> 00:27:27,039 because the CAC is not worth it. 553 00:27:27,119 --> 00:27:29,599 Um so you could evaluate all of those elements. 554 00:27:29,680 --> 00:27:32,079 And so when we started to look at, you know, all of the 555 00:27:32,079 --> 00:27:34,480 different segmentation, you started to almost see, okay, 556 00:27:34,559 --> 00:27:36,720 here's where we're going to organize, here's how we're going 557 00:27:36,720 --> 00:27:38,799 to organize, here's how we're going to support it, and then 558 00:27:38,799 --> 00:27:40,720 here are ones that we're just going to exit. 559 00:27:40,799 --> 00:27:44,079 Um so it was a really interesting kind of RevOps 560 00:27:44,319 --> 00:27:47,839 finance product and sales marketing and customer success, 561 00:27:48,000 --> 00:27:51,599 um, you know, kind of cross-functional initiative that 562 00:27:51,599 --> 00:27:54,799 made us stronger and got us growing again. 563 00:27:55,200 --> 00:27:57,279 SPEAKER_02: Why do you think, in the example that you use, which 564 00:27:57,279 --> 00:27:59,359 is an excellent one with Shutterstock, why wasn't that 565 00:27:59,359 --> 00:28:00,640 happening already? 566 00:28:01,119 --> 00:28:04,079 SPEAKER_00: I think they had just had so much chaos. 567 00:28:04,319 --> 00:28:08,400 There had been so much chaos in adding all of these companies. 568 00:28:08,559 --> 00:28:12,240 And they had been on a growing spree, you know, they had been 569 00:28:12,400 --> 00:28:14,240 on an acquisition spree, frankly. 570 00:28:14,559 --> 00:28:16,880 And so they were bringing all of these people together. 571 00:28:17,039 --> 00:28:19,440 And so if you had been there for eight years, which as I 572 00:28:19,440 --> 00:28:22,799 mentioned was the average tenure, you could just kind of 573 00:28:22,799 --> 00:28:25,359 keep doing your thing and not add all of these. 574 00:28:25,440 --> 00:28:29,200 And then it it only, you know, it only became apparent once you 575 00:28:29,200 --> 00:28:30,640 weren't hitting your number. 576 00:28:30,880 --> 00:28:33,119 Why you weren't hitting your number was because you were 577 00:28:33,119 --> 00:28:36,079 selling the thing you had eight years ago, as opposed to all of 578 00:28:36,079 --> 00:28:37,519 the new stuff that you had to sell. 579 00:28:38,160 --> 00:28:40,480 SPEAKER_02: Did you come in after all those acquisitions? 580 00:28:40,720 --> 00:28:41,039 SPEAKER_00: Yeah. 581 00:28:41,200 --> 00:28:43,119 So I came in after all the acquisitions. 582 00:28:43,440 --> 00:28:44,720 SPEAKER_02: What an interesting dimension. 583 00:28:44,799 --> 00:28:47,279 And I think we're starting to see consolidation and 584 00:28:47,279 --> 00:28:48,240 acquisitions happening. 585 00:28:48,559 --> 00:28:53,039 Acquisitions are um so difficult to execute because of all the 586 00:28:53,039 --> 00:28:54,400 examples that you just gave. 587 00:28:54,559 --> 00:28:57,680 It's like fun to get the deal done, but then making it work 588 00:28:57,680 --> 00:29:00,079 afterwards is like way harder. 589 00:29:00,240 --> 00:29:04,480 Oh, and so I mean, I had to multiple times over, it does 590 00:29:04,480 --> 00:29:08,720 just naturally create a high state of unsettledness, and 591 00:29:08,720 --> 00:29:10,799 that's being you know optimistic. 592 00:29:11,119 --> 00:29:11,519 SPEAKER_00: Absolutely. 593 00:29:11,680 --> 00:29:14,799 Well, and I've had to do that short held before that. 594 00:29:15,039 --> 00:29:18,799 We were a premises-based unified communication solution, and we 595 00:29:18,799 --> 00:29:20,480 bought a cloud company. 596 00:29:20,799 --> 00:29:23,039 Everything about us was different, right? 597 00:29:23,119 --> 00:29:26,720 Uh, it was monthly recurring revenue versus upfront CapEx 598 00:29:26,799 --> 00:29:30,319 investment, making all of your money through partners uh and 599 00:29:30,319 --> 00:29:33,359 through that upfront investment, in fact, selling against each 600 00:29:33,359 --> 00:29:34,720 other a lot of the times. 601 00:29:34,880 --> 00:29:37,440 Um, and so it was really interesting to watch that 602 00:29:37,440 --> 00:29:37,759 happen. 