Bridget Winston on this episode
Bridget Winston is the Chief Revenue Officer of PatientNow and previously led revenue operations at Chief (the membership platform for executive women), Shutterstock, and ShoreTel. Her career spans unified communications SaaS, stock content marketplaces, membership platforms, and vertical SaaS—a range that gives her an operator's perspective on what works when legacy playbooks fail.
In this episode of CRO Stories, Rachael Bueckert and Bridget discuss how she scaled Chief from 1,500 to 20,000 members and a $1.1 billion valuation. The core claim: ideal customer profile (ICP) is everything—and most companies think they know theirs when they haven't gone deep enough into retention, unit economics, and actual customer composition.
Bridget emphasizes that discovering your true ICP requires financial analysis across customer segments, not just survey responses or surface-level data. She deployed AI data enrichment at Chief to uncover that solo entrepreneurs represented roughly 25% of the member base, not the 5% initially assumed—a realization that fundamentally reshaped product and go-to-market strategy. The deeper insight is that a true CRO operates across marketing, sales, and customer success, aligning all three functions around shared metrics (not just top-of-funnel vanity metrics) to ensure you're acquiring and retaining the right customers.
The episode also covers pivots driven by COVID-era market shifts, the UK expansion failure, why Bridget intentionally took a customer success role to become a better revenue leader, how she uses AI to accelerate segmentation and capacity planning, and her discipline around organizational change management—including how to diagnose team underperformance by looking inward at process and structure before blaming talent.
What we cover in this episode
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3:10
What Broke During Scaling Chief pivoted from in-person NYC-only to national to virtual and back, revealing product-market fit is never static.
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5:29
UK Expansion Failure Despite planning and research, UK market dynamics—funding, pricing elasticity, comfort with vulnerability—didn't match US model.
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8:00
AI Data Enrichment for ICP Good Work tool revealed true customer segments and lifetime value patterns that surveys and assumptions had masked.
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10:35
ICP Is Everything True CRO work is finding the customer profile where acquisition, retention, and word-of-mouth flywheel work together.
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13:48
CRO vs. VP of Sales Test If you're not doing financial analysis by segment and aligning compensation across marketing-sales-CS, you're a glorified VP of Sales.
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16:00
The ShoreTel Case Study Aligned comp plans across teams to stop selling to law firms who churned immediately, shifting the entire company ICP.
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19:00
Why She Took a CS Role Bridget intentionally moved to head of global customer success to understand retention—now her CRO differentiator.
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27:43
Two-Way Doors vs. Big Solutions Test and iterate on most decisions; only commit big resources to irreversible one-way-door choices.
The lines worth sharing
ICP is everything. If you are a true chief revenue officer, the thing you care most about is finding that product market fit with your ICP.
Bridget Winston · 10:35
That's the secret test to me: if you're operating as a CRO or if you're just operating like a VP of sales—a glorified version of VP of sales.
Bridget Winston · 13:48
I purposely went and did a stint as a head of global customer success. It was the most enlightening thing, and it is my differentiator as a chief revenue officer.
Bridget Winston · 19:02
You are never done with product market fit. You are always evolving it. It's the biggest lesson from Chief.
Bridget Winston · 25:38
Common questions from this episode
How did Bridget Winston scale Chief from 1,500 to 20,000 members?
Through COVID-driven pivots from in-person to virtual to national, AI-enriched ICP discovery that revealed hidden customer segments, and intentional product-market-fit evolution. She aligned marketing, sales, and CS compensation around shared metrics to stop selling to wrong customers.
What is a true CRO vs. a VP of Sales?
A true CRO operates across marketing, sales, and customer success with aligned financial metrics and compensation. A glorified VP of Sales focuses only on quota and lead volume without analyzing customer lifetime value, retention, or unit economics by segment.
How do you find your real ideal customer profile (ICP)?
Go beyond surveys and surface data. Use AI tools to enrich customer data, then analyze lifetime value, churn rate, CAC, and referral strength by segment. Most companies discover their true ICP is different from what they assumed.
Why did Bridget take a customer success role?
She wanted to deeply understand retention, net retention, and the customer journey—gaps she had as a sales-first leader. She says it's now her biggest differentiator as a CRO because few revenue leaders truly grasp how CS drives recurring revenue.
What is a two-way door decision in go-to-market strategy?
A reversible bet you can test, learn from, and pull back on without major cost or loss. Opposite of a one-way-door decision (like hiring a full team) that commits you permanently. Use two-way doors to test AI tools, pricing, or market expansions.
What happened when Chief expanded into the UK?
Despite careful planning and user research, UK market dynamics—willingness to fund memberships, pricing elasticity, and comfort with vulnerability in small groups—didn't match the US. Chief pulled back, learning that speaking the same language doesn't mean product-market fit translates.
SEO meta description
Bridget Winston, CRO of PatientNow, on scaling Chief 13x: ICP is everything—and most companies haven't gone deep enough into unit economics and retention.
Target keywords
Bridget Winston CRO
Chief membership platform
ideal customer profile ICP
CRO vs VP of Sales
SaaS unit economics
customer success retention
AI data enrichment go-to-market
product market fit scaling
two-way doors decision making
revenue ops segmentation
net retention metrics
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Read the full transcript · 87 KB · Bridget Winston
Bridget Winston0:00So one of the examples that I have here is at Shutterstocks.
Bridget Winston0:03So all of the enterprise growth had stalled.
Bridget Winston0:05No one was hitting their quota, we'd had thirty five percent attrition, and the employee NPS was a two out of ten.
Bridget Winston0:13So pretty abysmal.
Bridget Winston0:14And what I found when I dug in was that the team was working hard, but there was really no structure.
Bridget Winston0:20There was no segmentation.
Bridget Winston0:22There was misaligned hiring.
Bridget Winston0:23There was no repeatable process and truly what I would say is no one was actually looking internal.
Bridget Winston0:29Like, what are we doing that's maybe contributing to the fact that we are not actually seeing success here.
Rachael Bueckert0:40Welcome to Go To Market Science.
Rachael Bueckert0:41There's an art and there's a science to go to market.
Rachael Bueckert0:44In this podcast, we talk about the science by interviewing CRO, private equity investors, and other sales and marketing experts as well as talking about what we learn every day in the trenches is helping to build go to market engines.
Rachael Bueckert1:02Welcome back to another CRO Stories segment.
Rachael Bueckert1:05I'm your host, Rachael Bueckert.
Rachael Bueckert1:06And with me today is Bridget Winston.
Rachael Bueckert1:09She is the current CRO of PatientNow.
Rachael Bueckert1:12Formerly, the chief revenue officer of Chief, as well as Shutterstock.
Rachael Bueckert1:16Bridget, thank you so much for joining me today.
Bridget Winston1:18I'm thrilled to be with you, Rachael.
Rachael Bueckert1:20Yeah.
Rachael Bueckert1:20It's so great to have you on file.
Rachael Bueckert1:21I know you kept missing each other a little bit.
Rachael Bueckert1:23I had to reschedule you had her reschedule, but it was for good reasons.
Rachael Bueckert1:26Yeah.
Bridget Winston1:27It was.
Bridget Winston1:27I mean, I I was in between roles in between chief and PatientNow, and so I had a little bit of time to myself, and so I was able to take some vacation and go to Tuscany and do a cooking course, and then also take a week and hike the camino des Santiago in Spain.
Bridget Winston1:44During a little pilgrimage.
Bridget Winston1:46Yeah.
Bridget Winston1:46So it was fun.
Rachael Bueckert1:48Yeah.
Rachael Bueckert1:48So you're you're fresh.
Rachael Bueckert1:49You're back at it now.
Rachael Bueckert1:50You're ready to go.
Bridget Winston1:51Yes.
Bridget Winston1:51I'm, like, a week and a half, two weeks in a PatientNow now.
Bridget Winston1:55So it's like, back to work back to the grind.
Rachael Bueckert1:58Back to work.
Rachael Bueckert1:58Yep.
Rachael Bueckert1:59So...
Rachael Bueckert1:59Yeah.
Rachael Bueckert1:59So you just started a recently a PatientNow, and I'm really excited to talk about that.
Rachael Bueckert2:03But we're gonna get that later.
Rachael Bueckert2:04First, let's kinda like, rewind a little bit and take a look at your previous role at chief.
Rachael Bueckert2:09So you took...
Rachael Bueckert2:11And she is for people listening.
Rachael Bueckert2:12It's a a membership kind of program.
Rachael Bueckert2:15It's B2c as well as enterprise sales.
Bridget Winston2:18Absolutely.
Bridget Winston2:18Yeah.
Bridget Winston2:18It's a consumer as well as enterprise.
Bridget Winston2:20But even the consumers usually get their companies to sponsor it.
Bridget Winston2:24So it's almost like a B2c to b type sales.
Bridget Winston2:27So it's a it was such an interesting mix of consumer and and enterprise.
Rachael Bueckert2:31Yeah.
Rachael Bueckert2:31It's a really interesting go to market model.
Rachael Bueckert2:33So you took chief from fifteen hundred members to over twenty thousand members in the time that you're with them and helped the company reach a one point one billion dollar valuation.
Rachael Bueckert2:44So that's a thirteen x scale and membership.
Rachael Bueckert2:46That's crazy.
Rachael Bueckert2:46So my question about that is as you were scaling, were there any, like, specific moments or metrics that told you what we're doing right now, this isn't gonna work for or five thousand members or ten thousand members.
