Kathleen Booth on this episode
Kathleen Booth, former SVP of Marketing and Growth at Pavilion, shares how microsegmentation is becoming the defining GTM tactic in B2B tech right now. After hearing from a prominent VC operating partner that "the things that used to work are not working anymore" and that microsegmentation is what actually works, Kathleen breaks down how to do it at scale without becoming another spam machine.
Microsegmentation means moving beyond broad demographic targeting to create highly specific, contextually relevant messaging for increasingly narrow audience slices, powered by enrichment tools, AI, and automation. What once required writing dozens of email variations manually can now be done programmatically, but the line between personalization that resonates and creepy invasiveness comes down to judgment and effort. Kathleen explains how Pavilion used tools like Clay to identify not just who to target, but what "moments that matter" (a new job, a promotion, a fundraise, a job loss) drive people to seek out community and solutions.
The breakthrough strategy Pavilion deployed combined ungated pillar content (meaty 30-page guides Google couldn't summarize) with gated toolkits (templates, checklists, sample decks), then layered microsegmented outreach on top using de-anonymization, enrichment, and AI-powered copy generation. The result was significant improvements in open rates, click-throughs, and conversion rates across all email campaigns. Kathleen walks through the testing methodology for small segments, how to avoid the "congratulations on your raise" trap, and why imagination, not tools, is the real limiting factor. She also previews how the future will likely consolidate these scattered integrations into unified platforms and raises the provocative question: in a world where bots buy from bots, humanity becomes your competitive edge.
What we cover in this episode
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0:46
Kathleen's Background at Pavilion Former SVP of Marketing and Growth who spent three years building Pavilion's GTM conference from scratch and creating an AI-first marketing engine.
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1:36
Building GTM Conference from Ground Up The challenge of creating an executive-only B2B tech conference with 800 attendees, learning that people want time to connect with peers, not just keynotes.
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7:45
Community Impact and Personal Fulfillment How Pavilion's community drove real life-changing moments, from job placements to compensation negotiations to career recovery after layoffs.
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7:45
Defining Microsegmentation Evolution from broad demographic segments to persona-of-one targeting using enrichment, de-anonymization, and AI to layer criteria (title, company size, recent fundraise, open job postings).
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14:22
The Line Between Helpful and Creepy Using personal LinkedIn posts or family tragedies for cold outreach is gross; layering in effort and business logic (press release scraping, budget identification) feels human.
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18:14
Using Clay for Enrichment and Research Pavilion used Clay to scrape press releases, job postings, and company data to identify funding rounds, budget levels, and ICP targets at scale.
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21:25
Moments That Matter Framework Inflection points (new job, promotion, fundraise, job loss) that drive people to seek community; using these as segmentation criteria and content pillars.
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24:04
Ungated Pillar Content Plus Gated Toolkits 30-page meaty guides left ungated to prove quality and rank on Google; follow-up templates, checklists, and samples gated to capture email addresses.
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28:40
Tech Stack for Microsegmentation De-anonymization tools, Clay for enrichment, Copy AI for generative messaging, integrated with email and sales platforms; RevOps orchestrates the entire flow.
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31:04
Imagination, Not Tools, Is the Bottleneck Tools are all available; the limiting factor is creative vision and understanding what's possible when platforms are connected and what to test next.
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35:14
Measuring Success Beyond Open Rates Leading indicators: open rates, click-throughs, meeting requests; also tracked conversions on gated content and improvements in enrollment and membership.
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40:05
Common Mistakes in Microsegmentation Using lazy personalization (college mascot mentions), copying everyone with 'congrats on raise,' skipping the effort of understanding buyer moments and pain points.
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44:04
The Future: Bots Buying from Bots Unified platforms will automate enrichment, scoring, and sending; humanity and emotional connection become the only real differentiator as everything becomes possible with AI.
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45:27
What's Next for Kathleen Starting as head of marketing at an early-stage B2B SaaS company on November 3rd to build an AI-first marketing team that balances brand and automation.
The lines worth sharing
Microsegmentation is what's working. Everything else? Not so much.
Kathleen Booth · 1:15
Every individual person you interact with is becoming a persona of one. We have the tools to target them with something completely bespoke.
Kathleen Booth · 12:30
Don't just start with congrats on your recent raise because everyone's doing that. Look at what they're planning to use the money for.
Kathleen Booth · 18:45
The limiting factor right now is not the toolset. The limiting factor is our own imaginations.
Kathleen Booth · 31:35
Humanity is going to be the edge in a world where everything's possible with AI.
Kathleen Booth · 44:30
Common questions from this episode
What is microsegmentation in B2B marketing?
Microsegmentation breaks your audience into highly specific, small populations based on multiple criteria (title, company size, recent fundraise, job postings, location, ICP). You then use AI and enrichment tools to craft contextually relevant messaging for each micro-segment, moving beyond broad demographic personas to persona-of-one targeting at scale.
How do you avoid creepy personalization in microsegmentation?
Use business logic and effort: scrape press releases to understand what funding will be used for, identify true buyer pain points and inflection moments, avoid lazy mentions of personal details. The difference is between research-driven relevance and invasive scraping of private LinkedIn posts or family tragedies.
What tools do you need to execute microsegmentation?
De-anonymization (identify website visitors), enrichment (Clay, etc. to layer company and person data), generative AI (Copy AI to write contextual emails), and integration with email and sales platforms. RevOps orchestrates these; no single platform does it all yet.
Should your pillar content be gated or ungated?