603 00:29:37,839 --> 00:29:40,640 And that was the first place that I became, frankly, uh it 604 00:29:40,640 --> 00:29:44,079 was a VP of sales and customer success where I saw the impact 605 00:29:44,079 --> 00:29:48,079 across marketing, sales, onboarding, customer success, 606 00:29:48,319 --> 00:29:48,880 support. 607 00:29:49,039 --> 00:29:52,079 I saw the impact of selling to the wrong type of customer. 608 00:29:52,160 --> 00:29:56,480 Um, we had an example of we used to sell to law firms as an 609 00:29:56,480 --> 00:29:59,359 example in our cloud solution. 610 00:29:59,519 --> 00:30:03,279 And you You would do so much work to market to them, to then 611 00:30:03,279 --> 00:30:06,319 go through the months of red lines with this law firm, right? 612 00:30:06,480 --> 00:30:09,839 Then it would take months and months to onboard them. 613 00:30:09,920 --> 00:30:13,920 Um, and then the second that you got them live and there was any 614 00:30:13,920 --> 00:30:16,880 disruption in service at all, they churned. 615 00:30:17,039 --> 00:30:19,759 And so it turned into, it was actually very fascinating. 616 00:30:19,920 --> 00:30:22,400 This was my entire career, had just been in sales. 617 00:30:22,480 --> 00:30:25,119 And so here I am thinking, well, we did our thing right. 618 00:30:25,200 --> 00:30:28,000 We got that, we got that deal closed, right? 619 00:30:28,160 --> 00:30:29,839 Um, we got our commission. 620 00:30:30,079 --> 00:30:33,279 And it turned into this was the first time where I really went, 621 00:30:33,359 --> 00:30:36,960 oh my gosh, it's not about doing your thing right, it's about 622 00:30:36,960 --> 00:30:37,920 doing the right thing. 623 00:30:38,160 --> 00:30:43,599 And so we evolved and changed our entire 150-person team to 624 00:30:43,599 --> 00:30:47,839 where no longer was anyone able to sell to law firms or market 625 00:30:47,839 --> 00:30:52,000 to law firms or keep a law firm because we now went, who is the 626 00:30:52,000 --> 00:30:55,920 longest, who's the LTV, who has the longest tenure, retention, 627 00:30:56,000 --> 00:30:56,799 et cetera, with us? 628 00:30:56,960 --> 00:30:59,519 Who is the right ICP for us to be selling to? 629 00:30:59,759 --> 00:31:03,839 And so not only did we change who our ICP was and like all get 630 00:31:03,839 --> 00:31:06,559 aligned to it, but then I also changed the compensation model 631 00:31:06,559 --> 00:31:07,200 for everyone. 632 00:31:07,359 --> 00:31:10,319 So everyone had the compensation that they were entitled, you 633 00:31:10,319 --> 00:31:11,680 know, that they were responsible for. 634 00:31:11,839 --> 00:31:16,559 So sellers, it was new ARR for the support team, it was their, 635 00:31:16,640 --> 00:31:21,039 you know, uh their uh first call resolution, uh, was their 636 00:31:21,039 --> 00:31:23,119 primary way of getting paid, right? 637 00:31:23,200 --> 00:31:24,960 Either for their bonus or their commission. 638 00:31:25,119 --> 00:31:29,680 But 25% of everyone's variable compensation had a retention 639 00:31:29,680 --> 00:31:30,559 element to it. 640 00:31:30,880 --> 00:31:34,240 So that you were not just doing your thing right, but you were 641 00:31:34,240 --> 00:31:36,480 doing the right thing holistically for the 642 00:31:36,480 --> 00:31:39,440 organization to succeed, which was all about retention and 643 00:31:39,440 --> 00:31:40,880 long-term value of the customers. 644 00:31:42,079 --> 00:31:44,640 SPEAKER_02: Bridget, you know, just in this conversation, it's 645 00:31:44,640 --> 00:31:48,000 clear you've walked into some tumultuous situations. 646 00:31:48,480 --> 00:31:51,599 Walk into acquisition-based tumult. 647 00:31:51,920 --> 00:31:55,200 That's probably like on the degree of difficulty scale as 648 00:31:55,200 --> 00:31:56,160 high as it gets. 649 00:31:56,319 --> 00:31:59,759 And if you can successfully navigate the change management 650 00:31:59,759 --> 00:32:04,480 or transformation in that context, imagine what you can do 651 00:32:04,480 --> 00:32:07,119 when you don't have the one hand, the one arm tied behind 652 00:32:07,119 --> 00:32:10,400 your back in terms of doing that. 653 00:32:10,720 --> 00:32:17,039 I wouldn't underestimate the um the skills that one acquires to 654 00:32:17,039 --> 00:32:20,880 be able to effectively um manage growth. 