Rachael Bueckert2:59And we need to change the way we're doing to support the scale in this growth that we want to see going forward.
Rachael Bueckert3:05What broke first or or what what needed to change first?
Bridget Winston3:10Yeah.
Bridget Winston3:10Oh, I love this question so much.
Bridget Winston3:11Well, I mean, there were a couple of pivotal moments that I think over the five years that we were able to really capitalize on and make some quick pivot.
Bridget Winston3:22So the first I would say is Covid.
Bridget Winston3:24Oh, yeah.
Bridget Winston3:25Chief started.
Bridget Winston3:26Yeah.
Bridget Winston3:27Exactly.
Bridget Winston3:27Chief started very much as an in real life experience.
Bridget Winston3:30We started in New York only.
Bridget Winston3:32We started in big cities only, and so we started in New York and then expanded it into some of the other left home Nfl cities.
Bridget Winston3:40Basically, where there was a pretty large total addressable market.
Bridget Winston3:43Of senior executive Women, Vp vpc suite women from Fortune five hundred executives.
Bridget Winston3:48Those were kind of the typical Ic, the ideal customer profile that we were going after when we started.
Bridget Winston3:53So, obviously, there was some change that needed to happen immediately of as we launched, we launched in twenty nineteen in New York only, we'd expanded to different different cities and then Covid happened.
Bridget Winston4:04And so we had to change that approach and go from something that very in real life experience into something that was much more virtual.
Bridget Winston4:12That is not unique so many organizations had to do that, but we found that that allowed us to really scale our operations because it that allowed us to not just be in real life in cities where we had club houses, But now we could offer this connection in this belonging and this feeling of community across the nation.
Bridget Winston4:31And so in twenty twenty two, we were able to scale that nationally, and not just be city by citi approach.
Bridget Winston4:36So you started to see us migrate into much more of a national play, I would say what was interesting about that though, is that then when Covid ended, I would say then we had to transition back into that desire for an in real life experience.
Bridget Winston4:52And now we had people who were in boise, people who were in New York, people who were all over the place who were now creating a much more in real life experience, and you just watched all of that community and so many tailwind in so many organizations that were like, investing in D, start to also pull back.
Bridget Winston5:11Right?
Bridget Winston5:12So they were pulling back a little bit on that commitment.
Bridget Winston5:14You also started to see them, see our members also start to say, hey, I want...
Bridget Winston5:19I want more of that in real life experience.
Bridget Winston5:21And so we had to pivot in that way as well.
Bridget Winston5:23The other thing I would say is right around that time, we had launched into the Uk.
Bridget Winston5:29And what we saw there and despite so much planning and so much user research.
Bridget Winston5:35I will say this to everyone.
Bridget Winston5:37Even just because they speak the same language as you does not mean that the experience is going to translate perfectly.
Bridget Winston5:43And so we saw a lot of different market dynamics there, both the willingness for companies to fund this membership the, kind of the pricing elasticity and availability of funding for a membership like this as well as their comfort level with being in small groups being very vulnerable.
Bridget Winston6:02And so you watched us kind of do a lot of learnings.
Bridget Winston6:05And then as we had to transition and think through how are we going to make the Us and, like, make our central market through our, kind of Us centric market succeed, we actually pulled back from the Uk, And so we had to make some really tough decisions about the growth and where our biggest areas of opportunity and how product market fit is never done.
Bridget Winston6:27You are always evolving it.
Bridget Winston6:29And I would say even now and you'll see it even with chiefs most recent campaigns we were originally designed for a fortune five hundred executive after Covid, not everyone's a fortune five hundred executive anymore.
Bridget Winston6:40Either there were layoffs or macroeconomic climate shifts that made those people either not have a role in that Fortune five hundred corporate executive.
Bridget Winston6:48Or you just watched people say, I don't wanna do this anymore, and going into business for themselves.
Bridget Winston6:53And so that profile of member has changed.
Bridget Winston6:56And so I think there were so many interesting lessons and I will forever, take chief as, like, being the one of the most formative things I've ever done in my career because despite the great numbers, fifteen hundred to twenty thousand, despite going from a single city to national then to international, despite the one point one billion dollar valuation.
Bridget Winston7:18There were so many interesting both pivot but also mistakes and learnings that I was able to have along the way.
Rachael Bueckert7:26That's awesome.
Rachael Bueckert7:26So do you think you would attribute a lot of that scale kinda during and after Covid to a re analysis of your best Ic and, like, segmenting that analysis and changing it.
Bridget Winston7:39Absolutely.
Bridget Winston7:39And it's really interesting And I would say was actually...
Bridget Winston7:43I was able to partner with amazing, and I will I I will pitch them forever.
Bridget Winston7:46It's a company called good work.
Bridget Winston7:48They use an Ai tool that helped us not because typically, we were just being able to get some of the feedback through surveys.
Bridget Winston7:54That of our members at chief.
Bridget Winston7:56And so a lot of that relies upon the busiest women in the world answering a survey about how their position has changed.
Bridget Winston8:02So are you still at Pepsi?
Bridget Winston8:05Are you still employed by the Fortune five hundred management consulting firm?
Bridget Winston8:09So a lot of those people typical survey results are pretty low.
Bridget Winston8:12And so we were able to use an Ai tool to enrich our data to actually give us more information about our customer base so that something where I thought, maybe let's call it.
Bridget Winston8:22Sub five percent of my members were solo or entrepreneurs and then to find out that maybe it was more like a quarter of them.
Bridget Winston8:30And so what that did then is start to evolve our product market fit and start to evolve our product.
Bridget Winston8:35Because all of a sudden, now, that member wants something different than the corporate executive once.
Bridget Winston8:42And so we really informed initially it started off as just something we were using for lead scoring as an example.
Bridget Winston8:49But boy, it informed everything about the way that we went to market, product included.
Rachael Bueckert8:55Okay.
Rachael Bueckert8:55That's really cool.
Rachael Bueckert8:56How did that work?
Rachael Bueckert8:56How did that tool work?
Rachael Bueckert8:57How did it get the information?
Bridget Winston8:59It was basically...
Bridget Winston8:59It went into our Crm, and then it enriched all of the data that it can find throughout the Internet to actually start to help us with differentiated segments.
Bridget Winston9:08Segments we thought, we thought that our our segments were this.
Bridget Winston9:12This tool good work was able to tell us, actually, you have these segments And here are your micro macro, you could filter it up by all sorts of things just to be really informed about, who is your Ic?
Bridget Winston9:23What are those engagement patterns that suggest that they stay with you longer?
Bridget Winston9:26And also, what do they do that's maybe different?
Bridget Winston9:29And how do they show up differently both in their engagement patterns in their Lt tv?
Bridget Winston9:35Like, their lifetime value with you.
Bridget Winston9:37So fascinating, I cannot recommend Tom's Amp at good work enough?
Bridget Winston9:41I am even thinking about using him in future projects and I recommend him constantly.
Rachael Bueckert9:47Yeah.
Rachael Bueckert9:47That's that's awesome.
Rachael Bueckert9:48And I'll actually probably look into that myself after a call because we do stuff like that manually all the time here at Usc.
Rachael Bueckert9:54And I mean, we don't have, like, ten thousand or five thousand customers or anything like that.
Rachael Bueckert9:59So it's a much smaller number and a much easier to work with, but still, like, very interesting to see, like, how an Am I may be able to hone in the Ic.
Rachael Bueckert10:07Because for us, like, last year, we did a a huge project on figuring out who our true Ic was and our true, like, ideal buyer our persona was, and it made a huge huge difference in everything from the way we markets to the way even we deliver our product, and we've been seeing a huge lift from it.
Bridget Winston10:25So I love it.
Bridget Winston10:26That's that's what he says.
Bridget Winston10:27That's exactly what he says, And I will say, that's probably the thing I've learned most as being a chief revenue officer is Ic is everything.
Bridget Winston10:35If you are a true chief revenue officer, as I say, across marketing sales customer success, the thing you care most about is finding that product market fit with your Ic, those folks where you not just acquire them, but you retain them and that they become that flywheel of a word mouth for you.
Bridget Winston10:54It makes everything so much easier that your Lt to c ratio is much easier where you are looking at what's my lifetime value versus the customer acquisition cost to acquire them.
Bridget Winston11:04Everything becomes so much more efficient if you are selling to the right type of customer.
Bridget Winston11:08And it's hard though at the beginning, Like, if you are a startup up, you are selling to anyone because you're evaluating what's my product mark fit.
Bridget Winston11:14Where do I have that?
Bridget Winston11:16And so as you grow as you scale, that's probably another thing that obviously became very critically important for us at chief as we grew, it became much more important for us to understand?
Bridget Winston11:27Okay, there's an, and how has our customer changed as well so that we are also designing products to fit that customer who wants to stay with us longer.
Rachael Bueckert11:37And that was a really good point you made.
Rachael Bueckert11:38Like, I think a lot of people listening to the bit this might think like, oh, Ic.
Rachael Bueckert11:42You know, we know our Ic.
Rachael Bueckert11:43We...
Rachael Bueckert11:44We understand who our Is We're we're, like, a fifty million hundred million dollar company.
Rachael Bueckert11:47But it's like, you think you know who your Ic is because you're looking at, like, customer sold to, But have you gone deeper?
Rachael Bueckert11:54Have you looked at, like, the actual lifetime revenue you've received, you know, the the cost benefit analysis of, like, do these...
Rachael Bueckert12:02How how quickly do these people churn, how much customer success resources do they need to use up?