Gate the main pillar content (meaty 30-page guides) when it answers search intent better than Google SERPs. Leave it ungated on your site, but offer a PDF download for email capture. Gate the follow-on toolkits (templates, checklists, decks) since readers know the content is good and will trade email for practical assets.
What are moments that matter in microsegmentation?
Inflection points when people seek help or solutions: getting a new job, earning a promotion, their company raising funding, losing a job. Identify these for your buyer, build content around each moment, and use them as micro-segment criteria to reach people when they're most receptive.
How quickly do you see results from microsegmentation?
Leading indicators (open rates, click-throughs, meeting requests) can improve within weeks if your sales cycle is short and volume is high. Results depend on average contract value, sales cycle length, and visitor throughput; longer cycles and higher ACV mean longer testing windows.
SEO meta description
Kathleen Booth on building microsegmentation engines: ungated pillar content, AI-powered enrichment, and why humanity beats bots in B2B GTM.
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microsegmentation B2B marketing
Kathleen Booth Pavilion
GTM strategy personalization
Clay enrichment automation
ungated content gated toolkits
moments that matter buyer personas
AI cold email outreach
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micro-targeted email campaigns
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Read the full transcript · 49 KB · Kathleen Booth
KATHLEEN BOOTHI actually had coffee with an operating partner at a pretty well-known VC firm in B2B Tech recently, and he said the same thing. He was like, there's a lot that's not working right now. Let me start with that. That was the theme of the conversation is the things that used to work are not working anymore. So my question to him was like, well, what is working? And his answer was microsegmentation.
SPEAKER_02Welcome to Go-To-Market Science. There's an art and there's a science to go to market. And in this podcast, we talk about the science by interviewing CROs, private equity investors, and other sales and marketing experts, as well as talking about what we learn every day in the trenches helping to build go-to-market engines. Welcome back to a very special CMO story segment
RACHAEL BUECKERTthat we're doing today with my very special guest, Kathleen Booth, who is the former SVP of Marketing and Growth at Pavilion. Kathleen's also a CMO, founder, and brand evangelist known for her work turning brands into media powerhouses and fostering wildly successful communities like Pavilion's 10,000-plus go-to-market leaders and Impact's 5,000-plus marketers. Kathleen, welcome and thank you so much for joining me today.
KATHLEEN BOOTHThanks for having me, Rachel. I'm really excited to be here and have this conversation with you. Yeah, me too. And before we get into our topic today on micro-segmentation, I am so curious about
RACHAEL BUECKERTyour work at Pavilion and everything you guys do there. So I really wanted to ask, what would you say was your greatest achievement at Pavilion?
KATHLEEN BOOTHOh gosh. I mean, it was such a fun three years. Honestly, I probably like one of the top highlights of my career. And I think if I looked back, and there's a lot of things I could pick, but for me, the highlight was really our three GTM conferences. When I came to the company, they had committed to doing a conference, but didn't really have a plan in place for it. And I got to sort of build it from the ground up and create a major industry event. And we held it three times and we iterated it over the course of three years, always trying to make it a little bit better. And I'm sure they're going to keep iterating and making it even better following my departure. But the opportunity to build that and to have all of those people come together. I mean, we had about 800 people each year attend. And as far as I know, it's the only executive only B2B tech conference. And so that was just great. I mean, the feeling of bringing the community together, seeing people hugging, you know, when they meet each other for the first time in person, and they've known each other on zoom, like, I always say, if you see any of my LinkedIn posts after the conference, I always say there's like a lot of love in that room. And it sounds kind of corny, because you're talking about a B2B tech conference. But it's true, there's a lot of love in the room. And there's just a lot of amazing people who are there to help each other to lift each other up to support each other. And the opportunity to be a part of that is something that I will always be very grateful for.
RACHAEL BUECKERTYeah, that's amazing. And I think a lot of people forget when we're all kind of stuck on the computer, only knowing other people through a screen, that there are actual like human beings on the other side of that. And so it can be very emotional, even if it is like business stuff, right? That's so cool. So you were a part of the very first one that Pavilion did?
KATHLEEN BOOTHYeah. So when I came, they had the contract with the Hyatt Regency in Nashville, Tennessee, they knew they were doing an event, but they didn't even know what it was going to be called. They just knew they were bringing the community together for a conference. And so I came up with the name GTM and the focus on that and was very involved really from day one and just determining what should the conference look like? How should it be structured? Who should we design it for, et cetera? So it was a lot of fun.
RACHAEL BUECKERTAlso, what was like the biggest thing that you learned from doing that? Like any huge issues or challenges that happened in the beginning and you had to like figure something out? Yeah. I mean, the biggest thing, honestly, is that you can never build in enough time for
KATHLEEN BOOTHrelationship building. People think of conferences and they usually, the first thing that springs to mind is like the keynotes and the sessions. But I think, especially because we had an executive level event, people certainly are interested in who's speaking and they do want to learn, but what they're really coming for is the other people that are going to be in the room with them. And in the beginning, I think we had the first year we did it, we had 15 minute breaks between sessions. And that was just like nowhere near long enough. And for the last two years, we increased it to 30 minutes. And I feel like that's still not really long enough. Like we could have 45 minutes to an hour between sessions and people would still be lingering in the hallways having conversations. And so I, you know, I don't know that there's any perfect number, but building in more time for people to get to know each other, you never go wrong with that. That's awesome. And what do you think will be the hardest part of leaving Pavilion? What are you
RACHAEL BUECKERTgoing to miss the most?
