#113 - Jillian Bejtlich - Community Lead at Calendly - Supercharging GTM with the Community

Sales, marketing, RevOps, and customer success. It's sink or swim out there, and yesterday's strategies and tactics won't help you today. This is Revenue Today, and I'm your host, Jared Robin. Join me as we interview top revenue leaders in our community to learn what steps we could take right now to help you scale more effectively. Revenue Today is sponsored by Rev Genius and Rev Room, and we're on a mission to build trusted spaces for curious revenue professionals who are collaborating on the future of B2B GTM. Hey friends, welcome to another episode of Revenue Today. I'm, I'm really excited about this one. Um, we've been diving into community leaders and lately, um, and how community contributes to a big part of go-to-market. And today's guest has been Contributing to communities since 2007, working in it since 2011. She's helped architect many communities ranging from software as a service base to even the defense industry. Most recently, she's taken the lead at Calendly, uh, following a long stint running community at Zapier. So she's got a plethora of experience. Welcome, my guest today, uh, Jillian

Hey, thanks for— yeah, I'm super happy to be here.

Awesome. And, you know, I have so many questions to ask you because, you know, community being a part of GTM is misunderstood or not always understood fully, right? Yeah. And it's the challenges we have, you know, with dealing with others and, you know, in our company and in the space. Diving right into it, if I were to ask you to debunk a myth about GTM or generating revenue, what would it be?

So when it comes to community specifically, I think the one that I see the most that I always want to debunk is that people assume that community can only live at the top of the funnel. They think that community is simply there for awareness and acquisition, and once you've done your job there, You're good, you're done, that's it. And you see a lot of communities try to launch with this in mind. They're pretty much there just to kind of like generate leads or to kind of like get people in the door. The reality is that community is so much more than that. Most of what I do, I tend to focus on— if awareness and acquisition are the first 2 phases of the customer lifecycle, I really love hanging out in adoption and advocacy. Because this is where you actually see cost savings happen. You see transitions happen, and you really see that stuff that you're like, oh my gosh, this is doing something. This is actually having an impact on the business. It, you know, it saves you money, it's free advertising, but you gotta get there. You actually have to get past that initial strategy of awareness and acquisition. And you really have to lean in and be like, I trust that bigger things are coming. And too many communities, don't do that. They only focus on those first 2 phases because they're like, community is part of GTM, and GTM is all about that. They forget about the rest of that customer lifecycle.

So, how do you get started, you know, being a head of community, coming in and helping the team realize the importance?

You know, I think it's funny, kind of like a superpower you have to have is actually realizing when to It's gonna sound a little crazy. Shut up and listen. It's actually really important. So, one of the things, you know, I've been at Calendly now for either 7 or 8 weeks. I actually don't remember. It's less than 2 months. That's all I know. I was just talking to my boss this morning, and I was like, I know it's more than 6 weeks, but it's less than 10. So, it's somewhere in there. But my time here so far has been about listening. I have been talking to people across the organization. I have been interviewing customers. I've been interviewing non-customers. I've been talking to other community leaders. And it's a lot of me asking 4 or 5 questions, sitting back, and letting those people tell me about what it is they want to see out of a community, what they don't want to see out of a community, how they feel about Calendly, how they found Calendly, why they don't want to use Calendly. That's actually where you got to start, which is really kind of counterintuitive to a lot of people because they come in and they're like, the organization wants this. And they go sprinting off with that information, when the reality is that if you start a community and it's not perfectly aligned between the organizational needs and the customer needs, you're not going to get to those last 2 phases I'm talking about. In fact, you may not even get to the first 2 phases.

Yeah. How do you reset expectations? Like, if you're hired and they want the first 2 phases, they want top of the funnel, they're like, yes, we want to increase Calendly users. 30% YOY, and community is the newest thing we're adding. It's a tough market. How do you, how do you help with that or help level expectations?