Rachael Bueckert12:07How hard it is to sell them?
Rachael Bueckert12:08Are you trying to...
Rachael Bueckert12:09Are you having to discount them to even, like, close these deals.
Rachael Bueckert12:12So you never...
Rachael Bueckert12:14You don't really know.
Bridget Winston12:15If that's why it's so important, like, not only getting your segmentation.
Bridget Winston12:18Right, but then start to do all of that financial analysis, do by your segments.
Bridget Winston12:23So To cap by each of those segments.
Bridget Winston12:26Because you might start to determine that, like, oh, this segment is much more likely to be a referral engine for me.
Bridget Winston12:34So it's much cheaper to acquire them and they stay for longer.
Bridget Winston12:37Right?
Bridget Winston12:37Versus this is, like, god, I've gotta spend so much.
Bridget Winston12:40I've gotta do paid marketing to get to this to this customer.
Bridget Winston12:43And so you just started to be much more informed about the decisions that you are making and more intentional about the Ic first off that are in your base.
Bridget Winston12:52Or let's call it the different segments that are in your base?
Bridget Winston12:55Where do you want your Ic to be?
Bridget Winston12:57What do you want your financial metrics to look like?
Bridget Winston12:59Those unit economics still look like?
Bridget Winston13:00And then how do you design a product that actually fits that?
Bridget Winston13:04And sometimes that takes, like, a couple of reps to figure out.
Bridget Winston13:07Obviously, we needed to a couple of years to kinda figure out, okay, where are we best designed for, and then you can start to just iterate on it.
Bridget Winston13:15And then to explore your ad.
Bridget Winston13:17Intentionally, not just by happens stamp because that just happens to be when you threw a wide net who came in.
Rachael Bueckert13:25Exactly.
Rachael Bueckert13:25Yeah.
Rachael Bueckert13:26We call it un blending the funnel.
Rachael Bueckert13:27We've written like a bunch of content and stuff on this as well.
Rachael Bueckert13:30And I think a lot of revenue leaders look at the idea of, like, segmenting and breaking all these things down is, like, such a chore.
Rachael Bueckert13:36Like I don't have time for that.
Rachael Bueckert13:37I don't have if the resources for that.
Rachael Bueckert13:38And what's the point is just, like, another dashboard that our, a, Ceo isn't gonna really care about.
Rachael Bueckert13:43But it does matter so much.
Rachael Bueckert13:45And like, if you're a Cro,
Bridget Winston13:48that's the secret test to me if you were operating as a Cro or if you were just operating like a Bp sales.
Bridget Winston13:54And a lot of times when they promote someone to a Cro position, that is just a glorified version for Vp of sales.
Bridget Winston14:02To me, even if you don't own all of these functions, the best chief revenue officer is going across all of those functions, marketing, sales, customer success.
Bridget Winston14:11And understanding the financial mechanics of acquiring a customer efficiently and creating lifetime value.
Bridget Winston14:19I always talk about it.
Bridget Winston14:20There's a book by general...
Bridget Winston14:22General Stanley Mc crystal, which, you know, I'm no war for anybody who knows this, but like, He wrote a book called team of teams and what was so fascinating about it is he calls it doing your thing right versus doing the right thing holistically.
Bridget Winston14:34And so when you can have those teams operating and concert, marketing sales and customer success.
Bridget Winston14:40And everyone is basically let's call it financially aligned to, yes, we are trying to get everyone's trying to get their leads.
Bridget Winston14:47Their cost per lead, their their sales, their Mr, their Arr, and these people are focusing customer success is trying to get, you know, retention and expansion.
Bridget Winston14:56But if you can actually start to blend across those incentives, and I've done that a couple of times where I've actually aligned marketing sales and customer success on...
Bridget Winston15:05They've got their primary metric that they're responsible for, but somewhere in the twenty five percent of their comp, is based upon a shared metric that usually is tied to Lt tv or net retention or gross retention.
Bridget Winston15:17Something that reminds everyone.
Bridget Winston15:20The thing that we are going after here is a retained perfectly fit customer.
Bridget Winston15:26And so it kind of changes the the motivations, and you stop selling to the wrong type of customer.
Bridget Winston15:33I did that at Shore tell prior to my time at Shutterstock.
Bridget Winston15:37Where I was able to align those teams together because of those those align comp plans.
Rachael Bueckert15:42Yeah.
Rachael Bueckert15:42Absolutely.
Rachael Bueckert15:43And, like, as a Cro, you're...
Rachael Bueckert15:44Like you said, is it's not, like a Vp of sales position.
Rachael Bueckert15:47That's that's not what you're supposed to be doing.
Rachael Bueckert15:48You're, like, a steward of capital, your steward of revenue.
Rachael Bueckert15:51And especially in a recurring revenue business, that means looking at the entire system, like, what happens after you sell a customer.
Rachael Bueckert15:57If your business model is recurring revenue, that revenue has to recur.
Rachael Bueckert16:00So you need to figure out, like, how do we make sure that it it keeps recurring and people stay and expand.
Rachael Bueckert16:06Hopefully.
Bridget Winston16:07Well, and I'll tell you, even at Short tell...
Bridget Winston16:08That was, like my first time actually experiencing this.
Bridget Winston16:11And so it was the first time I I had come up through sales.
Bridget Winston16:14That was my background, sales, channel partnerships, all of that Right.
Bridget Winston16:17And so I was promoted into a role where it was a Vp of sales of customer success.
Bridget Winston16:21So I had all of these roles under underneath, Like, the marketing Sdr str, the, sales, partnerships, onboarding, client success support, all of these functions.
Bridget Winston16:31And so I'm was it was the first time that I was having to understand okay?
Bridget Winston16:35Recurring revenue.
Bridget Winston16:35It's not just doing my thing right, but doing the right thing holistically.
Bridget Winston16:38And what we started to see was, like, we would do all of this work, we would market.
Bridget Winston16:42And we sold a unified communication Saas solution.
Bridget Winston16:45So if this was also we had adjust gone into the Saas world.
Bridget Winston16:48We acquired a company that was a Saas platform versus, a, a premises based Capex expenditure.
Bridget Winston16:54And so we were kind of all learning this muscle at the same time, me and a hundred forty if the the team folks who worked on my team.
Bridget Winston17:02So what we found was marketing was marketing to law firms as an example.
Bridget Winston17:07The Sdr str were getting that on a calendar.
Bridget Winston17:09The sales reps were selling it.
Bridget Winston17:10They were going back and forth, doing red lines back and forth.
Bridget Winston17:13Right?
Bridget Winston17:13Getting the contract signed.
Bridget Winston17:15Onboarding would come in forty five days it would take so much work to, like, get them switched over and everything onboarding would do it.
Bridget Winston17:21And then, they would go on to customer success or call support.
Bridget Winston17:24And the first time that they had an outage or some blip and service.
Bridget Winston17:28They would turn immediately.
Bridget Winston17:29And because they were law firm too.
Bridget Winston17:32Like, they had everything written in the contract to where they...
Bridget Winston17:34If it wasn't, like, a hundred percent uptime, they could get out of their contract.
Bridget Winston17:38And so because we could see that entire thing.
Bridget Winston17:42I was paying commission to all of these people.
Bridget Winston17:43Right?
Bridget Winston17:43There was so much energy and effort.
Bridget Winston17:45And so once we started to see that, this customer turns, we stopped marketing to them.
Bridget Winston17:50We stopped selling to them, we stopped onboarding them.
Bridget Winston17:53Right?
Bridget Winston17:53Because the Ic was no longer going to be law firms for this product in particular.
Bridget Winston17:59It was not the right thing to do.
Bridget Winston18:01And so it was hard for the salespeople people to understand that.
Bridget Winston18:04Right?
Bridget Winston18:05They wanted to sell to these people, the onboarding people wanted to onboard.
Bridget Winston18:07But once you aligns that compensation model.
Bridget Winston18:10Let me tell you.
Bridget Winston18:11Things started changing it.
Bridget Winston18:13Right?
Bridget Winston18:13Because the most important thing was not just doing their thing, but doing the overall right thing.
Bridget Winston18:18And so it was a really good example of, like, changing behaviors, changing outcomes based upon, like, a aligning compensation, but also just aligning on the most important metric.
Rachael Bueckert18:29Absolutely.
Rachael Bueckert18:29I love that so much.
Rachael Bueckert18:30Like that's...
Rachael Bueckert18:30It boils down validates kind of like, all the the principles that we try to a spouse at Usc.
Rachael Bueckert18:36Like, though the whole revenue system is Not just sales guys.
Bridget Winston18:40Yes.
Rachael Bueckert18:41Nobody wants to hear about, like, customer success stuff though.
Rachael Bueckert18:43But we...
Rachael Bueckert18:44We still produce it.
Bridget Winston18:45Oh, I love.
Bridget Winston18:45No.
Bridget Winston18:46I mean, I will tell you.
Bridget Winston18:47I purposely let...
Bridget Winston18:48So I will say like, for me to be a chief revenue officer the most defining time of my career was going into being ahead of global customer success because it was lightning, and I purposely did it.
Bridget Winston19:02Like, I came up through sales like I mentioned, and then because I saw marketing encroaching on Sales territory, and customer success is now going to own most of the revenue in a Saas world.
Bridget Winston19:14So I went, I was like, I've got an understand this customer success motion.
Bridget Winston19:18And everything that's tied to retention and an expansion and net revenue and gross revenue, all of that.