655 00:32:20,960 --> 00:32:25,359 Um, but if you think about coming into a situation in a you 656 00:32:25,359 --> 00:32:28,640 know more favorable starting point, so to speak, um, you 657 00:32:28,640 --> 00:32:31,440 know, that the idea of accelerating growth might be 658 00:32:31,440 --> 00:32:34,240 really compelling and exciting based on what because you've 659 00:32:34,240 --> 00:32:37,680 already seen the harder uh you know, sort of picture. 660 00:32:38,000 --> 00:32:41,039 Another thing that kind of comes to mind for me is in order to 661 00:32:41,039 --> 00:32:45,920 effectively transform an organization in any way, I 662 00:32:45,920 --> 00:32:49,680 imagine you you talked about this cross-functional dynamic 663 00:32:49,920 --> 00:32:53,519 working with finance and working with RevOps and looking at LTB 664 00:32:53,519 --> 00:32:57,119 and cat to cat and making the tough decisions that you can't 665 00:32:57,119 --> 00:33:00,319 make on your own about what are we not going to do anymore? 666 00:33:00,480 --> 00:33:02,559 Law firms, in your example, being the perfect thing. 667 00:33:02,720 --> 00:33:05,279 We're able to close deals there, but it's not good business. 668 00:33:05,440 --> 00:33:09,599 It takes a village, so to speak, to come to agreement that we 669 00:33:09,599 --> 00:33:10,640 can't do this anymore. 670 00:33:10,799 --> 00:33:14,400 Can you talk a little bit about um you know how you pursue now 671 00:33:14,400 --> 00:33:18,160 cross-functional relationships at the executive level and maybe 672 00:33:18,160 --> 00:33:21,119 the learnings that have gotten you to your worldview today? 673 00:33:21,599 --> 00:33:27,759 SPEAKER_00: Yeah, I mean, I'm a big, let's say, management book 674 00:33:27,759 --> 00:33:28,319 reader. 675 00:33:28,480 --> 00:33:29,920 I love books on leadership. 676 00:33:30,000 --> 00:33:36,000 So one of my favorite ones is uh shockingly, Stanley McChrystal, 677 00:33:36,240 --> 00:33:39,359 General Stanley McChrystal's book called Team of Teams, where 678 00:33:39,359 --> 00:33:43,519 he talks about how they were able to defeat Al-Qaeda in Iraq. 679 00:33:43,599 --> 00:33:50,960 And he uh he managed the joint operations special forces, and 680 00:33:50,960 --> 00:33:53,519 it was all of these individual branches of the government, 681 00:33:53,680 --> 00:33:53,920 right? 682 00:33:54,000 --> 00:33:56,640 And so they were all in Iraq trying to, you know, kind of 683 00:33:56,640 --> 00:33:58,720 defeat this very nimble enemy. 684 00:33:58,960 --> 00:34:02,240 And he found that this, you know, we're the US had the 685 00:34:02,240 --> 00:34:05,119 strongest military in the world, and we're getting beat every day 686 00:34:05,119 --> 00:34:08,320 by a more nimble, flexible, you know, adversary. 687 00:34:08,480 --> 00:34:12,159 And it was because of the things they were doing internally to 688 00:34:12,639 --> 00:34:13,679 make things harder. 689 00:34:13,840 --> 00:34:19,440 So one branch of the military had like an informant and 690 00:34:19,599 --> 00:34:23,119 someone who was, you know, kind of their their go-to guy. 691 00:34:23,280 --> 00:34:25,920 Another branch of the military was like targeting that person. 692 00:34:26,079 --> 00:34:29,840 So, you know, they it everything was misaligned. 693 00:34:30,079 --> 00:34:33,679 And so I think of that book a lot, and that's where I got that 694 00:34:33,679 --> 00:34:38,000 whole, you know, do the right thing versus doing your thing 695 00:34:38,000 --> 00:34:41,119 right, um, because he basically changed it to where he said, now 696 00:34:41,280 --> 00:34:44,480 we are a team of teams, we are doing missions together, we are 697 00:34:44,480 --> 00:34:47,519 aligned on what our missions are, and the ultimate goal is 698 00:34:47,519 --> 00:34:51,840 the, is like, is the is to defeat al-Qaeda and Iraq. 699 00:34:51,920 --> 00:34:54,880 Uh, in the same sense, I think of, you know, the ultimate goal 700 00:34:54,880 --> 00:34:58,159 is the organization's goal, not just your sales goal or not just 701 00:34:58,159 --> 00:34:59,440 your product team's