Yeah. So, I kind of like to use a bit of a sandwich method, which is tell them what they want to hear, tell them how it's going to be, and then tell them what the future looks like. And a lot of times, that is kind of reinforcing the whole, yeah, community can help you with the top of funnel. Absolutely. I'm happy to help you do that. Research shows that our customers are looking for this and the organization is looking for this. This is the overlap. There are some dogs in the background. That is all right. I'm totally a dog person. Sorry about that. No, no worries. But yeah, like really kind of doing that sandwich method of like, hey, we're here, we're here, we're here, and kind of telling them how it's going to be. And, you know, I love my management crew at Calendly. But I even had to do that there. I had to, you know, even during the interview process, they were like, this is what we want to do with the community. And I was like, yo, that is so exciting. But I also had to remind them and say, okay, there's actually elements of this that we need to change how we're going to do it. We need to try to do things like this. You know, to give you an example, one of the things they'd asked for was they're like, what about gamification? Wouldn't gamification be cool? And I was like, You want to have a support community and gamification. Those 2 don't jive. And really kind of talking through why that is, showing them the research. And then also now at this phase, bringing in the user research, like actual testimonials from customers and non-customers, and being able to say, actually, this isn't what they want. This is what they want.

The biggest question I'm hearing, like, like early-stage companies, let's go like Earlier, they really want that top of the funnel, and they're, and they're pushing for more. How do you set up, you know, a program for them? And what, what are the important KPIs? And then, and then we'll go with, you know, the, the later stage companies after. But I'm curious.

Yeah, so I mean, actually, the most important thing for an early stage company is advocates. So, someone out there loves your product. Someone out there is super excited that you exist. And this is actually really fun when you're a small-stage company, because you have a much smaller user base. You get to know these people, you can build real relationships with them. And the reality is that these are the people who start your community. They're the ones who are going to help grow it and make it what it is. And like, for instance, right now at Calendly, we have this amazing program called the Calendly Collective. It is our advocacy program. That's who I am leveraging. Like, these are my early-phase people. I mean, granted, Calendly is much bigger at this point. We're not a startup anymore. But that's the same type of notion where I am leaning on these people and telling and asking them, what do you want? What can I give you? What are your needs? What are your wants? What are your motivators? And it doesn't matter at this point that, you know, we've been around for as long as we have, or if we'd been around for 1 year, I'd still be leaning on that group of people. And that's probably like my biggest piece of advice for early-phase companies that are going, oh my gosh, we need a community. Go find your advocates first. Like, you literally can start off in a Slack channel. You can have a weekly roundtable with them. Doesn't matter to me, but you need to create meaningful relationships because those are going to be your original community members. Those are going to be the people that bring in their friends, that bring in their networks. That's going to be how you grow that community.

How can you best, outside of giving them community vibes, how can you best encourage them to help you drive those top— I'm pushing on the top of the funnel because I do think I'd love to hear your point of view on how to make it really organic. It's the trickiest thing.

Yeah. Yeah. No, it is.

Because by nature, it's Not super organic.

Yeah, it's not super— it's funny, it's not super intuitive, but it's— you really have to get to know those people and understand what it is they want, like their intrinsic and extrinsic motivators. Once you've figured that out, you're going to be able to get them to speak more freely to you, and they're going to feel more amped up about that personal connection. They're going to feel more positive about that company. And that's when they start recommending you. That's when they start talking about you in places, that's organic top-of-funnel growth. Now, sending them a piece of swag and saying, hey, you got to go bring in 50 people now, that's not organic. And that's another big mistake I see a lot of early communities make is the whole like, we need swag. Oh my gosh, we need swag. We have to send out swag, swag, swag, swag. And I'm like, oh no, that's actually not organic growth. Like, it can be a motivator for some people. And that's why it's important to ask those questions. But really get to know what these people want. And I mean, for instance, some things that you can use to motivate people, being able to influence product growth, transparency into your product roadmap, you know, getting a chance to understand the company's strategy, meeting other people just like them. Pretty much anything where people feel like they matter is going to be a motivator, especially in those early-phase companies, because we all want to feel like we've had an impact. And that's, That's pretty cool.

How do you leverage a calendar tool to rile up advocates? I'm curious what you all do with that.

