Messaging is a moving target, MQL purgatory, growth marketing hubs | Kaylee Edmondson @ BrightWheel

February 2, 2023

Episode Description

Demand Gen Chat is back for a new season! In our first episode of Season 3, we introduce you to our new host and catch up with Kaylee on what she’s been up to since joining the marketing team at BrightWheel. We also chat about a few of her favorite episodes from last season of the podcast, and the tactics she'll be bringing with her as she builds out the demand gen function in her new role.

Show Notes

Listen to Ben’s episode to heart how he approaches MQLs:

Listen to Jason & Mark’s episode to learn more about how they got their CAB’s help to test out their messaging:

Listen to Julia’s episode to hear more about Toast’s Growth team:

Follow Tara:

Follow Kaylee:

Subscribe to DGC:




About Demand Gen Chat

Demand Gen Chat is a Chili Piper podcast hosted by Tara Robertson. Join us as we sit down with B2B marketing leaders to hear about the latest tactics and campaigns that are driving pipeline and revenue. If you’re looking for tactical ways to improve your marketing, this podcast is for you!

Episode Transcript

[00:00:00] Hello, welcome to Demand Gen Chat. I'm very excited to be kicking off Season Three of the podcast. Before we get started, you've probably noticed that I'm not Kaylee, my name is Tara Robertson, and I'm the Senior Manager of Demand Gen at Chili Piper. So for many of you, she near- needs no introduction, but if you're new to the show, Kaylee is the Director of Demand Gen at Brightwheel. She's also the mom to two adorable little ones, and a brilliant marketer. So Kaylee, why don't you tell us a little bit about your new role, and the op that took you away from Chili Piper.

Yeah, oh my gosh, hi. Welcome, it's so nice to be back, um, in this space, chatting with you. Um, yeah, a little bit about Brightwheel. So, I had an opportunity to lead up a Demand Gen function over at Brightwheel, and do some of the very similar work that drew me to Chili Piper. Um, Brightwheel for those of you who've maybe never heard of it is an early eduction software that helps with, um, childcare management. For Montessori schools, preschools, anything, um, pre-kindergarten.

And, as Tara alluded to, I have two young girls. [00:01:00] So that's very much so, um, a place that's near and dear to my heart on a personal level, just with where we're at with our family right now. And then of course, the opportunity to build the Demand Gen function from the ground up is- is truly a passion of mine that I love. Um, so yeah, Tara and I had the opportunity to work together at Chili Piper, and I'm really excited to be passing the reigns back to you.

We're so happy to have you back, and so glad you agreed-


... to come back for this, kind of transition episode. Um, so as Kaylee mentioned, I joined her team, um, the marketing team, actually, at Piper around eight months ago. And before this, I had around 10 years of experience at all different types of startups, but all in the SaaS space. So, I was fair- a fairly early marketing hire at both Uberflip and Top Hat, so both of those are based in Toronto. So very familiar with, obviously, MarTech and the content marketing space. So, Chili Piper was just a brand that I was really excited to come join, And Kaylee kind of made the case to join her team. So I couldn't say no. [laughing].

Fair enough.

Um, so I'm really excited to be taking the reigns. Kaylee did an awesome job last season, as all of you know. [00:02:00] So, really excited to just kinda keep it going. And hopefully this season, looking to dive a little bit deeper and have some more tactical takeaways for our audience to take back to their teams.

So, I thought the best way to handle this episode would be to chat about last season. Um, I know we got a ton of great feedback on last season and you as a host, so why don't we start with just a couple of your favorite episodes. And I know we have a couple of them in common, too. So, one that we both really liked was Ben's episode. So, Ben from ChartHop joined. Do you want-


... a little bit about you liked?

Yeah, absolutely. So, just on a personal note, I think Ben is top... Like best in class. One of the-

Mm-hmm [affirmative]

... best in class Demand Gen marketers that I've ever had had the opportunity to network with, and really get to know on a personal level. Um, he and I had started just like a very casual, like pinging back and forth after he had, um, followed up from The Sauce, which is a- a monthly newsletter that we send out at Chili Piper. Um, and he just loved the content, and it sparked this really natural, um, relationship between the two of us. We're just like [00:03:00] really entertained by trying to question the status quo.