KATHLEEN BOOTHOh my gosh. It was just such a unique circumstance to work in a place that the entire mission, the product really was around helping people. And I mean, you could argue that every product is around helping people, but this was a place where on a daily basis, I could log into our Slack community and see messages from people who had gotten jobs because of their participation in the community, who had negotiated better compensation, who had solved a really complicated problem, like just real gratitude and real life-changing things that would happen every day. And that was just very motivating. And to be in a position to personally help people and to do it on, even on a one-on-one basis. Sometimes I think that's kind of rare as a marketing leader, especially, you know, like I come out of B2B tech, you're often selling software and I'm the type of marketing leader that needs to believe in the software I'm selling. Like I have to believe that it's helping people and changing their lives, but this really was at another level. And I mean, I'll never forget. There's one day that really stands out in my mind when it was a women of Pavilion calls. We have the sub community for all the women executives. And this was before we had women who were leading the community and I was running the call. And it was something that I had kind of stepped in to do as a passion project. And it was like a networking call and we got on and there was one woman who joined and she was just in tears. And she said, I just got fired. You are the first people that I'm telling this to. And to see the group of women rally around her and like, say, you're not alone. It's happened to all of us. Like, you're going to be okay. How can we help? Who can we make introductions to? And then two months later to see that same woman who had been in tears on the call, get a new job through the community, have it come full circle in that way. And today I talked to her recently and she just got promoted from CMO to CRO and now she's running marketing and sales and she's really thriving. And those journeys and understanding how they all stitch together and how the community played a part in it is, it was just so personally fulfilling.
RACHAEL BUECKERTThat's awesome. I love that so much. It makes the work so much easier when you know that you're actually affecting people's lives and bringing real value to people's lives. Absolutely. I love that. Well, onto our topic of the day, which is micro segmentation. And Kathleen, you and I chatted a little bit before this episode. I still not entirely sure what micro segmentation really means. So can you give us the full rundown?
KATHLEEN BOOTHYeah. So, you know, I think as marketers, we've always had this concept of segmentation where, you know, you're selling and marketing to an audience, right? A broad audience. And you ideally are breaking that audience down into sub segments and you're tailoring your messaging and your emails and your marketing campaigns by segment. And I think over the past five years, let's say our ability to target and to break those segments down has really evolved because five years ago, it might be very demographically based. You might say, oh, you know, we're selling to marketers at manufacturing companies, right? Like I'm just making this up. And maybe then you might segment by company size or by what they manufacture. But today, because of all these enrichment tools, because of de-anonymization tools for your website, because of AI, the ability to get so much more granular, it has really expanded and it enables us to really tailor our messaging and our campaigns and our content in a way that is so finely targeted. And when done well, that really moves the needle with things like email open rates, with conversion rates, with even like time to close deals, because you're giving people information that's so much more relevant to them. And so there's actually a concept that I've been toying with in my head of like, it used to be that we would develop buyer personas and those would be our segments. Like today we're marketing to Marketing Mary or Sales Sam that I really think is going away or maybe it's not going away, but it's a starting point. And we're almost at the point, if not there, where every individual person that you interact with is a persona of one. Meaning we have the tools at our disposal that we can target that individual as their own profile and come up with something completely bespoke for them. I mean, micro segmentation doesn't necessarily mean targeting one person, but I do think it's like smaller, much more targeted populations that have things in common that let you drive such greater impact with your marketing.
RACHAEL BUECKERTSo how micro do you tend to get or want to get with this? I think it depends. It depends on how micro you can get and not just how micro you can get in
KATHLEEN BOOTHidentifying the segments, but how well you can then take that information or that population and automate and scale messaging to them in a way that still feels really personalized. And so I can give you a couple of examples that we toyed with at Pavilion and that I'll certainly use in my next role. One example is looking at your population of prospects and at Pavilion, we marketed to go-to-market executives in B2B tech. So that's already a segment of the broader population of go-to-market executives, you know, B2B tech specifically. From there, you can drill down to geography. You can drill down to company size. You can drill down to the specific title of the person. So there's a lot of like parameters that I think have been available to us for a long time. So you could be like, I only want to, in this segment, market to CROs of tech companies selling software as a service that are in North America that are between 50 and a hundred million dollars. Like that's not new. That's always been there for us. But when you layer on top of that, an example might be, for example, a company that has just in the last month raised a new venture round. All of a sudden your population shrinks further and you have an additional criteria upon which to target your messaging. You know, you've just raised your round. And I think there's a lot of companies that are doing this, but maybe you even layer something further on that. And it's like just raised around and has an open job posting for a new chief marketing officer. And then you could go even further and their ICP is pharmaceuticals, right? There's just so much you can do now with tools like clay, for example, where you can do wonderful enrichment and you might maybe even drill it down further to say, and has visited our website and has visited a specific page on our website. And all of these additional data points that you're layering in allow you to further personalize the outreach you're doing. And that, I think a lot of that has always been possible, but what hasn't necessarily been possible in the way it is today is what do you do with that information? Before it would have been, oh my God,
SPEAKER_18now I have to write 50 different variations of an email to all these micro segments. But now with
KATHLEEN BOOTHenrichment tools, with AI, with generative AI specifically, we can take these micro segments and what we know about them. And we can essentially write prompts and scripts and automations that say, okay, I know that this company is 50 to 100 million B2B tech. I know they just raised a series C. I know they're hiring a CMO and that brings with it certain challenges. And I know they were recently on this particular page of our site, looking at this specific part of our platform. All of a sudden, if you know those things and you can feed it into an AI, it can craft a pretty darn good specific email and automatically send it out to that person. So that's what I mean by micro segmentation. It's like going to that next layer and getting really, really contextually relevant to the recipient and doing it in a way that's automated with a degree of personalization. Now, and I think a lot of marketers would say like, don't just run it and set it and forget it, run it, come up with the draft emails, and then like quickly review and add in a personal note or an anecdote or check it. But again, the amount of time it takes to do that compared to what it might have taken five years ago is dramatically different. Yeah, no, so much is changing in such a short period of time. Even
RACHAEL BUECKERTa couple of years ago, like we wouldn't dream of having this kind of granularity in the way that we could market. It would have been a time suck and a resource dream. And it's similar to like what we
KATHLEEN BOOTHused to see with SEO, where you'd hire people to sit around and write like 150 variations on a landing page. Now all that can be done by generative AI. And that's another form of micro segmentation, by the way, it's like this programmatic SEO, where you're targeting different audiences with your content, it's so much easier to do it at scale now. And I think the danger in all of this, of course, is just because you can doesn't necessarily mean you should. And like, everybody has these tools at their disposal. So anybody can spray and pray. So it's really about the judgment you use and how you craft that email or how you write that copy on the landing page so that it still feels like you did the work and made it really relevant to them.