So, you know, it's really funny. I've done a lot of user interviews, and one of the things that's come up as a bit of a theme is that we get really excited about Calendly. Like, we're really excited about how efficient it is. We're excited about what it does for us. We love the fact we don't have to go back and forth about, you know, this time at that time, and all of that great stuff. But the funny part is that you couldn't go to Thanksgiving dinner and you're having a conversation with your grandma and she's like, oh, what have you done recently? And you're not going to be like, I made my calendar more efficient. It's just not something you're going to be able to do. But the reality is that community, Calendly community, these are other people who are just as ludicrously excited about these cool calendar automations and efficiencies as you are. So, that's kind of like how you generate some of this buzz, some of this excitement, is it's a network for calendar automation and scheduling aficionados. Like, that's kind of cool, you know, it's such a niche. But that's actually where community tends to be most successful, is that when you can give people something they can't get anywhere else.

Now, what's the impact you hope to have on, like, the Calendly user?

Yeah. So, basically—

Or is the outcome that you're hoping to generate? Yeah.

Yeah. It's kind of twofold to start, threefold long-term. The first one being is that as the company grows, people need information, they need support, they need how-to, they need troubleshooting. And we have an amazing support department. They are top-notch, world-class, super, super brilliant people, very, very kind, but there's only so many of them. And that means that sometimes, even though you're in the moment, you're working on the thing, you're not gonna get an answer as you're working on it. You're gonna have to put in a support ticket, you're gonna have to wait a bit. And at that point, maybe you're already out of the workflow, et cetera. Community is going to really let you get more information in the moment by having an ever-growing collective knowledge base. So, that's kind of number one, is really around changing support, changing knowledge access, and everything like that. The second part is around inspiration. People really, I mean, it's amazing all the time say to me things like, yeah, I have one event type. I have my like one-to-one meetings, but I've heard about collective. I've heard about round robin. I've heard that I can have all of these different like calendars, blah, blah, blah. How, what do I do? Like, I don't even understand where to start. And that's really cool because this is an opportunity for us to connect, you know, solo entrepreneurs to small business owners, small business owners to enterprise people, and kind of everyone share that knowledge in ways that really pass geographical, industry, socioeconomic barriers, really kind of get around all of those. So I think inspiration is going to be a huge, huge piece of that. And the third part is ideation and feedback. This is a really cool opportunity for people to tell us how they want to use Calendly and how that they'd like to use Calendly, and for us to get a lot more visibility into all of that, and also for us to be more transparent with users. So, kind of like 3 really big impact areas.

I love it. And I love how you've broken this down. Let's take a step back. We have our advocates, and it's so interesting that this is the first step. And, you know, thinking logically, going back even before that. Like, let's, let's say you don't have product-market fit as a company. Does it make sense to build community, or what's, what's the starting point? Like, when does it click in that now we should start, start a community for our product on the early side? Because there's people that are like, right away.

Oh, yeah, no, for sure. I actually really think you have to have advocates first. If you don't have advocates, you shouldn't be having a community yet, because communities are for conversation, collaboration, and connection. Like, that is the big things. If you don't have advocates, you don't have people yet that wanna have organic conversations about your product. Now, with that being said, your advocates could be people you don't know of yet. They could already be on Reddit, they could already be on Stack Overflow, they might be on the app formerly known as Twitter. I just can't seem to call it X.

I just re-updated my app, and the old logo's still there. I'm wondering when that's gonna turn.

Yeah. Mine just changed the other day. But yeah, your advocates could be in a lot of different places, but more than likely, they're not on your platform yet. You need to go find them and give them a compelling reason to be on your platform. And when I say your platform, I mean your Slack, your community, heck, even your email, your Zoom. Like, there are a lot of ways to build community that don't necessarily mean that you have to have a community platform yet. But if you don't know who those people are, You're going to have one of those, you know, that movie from like, what, the '90s, Field of Dreams. You can build it. It does not mean that they're going to show up and play ball. You really have to actually have players there before other people are going to start showing up.

How do you find them? Do you just scan all the socials or do you shoot an email to all of your users and say, are you that person?