So it seemed natural to bring him on. Um, and of course he followed in his footsteps, and delivered some pretty spicy takes on how they're interpreting Demand Gen over at ChartHop. I think the... One of maybe the maybe interesting concepts that he had posed, that was very different from, um, things that we were doing at the time at Chili Piper was this concept of an MQL purgatory, where he had outlined two, um, two different MQL paths. Um, one being an implicit path, and the other being explicit. Um, obviously it was very... I made it very public, uh, during my time at Chili Piper that I had kind of de- abolished the- the concept of lead scoring.

So, implicit MQLs were not a thing for us. Um, but he was very much so passionate about it, and it's- it was really interesting to her his take on how their operationalizing that, and why he felt very passionate that MQLs in MQL purgatory, and getting stuck there, is definitely not where you need to be. But, operationalizing the concept of an explicit hand-raiser versus those that aren't yet ready for a demo. [00:04:00] Um, and just how that was working for their business and down funnel metrics.

Yeah, I related a ton to when he called it purgatory, and a couple of [inaudible 00:04:07] we would spend just hours as a Demand Gen marketing team in a room talking about lead scoring. And how we would score different people that download different e-books, or people that attended a webinar. And then I would chat with sales later on and they just did not care, at all. So-


... I thought it was a really good take.

And I think something that's even more interesting is that it seems like every company is- is really on board with the concept of testing, and like optimizing through some type of like-

Mm-hmm [affirmative]

... A/B test, or even like an MBT or whatever that it... Whatever it is that they're trying to put in front of them. And with lead scoring, there are so many variables that go into it, how do you ever really feel? Like to your point about going around the room a million times on like, "Well, how much scoring or weighting should this activity get? Or these series of activities?"

It... There are so many variables that go into it that I really feel like it would take, I don't know, a large volume, like high quantity, to be able to even get to a place where [00:05:00] your lead scoring model is statistically significant on all fronts.

Right, I think-


... I mean that's the case across a lot of different tests that marketers do, is we just say, "It's a test, we'll figure it out later." But if you do that over and over, especially for something like a lead score, you're never going to get anywhere. Because-


... you're constantly changing it, so you're never gonna have results that are significant.

Exactly, exactly. And I- I think, yeah, his- his entire take, if anybody listening to this episode hasn't listened to Ben's episode, I would highly recommend-

Mm-hmm [affirmative]

... um, going back and listening. When Tara was asking for some of my, like, top takeaways, um, Ben's was the first that came to mind. So, um, the entire episode is really good. He drops a lot of knowledge just outside of MQL purgatory, as well. Um, and ChartHop is doing some status quo questioning activities, which are good.

Another episode that I really enjoyed, and I know you did, too, was... I think it was the last on of the season you interviewed Julia from Toast.


She's just such a smart marketer, I really loved hearing from her.

Yeah, it's so interesting. So obviously, Toast had a huge year last year, um, and they [00:06:00] IPO'd at, um, a c- a crazy value. It was a really, really, um, successful year for them in terms of growth. And being able to provide more insights and more resources for their customer base, um, Julia, interestingly enough, has been at Toast through so much growth. Um, maybe to try and quote off the fly, I believe she's been there for six years, um, and in the world of SaaS, six years is like 16 years, at least. Um, so she has seen Toast through so many stages of growth.

And I think that, um, one of the main reasons I wanted to have her on is because Toast envisions the growth marketing role very differently than the traditional, like, Demand Gen function, um, in that she is almost like, um, like an operating hub that sits outside of marketing and can really move as a nimble team across the funnel to work on really specific initiatives for optimization. Which I thought was a really cool concept.