RACHAEL BUECKERTAbsolutely. I get cold emails almost every day from all different types of companies. And I can just
RACHAEL BUECKERTtell that they used an AI to do a really rudimentary scrape of the homepage of our website. And not even like a good scrape, because they assume that we are a B2B SaaS company when we are not actually a SaaS company. So they'll say like, Oh, I know that you do marketing at a B2B SaaS company. And I'm like, no, I can tell you actually, but actually, I don't. Yeah, absolutely.
SPEAKER_28Yeah. And I the worst ones are the ones that are like that start with go Blue Jays,
KATHLEEN BOOTHwhich is like my college mascot. And it's such a lazy personalization. Yeah. So I think that there is a way to do this that feels like you put the effort in and you've gotten to know the person a little bit. And then there's ways to do it that are just creepy.
RACHAEL BUECKERTYeah. Yeah. Creepy. And also just like, I don't know, like just abusing it, just like spamming people and bringing up things that you don't need to bring up. There, I remember this story that I read on LinkedIn, somebody posted about how she got a cold email, because she posted on LinkedIn, like a personal story of hers. I can't remember exactly what it was, but it was very personal. You know, some people like to do that, which is fine. But you could tell this person just used AI to scrape her LinkedIn posts because they used this very, very personal thing that happened to her. I can't remember if it was like a death in the family or something like that, like something very serious. Right. And they use that as like their opener to try and sell her their product in like a really gross way. I wish I could remember exactly what it was, but that just really stuck with me. And I was like, man, there's gotta be some humanity in the AI that you use, or you're in for a PR catastrophe potentially. Yeah. And I think, like I said, anybody could really do this micro
KATHLEEN BOOTHsegmentation. It's not rocket science. I would say if you're not micro segmenting, that's a problem today because what you're up against is companies that are. So you certainly have to do it. But I think the real art comes into how you do it and like how you create these prompts to like build contextually relevant messaging without just checking the box again. And without just like, there was a post earlier today by Jen Allen, who's a big LinkedIn influencer in sales. And she actually talked about this with the venture rounds because she has seen a lot of companies do this kind of segmentation as well. And she was like, don't just start with congrats on your recent raise because everyone's doing that, right? Like that's the truth. Everyone is sending these emails saying you just raised money. There's a different way to do it. And she had some suggestions around scraping the press release to understand what they said they were going to use the money they raised for. So it's like, oh, we're going to hire engineering talent or we're going to be building this other feature. And, you know, like that's an example of going the extra mile and saying, you know, I see that you're planning to use the money for X, Y, Z. And in her example, it was like, did you know that this other company did the same thing? And this is again, all possible automatically because with the tools available today, like we've used clay at Pavilion quite a bit, and we have an incredible person on our team who's really great at building out these automations and he feeds it our customer list and he's able to then identify similar companies that have had similar challenges or experiences or in similar industries and like automatically reference them, particularly if they have happy members or customers, high NPS, if you will. And so that like same motion can be done anywhere and populate your emails to make it really feel very personal. Yeah. I'm curious how that's possible to do that at
RACHAEL BUECKERTscale. I only have like a bit of a knowledge with clay. We use clay a little bit, but I'm not, I'm nowhere near like an expert in it at all. And I know there's like so many layers to it that I haven't even touched on yet. Do you guys use the AI agent, like have it read the press release of this and pull out, you know, why they're getting this funding, like something like that?
KATHLEEN BOOTHYeah. I mean, it's unbelievable what it can do. So there's quite a few use cases that we've used it for we have it scrape websites and tell us who our prospective customer is selling to. So like who's their ICP. We've also, a lot of people who join Pavilion have their company pay for their membership. And so we're able to scrape the company website and see if they have like, look at the job postings. And usually it'll say whether they have a learning and development budget. Very often it'll say how much of a budget they have. And so we can actually tell the prospective member, Hey, did you know you have a development budget of this much? So those are some examples, but yeah, you can have it scrape press releases, LinkedIn announcements. You can do S1 filings for bigger companies. So there's just like a lot of information out there that companies make available and tools like clay. It's certainly not the only one, but it's happens to be the one that we were using are just great at mining that information. And over time, you're going to, you know, you can tweak the prompts to make sure what it's returning is logical and makes sense, but it's all out there for you to build on.