Bridget Winston19:25And so I purposely went and did a stint as a head of global customer success, It was the most enlighten thing, and I will tell you as a chief revenue officer, it's my differentiator.
Bridget Winston19:36When I go for at my job at PatientNow, it is because I know onboarding support and client success.
Bridget Winston19:44That I am a chief revenue officer a PatientNow right now because that is so critically important.
Bridget Winston19:50Anyone can hire and anyone can...
Bridget Winston19:52I don't wanna say anyone.
Bridget Winston19:53But it's easy to find a Vp of sales.
Bridget Winston19:55It is rare to find someone who cares about the full customer journey.
Rachael Bueckert19:58That is so awesome.
Rachael Bueckert19:58I love that.
Bridget Winston20:00So keep on producing that customer say oh, not producing that customer success content.
Bridget Winston20:04It's so critically important.
Bridget Winston20:05So I did it exclusively for a year, but now since then, it's been in every single role I've had.
Rachael Bueckert20:11Nice.
Rachael Bueckert20:11That's so that's so valuable.
Bridget Winston20:14So for the last, I would say, yeah, Of the last maybe five six.
Bridget Winston20:18So eight years, I've had customer success under my under my.
Rachael Bueckert20:23Nice.
Rachael Bueckert20:23Awesome.
Rachael Bueckert20:24Okay.
Rachael Bueckert20:25So in line with looking at like, segmentation and all that stuff.
Rachael Bueckert20:28But I had a question about still looking at, your time at chief.
Rachael Bueckert20:31So you ran both B membership and enterprise sales.
Rachael Bueckert20:34But was there ever a time when the B2c motion and the debt enterprise motion competed for resources or you had, like, choose between favoring one of the two or how did that work?
Bridget Winston20:45Yeah.
Bridget Winston20:45One of the things that is so critically important to me is this concept of that you see in five just dysfunction of a team if you've ever read that focus.
Bridget Winston20:54Wanna...
Bridget Winston20:55Yeah.
Bridget Winston20:55I feel like I'm, like, pitch pitching all these books and podcasts and everything.
Rachael Bueckert20:59That's us totally fine.
Bridget Winston21:00Yeah.
Bridget Winston21:00Yeah.
Bridget Winston21:00So I will, and customer success is a discipline.
Bridget Winston21:03So five dysfunction of a team talks about how the team that you are on, the team that you are on is not the team that you've lead.
Bridget Winston21:10It's the highest ranking team that you are a part of.
Bridget Winston21:13So I had two people on my team, my B2c membership team, and my B2b enterprise sales team.
Bridget Winston21:20And what became really interesting was, yes, there was fight for resources.
Bridget Winston21:24There always is just because, you know, you have to do some capacity planning.
Bridget Winston21:28Typically, the capacity planning was very model in the B2c world because it's much more high volume high velocity.
Bridget Winston21:35There's a set number of calls a day.
Bridget Winston21:37There's certain hours in the day.
Bridget Winston21:38We know how many leads convert into opportunities.
Bridget Winston21:42We know how many...
Bridget Winston21:43Opportunities convert to close business.
Bridget Winston21:45So it's actually a very model thing to predict.
Bridget Winston21:49The b to b side is much more lumpy.
Bridget Winston21:51Right?
Bridget Winston21:52And so the res sourcing plan for the B to b model was much more tied to advance understanding of pipeline.
Bridget Winston22:00And a target list.
Bridget Winston22:02And so we had very specific targets because if you break it down to Ic, you were able to know who has a pretty large Tam, a large total addressable markets of senior executive women who are Vpn and C suite, and those are our top targets.
Bridget Winston22:17Now, that does not mean that between the consumer and enterprise side of the business that there weren't sometimes people who are on that target list who came in through the consumer side as an option.
Bridget Winston22:29So we had a lead flow process where they would share leads, usually aligning incentives, but even just aligning culturally around this five dysfunction of a team, the first team mentality, where we are both aligned on the revenue that we are adding to the business, not everyone's individual goal.
Bridget Winston22:48So it's that same mentality of don't just do your thing right, do the right thing holistically.
Rachael Bueckert22:54Absolutely.
Rachael Bueckert22:54And, like...
Rachael Bueckert22:55We we talk about that all the time here too.
Rachael Bueckert22:57Like, I'm marketing.
Rachael Bueckert22:58I'm I'm the marketing team for Usc.
Bridget Winston23:02Got it.
Bridget Winston23:02I'm looking at her.
Rachael Bueckert23:04Yeah.
Rachael Bueckert23:04And I'm not judged On.
Rachael Bueckert23:06You know, how many leads I get into the pipeline.
Rachael Bueckert23:09I'm judged revenue.
Rachael Bueckert23:10So that kinda changes my entire my mindset.
Rachael Bueckert23:12Right?
Rachael Bueckert23:13Yeah.
Rachael Bueckert23:13That kinda changes my entire mindset around, the type of leads I want to get into the pipeline.
Rachael Bueckert23:18So I'm looking at that.
Rachael Bueckert23:19I'm looking at customer success, the type of leads that stick around and, like, stay with us, like our true Like we talked about.
Rachael Bueckert23:26And I know it's not fully feasible for every single company to do that, and I don't think there's, like, one playbook that every company should follow obviously.
Rachael Bueckert23:34But having every team in in, like, your direct revenue organization, have some kind of goal or, like, expectation against revenue is so critical.
Rachael Bueckert23:46Just because of that because it gets you thinking about, yeah.
Bridget Winston23:50And even if sometimes what you see is, like, the entire organization has some...
Bridget Winston23:54Typically, the sales teams or anybody's who's carrying Quota has, obviously, their compensation.
Bridget Winston23:59I think there's a way to change that variable compensation to where let's call it, seventy five percent is on the primary metric and twenty five percent is on that shared metric that the that aligns everyone across the customer journey.
Bridget Winston24:10But even like people who are in engineering, People who are in product, people who are in Hr, Like, there is a way that that bonus plan is structured in a way that the most important metric that funds the bonus pool could also be revenue, retention, net retention, whatever it might be that is, like, the most important guiding metric for the organization.
Bridget Winston24:30That is that gal price across the organization of, like, the most important thing that we can be doing is being customer centric, that's fueling it.
Bridget Winston24:37So that's a...
Bridget Winston24:38That's one way to do it as well.
Rachael Bueckert24:40Yeah.
Rachael Bueckert24:40Absolutely Even, like, like, product teams, you know, if...
Rachael Bueckert24:42If they get some kind of incentive for renewed contracts.
Rachael Bueckert24:46So, like, every customer that renew their next term.
Rachael Bueckert24:48You get, like, a bit of a bi or, like, something like that because that's just gonna is gonna make people focus so much more on making the product something that people wanna keep coming back to and totally.
Bridget Winston24:58Is it something that's ga?
Bridget Winston24:59Is it something that makes the payment processing easier, all those things that you can do to, like, care about the Ux to make people more often to stay with you?
Bridget Winston25:09All of those elements, I think are are components that contribute to net retention as an example.
Bridget Winston25:14So...
Rachael Bueckert25:15And so before you mentioned that you learned so much achieve.
Rachael Bueckert25:17I wanted to ask, like, what was the biggest lesson that you learned at your time achieve specifically around, like, go to market operations and structures and stuff like that.
Rachael Bueckert25:26Gosh.
Rachael Bueckert25:27It's a big question.
Rachael Bueckert25:28Yeah.
Bridget Winston25:30My it is a big question.
Bridget Winston25:32Well, I'd say number one, you are never done with product market fit.
Bridget Winston25:38So echoing that a little bit, you are never done with product market fit.
Bridget Winston25:43And, you know, the other thing, I would say that I always compliment our c founder and Ceo, Caroline on.
Bridget Winston25:51That she taught me personally that I had a lot of growth around is I used to when there was a big problem, I would propose a big solution.
Bridget Winston26:02And I would always come in hot with, like, alright.
Bridget Winston26:07We wanna solve the enterprise problem.
Bridget Winston26:09We wanna get to ten million.
Bridget Winston26:10Let me tell you how we're gonna I need a team of three, then I'm gonna have this.
Bridget Winston26:14And then we're gonna do this marketing, and I would go big.
Bridget Winston26:17Because to me, ten million dollars.
Bridget Winston26:20That's what we wanna do.
Bridget Winston26:21Great.
Bridget Winston26:21Big problem.
Bridget Winston26:22Big solution.
Bridget Winston26:23Let's go.
Bridget Winston26:23She taught me the value of testing iterating before, and it's because she was startup founder.
Bridget Winston26:31Right?
Bridget Winston26:31Like a startup founder is always doing that.
Bridget Winston26:34And she created that muscle in me.
Bridget Winston26:36And it was because I had worked at bigger companies, more established companies less at the startup up stage.
Bridget Winston26:41And so she created that muscle for me so that now I can actually create it with my leaders.
Bridget Winston26:47Like, as they are proposing solutions to me.
Bridget Winston26:50There are...
Bridget Winston26:51The only thing I I say, like, that we won't do are those things that are one way doors.
Bridget Winston26:56But again, imagine, a one way door of, like, investing to get to ten million, we have to do I have to hire a team of seven and starting, but, like, what a one way door decision.
Bridget Winston27:08Right?
Bridget Winston27:08Like, why don't you do those things that are two way doors?
Bridget Winston27:10And...
Bridget Winston27:11That's a Jeff Bezos concept.
Bridget Winston27:12Right?
Bridget Winston27:13That, like, there's no test, iterate two way door.