goal. 702 00:34:59,679 --> 00:35:03,119 The other thing I've read was Five Dysfunctions of a Team. 703 00:35:03,199 --> 00:35:04,960 That's one of my favorite books ever, too. 704 00:35:05,119 --> 00:35:08,079 And they always highlight that the team that you are on is your 705 00:35:08,079 --> 00:35:13,199 most senior team that you are on cross-functionally, not the team 706 00:35:13,199 --> 00:35:13,760 you lead. 707 00:35:13,920 --> 00:35:17,920 And so, again, my team is not my sales or my customer success or 708 00:35:17,920 --> 00:35:18,960 my marketing team. 709 00:35:19,199 --> 00:35:22,559 My team is me and my chief product officer, my chief 710 00:35:22,559 --> 00:35:23,519 financial officer. 711 00:35:23,760 --> 00:35:28,239 We are solving the CEO's problems, uh, not necessarily 712 00:35:28,239 --> 00:35:32,239 just the problems of our team, um, or only answering that. 713 00:35:32,320 --> 00:35:35,519 And so, and I think there's no better, you know, kind of 714 00:35:35,519 --> 00:35:39,519 definition of that than aligning on, let's say, an ideal customer 715 00:35:39,519 --> 00:35:40,159 profile. 716 00:35:40,480 --> 00:35:43,760 That I would be, you know, that is like one of the perfect 717 00:35:43,760 --> 00:35:46,480 examples of you think that maybe that's just a go-to-market 718 00:35:46,639 --> 00:35:47,280 challenge. 719 00:35:47,519 --> 00:35:48,559 Absolutely not. 720 00:35:48,719 --> 00:35:53,920 Your CFO, your chief product officer, your CEO, um, everyone 721 00:35:53,920 --> 00:35:58,000 within your organization needs to be aligned on who your ICP is 722 00:35:58,159 --> 00:36:01,440 and what that means if you are only selling to that or if you 723 00:36:01,440 --> 00:36:03,119 are choosing to go beyond it. 724 00:36:03,280 --> 00:36:07,199 Um, so even something like the ICP work that I think is 725 00:36:07,199 --> 00:36:10,239 probably the most important thing, allows you to know where 726 00:36:10,239 --> 00:36:15,199 are we, where are we targeting and and what are we willing to 727 00:36:15,199 --> 00:36:19,360 spend to get that customer and what are we doing, you know, to 728 00:36:19,360 --> 00:36:22,079 service and support and keep that customer. 729 00:36:22,159 --> 00:36:25,599 Uh, and I think there there's there's no more kind of example 730 00:36:25,599 --> 00:36:29,760 of something where it aligns the entire executive team more than 731 00:36:29,760 --> 00:36:30,880 something like ICP. 732 00:36:31,599 --> 00:36:33,360 SPEAKER_02: Yeah, I mean, that's a great example. 733 00:36:33,440 --> 00:36:36,480 Um, you know, Lencioni's five dysfunctions of a team. 734 00:36:36,559 --> 00:36:40,400 Um, I've heard a lot about this, that the idea that your team is 735 00:36:40,400 --> 00:36:43,039 your peers and not the folks that roll up to you. 736 00:36:43,199 --> 00:36:46,239 And I think everybody nods and you know vigorously agrees, 737 00:36:46,400 --> 00:36:46,960 yeah, sure. 738 00:36:47,119 --> 00:36:50,880 But the actual like application of that in the real world is 739 00:36:50,880 --> 00:36:53,119 much tougher than it sounds. 740 00:36:53,360 --> 00:36:58,559 It's very easy to live within your um your silo of 741 00:36:58,559 --> 00:36:59,519 responsibility. 742 00:36:59,679 --> 00:37:02,639 Uh, first of all, those folks report up to you, and so if you 743 00:37:02,639 --> 00:37:07,119 call, they answer, and you understand the deep context of 744 00:37:07,119 --> 00:37:09,760 the things that A, that they should be doing, B, the things 745 00:37:09,760 --> 00:37:12,559 they are doing, and C the struggles or challenges or 746 00:37:12,559 --> 00:37:15,199 objectives or obstacles that they might be facing. 747 00:37:15,440 --> 00:37:19,679 And so the inertia is pushing you at all times to work within 748 00:37:19,679 --> 00:37:20,400 that silo. 749 00:37:20,719 --> 00:37:20,960 Yeah. 750 00:37:21,119 --> 00:37:24,159 Like, for example, you might not be the head of engineering, you 751 00:37:24,159 --> 00:37:26,239 might not have any idea how to write code. 752 00:37:26,320 --> 00:37:29,039 So, like, what are you gonna talk to the head of engineering 753 00:37:29,039 --> 00:37:29,280 about? 