Yeah, I wonder how much of that is just due to her being [00:07:00] there for so long. Because it's, to your point, it's so rare to have a marketer stay anywhere for six years, so once you have that credibility I feel like you can start to come up with creative ideas like that. Where people will... They'll just take your word for it that you'll figure things out. And you can build this team that might not have clear goals that you deliver on today, but you will have something to show for it at the end of the day. And it's tough to build that credibility when everyone bounces around every couple of years. [laughs]. So...

Yeah, yeah, yeah. I think tenure probably has a lot to do with it, but also just like the mindset... I think it also just might be like an individual skill that she holds to-

Mm-hmm [affirmative]

... some degree, too. Um, the mindset-


... that she takes to not only like the marketing function, but honestly the entire gr- uh, growth at Toast as a business is really interesting. Um, she's r- a- and I think that her- her case around being separate, and having separate KPI's and initiatives from the marketing team really provides them that flexibility to dive deep on one specific area of the business, and make a true impact that can be [00:08:00] measured without feeling like what I'm sure we all feel at most points in our day, really torn between priorities, right?

Um, and I think it allows them to go deep fast, so that they can really make an impact that is measurable and is statistically significant, because obviously Toast has enough traffic and velocity be- to be able to proof things out. Um, and then move on to the next tasks. Um, which is like, obviously, just not always how startups are structured. Like, naturally resources are-

Mm-hmm [affirmative]

... pretty slim in the early days. But, um, I know that she started with a really small team, and has really proven out that notion. And her team is continuing to grow, which just means that they're- they're getting the results they expect, which is awesome to see.

Right. I also really liked how she spoke about... I mean a lot of industries during COVID would just kinda put things on pause and figure it out later. But she was very much like we need to support our customers now, they need us now. Toast was supporting the restaurant industry, obviously, so it was a really tough time for them. So, rolling out new tools, she even mentioned Chili Piper specifically, but instead of waiting and palleting things, they were [00:09:00] just moving on it to support not just the customers, but the sales team, too. Because they knew that they had a tough couple of quarters ahead, and I think that was super smart. Versus a lot of other people I've talked to who are just kind of very cautions, dipping their toes in things, pausing a lot of programs.

I think there's something to be said for that, too, because it's... Uh, obviously COVID impacted several industries, and, um, yeah, there's something to be said for like being able to use that time really in a- in a really wise way to really lean in and support-

Mm-hmm [affirmative]

... because all that does in, obviously in the grand scheme is bro- build trust and credibility with your existing customer base. Who will then, naturally, especially in the restaurant business, go and tell their restaurant friends, "Hey, this is what we're using." Um, so it's a really impactful flywheel for more substantial growth, ironically enough.

Right, and she talked a lot about it also being the time to focus on community, which I-

Mm-hmm [affirmative]

... think is just a natural fit for the restaurant industry, too. But, it's interesting to focus on building out community in a time when I'm sure, internally, they were struggling to hit numbers. And they just knew th- they [00:10:00] had to focus long-term, and not go for the short-term wins. So, I know you had mentioned s- um, just having that growth motion, not just for enterprise but all types of sizes of companies. So you mentioned that it's easy enough for a brand like Toast, when they have a ton of users and they can get that statistically significant traffic to their site. How do you think we could learn from someone like Julia?

Yeah, I still think that, like, even though a growth motion is very much so like you're website is a huge lever, right? Um, and I think that if growth is sitting like within marketing, your f- your scope that you're, you know, thinking about in terms of like growth and optimization levers, is pretty small. Just like, it's very narrowed into like acquisition only. Um, whereas if you can validate the right... Like validate with your right stakeholders early on, to hire one person that's like maybe mid-level to senior-level, um, that can really just standup small versions of a test.