Bridget Winston27:16Go in come back.
Bridget Winston27:17Go and come back.
Bridget Winston27:18So that you start to learn what is working, and then you can start to, like, iterate, change, pivot, and then get to the point where there's a bigger solution to a bigger problem.
Rachael Bueckert27:32Yeah.
Rachael Bueckert27:32I love that so much.
Rachael Bueckert27:33And our Ceo, Eddie was just talking to about that recently actually, the two a door thing because we're strat on all these different things and I'm like, yeah.
Rachael Bueckert27:40It makes so much sense.
Rachael Bueckert27:41Let's do that.
Rachael Bueckert27:42Yeah.
Rachael Bueckert27:42I love that.
Bridget Winston27:43Well, yeah.
Bridget Winston27:43I love it.
Rachael Bueckert27:45This next question is Skip be about any company worked at.
Rachael Bueckert27:47But on that line of thought, what was an experiment you did or a go to market bet, you made that failed in the experiment, and you had to, like, kinda, like, go back through that one that two eight or?
Rachael Bueckert27:57And look at the post mortem and figure out what went wrong and what was the result of that?
Bridget Winston28:02Well, I can use the Uk as the example at chief.
Bridget Winston28:06That's one, gosh.
Bridget Winston28:08I mean, I failed so much.
Bridget Winston28:10And I think that's actually, like, one of the other things just to highlight is, like, the failure muscle, we should not be so scared to fail, especially in a world where, as a Cro, my playbook is outdated.
Bridget Winston28:24Right?
Bridget Winston28:25Everything that got me here is now in this world of Ai, gonna have to change, and I need to be comfortable with that.
Bridget Winston28:32I need to have that growth mindset and be excited about testing and learning two way do it, and to actually get more comfortable with that.
Bridget Winston28:39So I could talk about the Uk.
Bridget Winston28:41I can also talk a little bit about something that happened at Shutterstock.
Bridget Winston28:44That's helpful because something that just to kind of do a little bit of a different take on it.
Bridget Winston28:50One of the things that we can fall prey to and you do it at every organization, especially if you're interviewing first Cro position.
Bridget Winston28:58When you come in consistently, especially if the team is not hitting numbers.
Bridget Winston29:02What you will hear in every element of your interview is the people.
Bridget Winston29:08They're just not good.
Bridget Winston29:09They're just not motivated.
Bridget Winston29:10They just don't have what it takes to succeed in what we were doing.
Bridget Winston29:15And I would say that I felt for that a couple of times.
Bridget Winston29:19And what I will say is that that is not my hot take is that that's not true.
Bridget Winston29:26And I can tell a couple of examples if it's helpful of, like, what I did to kinda change change the game on that and to actually assess it.
Bridget Winston29:34So one of the examples that I have here is at Shutterstocks.
Bridget Winston29:37So our enterprise growth installed, Shutterstock is the content platform where marketplace where we connect creators to people who are looking for stock images, photo footage, music, custom editorial, all of these different types of stock content.
Bridget Winston29:53And we were selling...
Bridget Winston29:55It was a consumer play, but then also grew into an enterprise play, and what we had found was despite all of these acquisitions, footage companies, music companies.
Bridget Winston30:03All of the enterprise growth had stalled.
Bridget Winston30:06No one was hitting their quota.
Bridget Winston30:07We'd had thirty five percent attrition, and the employee Mps was a two out of ten.
Bridget Winston30:14So pretty ab, pretty ab.
Bridget Winston30:17And so people were leaving because they weren't hitting their number.
Bridget Winston30:20I think it was, like, maybe ten percent of the people were hitting their number.
Bridget Winston30:24And what I think we saw was that the team was working hard and, of course, upon coming in, everyone's was, like, you know, it's the talent.
Bridget Winston30:30But that's what the problem is.
Bridget Winston30:32Right?
Bridget Winston30:32And what I found when I dug in was that the team was working hard, but there was really no structure.
Bridget Winston30:36There was no segmentation.
Bridget Winston30:38There was misaligned hiring.
Bridget Winston30:40There was no repeatable process and truly what I would say is no one was actually looking internal.
Bridget Winston30:46No one and I always say, first look inward.
Bridget Winston30:48What are we doing that's maybe contributing to the fact that we are not actually seeing success here.
Bridget Winston30:53And what you started to see was there was unclear segmentation, as I mentioned, there was no rhyme a reason to how many reps were assigned to any of the any of the accounts.
Bridget Winston31:05You would have an account who was managing a five thousand dollar account as well as a million dollar account.
Bridget Winston31:10It just didn't make sense.
Bridget Winston31:12There were all different types of industries and verticals that you could segment by that we were not segmenting by.
Bridget Winston31:17There were a couple of people who had been there for a long time and just were absolutely adamant that they were not going to sell the new stuff that we had brought in.
Bridget Winston31:25And so there was no expectation of that And so because of that, they were not hitting their number because all of the numbers were at least built with some version of growth on these existing accounts.
Bridget Winston31:35But there were a lot of people who were bright spots.
Bridget Winston31:37There were so many people who were actually doing the things we wanted them to do.
Bridget Winston31:41And so, I mean, it was very clear what you had to do at the beginning, like, first look inward and go, yes, it's not that there's not a talent problem.
Bridget Winston31:49But also, have we done the plan for the plan.
Bridget Winston31:52Have we made it understandable about first off, what are the clear segments.
Bridget Winston31:57Where should we...
Bridget Winston31:57Where is their performance already that that should be, you know, executed on and then where is their potential in terms of the account growth that we could be expecting.
Bridget Winston32:06Let's organize for that in terms of the segments.
Bridget Winston32:09Let's organize by industry in vertical and maybe size of customer.
Bridget Winston32:12So we first had to do that.
Bridget Winston32:14No names and boxes at all just what would be the right capacity plan to support this existing customer base and the opportunity that we see?
Bridget Winston32:21Secondly, what about the talent?
Bridget Winston32:23Now let's look at the talent?
Bridget Winston32:24Now let's look at, like, who is best suited for each of these industry verticals, size of customer?
Bridget Winston32:31And where are we seeing bright spots?
Bridget Winston32:33Who is selling that full portfolio versus somebody who just wants to sell something much more transactional and quick hitting?
Bridget Winston32:39And then how do we leverage the talent to help coach the other talent?
Bridget Winston32:42How do we make this fun?
Bridget Winston32:44How do we make the change fun?
Bridget Winston32:45How do we make it to where they're helping with the interview process as people start to leave?
Bridget Winston32:50Like, how are they helping with the interview process and being that leader who we either promote to the position or actually just being somebody who's a subject matter expert?
Bridget Winston32:58That we can call upon to help coach in and on ramp someone.
Bridget Winston33:01So in the end, we were able to kind of change the approach.
Bridget Winston33:05We realized we didn't need as many heads.
Bridget Winston33:08So we were able to repurpose some, that we were also seeing such attrition that we were able to go.
Bridget Winston33:12Let's keep the best of the best of some of these.
Bridget Winston33:14We were able to, kind of re hire for the types of, let's call it sales motions that we needed.
Bridget Winston33:20And then we were able to kind of transition away from attrition of thirty five percent.
Bridget Winston33:25We were able to get it to two percent.
Bridget Winston33:27And change that ramp time for anybody who was hiring from five months to three.
Bridget Winston33:33And then we were able to get the employee n p score because we started doing celebratory things.
Bridget Winston33:38We started making it fun.
Bridget Winston33:40We started coaching each other about how to win.
Bridget Winston33:42We're able to grow that employee P score to a seven out of ten.
Bridget Winston33:46So not perfect, but progress from that two that I came in and inherited a little bit.
Bridget Winston33:52So lots of, like, learnings around people will tell you it's one thing, do your due diligence, listen to customer calls, listen to do ride along, and then also just first get work and go, what have we done to actually set this org in this team up for success.
Bridget Winston34:08Because if I had just come in and fire everyone.
Bridget Winston34:11I'd be in the same exact position that I was when I when I started accept worse because I would have now had to do a ramp.
Rachael Bueckert34:19Yep.
Rachael Bueckert34:19And that mindset, I think is so so important for any kind of, like, revenue leadership to have, like, not just just coming in and looking at a problem at face value, but really digging into the processes and what's broken underneath on, like, an operational level.
Rachael Bueckert34:34And being responsible for organization structures, Like, I've...
Rachael Bueckert34:38I'm not personally zero, but I've I understand talking to their Cro.
Rachael Bueckert34:42It's, like a huge huge part of the job.
Rachael Bueckert34:44Oh, yeah.
Rachael Bueckert34:44Yeah.
Rachael Bueckert34:45Knowing who you're hiring, making sure.
Bridget Winston34:47And I will say that's why Rev ops partner is the most critical hire for a Cro.
Bridget Winston34:52It's the most...
Bridget Winston34:53Like, that is what they help with.
Bridget Winston34:54And I will tell you with, like, at Shutters socket would take five months of planning.
Bridget Winston34:59To actually get the accounts right to do the segmentation correctly.
Bridget Winston35:02I will say now with that good work tool.
Bridget Winston35:04Oh, my gosh.
Bridget Winston35:04That that stuff is, like, two weeks now.
Bridget Winston35:07So, I mean, Ai has changed the game on your ability to segment to capacity plan to do all of the stuff that's, like accompanying your org structure and, like, and even quote mechanics, all of those things, the modeling that you can do.
Bridget Winston35:21Gosh, it becomes invaluable.
Rachael Bueckert35:23Yeah.
