

17 Sep 2026 · 39m · 13 chapters

Sprout Social’s revenue marketing approach—building predictable pipeline by aligning segmentation across sales, marketing, product, and customer success, then mapping segments to solutions and prioritizing spend by expected revenue contribution (modeled back from NRR).
Hailey McDonald, VP of Revenue Marketing at Sprout Social. Background: revenue marketing/demand gen leader; joined Sprout ~5 months prior; sits in a ~75-person marketing org with three arms reporting to the CMO (revenue & growth, product & customer, brand experience). She’s responsible for pipeline and says the role is hard to hire because it must connect “authentic” marketing to revenue outcomes and product experience.
segmentation misalignment across departments creates “leaky funnels”; campaigns are “quarterbacks” that translate segment priorities into coordinated digital, events, and lifecycle work; measure marketing by modeling back from NRR (not just pipeline), to avoid incentivizing the wrong behaviors; use market “signals” to adjust segment bets when deals stall.
retail/e-commerce vs technology orgs use Sprout differently (social for selling vs publishing/listening/analytics); sales-led motions become expensive at broad scale, so Sprout threads product-led growth alongside sales-led.
Written by AI. May contain mistakes.
Hailey discusses the challenges of hiring demand generation leaders.
“which seems to be this unicorn type of hire today.”
Discussion on the structure of the marketing team and the role of the chief of staff.
“There's product and customer and there's brand experience.”
Hailey explains the strategy behind segmentation at Sprout Social for revenue growth.
“It looks like this whole thing around segmentation and rethinking how the company is going to generate pipeline.”
Hailey elaborates on the importance of aligned segmentation across teams.
“rather than just kind of having a one size fits all, which gets a little unwieldy and isn't effective.”
Learn how to align different departments in a revenue organization for effective segmentation.
“Sales is thinking about segmentation in a different way.”
Explore how a well-structured campaigns team can drive marketing strategy and execution.
“I think that I feel pretty passionately that you can like design your org how you feel is necessary, like just whatever works for your team.”
Explore the importance of Net Revenue Retention (NRR) and how incentives affect sales behavior.
“Yes, we still use MQLs where I am today.”
Delve into how marketing can influence NRR through customer engagement and expectations.
“And so it's like things like that, you, you, you start to unpack and realize like, oh, what's actually driving the behavior here?”
Learn the importance of paying attention to market signals to avoid misalignment in marketing efforts.
“And like, that's why NRR is the true definition of success.”
Discuss the transition from executing marketing campaigns to adopting executive responsibilities.
“on these sort of segments and we've learned, we've made our bets on like, Like we're going to make the, this is our tier one.”
Examine the influence of AI on marketing strategies and the challenges faced by established organizations.
“But if you want to be a CMO, a VP or an executive treated like an executive in marketing, the real ones that I've worked with, they treat the company as their job.”
Explore the challenges of adapting to new marketing technologies and maintaining competitive agility.
“Speaking of that topic, give me Haley's take.”
The hosts discuss upcoming events and the importance of segmentation in marketing.
“But yeah, I'm heading to Boston right now.”

Get the gist, explore an idea or ask about something said.
On The Exit Five Podcast, what are the key points of this episode?
Automatic transcript. May contain errors.
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2:52One, two, three, four, exit. One, two, three, four, exit. Hey, my guest on this episode is Haley McDonald. She's VP of Revenue Marketing at Sprout Social. They're a social intelligent platform with 30 ,000 customers. They've been around 16 years. She sits within a 75-person marketing org, three marketing leaders that report to the CMO. Her job is all about revenue marketing. She's the one responsible for the pipeline. This is the hardest role to hire for in B2B right now that we're hearing revenue marketing, demand gen. So we talk about her approach at Sprout Social, why it's all about the strategy and the segmentation, not the channels.
3:32Enjoy my conversation with Haley McDonald. Seems like this role, which you are, you're VP of revenue marketing, but this is like demand gen, which seems to be this unicorn type of hire today. Why is this role so hard to hire for? This is off the cuff, not in our prep, but like this role of like a demand gen leader. This is you. Why is this role so hard to find? Yeah. Well, I mean, I think there's a lot of people, you know, like the man done isn't new. It's been like the favorite child they think of, especially B2B tech for a while. I do think right now it's, you know, there's a lot of pressure on hiring this role because ultimately you're responsible.
4:07I view it as my responsibility to attach all of marketing's activity into some sort of like revenue generating machine, right? Like ultimately, for the most part, if you're in B2B tech or B2B marketing, you're there to like like sell a service or sell a product, you're not there to just have fun and games. And so it's the seriousness of connecting all of that together. And that can be really challenging when you also want to do good marketing, you know, that like feels human and you're connecting with people and you're making people feel things. It's like, I'm crunching the numbers in the background and someone else has to make that experience work too on the other side.
4:40Well, yeah, or it's like, there's just this fundamental tension between the channels that like this podcast would be one example of it, right? Like the ROI of doing this podcast for a company. It's a little bit muddy. It's not just like because we did 12 episodes this month, we're going to book three sales meetings, but there's lots of like implications that you can get from doing this podcast. And so I think like the reason it's become that darling of the B2B world is because you want someone on the team who you feel like is responsible for like making sure sales gets fed. 100%. Like it's my job to kind of engineer that connective tissue.