You know, there's different ways of doing it. I find more often than not, you're going to look on your socials and you're going to find them. Right. Like, that is more often than not. I mean, like, I can tell you right now with Calendly, I've been like crawling YouTube and Reddit, the app formerly known as Twitter, you know, all of those. And I'm finding people, I'm finding people that aren't even part of our Calendly Collective. And then I am finding our Calendly Collective people out there in the wild. And it's really cool because sometimes I'm like, I'm going to go check. I want to go see if this person is already in our network. And a lot of times they are, which means that That approach works. Like, these people do have traits and attributes that they display organically without us even interacting with them, and it does correlate to them actually being an advocate.

That's badass. So, I have my advocates. I found them under a rock. What KPIs internally do I need to— are the most important, in your opinion? for me to look at and try to like maximize on?

Yeah, I mean, I think now it depends on what it— what is you want to do. And that kind of sounds a little weird to say, but, you know, for instance, this is the other kind of like, you know, if there was another myth to break is that when we also say, oh, I want a community. Great, I'm so happy for you. Which one? Which community do you want? Do you want a community practice? Do you want more support? Do you want knowledge? Do you want ideation? Do you want education? There are so many types of communities. I mean, like, just to give you an example, for fun outside of work, I am an admin for a Facebook group for female mountain bikers. We have 38,000 members. It's sheer chaos and mayhem. And then I also am an admin for another group that's a local group that has 2,000 members and a huge in-person element to it. Those communities are actually 2 types of communities. And then the community that I ran at Zapier and the community I'm running at Calendly, are actually 2 other types of communities. So, your KPIs are tied to your type of community.

Got it. So, there's no repeatable playbook you've done?

No. I hate to say, but no. I mean, there's elements that you can repeat, but there's no silver bullet.

Walk us through it. It sounds like talking to people. Is critical. How do you build your playbook when you come in?

Yeah. I mean, so, the first thing you should do, so, let's say, for instance, you've just started at a company, you're not employee number 1, you're probably not employee number 3, you're probably a little bit further out. Get to know the people that already are there. Understand where that product has been, understand how that product came to be, what niche were they trying to fill, everything like that. You need to put on your business strategist hat for a while and ask all those questions. I mean, can I give you an example? I've been running around Calamity right now asking about our business KPIs. I have a whole list of business KPIs, and I'm asking for definitions, I'm asking for formulas, things that people are like, why do you need that? Like, you're a community person. And I'm like, well, I want to understand if I can impact those. So, that's number one, no matter who you are, where you work, You got to understand business strategy.

Could we? Could we? I hate this phrase. Double click on that a little bit. The one line: You're a community person. Why does this matter? Myth I want to bust: Community needs to align with core KPIs.

Yeah, yeah. So it's funny because every company I've worked at, I've always had people push back and be like. Why are you asking about our revenue? Why are you asking about our churn? And I'm like, because I need to know. I need to understand how these things are happening. And the reason being, like, to give you an example, I'll use churn. I've been digging into churn at Calendly. There's a variety of reasons why people churn. Some of them are completely normal and natural. And it's like, well, duh. Yeah, of course. But like, let me give you a real example one. People tend to churn, not, not a huge number, but some people churn because they assume that Calendly is missing key functionality that they need, when in fact it actually turns out that they're not using their calendars correctly. So this was a light bulb moment. I was like, oh my gosh, I have an opportunity to have a calendar etiquette section of the community where we talk about How blocking off time on your calendar impacts Calendly functionality, or how buffers, or how time zones. There's all these intricacies that people assumed were our fault, when in fact they were actually just people not knowing how to use their calendars. So by understanding churn metrics, I'm able to actually develop my strategy, and that's why community people. need to know everything, which is,

I mean,

kind of awkward at times.

Theoretically, you could work with the growth people and say, okay, you're getting this drop-off at this certain point. Do you want to send them an email to join the community to test if that's going to solve it? Right? Like,

right, right. But even before then, like, now I know specifically in my community I need to build this proactively. So even though my community is probably not launching for like another 4 to 6 weeks, I have already started building this part of the community. I am already proactively building content around calendar etiquette so that the moment I open up the doors to my pilot, to my restricted group, they're going to be like, oh, time zones, oh, buffers. Like, this is already going to be there for them, which means that I am going to hit the ground running when it comes to all aspects of GTM, not only awareness and acquisition, but I'm already hitting the ground running on adoption. And activation.