Rachael Bueckert35:23Absolutely.
Rachael Bueckert35:24I always love hearing that from miss Hero because like, that's what we do at Usc.
Rachael Bueckert35:27So, yes.
Rachael Bueckert35:28Validation boom.
Bridget Winston35:31It's the best.
Bridget Winston35:31It's the number one.
Bridget Winston35:32It's the number one most important role I would say.
Rachael Bueckert35:36Awesome.
Rachael Bueckert35:36So looking back at, like, all of your Cro roles and even the roles that you had before you transitioned to being a zero, what did you learn from all of that that you plan to take into PatientNow?
Bridget Winston35:50Oh, I love this.
Bridget Winston35:51Well, I think it is a little bit of that that element of the two way doors and testing and learning, especially in this time of Ai.
Bridget Winston36:01I would say, that had been something maybe I've been a little more reluctant to do in terms of, like, automation and and being quick with the tools.
Bridget Winston36:10Now I...
Bridget Winston36:11Am evaluating three Ai tools, and I'm a week and a half to in.
Bridget Winston36:15Right?
Bridget Winston36:15So I have three Ai tools that are on the docket for me to either do a pilot with or is already underway.
Bridget Winston36:22So a week and a half in, Ai is becoming a very critical component to my go to market motion.
Bridget Winston36:29And I think before we would have called it automation or tools or anything, and I think it would taken months to get ramped.
Bridget Winston36:36So I would say not being scared of the test, learn, iterate an Ai, forward companies make that very easy for you to test and learn and pilot.
Bridget Winston36:47So not being scared of that and embracing that that what I learned at chief from from Carolyn around, you don't have to have a big solution to a big problem.
Bridget Winston36:55You can test learn iterate and Ai makes that even easier.
Bridget Winston36:59The second thing I would say that I learned at chief in that I am applying to pretty much every conversation I'm having with Cro and to myself, is what I learned actually being at chief because it was such a consumer marketing play.
Bridget Winston37:18So I'll go into this a little bit.
Bridget Winston37:20This is my biggest hot take, I think.
Bridget Winston37:22And biggest take that I would say, people should take even as a b b Saas marketer or, chief revenue Officer.
Bridget Winston37:30So the consumer world do you think of, like, the way that you market to that person's it's much more...
Bridget Winston37:35The perception is that it's much more of an emotional play that you're playing on the emotional side that because they have to identify with your brand and all that.
Bridget Winston37:43Whereas the perception of a B kind of marketing and positioning as much more rational.
Bridget Winston37:48Usually, it has to make you money save you money to do to to get an enterprise buyer to say yes.
Bridget Winston37:54And that's not completely untrue.
Bridget Winston37:57But in a world where Ll are becoming the way that people are getting found more frequently.
Bridget Winston38:03I would argue that the world of consumer marketing and enterprise B marketing, are starting to complete a bit more.
Bridget Winston38:11And the tactics that typically motivate a consumer sale are starting to motivate a b to b sale.
Bridget Winston38:18So I'll give an example.
Bridget Winston38:19Now people are getting found in Ll, but the things that's feeding the Ll is earned media or reddit of all things.
Bridget Winston38:29Or any of those consumer review sites like g two as an example.
Bridget Winston38:35So your word of mouth matters more than ever, which is why Ic matters more than ever and why client success matters more than ever is because people who are leveraging this leveraging your solution and having a good experience with you.
Bridget Winston38:52Now is gonna be the thing that fuels the L, and therefore, that word mouth that buzz that you get from P r as an example.
Bridget Winston39:01All of those tactics that were much more consumer are now much more enterprise ready.
Bridget Winston39:07I'm seeing it play out in consumer led growth too.
Bridget Winston39:11Like, at chief, as you can imagine, the referral engine was pretty much everything for us.
Bridget Winston39:16I had a friend who is a Ceo of a of a b2b, Saas, cyber cybersecurity company, who he sells to are Cis.
Bridget Winston39:25So he sells to cybersecurity, folks who...
Bridget Winston39:29As you can imagine in that job, That's a very lonely position.
Bridget Winston39:32Right?
Bridget Winston39:33Because they are cis at a bank as an example at any moment if they get hacked, that is their job on the line.
Bridget Winston39:40Their name is in the paper.
Bridget Winston39:41And so that's a very, like, scary position to be.
Bridget Winston39:44Their entire growth engine comes from community led growth and referrals and talking to each other.
Bridget Winston39:52So I said to him.
Bridget Winston39:53I was like, I would stop spending money on paid ads.
Bridget Winston39:56And I would actually just lean into your community led growth strategy.
Bridget Winston40:00Get these systems together.
Bridget Winston40:02Have them talk to each other, have them learn from each other.
Bridget Winston40:05And the flywheel that now that has created for him is he's spending that money that he would have spent on let's call it any of that paid marketing.
Bridget Winston40:13And now putting it into retreats.
Bridget Winston40:15Gatherings for them, bring them together.
Bridget Winston40:18They're in a Whatsapp group together already, just allow for them to learn from each other to find community with each other, and naturally, the flywheel of that acquisition engine will will start to build.
Bridget Winston40:30So I would say that in particular at PatientNow is probably the thing I'm bringing in because the people who I'm selling to are med spot owners.
Bridget Winston40:41Those are people...
Bridget Winston40:41Those are the consumer...
Bridget Winston40:42Those are the customers that we are helping every day.
Bridget Winston40:45Med spa owner, traditionally is seventy percent, are women owned entrepreneurs.
Bridget Winston40:48They may be a nurse practitioner, or they may be a provider themselves.
Bridget Winston40:53Every minute they're on the call with me or my team.
Bridget Winston40:57Is a minute they are not making money for their med spot practice.
Bridget Winston41:00So in some ways, what I am selling to them and giving to them as our value proposition is not necessarily back end software that helps with with their practice management Emr marketing tools all of that.
Bridget Winston41:12I am giving them the confidence that we've got you.
Bridget Winston41:14And that is best told by people who I got.
Bridget Winston41:19Right?
Bridget Winston41:19My customers who I deliver for every day.
Bridget Winston41:22So I will be bringing in that consumer, that consumer kind of motion of community led growth into what is effectively a B to b Saas like.
Rachael Bueckert41:31Yeah.
Rachael Bueckert41:31I love that so much.
Rachael Bueckert41:32And I think a lot of people in B, resell B rather forget that buying committees, each individual is a c.
Bridget Winston41:40Yes.
Bridget Winston41:40Exactly
Rachael Bueckert41:41it's, like, a bunch of little B2c inside your B2b.
Rachael Bueckert41:44So other people that you're talking to and and people want connection, and they want to feel supported, especially nowadays in in the era of Ai, and it feels like so much content that we're seeing in our our regular meeting places like Linkedin.
Rachael Bueckert41:57It feels so much more dis genuine because you can just tell the people are just creating, like, Ai content.
Bridget Winston42:03Totally, what is the Ai slot as they're saying,
Rachael Bueckert42:06the Ai swap.
Rachael Bueckert42:07Yep.
Rachael Bueckert42:07Well, I mean, nothing needs to Ai.
Rachael Bueckert42:09Like, I...
Rachael Bueckert42:09We use Ai to help with stuff here, but when everything you're doing and producing is Ai, people can tell.
Rachael Bueckert42:14And I think there's gonna be a huge craving for that human connection.
Rachael Bueckert42:17And, yeah, we were just talking today or throwing there on the idea of, like, creating our own, like, slack communities or something like that for for Cro and revenue leaders.
Rachael Bueckert42:25And and and that's what it'd would be about.
Rachael Bueckert42:27It would just be about them connecting with each other and, like, networking
Bridget Winston42:32absolutely.
Bridget Winston42:32Absolutely.
Bridget Winston42:33I couldn't agree.
Bridget Winston42:34I mean, because in a world where there is no more playbook anymore.
Bridget Winston42:39I truly do say that.
Bridget Winston42:40Like...
Bridget Winston42:40And this is how how we talked about cheap too.
Bridget Winston42:43Like, and maybe the first time that you're facing a problem.
Bridget Winston42:46But I guarantee it's not the first time that thousands of my members are facing that problem.
Bridget Winston42:51So in a world where, like, I would say, maybe even you're...
Bridget Winston42:55If you went to and got your Mba.
Bridget Winston42:57That playbook may not working or all of that education or all of your twenty years of experience may not working anymore.
Bridget Winston43:04So you've gotta learn from others and those pure networks that in.
Bridget Winston43:08That's why I say the community led community becomes much more important in a world where people don't know what the exact right next thing to do is.
Bridget Winston43:16And so they asked their friends.
Bridget Winston43:17They ask people who are having some success with it.
Rachael Bueckert43:21Mh.
Rachael Bueckert43:21Absolutely.
Rachael Bueckert43:22So what attracted you to the position at PatientNow coming from chief?
Bridget Winston43:28Well, I love it.
Bridget Winston43:29So this question is...
Bridget Winston43:31Yeah.
Bridget Winston43:31I knew it was gonna be really hard to find the next opportunity that, like, rival my experience with with she It was so mission centric, and there was so so much to love about it, and I learned so much, and I loved my leadership team.
Bridget Winston43:45I am so thrilled to say that I found the exact right opportunity.
Bridget Winston43:52I was planning on doing my camino d des Santiago And my tuscany anything for months But this opportunity, I will say in Carrie Go, the Ceo was a very big part of that.
Bridget Winston44:02But I'll talk through a little bit of the opportunity.