Like for instance, obviously this is like-

Mm-hmm [affirmative]

... really speaks to Chili Piper, too, but, um, [00:11:00] it's like... You know, main levers could be something like one, obviously getting and growing traffic to the website could be an area that they look at. But even like website to MQL conversion, or form fill, or whatever we're calling it these days, but even outside of that, right? MQL to SQL, which is exactly where Cili Piper plays, like there- there isn't always enough time in the day for a Demand Gen team, or a marketing team, to come in and really operationalize all of those areas of the business that touch so many stakeholders. So I think Julia had-

Mm-hmm [affirmative]

... mentioned this in her episode, too, that it's like the sooner you can start a growth motion, even if it's one person, the more that flywheel takes off over time. And so it's like, I guess I look at holistically how CMO's, or even CEO's, prioritize like their first few hires. Um, and thinking about like what those first few hires really should be for your business. It makes a lot of sense to me to try and makes sure one of these top five to 10 marketers is a dedicated growth marketer that [00:12:00] sits outside of the regular marketing department, so the that they're hired in as like special projects.

And that is what they do. And they're not distracted by the-

Mm-hmm [affirmative]

... day to day priorities that the marketing team has to do to keep the business afloat.

Yeah, it's so easy for a role like Demand Generation, which is everything right now-


... instead of just... Instead of focusing on growth, or very specific KPI-


... it's, "We have a new case study we need to get eyes on. We have a new podcast we need to promote, we have a newsletter going out tomorrow." And so to have it separate from the team makes a ton of sense if you can carve out the resources for that.

Yeah, agree. Agree. And I think, too, it- it's just like- it's all about making the case and understanding like how can you build that case today around your specific use case, right? Like, "Hey, our business today is really struggling with web traffic to MQL." It's like, "Okay, cool, let's get in a dedicated person to really own this project, um, and see it through to fruition." Like you said, without getting like pulled away to focus on like the day to day must [00:13:00] haves.

Yeah, and you have to start the role that way or else your kind of already in it, right? I mean you know how it is in here.

Oh, exactly.

The first Demand Gen hire, you're all of a sudden you own the e-mail, you own paid, you own everything. So if you start the role saying, "This is their focus, let them do that." Prove out that that role works, then maybe you hire someone else to focus further down the funnel, or even more top of funnel to figure out what that conversation could be.

Yeah, exactly. And I think that it- it's gonna look different at every business, right? So like to provide like maybe a little bit more color just outside of Toast, I know that, um, Udi Ledergor, the CMO over at Gong, had done an interview at some point last year, or maybe earlier the year before. All of the periods we've been stuck at home for COVID kind of run together-

It's all... I'm just [laughing]

... but he talked in detail, um, about how he went about building his team. And he had actually at one point pretty early on in their growth over at Gong hired a dedicated person to focus specifically on building the brand and category creation. Um, and that was her role-

[00:14:00] Mm-hmm [affirmative]

... she sat, like basically, entirely separate. She ro- reported up to him, but she was her own dedicated pillar within the marketing org, and that's all she was focused on. And in his interview, he said exactly that. The reason he hired her-


... and kept her as like a separate dedicated function, is so that she could focus on something he knew was going to be critically important to building the brand at Gong. Um, and not get pulled away into the like- the day to day, gotta do it, hamster-wheel type of tasks.

Mm-hmm [affirmative]. Yeah, I mean it's obviously worked out really well for them. Their brand is-


... amazing, and everyone knows it. So, she's doing a great job.


Um, but I could see if he'd just hired a more generalist brand marketer, she would be editing copy on emails, or-


... taking a second look at ads before they go. It's so easy to get pulled into those day to day tasks. So, that's a really interesting structure. And then, one episode that I know we both also really liked was Jason and Mark from Metadata. I mean, I think we both like everything that those guys work on, but it was just a really fun conversation, especially hearing just Jason talk about the interview process when he was bringing Mark on [00:15:00] from [inaudible 00:15:00]. But, I know the highlight for me was really all around just storytelling, and focusing on how they wanted to put that strategic narrative together.