If you know that, like, people are activated once they set, like, 5 meetings in a 2-week period, I'm just making fake numbers. You could show people how to set 5 meetings in a 2-day period, like, for all the other stuff.

That's exactly what it is. We can influence behavior. That's, like, the serious magic of community is, like, if we have the information that we need on all aspects of the customer lifecycle, we can proactively influence the behavior of our customers and help you get the desired outcome that you're looking for, which is so cool.

Felt like a relevant tangent. Let's go back to the playbook. We're coming up with the playbook now. I had to call that out because, geez, you've probably heard it multiple times, and I'm sure the listeners are thinking that, but we're listening now. What's the second aspect of building that unique playbook for your community or your company?

Yeah. So, after you've gotten past business strategy is when you start getting into having to actually understand your customers. And when I say your customers, that's kind of a very broad term, because actually, you want to understand your customers, your non-customers, your competitors. You want to understand people who have churned, people who have rated you poorly. You want to talk to everyone that you possibly can. Because what you're trying to figure out is, you've now kind of looked at some KPI-driven data around how are we acquiring people, how are we losing people, how are we retaining people, which ICPs or which personas are the most impactful. Now, you want to understand from the customer perspective, what are they actually experiencing? What's actually happening in their world? So, for instance, one of the questions I've been asking a lot is, do you remember how you found Calendly? And it's really funny because some people are like, oh my gosh, I remember the email that I got that someone had a Calendly link in, and I was like, what is this magic? Other people are like, I have no idea, it's just been here forever. But it's important to ask these questions because it helps you understand friction points and opportunities from the customer perspective, because they're the ones that are going to tell you, oh yeah, I tend to be setting up Calendly stuff on weekends because it's the only time that's quiet. Which means that they're going to have support access problems. Or they say things like, oh, yeah, I really don't like sending in tickets or using chat, I prefer to Google. Great, that's another friction point. And so, you kind of keep identifying these things, and you keep building up your strategy. So, now you understand the business side, now you understand, you know, your user side. So, that's kind of like chapter 2 in the playbook.

Is there chapter 3?

Oh, yeah. There's, like, 25 chapters to this book, and it just never stops growing. But, you know, when you start getting, like, chapter 3, this is now where you're kind of doing that overlap, and you're like, all right, cool. I understand the company, I understand the users, what's the community strategy? And that's kind of where right now, you know, we've taken all this information, we've picked a platform, We've picked an overall strategy, we've identified the community personas. You know, we're at the point right now, we're working on the community architecture, we're working on the taxonomy, the navigation. These are all kind of, like, different chapters that you're gonna work on. They're a lot smaller. So, instead of being, like, you know, a textbook for each one of those, they're kind of, like, you know, like, actual chapters. But it's a lot of pieces. And I think that's also kind of the interesting thing about community is that, A lot of times, we try to get shoved into, like, some little corner of GTM, and they're like, yes, you, you're gonna report to marketing, or you're gonna go sit in customer support, whatever. And it's like—

Those are the two big ones.

It is the two big ones, but the reality is that community touches everything. And so, you know, I hope if there's any founders that are listening to this eventually, I want you to remember that because you're gonna have this person, probably way too enthusiastic like I am. What you can't see is the amount of hand waving and hand gestures going on. We're very cross-functional. We're very happy to talk to people. We're very happy to do research. But we also need to have the autonomy to say, hey, I need to go talk to engineering. I need to go talk to growth. I need to go talk to finance. I need to go talk to security. Like, that's how community works. And that's the interesting part about the playbook, because the playbook starts crossing into all of these different functions. And yeah, so much.

How do you, how do you align? Right? Because parts of you align one way, parts of you align another. Is that just like your hires? Like you hire one CS support community person, one marketing— I'm using the word support. It could be a different title, but you get the idea.

Like, how do you build out a team?

Like, community isn't often its own pillar in GTM, right? Like, it's, it's nestling somewhere under revenue. Yeah. You have customer success going to customer success, sales and marketing ops going to RevOps now.

Yeah.