Bridget Winston44:05I'd start to say with just the opportunity.
Bridget Winston44:06So number one, it's a twenty billion dollar market that's growing fifteen percent a year.
Bridget Winston44:12It is a market with tailwind.
Bridget Winston44:14And it is so fun as a Cro to sell in a market with tailwind in a market that is growing so fast and in a market where I actually even know know the solution.
Bridget Winston44:25So selling to Med, Guess what?
Bridget Winston44:27I'm a customer.
Bridget Winston44:28So I understand.
Bridget Winston44:30And so I would start to say with, like, selling into a market with tailwind where every every minute you're seeing another men's ball or Gl one clinic or dermatologist, plastic surgery center, like, It's a market with tailwind, and it's becoming one of those markets where even younger people are going, even men are going.
Bridget Winston44:47And so you're starting to see both the opportunity where there's real commercial success, but it's also impacting people.
Bridget Winston44:53And that's brings me to the mission element of this.
Bridget Winston44:55As I mentioned, seventy percent of Med hunters are women in.
Bridget Winston44:58And these are thriving entrepreneurs who just need help, making their practice run smoother.
Bridget Winston45:04What I do is help make these these business owners more money.
Bridget Winston45:08So that they can do the thing that they care about.
Bridget Winston45:11Right, every day.
Bridget Winston45:12And so that's where, like, that mission alignment that...
Bridget Winston45:14That comes from chief, I think is really really aligned.
Bridget Winston45:17And then lastly, I would say the team.
Bridget Winston45:19Everything from Carrie, the Ceo the second we met, I was, like, this is someone I want to follow.
Bridget Winston45:25She has a lot of people who have gone with her from organization to organization.
Bridget Winston45:30When you find a Ceo who has that level of followers ship.
Bridget Winston45:34You follow them, you get on that...
Bridget Winston45:36You get on that rocket ship with them.
Bridget Winston45:38And then everything I've done in my first weeks have been all about diving in to the customer facing teams.
Bridget Winston45:44So everything across marketing sales, onboarding, support, client success, And as I dive in, and we talked about the things that are important for the customer, our team has a real pulse for what our customers are craving and real empathy for that business owner who is trying to do the best thing for her practice.
Bridget Winston46:04And that we are that that support engine to kind of be there with it.
Bridget Winston46:09I got you.
Bridget Winston46:09And so they've got great ideas about when we show up our best.
Bridget Winston46:13And also, how can we continue to iterate on this and and improve that even more.
Bridget Winston46:18So I'd say, honestly, the opportunity, the mission and the team are the things that I just...
Bridget Winston46:24I couldn't say no.
Bridget Winston46:25I'd come home from Europe and take this job quickly and get ready for this year.
Rachael Bueckert46:30Yeah.
Rachael Bueckert46:30Absolutely.
Rachael Bueckert46:31I love that.
Rachael Bueckert46:31And I feel like the...
Rachael Bueckert46:32The world just needs so many more businesses that are like that and are so connected to their customers, and it just doesn't feel like like a sterile robotic transaction, You know, but you're actually feeling supported by the businesses that, you know, you use and the tools that you use.
Bridget Winston46:48Yeah.
Bridget Winston46:48Yeah.
Bridget Winston46:48Absolutely.
Bridget Winston46:49Because I mean, I sit there and I, like, technically, we sell software.
Bridget Winston46:52But really, what we're selling is the feeling of trust that we're gonna help you.
Bridget Winston46:57We will help you, and we will.
Bridget Winston47:00And that's...
Bridget Winston47:00That was just...
Bridget Winston47:01Like, to find that alignment with an organization and and in support of And smb businesses that are trying to grow in a in a in a market where they're just really trying to execute on the demand.
Bridget Winston47:14That they have, signed me all day.
Rachael Bueckert47:18Absolutely.
Rachael Bueckert47:18I love it win, like, values mash.
Rachael Bueckert47:19You always want your values to match the company at?
Rachael Bueckert47:22So what kind of goals are you hoping to achieve in the coming quarters or years that you're there either for revenue numbers, percentage increases or or just, like, operational projects.
Bridget Winston47:34Yeah.
Bridget Winston47:34I'd start to say there are certainly revenue goals that we have that are that are very in aligned to the high tailwind opportunity that we see.
Bridget Winston47:45But I think that there's always refinement that you can do with making sure that you are targeting the exact right Ic and that you are delivering the product enhancements that that Ic is most desi.
Bridget Winston47:57So that, I would say is probably my most critical element, which is customer centric, so aligning all of these teams and the company around the customer centric of those that we are designing around Therefore, it shows up, as I always say, I'm chief revenue officer, but revenue is a lagging indicator of customer centric.
Bridget Winston48:18And so aligning the entire company around.
Bridget Winston48:21How are we designing products that answered the call of that customer?
Bridget Winston48:25And have empathy for that customer?
Bridget Winston48:27Because as I mentioned, every minute that, Med thought owners on a call with me is a minute that she's not able to generate revenue for her business.
Bridget Winston48:35And so how am I always constantly showing up with that in mind where I am there to make her more money or save her money or time.
Rachael Bueckert48:44Yeah.
Rachael Bueckert48:44I love that.
Rachael Bueckert48:45So looking across chief Shutterstock, PatientNow the other rules you've had before.
Rachael Bueckert48:51What kind of skills and expertise Do you think Cro need to build universally?
Rachael Bueckert48:55That would allow them to work at such a wide variety of different types of companies that have different, you know, go to market motions and and structures and stuff like that?
Bridget Winston49:06Oh, I love this question.
Bridget Winston49:07So some people call my...
Bridget Winston49:09Let's call it disparate experience, a liability.
Bridget Winston49:15And what I would say is it is the thing that is going to make me nail every role that comes up, especially in a world where there's no playbook.
Bridget Winston49:24Again, I'll throw out another book that Carrie actually recommended Carrie Gomez our Ceo a PatientNow.
Bridget Winston49:30Recommended it's a book called Range, and it talks about the importance of having in a world where there is no defined path of success, people with range are best suited to solve those problems.
Bridget Winston49:44There are other times where there's a very defined path where someone who's, like, more like a tiger woods who, from the age of two, practiced and got better where there's a defined path of success.
Bridget Winston49:54Then that is...
Bridget Winston49:55It's actually better for you to just practice a lot and have subject matter expertise just on your golf swing and to get better on that.
Bridget Winston50:02But in a world where there is no playbook.
Bridget Winston50:04People with range actually do better.
Bridget Winston50:06So what I would say is I believe that my background in being in sales, partnerships, marketing, customer success, b to b Saas, unified communications, technology, membership org, and now into a vertical Saas play, I actually believe that that is what allows me to come at these problems with pretty standard because it's not...
Bridget Winston50:30The playbook doesn't change in the sense that, like, you still do very similar things.
Bridget Winston50:35The ways to improve, let's call it new Arr are all the same.
Bridget Winston50:39Increase your pipeline, increase your average selling price, increase your conversions and win rate.
Bridget Winston50:43It's pretty standard no matter what what business you're around.
Bridget Winston50:47Those are kind of the the levers you pull and they're are just different tactics.
Bridget Winston50:51And the range can be the thing that gives you creativity in those tactics once you've got sort of the the understanding of the fundamentals.
Bridget Winston51:00Second thing I would say is you've gotta have a financial acumen.
Bridget Winston51:04That financial acumen is so critically important so that you can actually make good decisions based upon the data.
Bridget Winston51:11So yes, you've got to have lots of range to understand your creativity.
Bridget Winston51:15So you've gotta have sort of left brain right brain at the same time.
Bridget Winston51:19So you've gotta have that creativity that comes from diverse experiences.
Bridget Winston51:22But as long as you are anchoring everything into financial acumen and data, that always helps make your recommendations go very far.
Bridget Winston51:31And then I say the last thing is, like, a little bit of grit and resilience.
Bridget Winston51:35I was a d one athlete, I bring that up in every interview, that I...
Bridget Winston51:40That I have because just having, like a little bit of grit and resilience in, like, ability to, like, pick yourself back up when things are hard.
Bridget Winston51:48I'd say, and you don't have to be an athlete to do that.
Bridget Winston51:52There's plenty of experiences that can give you that childhood, like, whatever it might be But Childhood.
Bridget Winston51:58I always say...
Bridget Winston51:59Yeah.
Bridget Winston51:59Exactly like there's all sorts of things that I'm sure people who dancers, people who were musicians.
Bridget Winston52:05Like, there's just a little bit of that written resilience when things got hard.
Bridget Winston52:08And those are the things I would say, I look for and that I I will be.
Bridget Winston52:12Caring with me throughout because I think in a world where it's uncertain.
Bridget Winston52:17You've gotta believe in yourself, trust yourself and, like, leverage your skills and competencies, but also just have the character of someone who's constantly, like learning,
Rachael Bueckert52:28I love that.
Rachael Bueckert52:28And I was interviewing Cal Norton yesterday for the podcast.
Rachael Bueckert52:31He did mention something.
Bridget Winston52:33Oh, love him.
Rachael Bueckert52:34Yeah.
Rachael Bueckert52:34He's great.
Rachael Bueckert52:35And he mentioned something along the similar lines of having having some kind of outside hobby.
Rachael Bueckert52:41Where you you go into it not knowing if you'll succeed at it.
Rachael Bueckert52:45So it's not something that's, like, easy or something that's like, oh, yeah.
Rachael Bueckert52:48I'll, I'll just gonna do this.