Yeah, I think so, too. And I think the- the really like actionable piece, especially from that conversation-

Mm-hmm [affirmative]

... that I took from them, was how Mark went about like breaking down this like fourth wall, almost. Um-

Mm-hmm [affirmative]

... to get to a place where their website really meant something to the customer base that they were trying to get in front of. Um, so often in marketing, and especially marketing where you're marketing to marketers, it's really easy to get into this jargon-heavy-

Mm-hmm [affirmative]

... situation where you think what you're saying makes total sense, but in reality, you're so muddied by being in the business, you have obviously internal conversations with your teammates through Slack, with customer success, with whoever, where you're unknowingly creating your own jargon and your own dialog that makes [00:16:00] total sense to you because you're in that business every day. You take that copy and you put it on your website, and your prospects and customers are like, "What is this?" [laughs] "What are you actually saying?"

Mm-hmm [affirmative]

"These words, like, you know, these words don't resonate with me, I don't know what you're saying." And so the way that Mark went about it, it was so, like... I don't know, it seemed so obvious, but in hindsight I've just never seen a website built this way. Draft copy in a word doc, share the word doc with members on the CAB, get direct feedback from them. Ways they would say it differently, does this mean something to you, tell me in a comment in this doc what this means to you. Um, how can we make this clearer, et cetera. And then, takes all that feedback, directly inputs into the doc, shares out a final draft. Like, boom. That's website creation.

And were you on their CAB through that process, or did you join the CAB after that part?

I actually joined the CAB after that process, but Mark and I had already started just chatting and networking on LinkedIn. And he was like, "Hey, we're working on some stuff for [00:17:00] our new website. Like I'd love for you to review this doc." And the way that he went about it is like he had a master doc, he cloned a new doc for, you know, the maybe 10 people that he circulated it to, so that I had my own like working draft, and I wasn't... Like my thoughts weren't being muddied by me reading other's comments, right?

And so like then he would collect-

That's smart, I could see it very easily just saying, "Oh I agree with what this person said."

Right, and so he like-

Or, "I don't like this part because they didn't like it." Mm-hmm [affirmative]

Exactly, so he like purposefilly- purposefully siloed us into our own document. So that we weren't like, yeah, not confused or like distracted by other's initial thoughts, and could provide like our own actual, um, thought process. Or like, "Hey, I need clarification. This doesn't mean anything to me." All those things. Um, and then compiled into one more draft, just to be like, "Here's all the feedback, this is what it looks like now. One more round."

Um, and he didn't do that for every page on the website, to be also clear that this is not a crazy [crosstalk [00:18:00] 00:17:59]

Right, "Hey, can you review every page on our website." Yeah probably-

Yeah, just 100 pages.

... probably not. But, he did do it for top, like high-priority, most trafficked pages.

Mm-hmm [affirmative]

Um, which I think was really helpful.


And this was also as their brand and their strategic narrative was evolving, their website was also getting a facelift at that time. So it was like all the things, but obviously the copy was key. Um, their website hadn't been updated in a year or so, or maybe two years before he started doing this exercise. And it was just a really practical way to go about building a website-

Mm-hmm [affirmative]

... that you know is actually going to resonate with your prospects.

Yeah. I really loved how Mark said... I think his exacts words were that "messaging is a moving target." And that really resonated with me because I think it's so easy to say, "Hey, we asked a CAB, this resonated, and now we're going to stick with this forever." And people's pain points do change over time, they find new tools to fill gaps that maybe weren't in the market six months ago, and now they are. So their pain point could be now I have too many tools and I need help-


... figuring [00:19:00] out how to use them all together. Just from their conversation, there's a ton you could learn from taking time out. So, that's the permanently strong takeaway for me.

Yeah, I know. I think there is. I think there is, and it's like not a- like, uh, your- your messaging is a moving target, because obviously the market is changing, but also I think that their product is evolving, right? Like the product like-

Mm-hmm [affirmative]

... when he and I and Jason chatted, I don't know maybe that was like six months ago, maybe more? I feel like the product itself they were trying to market to the- to- to their prospects was drastically different than the product that they're marketing today. Because obviously it's making evolution, and so I think all of those things kind of-

Mm-hmm [affirmative]

... move like a puzzle piece in tandem. Um, and yeah, I think that almost every marketing department that you chat with is like, "Oh, we're redoing our website." And it's like-

That's perfect, yeah.