RACHAEL BUECKERTThat's so smart. I love that. And I know I like that. Like there's no one playbook for doing this kind of stuff. You can't say like, Oh, this is specifically the kind of stuff you need to look for. It's going to be different for every company and every person you're targeting and their needs and desires and everything. Like you mentioned finding education budget. That's so specific for a company like Pavilion. And that's so smart to think of that. On that thread, what's the research that you guys did to be able to understand how you need to segment? Like, how did you figure out, Oh, we should look for companies that have this kind of budget for their employees? Yeah, I think it all starts with looking really deeply at the
KATHLEEN BOOTHcustomers you're already selling to the best fit customers, the ones that, you know, come on board, who quickly activate, use the product, who are happy with it, who get value out of it. And like, try and trace back what are the common things that tie those customers together? In our case, we knew X percent of new members pay for Pavilion with their L and D budgets. And so the question then is like, well, how do we find more of those? And so that then led us to focusing on that population. I think it's then also, this is where we do go back to that original concept of a buyer persona. Like if we know, for example, that we're selling to CMOs and we deeply understand that CMOs, especially in B2B tech, especially when they're venture backed, you know, when they raise a new fundraising round, that's often a moment of both opportunity and vulnerability for them, because it's either a great opportunity where they have more budget and the company is going to grow faster. And that's a great moment in their career. And, or the pressure ratchets up on them because the investors have given money. They want to see growth increase. And, you know, very often when you get a fundraising round, that's when your CXOs are replaced with somebody who's like done that next stage journey. And so we identified at Pavilion, something that I called moments that matter. And these were like the inflection points in people's careers that would drive them to seek out community. One was raised a round of funding. Another one was just got a new job. Another one was got a promotion. Another one was, they lost a job, right? Like these are all the moments when you think I need a community of peers to help me. And so that also helped us understand, like, how do we identify people who are at those moments? Like who've had a job change, who've had a promotion, who've lost a job, whose companies have recently raised. So it starts with deeply understanding your buyer. And a lot of that can come from research that you do as part of your buyer persona process. A lot of it can come from listening to sales calls. And this is another place where AI is really helpful, because you can take all of your if you're especially if you're using, you know, a call recording platform, many of them have built in the ability to query all of those transcripts and say, for example, tell me, you know, the top 10 reasons somebody is joining or the top 10 reasons that cause somebody to search for us and surface those things. And those all become then criteria you can use to further segment your audience of prospects to try and find audiences that look just like those people.
RACHAEL BUECKERTI love that. The find the moments that matter. I think without really knowing that we kind of did something like that when we were doing kind of a deeper look and overhaul at our own ICP for Union Square Consulting. And yeah, we like went through all of our sales calls and stuff. We noticed that a lot of the times we where we got a prospect that was like a really good prospect, either we won them or not. It was a CRO or another CXO who had just recently gotten to their role at that company and they were looking for help like strategizing and executing and stuff like that. And we were like, okay, so like being in a new role is one of those inflection points. That's awesome.
SPEAKER_18Yeah, definitely. And we actually formulated our content strategy around that. And so
KATHLEEN BOOTHnot only were we doing this micro segmentation and tailoring our outreach, but at the same time, we were building out topic clusters with pieces of pillar content for each moment that mattered. So over the summer, we built one for people who had just gotten into their first VP role, you know, or like their first CXO role, like they've, they were a VP of marketing. Now they're a CMO for a lot of people. They're like, I don't really know what the difference is. There's no book on this. So I need to learn. And so we built content and articles around that topic. And then the second one was your first 90 days in a new executive role. Cause that's something we saw all the time in our community. Like, Hey, does anybody have a sample 30, 60, 90, probably one of the most common questions. And then the third one was preparing for a board meeting. Again, these are all moments that matter. And so it's not just like, how do we do outreach to these audiences? It's like, what artifacts do we have that are useful and educational that will help answer the questions that someone has at that moment to give us a reason to reach out. So it's not all just like, Hey, you want a demo? You know, you want to join? It's like, no, we have, we built resources just for you. That's awesome. That is so validating. Cause we did recently do
RACHAEL BUECKERTsome content like that for, you know, CROs, the first 90 days is in a new CRO role. Like, should you be doing dah, dah, dah, dah, dah. So how do you use that pillar content? Those things you've made in your micro segmentation strategy and process?