Rachael Bueckert52:49But you go into it feeling like, I might actually fail this and then trying it and then seeing if you can push through and succeed at it, or seeing if you do fail at it and, like, picking yourself back up and, like, creating that grit and resilience.
Bridget Winston53:01I couldn't agree more with that.
Bridget Winston53:02And, like, it's it's something we teach our...
Bridget Winston53:04Teach kids to always end it's, like, you learn in that discomfort.
Bridget Winston53:08I will tell you on that Camino.
Bridget Winston53:10Day three when it was pouring rain for six hours.
Bridget Winston53:13I woke up, and I was like, on day.
Bridget Winston53:15I was like, I don't wanna do this.
Bridget Winston53:17I'm like, so annoyed at doing this.
Bridget Winston53:19And, of course, like, getting myself to go through it, and I will say it was only through, like, going through that hard day and kind of going, what is this meant to teach me?
Bridget Winston53:29What can I learn from this?
Bridget Winston53:31And I will say, gosh, I came out the other side, It was day three that I actually started.
Bridget Winston53:36Okay.
Bridget Winston53:37Enjoying myself a little bit more?
Bridget Winston53:39Talking to the other folks on the...
Bridget Winston53:43On the walk.
Bridget Winston53:43Giving myself small wins where I stopped and had some coffee and rested my feet.
Bridget Winston53:49There are things that you can do to kind of get yourself frankly motivated to do the things that are hard, And so even just finding out how you can motivate yourself during, like, times of being un or demo.
Bridget Winston54:04That was a learning experience in.
Bridget Winston54:06I was like, okay.
Bridget Winston54:07So on this date where I have to go walk six miles in the rain.
Bridget Winston54:10How about you stop on mile at the second hour and have a coffee.
Bridget Winston54:16And I was like oh, that's a little reward for myself.
Bridget Winston54:19Okay?
Bridget Winston54:19Let me shrink the change of this six hour walk.
Bridget Winston54:22And stop after hour or two.
Bridget Winston54:24And, like, there were little rewards.
Bridget Winston54:25And so these are all these little little tricks that you learn when you put yourself into uncomfortable situations that then you can...
Bridget Winston54:32That I've learned that now I will tell everyone.
Bridget Winston54:35You better go on this, You're gonna learn so much about yourself.
Rachael Bueckert54:38I love that.
Rachael Bueckert54:38And, it's is so important to too.
Rachael Bueckert54:39I mean, like, we we try to, like, just talk about the operational side of being a Cro, but I think these other things are so so important and they all bleed into each other.
Rachael Bueckert54:48Like, it's all connected.
Rachael Bueckert54:49It's not, like...
Rachael Bueckert54:50Just learn how to be, like, really good at operations are really good at finances or sailing or whatever.
Rachael Bueckert54:55It's like, you have to have this well rounded kind of personality and, like, inner world to really really succeed at all these other things because all these little pieces and experiences since you have.
Rachael Bueckert55:06They all lead up to, you know, other challenges you're gonna face in your your business in your career life.
Bridget Winston55:12Couldn't agree more, and you said it best.
Bridget Winston55:14We are all c's.
Bridget Winston55:15Right?
Bridget Winston55:16We are all consumer.
Bridget Winston55:17And so, like, every every I always am, like, you know, a company is just made up of in of people.
Bridget Winston55:23So truly, to be a good leader, you actually just have to love people.
Bridget Winston55:27And you truly do have to love people and know how to motivate people because your subject better expertise doesn't win the day anymore, like, once you become a leader, you are leading the people who are leading the people who are leading the people who are getting the thing done, so you've gotta have an expert understanding the data so that you don't have to be in every call to understand how things are going.
Bridget Winston55:47But you also have to be a lover of people, and that takes change management.
Bridget Winston55:52That takes grit that takes resilience that takes an understanding of the emotional side of, like, change management.
Bridget Winston55:57And so all so critically important.
Rachael Bueckert56:01Yeah.
Rachael Bueckert56:01Absolutely.
Rachael Bueckert56:01And so we talked a little bit about playbook kinda throughout the conversation.
Rachael Bueckert56:06But I wanted to ask what has changed in the playbook or the title of the Cro, the way that you work between it was like, on your first day at Shutterstock versus your first day at chief versus your first few days now at PatientNow?
Bridget Winston56:21Well, I'd say the acceleration of how Ai can augment my ability to execute the playbook and my my insight on what the playbook should be.
Bridget Winston56:31So I'd say Ai is probably most critical element, as I mentioned, the planning process used to take me five months to do at Shutterstock.
Bridget Winston56:40That is now accelerated into less than a month.
Bridget Winston56:43To get ready for a new fiscal year, capacity planning, the models of, like, what needs to be true from the marketing to, kind of retention models.
Bridget Winston56:53What insight can we learn about the way that we might wanna change the product.
Bridget Winston56:58So I would say, Ai has now not just been enabler for me on the marketing and sales and customer success side, but also getting those feedback loops into product into finance so that we are better informed so that we're better kind of aligned for an annual operating plan model.
Bridget Winston57:16So I would say that is probably the biggest change that I've seen and also just the growth that I've had.
Bridget Winston57:21I think, I was always the youngest leader person on my team, and I was managing people who had either done things that I hadn't done, or, you know, it was my first time doing it, so I had nervous about about leading a team of people who were...
Bridget Winston57:38I think I was thirty when I became a Vp, and I was leading fifty year olds.
Bridget Winston57:42And it was I was leading across so many segments and functions that I'd had never even done.
Bridget Winston57:48But what I find is that what I can bring into that first off now is more experience and, like, a comfort with myself.
Bridget Winston57:54And the fact that I'm, like, I got this.
Bridget Winston57:57I know this.
Bridget Winston57:58But secondly, like, once you align around the customer, like, it's no longer about you, the customer or the data about the customer and the funnel and all of those things, the tactics start to take care of themselves.
Bridget Winston58:09I'd start to say also, like, in that environment especially when you feel like you're trying to prove yourself.
Bridget Winston58:14You sometimes go too hard in trying to prove yourself.
Bridget Winston58:19I think it's also...
Bridget Winston58:20Don't be afraid to be wrong.
Bridget Winston58:21Don't be afraid to ask others what they think too.
Bridget Winston58:24As long as you've aligned sort of around a North star or something that should be kind of guiding principles, I think you can you can start to ask people questions that then get you to a an answer that solves the need for the customer or for the company priority in the best way and not just in a way that you're like, this is what we're doing because I'm having impostor syndrome and we should go this direction.
Bridget Winston58:49Right?
Bridget Winston58:49So it's, like, be not being afraid to solicit that feedback too.
Rachael Bueckert58:53Yeah.
Rachael Bueckert58:53I love that.
Rachael Bueckert58:54So we're a little bit over time, but that's okay.
Rachael Bueckert58:58I just had one more question for you, and I really love this question personally.
Rachael Bueckert59:02What's the story behind your revenue leadership that you don't get to tell often enough?
Bridget Winston59:08I think it's that my favorite thing is pivot and change management.
Bridget Winston59:13And if I had to say what aligns me across all of those disparate roles or industries.
Bridget Winston59:22What I would say, the the common bond across all of them is that there was a pivot to be done where what got us here won't get us there.
Bridget Winston59:33And my hot take is that change management is a discipline it's all well and good for me to be like, I love Pivot and that pivot superpower, but there is actually a structure to the way that you introduce change and not enough people give it that give it that due.
Bridget Winston59:53And I will say, if you want the book on it, go read, switch, how to change things when change hard.
Bridget Winston60:00This is the way that you can implement a change management discipline, with your leaders with yourself with your team, and actually hold yourself accountable, and I will say this is something that I did at Shore tell at Shutterstock at chief.
Bridget Winston60:17And I'm about to launch at a PatientNow too.
Bridget Winston60:20I have a deck that basically takes that book and walks my leaders through it.
Bridget Winston60:24We workshop something a switch.
Bridget Winston60:26They're trying to make with their team, and we walk through the tactics and very easy strategy that you can use to do that change management.
Bridget Winston60:35And so I would say, it can be all well and good that I love Pivot and a superpower of mine, but I also think that it is so critically important.
Bridget Winston60:43The responsibility of leadership.
Bridget Winston60:46Is to actually have an organized approach to change management.
Bridget Winston60:49Otherwise, she just came on across as chaotic.
Rachael Bueckert60:53Awesome.
Rachael Bueckert60:53I love that.
Rachael Bueckert60:54What a good answer?
Bridget Winston60:55Oh, good.
Rachael Bueckert60:56Alright, Bridget.
Rachael Bueckert60:56This has been so amazing.
Rachael Bueckert60:58What a great conversation and amazing amazing insights, where can people find you and follow you if they wanna follow along with your journey at PatientNow?
Bridget Winston61:07Linkedin is probably the best place.
Bridget Winston61:09So hit me up.
Bridget Winston61:10Linkedin with me.
Bridget Winston61:11Send me a dm.
Bridget Winston61:12Love
Rachael Bueckert61:12it.
Rachael Bueckert61:12Awesome.
Rachael Bueckert61:13Thank you so much.
Rachael Bueckert61:14Have a great rest of your day.
Bridget Winston61:16Thank you so much, Rachael.
Rachael Bueckert61:20Thanks for listening to the show.
Rachael Bueckert61:21If this resonated, and or you'd like help with anything we talked about in the show, please reach out to us.
Rachael Bueckert61:26You can find us at Union Square Consulting dot com and the info will be in our show notes.