5:14And I have to do it from a place of authenticity and also a place that connects onto the product side as well, right? Because ultimately, you want to get great customers. You want to get great customers that stay with you for a long time and spend more money with you. But you also want them to be getting the best experience and use out of the product. And so figuring out all of that pattern recognition and like, okay, well, what's the connective tissue? And therefore, how can we design our campaigns and make sense of our marketing activities? That's my bread and butter. That's what I do every day.
5:45Okay, so we're going to get into that. You're big in segmentation, apparently, from my prep doc. We're going to get into that. But just set the lay of the land for the Sprout Social Marketing org. Looks like 75-ish people on the marketing team. And there's kind of three arms that you report into the CMO. There's the revenue and growth. That's your piece. There's product and customer and there's brand experience. And then this is a note in my doc. Is this the team runs on a chief of staff who wrangles cross-functional? Can you give me the lay of the land? Give me the marketing org a little bit, overview.
6:15Yeah, yeah, yeah. So we've got kind of like our three arms that you described exactly. And we're all linked together in lockstep. Works really nice that way. And then we are very lucky that we also have an office of the CMO where we have a chief of staff who does in fact wrangle us and bring like structure to everything that we do and make sure that we're able to connect all three of our centers, but then also extends out into our other cross-functional groups too. So it's just, I haven't had that at every organization. But oh my gosh, it's like big shout out to having a chief of staff when you do get that privilege.
6:47Yeah, yeah. Well, that's why I wanted to ask. I don't have familiarity with that. You haven't had it before. So what is that the team? What is this office of the CMO? Is that like a... Does each company have a... Each team have a department? What does that even mean? I don't understand. Yeah. So I actually... I had a similar setup. I'm at my last company too at Miracle where we were marketing at a chief of staff. And there were a couple of departments that had it, particularly the ones that have to work incredibly closely together and particularly the ones that like your plans essentially need to fit like a puzzle piece with another department's plans right and making that happen both cross functionally as well all the way through your team is just like dude it's a full-time job and that's why we have a chief of staff that just like helps keep us honest around that I think dude we're also just a bunch of marketers and so it's like if we get into a room and we don't have a facilitator it's a mess.
7:37So we have, we have someone that helps us do that. Any marketing event I've been to ever. It's like you go around the room and you do introductions and next thing you know, the meeting's over. It's like everyone has their whole spiel. Yeah. It's like our chief of staff, AD, like teach us just like on point and just like really make sure that we get what we need out of everything that we do. And that we like, you know, whatever marketers also lots of big ideas, but what's realistic? How do you bring those to life? Like that's something that our chief of staff supports too. Okay, cool. So since you've been there for, I think you joined in the spring-ish, LinkedIn says five months, what's been your big task?
8:13It looks like this whole thing around segmentation and rethinking how the company is going to generate pipeline. Why don't you take me through some of that? Yeah. So I think another part, if I had to talk about revenue marketing in general at a higher level, I think a lot of it is around helping your marketing team create plans around how people buy. And that's both like you want to create a good experience for your customers, but you also want your activities to make sense, control your cost of operating, all of that. And so Sprout actually has been, we're a 15-year-old company. We've always been very trial-forward product where you go to the site, it's like, try it out, you can get right into it.
8:55But we've been a sales-led organization for a really long time. So you are an individual practitioner even, and you would go talk to a salesperson, right? Which has served us really well because we've created these amazing customer experiences. We've been able to move up market and work with some of the biggest brands in the world. but it also can get like, that's not the only scale so far, right? So I was brought in specifically to kind of thread out our product led growth motion and run that alongside. Sorry, can we go back to that? What only scale so far? Meaning like once you change the, are you talking about if there's like a trial or free experience or not versus like bridging the gap between either getting on the phone and talking to sales or not buying from you?
9:35I mean, just really honestly, sales and growth motion gets really expensive, particularly when you're, you know, like when you're serving such a broad market. Yeah, can you break that down? Like why? What does a sales-led growth motion mean versus another motion? And then why does it get expensive? No, that's a great call out. So I mean, sales-led, right? It's super human. So you go interact with a website, you request a demo, you start a trial and you have a human, your customer service person, like your account executive reaches out, holds your hand, tells you everything that you possibly need to know.
10:07It's a very concierge. experience, which feels good. That's fun, right? That's super great. That said, not everybody wants to buy like that. Number one, some people just want to interact. Look, I'll say it. For me, annoying is shit. I'm sorry. I understand this is the dichotomy of marketing where I'm allowed to have both thoughts. But I wrote about this the other day. It's like, and we don't even do this. Someone was asking the price of our community or whatever. And I was like, oh, it's not published. But as a buyer, I'm like, I want to know the price. And so this is like, yes, on the company side, we say, you're going to get a concierge.