KATHLEEN BOOTHI mean, I think with any outreach process, right? First, you have to understand where that buyer is in their journey. And if they're not at the bottom of the funnel, ready to talk to you about, in our case, it was about joining the community. Then you want to reach out to them. You want to stay in front of them, but you got to be careful how you do it. Because I think we're all tired of spammy outbound. You talked about it. You get a lot of emails, right? And so the question is, how can you be most helpful? And so when we would create this pillar content, it was all ungated. There were some things that were follow on offers that were gated, but the pillar itself, the most useful educational piece was available on the website. And so we would reach out first and foremost, just to be helpful and say, you know, Hey, we have this piece of information that we think will be useful for you. And it's incredible. I mean, and this is like repeated throughout my career. Every time I've ungated something, the conversions, the number of people that still request it and give us their email to get a, like a PDF of it is so much higher because they're able to see the content is good and high quality versus people who are like, well, they say they have this long forum guide. I don't know if it's going to be any good. So I'm not going to give my email, right? Like if you can show that the content is good, people will convert and tell you who they are. And that really proved true for us. And, and those pieces of pillar content were some of our most popular content that we've shared. Awesome. So what, uh, so this is my selfishly my own personal
RACHAEL BUECKERTquestions right now, which pieces of content did you decide to gate and ungate? How did you decide which ones to ask for an email for? Yeah. So we wanted the main pillars to all be ungated and we
KATHLEEN BOOTHwanted them to be in-depth enough that Google couldn't answer the question in the search results. So the zero click result. And very often, like when you do a listicle or a how to Google will just take it and like answer that person in the search engine results page. So we didn't want that. We wanted to have something that was in-depth that someone would want to click through and read. That was number one. And so our primary piece of pillar content was like, these were 30 pages long in a Google doc before they got designed. They were like meaty content. So that's all ungated, but we would tell people if you want a PDF, just give us your email and we'll send you the PDF of it. And a lot of people converted on that. But for every piece of pillar content we built, we created a number of, let's call them toolkit assets. So for example, preparing for the board meeting, we had a sample board deck. We had a downloadable cheat sheet on the definitions of the different KPIs and what a scorecard should include. We had a calendar for board prep. So how far out should you start planning? For VP to CXO, we gave kind of an overarching 30, 60, 90. But if you wanted a role specific one, if you wanted the 30, 60, 90, that was specific to a CMO, for example, that might be, it was like a checklist. You download that. So what worked about this is that the things that were gated were the very practical templates and tools. And everybody would have already read the long form piece of content to know that it was good. And therefore we would have instilled confidence that what they'd be getting if they downloaded the toolkit would be useful. Awesome. I love that so much. Now my brain is just
RACHAEL BUECKERTthe gears are turning thinking how we can do that on our side. That is so cool. Okay. I'll have to rein this back to micro segmentation and not just turn it into a marketing call. So I know we've been kind of talking about this throughout the episode already, but is there any other tooling or processes that you used to do your micro segmentation, either figuring out, you know, what segments to do or, or actually like inputting them into the system and having, you know, salespeople use them?
KATHLEEN BOOTHYeah. So I think the first was we put in place website de-anonymization tooling so that if somebody came to our site, we could identify who they were. And then as soon as we were able to identify who they were, we would put them into a clay table and use clay to enrich as much as we could about them to understand, you know, did they have L and D who was their ICP? Who are they selling to? What was the size of their company? Where were they located? Like all the different pieces of information that would help us score the lead as well as understand how to customize our outreach to the person. So de-anonymization, then enrichment, then we also have used copy AI extensively for generative AI to craft messaging. So the outreach we would do would be pretty bespoke to that person based on the information that we knew about them. And copy AI, we had it really trained on our company voice on all the information about pavilion and, and it would pull from clay, like the systems all talk to each other. And so in clay, we also had our existing member list. Again, you know, overlaid with location, role, company size, NPS score, so that for every potential member, we can say, here's one or two or three people that look just like you who are already happy members. We also would be able to say, based on where you live, here's the person that's your chapter head. Would you like us to introduce you to them? You know, and so all of that was done pretty automatically based on the information that we had in the system. And then those integrated with our email sending platform, our sales outreach platform. And, you know, we were able to TF emails for our sales team with that. Awesome. That's such a, like an awesome, like interconnected network of stuff working
RACHAEL BUECKERTtogether. How long did it take to settle that all up? Not as long as you would think. And it's because we
KATHLEEN BOOTHhave this amazing person who's now been promoted to be VP of RevOps who just was really curious to figure out the tools and dove in to clay to, I mean, he understood make.com and Zapier and copy AI and, and like really learned what these tools were capable of. And I think the biggest thing to me is like the limiting factor right now, in my opinion, in this world is not the tool set. The limiting factor is our own imaginations, because I think a lot of these tools are still fairly new. Their capabilities are still fairly new. And I just think most of us haven't even conceived of what we could use them for. And so the thing that was so great about him was he like really dove in to understand what were these platforms capable of. And when he understood that it kind of unlocked this, like, wow, there's all this stuff we could do with them. And then it's a matter of just testing. Like I think with micro segmentation, you know, because you can go quick, you test, you iterate, you see what works, and then you try and like roll out those lessons learned to other populations. And that is, by the way, also the beautiful thing about it being micro is if your test doesn't work, you're not emailing or reaching out to 1000s of people, it might be 10, it might be 50, it might be 100. And so the cost of a miss is much lower than if you're sending to a really large population, where you only have one shot.
SPEAKER_13Mm hmm. So how does that testing actually look like?