Sales, self-explanatory.

Right.

Community could report to multiple places too, for sure, cleanly, right? Like what you said. Yeah. How do you align internally?

This is going to sound kind of weird. You kind of just roll with it. I know it sounds really strange to say, but, you know, coming into Calendly, for instance, I knew that I was going to be sitting under customer success, which sat under customer experience. And I was like, cool, that's great. I've also sat under support. I've sat under product. Marketing, engineering. Yeah, I've worked for almost every function with the exception of finance and security. And what's kind of weird about that is that you stop fighting it eventually. I have this dream that someday community will be a pillar, or, like, collaboration will be a pillar of its own. But you kind of just let it be. And so, like, my advice is, like, you know, if you're someone who's looking to go hire this person, Just give them, put them wherever it makes the most sense and they're going to have the most support. But don't worry about really trying to make it perfect. So yeah, that's, that's kind of my advice there.

I think there could be potentially less pillars than adding community to a fresh one. I think, I think that's the way we're going and it seems like communities might just be the first to it. Like, yeah, super interesting. Now, the topic of measuring ROI on community is something that isn't lost on anybody that runs community. Like, I'm curious how to measure it 2 ways. One, the marketing way, and we're just using the last example. The other, the CS or You know, customer support way. And yeah, how'd you do that along the way? I know you had some pretty unique stuff at Zapier. And also, community tends to be part of this dark social thing, right? Or this dark funnel. And if you're doing it right, it gets real dark and it gets real potent, right? And how are you measuring all of this? The ROI?

So, yeah, ROI is so funky because it actually really depends on what data you have available. You can measure ROI to some extent, no matter what. But to give you an example, so, at Zapier, we had the most incredible data science team. I love them dearly. And they were able to do some amazing work where they were able to track the activity of a specific user across our entire domain. Pretty much, you know, had they visited a self-serve resource? What did they do in the 7 days following that? Did they successfully use our product in 7 days? Did they submit a ticket in 7 days? Did they upgrade in 7 days? And because of that, we're able to now start tying in things like, okay, did community likely impact retention? Did it impact upgrades? Did it impact churn? Did it impact cost deflection? Those are all different ROI methods. Some of those are obviously revenue generation, and some of those are cost savings. So, that's kind of part number one. And I'm going to say, most companies, especially younger companies, are not going to be able to have that level of data science, because that is tricky business right there. I mean, if you happen to be a data company, you'll probably figure it out from, like, the get-go, but that's hard.

Yeah. Give me lean and mean, early stage as well.

Yeah, early stages.

And this thing they call attribution. How do we deal with that?

Yeah, so I think probably the best thing to do is you can lean a lot into NPS and kind of say, okay, if someone's happy, like, more than likely, it meant this. You can also ask people directly, like, if they do upgrade, say, hey, what influenced your decision? And if there is an opportunity for someone to say, I found a really great use case in the community, do that. Put community in front of them as an option for attribution. That's one of the big things that I don't see people do a lot, and I'd love to see that happen is put community in there. As like, if you say, hey, why are you churning? Why are you upgrading? Why are you buying? You have like a multiple choice list, put community in the list. Like, that is a really, really easy way for small, young, lean and mean companies to figure out that attribution. And it's cool because you can figure out where to put your money too.

Spot on. What's keeping you up at night now? I'm curious, some of the challenges that even somebody so tenured in community has.

I think, you know, there's actually a lot of things like, I hate to say that I'm definitely someone who has like community-induced insomnia right now. I think one of the big challenges in our space is that community professionals are expected to do so many things. I mean, It's incredible. Like, just today alone, the amount of different areas that I've worked in already, like, I'm not even, what, 4 hours into my workday, and I have touched everything ranging from SSO to design. I've had a conversation about analytics. We talked about strategy. I have an executive presentation coming up next week. None of these things are similar. And community professionals tend to wear all hats. We try to be a master of all, but it's hard to do. And when you're in that process of setting up a community, there's definitely this really— it's not even imposter syndrome because it's actually literally, you're just like, oh my gosh, I'm actually not an analyst. I'm not a graphic designer. I'm not a business strategist. I'm a community professional, yet I'm being asked to do all of these things. And it's exciting. It's what keeps us here. It's why actually we keep coming in to do this job. But it's also really, really overwhelming. It's a lot to handle. So, that's probably number one.