... I think there's something to be said for like we're redoing our website, which normally means like six months of like no progress, you're doing all this stuff behind the scenes, you're not publishing anything. Versus like publishing an iterating small pieces of your website over time, to actually-

Mm-hmm [affirmative]

... like get that market feedback fronthand- like [00:20:00] firsthand, so that you can understand if it's actually resonating. There's nothing worse than like going behind the scenes, spending six months heads down, everybody's in like fire mode, creating this website and then you publish it, and it's a total flop, right? We've definitely seen that happen a lot in this space last year. Tons of that happening. Where it's-

Mm-hmm [affirmative]

... like, "Wow, okay, so like did this really impact our business in a good way, or did it not?" And I think the more impactful way to go about that is like something similar to this process that these guys did. Um, where you're like iterating over like short sense of time, like what can we do today on the homepage? What can we do in the next three weeks on the homepage? Okay, let's go, let's do the work, let's publish it. That way if it's really not working, you haven't wasted six months of your time trying to redo the entire website for nothing.

There's a lot that you can take away from the way that, um, the Metadata team just kept it pretty simple. Like you said, it was just a Google doc. And they worked from there versus hiring some flash- flashy agency to come help them take it to the next level. Which [00:21:00] could go either way, honestly.

Exactly, exactly. And like, in transparency, at the time when they were doing this, they were a two-person team, right? Like that- that was-

Mm-hmm [affirmative]

... the marketing team. It's just Mark and Jason. Um, and they did have a- a brand agency that they worked with because I don't think either of them are natural born designers. Maybe they are, they'll come for me after this. But...


... they did have an agency that they worked with, but like by no means like that person wasn't doing any of the strategic narrative work that they were actually leading. So-

Mm-hmm [affirmative]

... to also be able to- to break down the barriers, and- and create really fast and efficient work streams, to get that level of work done between two people while also maintaining the day to day newsletters, webinars, like all of those other things that they were also very much doing at the same time, to me just like speaks to the volumes of like efficiency.

Mm-hmm [affirmative]. And they did about how, and in some ways that's easier, with only two people. Because there's less process, so I'm really curious now that their team is [00:22:00] growing, if they've been able to stick to that. Or if they find themselves kind of-


... stuck in a little bit of a growth phase. Or... that'd be interesting to hear from them again. Because I know they are very happy with... I mean, it's- they are busy, but happy, both the two of them. So, they are really cautious about adding a lot of red tape and process.

Yeah, no, and I hear that, too. I would love to hear a follow up from them. I think at this point-

Mm-hmm [affirmative]

... they've at least doubled in size on their marketing head count, if not a little bit more than that. Um-

It must be, because I keep seeing people on LinkedIn popping up in my feed.


Mm-hmm [affirmative]

And- and- and they've made some really great hires, too, for whatever that's worth. But on, um... Just yeah, over- understanding like overall process, and how they've kept like the efficiency of their cycle time. Like is it-

Mm-hmm [affirmative]

... faster? Is it better? Like how has it changed, I think would be really interesting to hear. Because it's like the lessons that you can learn about scale as a two-person or a four-person team, are also very similar red threads that you can still learn if you're a 30, 40, 50 person size marketing team.

Right, exactly. And they're still putting out so much [00:23:00] great content, so it's clearly not slowing them down. But I'm sure there's things they would improve on as they grow. So...

Yeah, no, it's interesting. You should see if they'll come back around for round two.

I'll try.


I'll definitely try to talk to them at some point, that would be great.

I think, too, like another thing about them that I think they are doing really well that we could definitely chat about and just like understand the overall impact of, is obviously they stood up a CAB very early on-

Mm-hmm [affirmative]

... their... Some members of their CAB were part of this website process, but even outside of that the way that they are leveraging a CAB is just not like anything I have personally seen before. Um, a- and especially have not seen that early on for a company to start, you know, when the company itself was the size that it was. Um, I think they were less than 100 employees when they started a CAB. Um, and, you know, it started out pretty small, like five or 10 members, then of course grew over time as they it- invited more people into their Customer Advisory Board.