754 00:37:29,440 --> 00:37:32,719 It's like you don't want to tell him about or her about the 755 00:37:32,719 --> 00:37:35,440 quality of the engineers because that's not your role. 756 00:37:35,519 --> 00:37:38,079 So you don't want to be coming across like you're infringing, 757 00:37:38,239 --> 00:37:42,719 or the head of product, or finance, or whatever the area of 758 00:37:42,719 --> 00:37:44,000 specialization is. 759 00:37:44,159 --> 00:37:47,760 So I think the idea that, like, hey, your first team is your 760 00:37:47,760 --> 00:37:51,119 peers and not just like the folks that report up into your 761 00:37:51,119 --> 00:37:56,559 org is much harder to actually apply because all the inertia is 762 00:37:56,559 --> 00:38:00,079 also pushing them to focus on the things they need to do day 763 00:38:00,159 --> 00:38:01,519 to day and so on and so forth. 764 00:38:01,679 --> 00:38:06,480 So I think a challenge for leaders is a the recognition of 765 00:38:06,480 --> 00:38:09,519 what you described, but then B, how do I put that into practice? 766 00:38:09,599 --> 00:38:10,719 How have you done so? 767 00:38:11,039 --> 00:38:11,599 SPEAKER_00: Oh, yeah. 768 00:38:11,760 --> 00:38:14,239 Well, it's aligned compensation, number one. 769 00:38:14,559 --> 00:38:18,079 So, you know, the salesperson in me dies hard because I think 770 00:38:18,079 --> 00:38:22,559 aligned compensation always is a way to reinforce the the goals 771 00:38:22,559 --> 00:38:23,199 that you have. 772 00:38:23,440 --> 00:38:26,880 So, um, and I mean that company wide. 773 00:38:27,039 --> 00:38:31,519 Um, I think there's also um I think what is it, people have to 774 00:38:31,519 --> 00:38:33,679 hear something nine times before it actually sticks. 775 00:38:33,840 --> 00:38:37,039 Um so I think it's also every single I think yeah, exactly. 776 00:38:37,199 --> 00:38:37,760 Yeah, yeah. 777 00:38:38,000 --> 00:38:38,880 It was nine. 778 00:38:39,039 --> 00:38:39,840 I think it's nine. 779 00:38:40,000 --> 00:38:40,400 I don't know. 780 00:38:40,480 --> 00:38:42,960 It's either seven or nine, and I can never remember. 781 00:38:43,119 --> 00:38:43,679 Yeah. 782 00:38:43,840 --> 00:38:46,639 And I'm like, I clearly I need to hear it more often. 783 00:38:46,800 --> 00:38:52,880 So the um, but I think at every uh, you know, all team meeting 784 00:38:52,880 --> 00:38:55,840 that you hold, every organizational meeting that you 785 00:38:55,840 --> 00:38:59,039 have, every time you kick off a meeting, as a reminder, our goal 786 00:38:59,039 --> 00:39:02,639 is that we are getting to this revenue target or retention rate 787 00:39:02,639 --> 00:39:06,800 should be this, or ICP is this, and we are looking at our ICP 788 00:39:06,800 --> 00:39:07,679 penetration rate. 789 00:39:07,840 --> 00:39:11,920 Like whatever that one thing is, and I always usually, if it can 790 00:39:11,920 --> 00:39:13,360 be one thing, it's ideal. 791 00:39:13,519 --> 00:39:16,719 Uh, if it is one thing that you can find is the ruthless 792 00:39:16,719 --> 00:39:19,440 priority of the organization that you are galvanizing the 793 00:39:19,440 --> 00:39:23,039 team around, then it is it's the one thing that you are always 794 00:39:23,039 --> 00:39:23,599 talking about. 795 00:39:23,679 --> 00:39:26,159 It's the one thing you are paying them on, whether it's 796 00:39:26,159 --> 00:39:31,039 their bonuses for uh usually the non-commission carrying folks or 797 00:39:31,039 --> 00:39:33,760 the uh or the commission carrying folks having a 798 00:39:33,760 --> 00:39:37,599 component of it to be uh to be um uh you know something that 799 00:39:37,599 --> 00:39:38,960 they are incentivized to. 800 00:39:39,119 --> 00:39:41,280 And then the third element I would say, so it's you know, 801 00:39:41,360 --> 00:39:44,400 aligned compensation, number two would be the you know, 802 00:39:44,559 --> 00:39:46,320 relentless discussion about it. 803 00:39:46,480 --> 00:39:49,679 The third would be find some way to make it fun. 804 00:39:50,079 --> 00:39:52,480 Find some way to make it fun. 805 00:39:52,719 --> 00:39:56,480 Um, and that they care about it because I have done, I can't 806 00:39:56,480 --> 00:39:58,880 even tell you the amount of embarrassing things that I've 807 00:39:58,880 --> 00:40:01,760 done where like if we hit a certain goal, there's pie in the 808 00:40:01,760 --> 00:40:02,000 face. 809 00:40:02,079 --> 00:40:06,000 If we hit a certain goal, I'm doing chapel roan karaoke, which 810 00:40:06,000 --> 00:40:07,519 you don't have to ask me too much. 811 00:40:07,679 --> 00:40:09,440 I will, I will raise my hand to do. 812 00:40:09,760 --> 00:40:14,400 But the there's so many things that are, you know, ways to like 813 00:40:14,400 --> 00:40:18,880 make that fun, or you know, the whole company gets um, you know, 814 00:40:19,039 --> 00:40:21,199 I don't know, a what have we done? 815 00:40:21,280 --> 00:40:24,400 We've done like yoga class together. 816 00:40:24,559 --> 00:40:28,880 Um, uh the entire company gets to have a half day off or 817 00:40:28,880 --> 00:40:29,199 something. 818 00:40:29,280 --> 00:40:31,920 You know, like there were there were things like that that we 819 00:40:31,920 --> 00:40:34,239 would do, and there were always little small milestones. 820 00:40:34,320 --> 00:40:36,159 And I've also heard this is what they do. 821 00:40:36,320 --> 00:40:40,159 Um, that, you know, as you were in pursuit of a goal, you don't 822 00:40:40,159 --> 00:40:42,719 do milestones, you do inch pebbles. 823 00:40:44,159 --> 00:40:45,199 Love that term. 824 00:40:45,360 --> 00:40:48,880 Um, I stole that from my favorite book, Switch, How to 825 00:40:48,880 --> 00:40:50,159 Change When Change is Hard. 826 00:40:50,239 --> 00:40:52,079 That's another one of my books that I love. 827 00:40:52,239 --> 00:40:56,559 Um, and they basically are like, this is the this the way that 828 00:40:56,559 --> 00:41:01,599 you create success is to show that success can be uh can can 829 00:41:01,599 --> 00:41:02,079 happen. 830 00:41:02,239 --> 00:41:05,280 And so, for example, if you're showing a timeline, you never 831 00:41:05,280 --> 00:41:07,119 show yourself at the beginning of this. 832 00:41:07,280 --> 00:41:09,199 You show yourself, see, we've already started. 833 00:41:09,280 --> 00:41:11,119 We're about 25% of the way there. 834 00:41:11,280 --> 00:41:14,400 So you already show, look, success is is already begetting 835 00:41:14,400 --> 00:41:14,960 success. 836 00:41:15,199 --> 00:41:19,920 People would rather be in part way through a longer journey 837 00:41:19,920 --> 00:41:21,920 than at the beginning of a shorter one. 838 00:41:22,079 --> 00:41:26,480 That is one of the invaluable lessons uh that Switch teaches 839 00:41:26,480 --> 00:41:26,559 you. 840 00:41:26,639 --> 00:41:29,599 And so that's where these little inch pebbles of shrinking the 841 00:41:29,599 --> 00:41:32,159 change that you were trying to get to work. 842 00:41:32,400 --> 00:41:35,920 And I will tell you, on that third day, on that Camino de 843 00:41:36,000 --> 00:41:40,000 Santiago, when I did not want to do this, I was using inch 844 00:41:40,000 --> 00:41:42,480 pebbles to motivate myself on this journey. 845 00:41:42,639 --> 00:41:46,079 I was doing, I was like, just get to that place so that you 846 00:41:46,079 --> 00:41:47,280 can have a coffee. 847 00:41:47,519 --> 00:41:50,079 Just get to that place so you can wring out your socks. 848 00:41:50,320 --> 00:41:54,000 It was small little change, or and I was like, you know, giving 849 00:41:54,000 --> 00:41:56,480 myself, uh giving myself little treats. 850 00:41:56,639 --> 00:41:58,719 Oh, then you can get your protein bar. 851 00:41:58,880 --> 00:42:01,840 You know, I was doing little things to like motivate myself 852 00:42:02,000 --> 00:42:03,920 because I couldn't talk to her, you know, I wasn't really 853 00:42:03,920 --> 00:42:04,960 talking to anybody. 854 00:42:05,039 --> 00:42:08,239 Um, and so all of those things are, you know, all of these 855 00:42:08,239 --> 00:42:11,519 change management tactics that you use are things that you can 856 00:42:11,519 --> 00:42:13,119 use on yourself too. 857 00:42:13,440 --> 00:42:14,079 SPEAKER_02: Totally. 