That's a big one. Are there any other major ones?

I think the other major one is, you know, right now, if you look on LinkedIn, especially if you've got community professionals in your network, you're going to see all the layoffs, and it's scary stuff. And of course, there's some people right now running around, other, you know, experts and gurus that are saying, Oh, this is the end of community management. It's not. I mean, when I started out in this field in 2011, there was probably less than 2,000 of us across the world that did the type of work that I do. Nowadays, there are— I couldn't even tell you how many. There's a lot more than that very small number of people. And what that means is that we've got people, all sorts of backgrounds, and all sorts of levels of experience. Our titles aren't consistent, the type of work that we do is not consistent. And I think companies are starting to realize that, and they're trying to move towards the future, they're trying to get lean and mean. And it's just a really kind of chaotic place to be right now. You know, it's like, if you talk to a director of community at one place versus director of community versus somewhere else, a head of community, a community lead, sometimes we're the same person, sometimes this person has 2 years' experience, sometimes they have 16 years' experience. That keeps me up at night right now. Like, it's, it's kind of stressful.

I posted today on LinkedIn, like, like I called it like spread karma post because I wanted to build a community on LinkedIn. I'm like, a lot of people are out of work. Comment here, like, just because that is a big thing. And what I've seen from community leaders, they become to your, you know, connecting the dots, you know, with advocacy being a big part, at least early community, they become customer marketers, they become brand. Like, um, they're, they're very, very versatile. Is, uh, is that they, they probably become, uh, head of influencer marketing at some places and, and all of this.

Yeah.

Because that skill set's big now. What excites you about the future? Is it the ability to have AI running a community of AI bots, and the community called Meta AI or something?

Oh, man. I have thoughts on AI. Yeah, I can definitely say AI excites me.

What are your thoughts on AI?

Oh, gosh. So, we did an experiment at Zapier. This was really cool. I got to lead an experiment to see what would happen if we let an AI bot loose in Zapier community.

To manage it or to— what aspect? Give some context.

We wanted to see what would happen if we let it loose as a support agent. So basically, let it think it was a Zapier employee who was answering questions. And we initially were like, all right, let's just give it a go. And like, we really restricted it. We didn't want to like mislead anyone. So we gave it a very specific spot in the community. We're like, have First off, it was patronizing. That was the initial voice it had, was incredibly patronizing. And we're like, that's not gonna work. Wow. And so, we kept doing experiments trying to get the right voice and tone and trying to reduce hallucinations. We finally got it to a point where we were like, let's try some famous people and see if it can find a voice and tone that works. It turned out the voice and tone of Tina Fey was actually the best fit for Zapier community. Which is really funny.

Not a shocker.

I, yeah, it was kind of a shocker. So we're like, this is great. And we did a bunch of prompts to get the, like, the hallucinations down. And we got to a point where it was really good, but then it started getting confused. And we never told it that it was Tina Fey. We said that it sounded like Tina Fey. And it started actually signing all of the posts, love Tina, have a great day, Tina. It actually thought it was Tina Fey. Um, and so we actually had to shut it down. It was really entertaining, though. So, it's not ready. Like, AI is definitely not ready. I think it's a really cool tool to use, and I am excited about it. I think that one of the coolest parts about AI is that it brings together so much knowledge at such an incredible speed that no human will ever be capable of doing that. Like, I can type in, you know, top use cases for Calendly for lead gen professionals, and I'm going to have to sit there and read and read and read and read. I type that into OpenAI or ChatGPT or whatever it is, and it spits back this amazing comprehensive article on all of the things. That is so cool. I am so excited about that. Yeah, that's definitely like the AI side. And then, I mean, I'm also excited that this field keeps getting more and more official. I mean, I can say to people now, yeah, I'm a community lead, director of community, head of community, whatever my title is, depending where I am. And more often than not, unless I'm talking to, like, my parents, which will probably listen to this anyways, most people kind of know what I'm talking about now. Like, I can explain it and they're like, oh, yeah, community, I've used that before. And I think that's pretty cool. It's nice to actually not be, like, a mystery.