Um, but, meeting [00:24:00] monthly with C-Suite, all like senior-level executives for every division of the business, so like marketing, sales, um, customer support, product, and then of course like C-Suite as well, so CEO and everyone was on there too. Um, were the really small-

And that's still monthly?

Mm-hmm [affirmative], monthly.


Um, was a pretty intimate group of people. So like [inaudible 00:24:24] pure benefits, like outward facing or that like, "Wow, I want to be a part of this because these are some of the best Demand Gen leaders in this space today. And to get an hour with them a month to be able to learn, is incredible. And just hear what they're doing, what's working, what's not working." Like selfishly, as a marketer, I would love that. So of course if, you know, people are given that opportunity to join, that's a huge draw.

Um, but also being able to give direct product feedback into their product roadmap on what you would really love to see, versus maybe features or tools that they've rolled out in the past that you don't get a ton of value from. And just talking through like, "This is how I'm using it, this is what's working. I don't understand how to use this, what can I do [00:25:00] for it?" Is super, super valuable. And like, from that, of course, Mark and Jason are listening in and hearing pain points for their prospect base, like current-

Mm-hmm [affirmative]

... things they could solve for. Ways to phrase things that their direct prospect base is using. Like, um, getting away from some of the jargon that they think makes sense but doesn't. And I think that very much speaks to this flywheel effect of, like, the market is shifting, people may be coming up with like new ways of talking about things or explaining things. And they're getting a monthly check-in, ear to the ground with their customer base, which is also talking and thinking much like their prospect base. To be able to take that, and implement it into their marketing materials.

It's so interesting that they had a CAB so early on because Jason had a comment about not wanting to spend some of their budget on ads to customers, but they're clearly very happy spending the time and resources with customers. I think that's a smart way to go about it, because to your point it ends up powering a lot of their messaging on the prospect side, too.

Yeah, I think so. I just think it's like this really interesting, [00:26:00] um, cyclical loop that-

Mm-hmm [affirmative]

... not a lot of companies like latch onto that early.

Yeah, we'll definitely share those episodes out in the recap post for this so everyone can catch up on those three. All three have a ton of great takeaways, so worth listening to them in full. I know we're coming up on time here, so I definitely just want to say thanks again, Kaylee, for joining us. I know you put a lot of time and energy into the last season, and everyone really appreciated the great conversations you had. And just- also just for being an awesome boss and human, just... You're great, and so happy to have you here. Yeah, and what an emotional send off.

I'm just here to make you cry.

What an emotional send off event. Look what it does to me.

Look, for whatever it's worth, um, yeah obviously I hired Tara on in early days over at Chili Piper. Um, I didn't ha- I mean, just phenomenal hire. Tara is, um, one of the best and brightest Demand Gen marketers I've ever had the opportunity to work with. So it's like so bittersweet, um, to not be in an [00:27:00] office with you every day, doing the grind and working on projects. But obviously, full support and I'm so excited that you're taking the reigns to take this on for Season Three. I'm really excited.

Thanks so much, I'm super excited to pick up where you left off. And I do have couple quick fire questions for you-

Oh, let's do it.

... before you go, if you don't mind. Okay, let's do it. Um, so first one, is there another marketer that you're following in this space that you recommend our listeners check out? Could be on LinkedIn, or maybe they have a great blog or newsletter.

Ooh, man, yeah. This is always a tough question, I feel like I [laughs] I always caught people off guard when I asked it, and I'm-

Mm-hmm [affirmative]

... going to be caught kind of the same. I think what- there are a couple of classics that I'll still stand by, so if anybody is new and listening to this podcast and you haven't heard it, um, before, um, there are a couple of just classics that I feel like you just must follow and have to have in your LinkedIn feed. Um, Dave Gerhardt, top of the list. Um, he's doing a lot of cool things now with other B2B startups. And he's consulting strategically, and really driving home this like [00:28:00] strategic narrative, um, initiative that I found so insightful from Jason and Mark.