KATHLEEN BOOTHWell, I mean, it depends on what the medium is. So if it's email, for example, I think still most people are using email for their primary outreach mechanism. You're coming up with a hypothesis around like we have this population, we think this is how we should customize the messaging to them. You use your enrichment and your generative AI tooling to come up with these emails that are contextually tailored to the audience, you send them. And if it's a small population, like I said, maybe it's 50 people, you start to look at you mean, it's like any test, you look at the open rates, you look at the click through rates, if your goal is demos or meetings booked, you look at that, and you begin to start to compare it across all the other tests you're running. And I think it's becomes very easy to see pretty quickly, this one's exceeding our target and outperforming the others. And then it's a matter of figuring out why, right? Like, is it the perfect line? Is it the open rate that's higher? Is it something in the copy that's really resonating? That's where I think it gets interesting is like, what was it about that outreach that drove results? And then how can we replicate that? And so, for example, in the case of someplace like Pavilion, the questions that we would always have is what are the strongest motivators for someone to join, or to actually like pull the trigger and become a member? Is it the cost? So like, are people thinking about, do I need a discount? Or how am I going to pay for this? Or is it knowing that another peer that they really respect is already a member? Maybe cost doesn't matter if they're like, wow, that person I really admire is a member, so I'm going to join too. Or is it that there's an event coming up in their geographic location? Like these are all variations on messaging that you can test in your outreach. And when you start to see results from one, like, let's say it's, oh, every time we mention peers that are well known in the space that that seems to like really drive results, then let's say we're testing that with a population of chief marketing officers, well, you can do the same for chief revenue officers or chief customer officers, you can start to roll those results out more broadly. That's awesome. What are the challenges with
RACHAEL BUECKERTtesting such small focus groups, though? Because I imagine that, you know, you only send 10 emails out. Let's say you only get one response. Could it just be that five of those 10 people were just I wouldn't say they wouldn't all be on vacation, but, you know, just didn't see it that week or something. I feel like a small numbers is really hard. Yeah, I mean, I think that's where you do have
KATHLEEN BOOTHto think about what the population size is. And like, if it's truly a test around something like value proposition, you probably want to have a slightly bigger audience. But it doesn't need to be huge. I would say like 50 is a decent number where you can begin to see trends. But if it's really about like, hey, we know the value proposition, we just want to get like, we want emails that are very specific to certain circumstances. That's when I think the smaller audiences make sense. If you're confident in the overall value prop, and you just want to really nail the messaging, then go finer in your segmentation. If you're testing value props, or if you're testing some other element, then you might want to go a little bit bigger.
RACHAEL BUECKERTAwesome. I love that. So the question is probably on everyone's mind. What impact has micro segmentation had on Pavilion? Oh, it's been huge. I mean, you know,
KATHLEEN BOOTHlet's just talk about emails. Open rates are higher when we get really specific. But I think the most important metric for us was really the number of people that would convert and join. And we saw significant improvements in conversion rates. And if the exact number differs by campaign, but material impacts and conversion rates, when we would follow this process, like a great example being the telling them that they have L&D budget, because all of a sudden, you're educating people that they're not, they don't have to spend their own money, right? Like, that's pretty powerful. And our response rate went way up for those. So it's something that I think, I think it's the future for every company. And it just it all has to start with like deeply understanding your buyer and looking at those who've already bought and figuring out what those commonalities are and the tools all there. The tools are here, I should say, for us to do this.
RACHAEL BUECKERTAnd I know you talk a lot with other like VCs and CROs and stuff like that. Is anyone else talking about micro segmentation?
KATHLEEN BOOTHYeah, I actually had coffee with an operating partner at a pretty well known VC firm and B2B tech recently. And he said the same thing. He was like, there's a lot that's not working right now. Let me start with that. That was the theme of the conversation is the things that used to work are not working anymore. So my question to him was like, well, what is working? And his answer was micro segmentation. You just have to get very granular and very specific. And that works. So I think that's like reinforced by the experience that I had at Pavilion. It's definitely something I'm going to take with me to my next role and implement for sure.
RACHAEL BUECKERTAnd what were the key metrics that you saw that showed it was working before you saw like any big revenue changes or membership increases? What were some of the first signs? I think leading indicators, definitely email open rates, click-throughs, meeting requests. Like we have
KATHLEEN BOOTHwhat we call an enrollment team, which is sort of like BDRs. And so people who would request a meeting with them, like all of those leading indicators in the funnel began to improve. With the content, we also saw conversions on the content going up when it was included in those emails and as part of like an educational flow to those micro segments. So yeah, I mean, I think it depends on the channel. For us, the focus was very much on email because we found that there's a lot of fatigue. And so we
SPEAKER_21were trying to figure out how to get better results from our email campaigns. And we definitely saw improvements. How early did you start seeing those improvements?
KATHLEEN BOOTHOh, really quickly. But we also had a very short sales cycle. And so that was one of the great things about Pavilion. Short sales cycle, high volume. So we were able to see results really fast. I think for any company, it really depends on what's your annual or your average contract value. Like how much are people spending with you? The higher they're spending, probably the longer it's going to take to see results. How long is your sales cycle? That's going to impact how long it takes. And what's the throughput? How many leads, visitors to your website, et cetera, do you tend to see on a regular basis? And I was lucky because given that Pavilion is sort of a high velocity, high volume business, we were able to do a lot of really fast testing and iteration to prove out the concept.
SPEAKER_21Awesome. And I imagine like every department probably came together and collaborated in this,
RACHAEL BUECKERTright? Your marketing sales product. How did you guys all collaborate on this strategy and work together to make it work?
SPEAKER_21I think it started with working with our member success team and our ops team, because they were
KATHLEEN BOOTHdoing a lot of deep work on cohort analysis, on segmenting our existing customer base and looking behaviorally at what demographic properties did the customers with the highest lifetime value share, what they did some regression analysis on what were the things that customers who were churning had in common versus those who were not. And so like building on the data that they collected to understand like who are our best fit customers? That was the starting point. And that really lived with our member success and our ops teams. And once we had that data, then it was a matter of the marketing team, taking that, looking at the population, the full audience that we had to market to, which was quite large, and beginning to identify the subsegments that matched that criteria. And then it was really like RevOps that helped build the a lot of these motions around that. And product marketing helped a lot with messaging. So it definitely is a huge team activity and, of course, content weighing in with the assets that they used in the emails.