858 00:42:14,320 --> 00:42:16,000 Bridget, you're back here in New York. 859 00:42:16,159 --> 00:42:17,360 What's next for you? 860 00:42:17,679 --> 00:42:20,960 SPEAKER_00: Um I'll be uh the chief revenue officer at a 861 00:42:20,960 --> 00:42:22,559 company called Patient Now. 862 00:42:22,960 --> 00:42:29,519 Uh it is the back-end practice management uh for med spas and 863 00:42:29,519 --> 00:42:34,079 aesthetic practices, uh, an amazing vertical SaaS company 864 00:42:34,079 --> 00:42:39,599 that is in the hyper-growth$20 billion uh market and growing at 865 00:42:39,599 --> 00:42:41,440 15% every year. 866 00:42:41,679 --> 00:42:47,920 So extremely great space and uh allows for Patient Now to be the 867 00:42:48,079 --> 00:42:48,880 market leader in that. 868 00:42:48,960 --> 00:42:49,920 So I'm excited for that. 869 00:42:50,480 --> 00:42:51,360 SPEAKER_02: Fantastic, Bridget. 870 00:42:51,519 --> 00:42:53,920 I feel like we just got started here talking, but we have run 871 00:42:53,920 --> 00:42:54,400 out of time. 872 00:42:54,639 --> 00:42:57,360 Best wishes, and I'm sure you're gonna do an amazing job in the 873 00:42:57,360 --> 00:42:57,679 new role. 874 00:42:57,760 --> 00:43:00,880 It was fun talking about your personal experience and your 875 00:43:00,880 --> 00:43:05,199 personal reasons, about your experience with revamping 876 00:43:05,280 --> 00:43:08,880 process and incorporating talent into the bigger picture and how 877 00:43:08,880 --> 00:43:12,400 you sort of cross-functionally bring the org along with you. 878 00:43:12,559 --> 00:43:13,679 Um, it's been awesome. 879 00:43:13,760 --> 00:43:16,000 So, Bridget, thank you very much for joining. 880 00:43:16,159 --> 00:43:16,960 Where should people find you? 881 00:43:17,119 --> 00:43:18,079 LinkedIn the place to go? 882 00:43:18,239 --> 00:43:19,679 SPEAKER_00: Yes, LinkedIn is the place. 883 00:43:19,760 --> 00:43:20,960 My DMs are open. 884 00:43:21,039 --> 00:43:22,000 Feel free. 885 00:43:22,320 --> 00:43:22,800 Awesome. 886 00:43:22,960 --> 00:43:23,840 Thank you very much. 887 00:43:24,079 --> 00:43:25,199 Thank you so much, Rick. 888 00:43:25,440 --> 00:43:25,920 This was so fun. 889 00:43:33,760 --> 00:43:35,920 SPEAKER_02: Reflecting on the conversation we just had with 890 00:43:35,920 --> 00:43:40,000 Bridget Winston, so many little tidbits of wisdom that were 891 00:43:40,000 --> 00:43:44,400 shared, it's hard to sort of compile it down to three big 892 00:43:44,400 --> 00:43:46,239 themes, but I'm gonna attempt to do that. 893 00:43:46,320 --> 00:43:49,679 And the first thing that stands out to me, so much of this show, 894 00:43:49,840 --> 00:43:54,239 is about tactics to help us be better sales leaders, better 895 00:43:54,239 --> 00:43:56,079 leaders, better professionals. 896 00:43:56,239 --> 00:44:00,000 And there's a whole nother side to us beyond our professional 897 00:44:00,000 --> 00:44:04,400 selves that in our personal journeys outside of just work, 898 00:44:04,480 --> 00:44:08,320 and Bridget's sharing her story and her personal journey between 899 00:44:08,320 --> 00:44:11,840 roles, taking a trip on the other side of the world, stories 900 00:44:11,840 --> 00:44:15,440 of adversity, stories of loss, stories of meaning, stories of 901 00:44:15,440 --> 00:44:19,599 spirituality, it gives us an opportunity to reflect and think 902 00:44:19,599 --> 00:44:21,280 about what is our own journey? 903 00:44:21,519 --> 00:44:24,880 What is the meaning we are finding beyond the work that we 904 00:44:24,880 --> 00:44:25,119 do? 905 00:44:25,280 --> 00:44:28,559 And when you hear another leader, a successful leader, 906 00:44:28,719 --> 00:44:32,239 share a story with some vulnerability in it, with some, 907 00:44:32,320 --> 00:44:35,920 you know, unconventional or not, you know, not your typical trip 908 00:44:35,920 --> 00:44:39,840 that folks would take, it helps form thoughts about our own 909 00:44:39,840 --> 00:44:44,000 search for meaning in our humanity beyond our ambition and 910 00:44:44,000 --> 00:44:45,039 our professional careers. 911 00:44:45,119 --> 00:44:48,079 So thank you, Bridget, for that uh storytelling. 912 00:44:48,320 --> 00:44:52,800 The second thing, the difficulty in when you have a company that 913 00:44:52,800 --> 00:44:54,239 grows through acquisition. 