So, if you're not following him, he is kind of everywhere. I think he has a book now, he's definitely doing multiple-

Mm-hmm [affirmative]

... podcasts. Um, he does a couple of live events a months. There's like tons and tons of great content to consume from him. Um, LinkedIn, Twitter, Instagram are all the places he's active. And then, of course, Chris Walker. Um, he is like fundamentally reorganizing the way that Demand Gen functions should operate versus how they have been operating in the past. Um, and that is a mentality that I fully support and stand by. So, if you're ready for like disruptive, um, Demand Gen insights, he's the guy.

Yeah, the whole team at Refine Labs is great. I keep seeing these great posts on my feed, and every time I check who wrote it it's someone new from his team.


So he's doing a great job, whatever he's doing there to hire them. It's a great... Um, and what's an under the radar channel or tactic that your team is really loving right now? Could be anything-


... that you're testing.

So, interestingly enough, [00:29:00] I've been in B2B SaaS my entire career, but have somehow almost always found myself marketing to marketers. Which means that-

Mm-hmm [affirmative]

... we're like heavy on LinkedIn. Um, a- and heavy on like organic Twitter if you're like in marketing Twitter. However, I am now in a space where I am marketing to, um, early education providers. So center directors, teachers, admins. Um, very different mindset, and these people love Facebook. So honestly, for the first time, and this is like not a new thing, but for the first time in my career, I'm really having to explore the depths of Facebook. And under- better understand how to optimize those audiences, and really spend efficient dollars there.

Um, which is not new news probably to the market, but is very new to me. So it's a- an exciting new challenge. But, it's working really well for us.

That's really fun. It's such a different audience.


We had a similar experience at Top Hat because we sold to professors, so obviously they're not updating their LinkedIn every day because a lot of them have tenure, so they're not looking [00:30:00] for a new job.


But they are on Facebook connecting with friends and family, so-


... similar.

And like ECE groups-

And Facebook is a beast, too.

Yeah, Facebook is a beast-

Mm-hmm [affirmative]

... and these ECE groups are like new to me as well.


There are so many of them, and they spend so much time there networking with their peers.

Mm-hmm [affirmative]

So, um, yeah. Understanding the community of ECE is really interesting to me, and those communities take place in different places than B2B marketers spend time, too. Um, which is fun. It's just a- it's a-

It's a fun challenge.

Yeah, it's an entirely different challenge, but, very exciting.

Cool. And lastly, where can people go find you? Or fo- get updates on how things are going at Brightwheel?

Yeah, absolutely. Um, so, although our audience spends time on Facebook, I still am not ready to commit to that. Um, yeah, find me on LinkedIn, um I'll be pretty active there and will be sharing updates regularly on what we're doing over at Brightwheel.

Great, and I'll put that link in the notes as well, so people can come find you easily. Thank you so much, again Kaylee, it was such a nice time to catch up with you.

Ugh, this was so great.

It's always a pleasure.

So great, I'm so excited to cheer you [00:31:00] on from the sidelines. You're gonna crush it, Season Three is going to be great.

Thank you so much. And thank you everyone for listening. I really hope you can stick around for Season Three, and looking forward to learning more about world of Demand Gen with all of you. Thanks so much.

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About DGC
Demand Gen Chat is a Chili Piper podcast hosted by Tara Robertson. Join us as we sit down with B2B marketing leaders to hear about the latest tactics and campaigns that are driving pipeline and revenue.
If you’re looking for tactical ways to improve your marketing, this podcast is for you!
About Mastersaas live
MasterSaaS Live is the interview series that seeks to answer the question: What does it take to be a badass CMO? For our host Alina Vandenberghe, Co-CEO and Co-Founder of Chili Piper, this question is personal. A CPO-turned-CMO, Alina is on a journey to become a badass CMO — and is building in public as she goes. If you're a current or aspiring marketing leader, this is your only chance to learn from top marketing leaders, innovators, and big thinkers about marketing in 2023 — from CRO to brand to music and so much more.
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