RACHAEL BUECKERTAnd so did you oversee the whole thing or who was like, was there one person that kind of like
RACHAEL BUECKERToversaw all the departments working together? Or is it just really each department head
RACHAEL BUECKERTcollaborating together? I wish I could claim credit. I think the champion within our team who really propelled this
KATHLEEN BOOTHwhole thing forward was a guy named Josh Carter, who's now he's the one that just got promoted to VP of RevOps. I think he was the one that saw the possibility of how all these tools could connect to make this possible. And that was the vision that really served as the spark for all of it. And then, you know, I think we worked pretty cross-functionally and collaboratively. So we had access to the data, the member success and the ops teams were already sharing that data so that we can more deeply understand what the best fit customers were. I think the piece that I was really focused on was, and this was something that we as a leadership team were really focused on, was like, we wanted to bring in new members, but we didn't want to just bring in anyone. We wanted to bring in the people that were the best fit, that would get the most value out of Pavilion, that would give back and contribute and be great members and make the community a more vibrant place. And so that's why that data was so important, was to understand, like, who are the people that are going to really help and serve our mission by becoming a part of the community and how do we get more of those? Absolutely. I feel like that's really applicable to any company as well. Because, you know, if you're
RACHAEL BUECKERTlike a B2B SaaS company, you want to attract the best customers for you. Because if you have wrong
RACHAEL BUECKERTcustomers, you're going to spend a lot more money in, or going to lose a lot more money in churn, spend a lot more money in customer success tickets because they're having issues or your sales team is going to
RACHAEL BUECKERThave to give them special deals just to close it because they're not actually, like, the best customer for you. So yeah, that's so important. Were there any surprising insights you discovered throughout the
RACHAEL BUECKERTmicro-segmentation process? I think the most surprising thing, honestly, was how much was
KATHLEEN BOOTHpossible. It's almost like you have to, once you start going down this rabbit hole, you kind of have to, like, rein yourself in and decide what you're not going to personalize around. Because you can do so much. You can get so specific. And to my point earlier, I think it can get creepy if you go too far. And so that's, like, finding that balance of, like, well, we could talk about all these other things, but we're not going to. And zeroing in on the things that matter the most to the prospect, right? Like, what are the things that they care about the most that are causing them the most pain
SPEAKER_21that we can help solve? That's what's most important. And how do you think this is going to
RACHAEL BUECKERTevolve in the future, either the near future or distant future, with, you know, the onset of AI and how everything's becoming creepier almost? I think that right now we live in a world where you can manually sort of connect all these different
KATHLEEN BOOTHtools and build what I'm describing. And it's happening and people are doing it and seeing great results from it. I think we're quickly moving to a world, and in some cases we're already there, where you don't need to connect these tools, like, where there will be unified platforms that will be able to just look at your customer data. They'll be like, oh, I see that this person came to the website. I've automatically enriched them. I've compared them to the, you know, your database. I know they fit the ICP. I've scored the lead. I've created the email. I've sent the email. Like, I think a lot of that is just going to happen in the background. And we're not going to need to have RevOps teams building this all and connecting it because somebody is going to figure out how to just make it seamless or the AI will know how to make it seamless. I think that's the second stage. But again, like all of these capabilities, they're available to everybody. And so the classic trope is that marketers ruin everything and they will be abused. These tools will be abused. And so there will be a lack of novelty factor very quickly for this approach. And so I think at the end of the day, it's all going to come back to like, how do we make things more human? Humanity is going to be the edge in a world where everything's possible with AI. And so I think we're going to have to continue to ask ourselves, how do we inject a personalized element into this? I think there's also, we're quickly moving to a world where bots are just going to buy from bots. Like the goal is eventually not going to be to get a person on the phone. It's going to be like, how does my bot sell to your bot? And we're both training our bots with what we're looking for. And so there's like that whole other experience, which is going to be interesting, but there will still be things that there will still be opportunities to break through the noise and to build brands that people love, to build trust, to build that emotional connection. And that's where I think the most interesting opportunities lie for marketers. That's crazy that humanity is going to be like the biggest asset for
RACHAEL BUECKERTa company in the future. It feels so dystopian. I know. It's crazy how fast everything has happened
RACHAEL BUECKERTtoo. Yeah. Oh my God. I can't even imagine what it's going to be like even just a year from now. I know. Yeah. Well, this has been really awesome. I think our listeners going to get a lot from this. I mean, I definitely have, and I'm not even in the operational side, but just from a marketing perspective, this has been like super, super enlightening. I also wanted to ask what's next
RACHAEL BUECKERTfor you now? Well, I am starting a new role November 3rd. I haven't announced it yet. It's head of marketing role at a B2B tech company and it checked every box for me. So I wanted to go
KATHLEEN BOOTHback into SaaS and I wanted an early stage company that didn't have marketing all built out yet because I really want to build an AI first marketing team that also prioritizes brand. I want to see how I can strike that balance and I want to do it from scratch. But I wanted a company that has a great product and product market fit. And the place I'm going is someplace that I've been a customer of for a few years and have experienced the product firsthand. Love it. Believe in it. I think there's a ton of value there and it's something that I'm personally really excited to align myself with and to evangelize. So I'll be announcing it on November 3rd. That is so exciting. And where can people find
RACHAEL BUECKERTyou, Kathleen, if they want to like see where your journey goes? LinkedIn. I'm very active there. So just
KATHLEEN BOOTHsay that you heard me on this podcast and I will accept your connection request. Awesome. Well, thank
SPEAKER_60you so much, Kathleen. This has been amazing. Thanks, Rachel. This was fun. Thanks for listening to the
SPEAKER_02show. If this resonated and or you'd like help with anything we talked about in the show, please reach out to us. You can find us at unionsquareconsulting.com and the info will be in our show notes.