It's kind of cool to be a mystery too, as long as you're paying the bills. Yes.

Yes. But it's harder to find jobs.

Totally. And, you know, I want to, you know, learn so much about your strategy there. Want to learn a little bit more about you. I see a combination of passes and medals maybe behind you. I'm curious to learn more about community outside of work and what you're doing.

Yeah. So, I am a mountain biker and a trail runner outside of work and a splitboarder and a bunch of other sports. I'm basically always outside. I really like type 2, type 3 fun. So, things that are not exactly fun in the moment, but after the fact that you're like, that was cool. So, that's kind of me outside of work. I actually love volunteering for races though, which is kind of a really weird Flex, I guess you can call it. I volunteered for the Boston Marathon twice, which was mayhem, sheer and utter freaking mayhem. So, 2 of my things up behind me are actually my volunteer badges from that.

We spoke about some of the humor that happens with volunteering for the Boston Marathon. Anything you care to share? Funny stories?

Yeah. Boston Marathon is and continues or has and continues to be just absolutely nuts. For anyone who's not familiar with it, it's about 30,000 runners converge on Boston, Massachusetts for a single day for 26.2 miles. Most of the runners have earned their spot there, really, really rigorous qualifying times and everything like that. So, these are really, really, really strong athletes. And then, of course, there's some charity runners as well. I have volunteered in what's called Sector 10 before, which is about 2 blocks after the finish line. So at this point, you've gotten your medal, you got your heat blanket, you got your banana, your Gatorade. And by the time you get to me, the adrenaline has started to wear off and the cramps have started. And so both times I've worked in Sector 10, it has been about 5 to 8 hours of catching athletes before they hit the ground and screaming for medical and wheelchairs. Absolute sheer and utter chaos. It's like fun in a very strange way. I don't know.

How do you leverage this volunteer work, which very much has community components to it? It's drawn—

Oh, absolutely.

In a big way. Actually, the Boston Marathon is the culmination of these massive effing communities like, oh, you're wrong, preparing for it. And this is like the mecca. And then, and then, oh, side note, they're going to New York next month or whenever it is, right? Like, or they're traveling to other places. It's pretty wild. How do you take inspiration from that and those experiences, you know, outside of work? And bring that into Calendly in this case and, you know, your past cases?

It's a great question. I think a lot of it is basically when you work at these events, you volunteer at these events, you see so many types of personalities. It's not like a homogenous, I'm a runner thing. Everyone is so different. Everyone has different backgrounds. And I love to bring that into my community work. I like to make sure that people can have their own voice, their own tone, their own background. background, their own perspectives, and be loud and proud about it. I think that's probably the most important thing. And like, that's been really, really big for me is like, you know, even as I'm building out Calendly, as I built out Zapier, as I built out community, you know, in the defense industry, all of these communities, I have made sure that people have had room to be who they are and bring their unique qualifiers, skills, attributes, whatever it is. I want them to bring those to the table because that's what makes a community a community. Like, if we didn't have that, we would just knowledge base, no shade to knowledge bases, but I don't want everything to sound the same. I want some people to be typing in all caps, some people to be typing in slang, some people to be talking about trails and showing, sharing dog memes. Like, be yourself. Tell us how you being you has made you the person you are and bring that to the community.

Let's end on that. That is incredible, Jillian. It's been It's been a pleasure learning from you today. How can people get in touch with you?

I am all over LinkedIn, not as active as I should be, but definitely come find me on LinkedIn. Feel free to send me a connection, questions, requests, whatever. I don't care. I'm there for it. I do a bit of like a community nerd series on there where I just kind of like write different pieces. telling you how to run communities or kind of thought-provoking questions. But yeah, come, come find me on there. That's usually the best way to get a hold of me.

Thank you again, Gillian. This is— this has been awesome. We're opening, opening up for GTM leaders understanding community and collaboration and collaborative growth and all of this good stuff. It means the world to have you today.

Thank you. It's been awesome being here. And yeah, looking forward to chatting with more people.

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