914 00:44:54,320 --> 00:44:56,639 And I'm not saying just one acquisition, I'm talking 915 00:44:56,639 --> 00:44:57,760 multiple acquisitions. 916 00:44:57,920 --> 00:45:01,840 And Bridget told stories that reflect the challenges 917 00:45:01,840 --> 00:45:05,039 associated with digesting and consuming and moving forward 918 00:45:05,039 --> 00:45:07,519 successfully when you've been in an acquisition-heavy 919 00:45:07,519 --> 00:45:08,159 environment. 920 00:45:08,320 --> 00:45:11,599 She told stories of having to like take a step back and get to 921 00:45:11,599 --> 00:45:14,719 the fundamentals of how would we run this business if we were to 922 00:45:14,719 --> 00:45:19,119 start it today and having to do basic things that weren't being 923 00:45:19,119 --> 00:45:22,480 done in an environment that you know might be described as 924 00:45:22,480 --> 00:45:23,280 chaotic. 925 00:45:23,360 --> 00:45:26,719 Um, and so that you know, I want to tip my hat to all of the 926 00:45:26,719 --> 00:45:30,079 sales leaders out there that are leading businesses that have 927 00:45:30,079 --> 00:45:32,960 been acquisition heavy, and I want to acknowledge the 928 00:45:32,960 --> 00:45:33,920 difficulty it is. 929 00:45:34,000 --> 00:45:38,639 And now I kind of understand at a greater level why such a large 930 00:45:38,639 --> 00:45:43,519 percentage of deals that get done don't translate into the 931 00:45:43,519 --> 00:45:47,039 value creation that was sold as part of that acquisition effort. 932 00:45:47,119 --> 00:45:49,360 Now, if you have a leader like Bridget, you have a better 933 00:45:49,360 --> 00:45:52,559 chance of being able to take a step back and then execute 934 00:45:52,559 --> 00:45:53,119 accordingly. 935 00:45:53,199 --> 00:45:56,880 But boy, her stories uh showed the difficulty in doing that. 936 00:45:56,960 --> 00:45:59,360 And so it's like almost operating with one arm tied 937 00:45:59,519 --> 00:46:00,079 behind your back. 938 00:46:00,159 --> 00:46:04,719 And so um, for me, it's like, okay, uh acquisitions sound fun, 939 00:46:04,800 --> 00:46:07,840 and when you see them happen on LinkedIn, people are celebrating 940 00:46:07,840 --> 00:46:10,880 them, but the there is hard work that has to happen on the other 941 00:46:10,880 --> 00:46:11,679 side of that. 942 00:46:11,840 --> 00:46:15,679 Um, the last reflection I have from the episode is when Bridget 943 00:46:15,679 --> 00:46:18,480 was talking about cross-functional leadership. 944 00:46:18,639 --> 00:46:20,639 And she made the point of making it fun. 945 00:46:20,800 --> 00:46:22,639 And I think it's a super important point. 946 00:46:22,800 --> 00:46:26,239 We all are trying to make the biggest impact we can on our 947 00:46:26,239 --> 00:46:28,239 organizations and develop the right relationships. 948 00:46:28,320 --> 00:46:31,199 And it's difficult when we are in a large group of humans 949 00:46:31,199 --> 00:46:33,360 working together towards a common goal. 950 00:46:33,599 --> 00:46:37,440 And it is important that the journey doesn't just have to be 951 00:46:37,440 --> 00:46:37,679 hard. 952 00:46:37,760 --> 00:46:39,119 It can be hard and fun. 953 00:46:39,199 --> 00:46:42,320 And it can be fun to be in a challenging environment. 954 00:46:42,400 --> 00:46:45,280 And I loved Bridget uh emphasizing the importance of 955 00:46:45,280 --> 00:46:45,440 that. 956 00:46:45,599 --> 00:46:49,280 I think we all need to be having fun along the way while we do 957 00:46:49,280 --> 00:46:53,440 the hard work of being great leaders, of learning how to be 958 00:46:53,679 --> 00:46:57,519 positive impacts across the areas of responsibility that we 959 00:46:57,519 --> 00:46:58,239 are working through. 960 00:46:58,320 --> 00:47:00,320 So thank you, Bridget, for a great discussion. 961 00:47:00,559 --> 00:47:01,760 Really appreciate it. 962 00:47:01,920 --> 00:47:03,840 Thank you to Ari Smolin for producing. 963 00:47:03,920 --> 00:47:05,760 Thank you to Sons of Summer for the tunes. 964 00:47:05,920 --> 00:47:07,679 Thank you, listener, for being here today. 965 00:47:07,760 --> 00:47:10,000 We will see you next time on Pillow Talks.