10:39I'm like, no, I don't want that because I know what that means. That means that this person is going to call me. Literally, my phone is in my pocket right now because God, my phone number is plastered across the internet. My wife won't let me change it. She's like, dude, we've been together for 15 years. I finally memorized your phone number. You can't change it just because you get a lot of spam. But yeah, I don't want to say that out loud. I think it's totally fair, right? Like some people don't want to buy like that. And then there's other instances where it's just like, you can move faster exploring a product on your own through more like product-led growth where, you know, like the product is designed in a way for self-discovery that just like suits people's needs a little bit better.
11:13In addition to like, if you do it well and you do it right on the company's side, it's more affordable to run a product-led growth. And so many organizations, so many startups, startup like that. So we're kind of in the opposite where we started out sales-led and now we're kind of really developing that product-led motion to run alongside it. Okay. And is your ICP like an enterprise customer? Because typically the sales led motion is more of like an upmarket customer. Or are you selling to multiple? Who is your ICP? That's the question I meant to ask. Dude, that's the tough thing about a place like Sprout is like we serve such a broad, such a broad audience.
11:48So we go all the way down from like individual practitioners or like creators that can use like our software for like publishing and analytics and like managing all of the different inboxes across like 10 different platforms that they might have. And then we have some of the biggest brands in the world too. So our ICP is enormous, which is why I like always laugh. Like someone is gonna punch me in the face if they hear me say segmentation one more time on my team or my company. But it's like, this is why segmentation is so important for us so that we can really drive effectiveness through our marketing rather than just kind of having a one size fits all, which gets a little unwieldy and isn't effective.
12:25It's like people need a special message on a special channel. That's cool. One of the reasons I like doing this podcast is because I think when I've, you do it so much I've now seen all different types of companies. And I take somebody, I think of someone like Claire, who's a VP of marketing at TechMetric. They have a very specific ICP. It's like this type of has to be an auto repair shop, has to be doing this, has to be in this location, has to be this. Then just last week, I do a podcast with Katie, who runs marketing at SurveyMonkey. She's more similar to you, which is like, well, we have enterprise customers, we have small business customers.
12:58And it's like, okay, well, what do you show on the website? And who do you argue with? You know, the VP of this segment is like mad that there's not enough product marketing material for this. And it's like grass is always greener. So for you, though, this path to driving more predictable revenue in these segments has been segmentation. Maybe your team is sick about hearing you talk about segmentation, but we're not. So bless us with some of that. What are you doing? Take us into the mind. How do you go and attack this? How do you build a marketing strategy here? What are you doing? Yeah. So I like to describe this.
13:28Like if you don't know what your segments are, or like, I think in some cases, organizations will be in a situation where people are thinking about segmentation out of necessity. Like maybe the marketing team is thinking about it because at some point you have to, when you go to like distribute your activities and like what email lists you're sending to and, you know, like things like that. And you may find yourselves orienting around personas or something like that when you think about segmenting and creating unique groups, right? And your company might be in a situation where marketing is doing that.
14:01Sales is thinking about segmentation in a different way. Product is thinking about it in another way. That is where I see, like, I mean, efficiency go to die, basically, when everyone is either not thinking about segmentation at all or all doing it differently. So my first sort of principle is that you really need alignment across your revenue organization. So, you know, sales, marketing, customer, as well as product on like who are your key ideal customer profile segments. And that can be, I mean, there's more than one way to peel a potato. It can be done in a lot of different ways. Sometimes you'll see it show up in verticals.
14:37Sometimes you'll see it as like business types. I generally try to leave that conversation around how are your customers buying? Like, how does that happen? How do they think about themselves? What are they coming to you about? And a lot of times that will show itself in like use cases. Like, so when we think about Sprout Social, I think like, think about retail and e-commerce. When they want to use social media, they're thinking about it oftentimes as a channel where they're selling their products. So like on the TikTok shop or like, you know, like e-commerce sort of things. And that's the use case that they're really getting out of us.
15:13And so they use, you know, A, B, and C product or solution. Whereas like, if you look at a technology organizations, like, you know, in B2B, they use social for an entirely different reason. They might be using it more as like a publishing mechanism, reporting, listening, analytics. And so they use more often our products, you know, D, E, and F or something like that. And that sort of alignment, like where you're looking at this visual here, if you can get your segments on your kind of, what did I put it on the top? Yeah, your segments across the top and your solutions down the other side, you're able to kind of create this heat map of like, what are we selling to who?
15:51And what is the priority? Like, which one are we selling more of to who? Okay. And so does this, is this like 101? The point is that this is like the foundation, right? If you just started firing off, making TikTok videos, making ads, choosing what events to go to. You can't really do that effectively without first sitting down and mapping this out. Is this your sheet of music for figuring? Because I think the question I'm trying to ask is like, how the heck do you figure out what to do with so many segments and so many different personas? You know, you could make the case to do or not do all these events, to do or not do all of these influencer campaigns, to do these ads or not.
16:28It's like, how is that? How do you go and execute on that stuff? I mean, like, I think this is there's kind of two things to say about that. One, yes, I do think this is the 101. If you can orient and look, this is just one view. I have found this view very clear and helpful and kind of used it in a few different scenarios effectively. And this is your map. This is where it kind of like all begins and where you're able to attach every single marketing activity into something that you know is geared up into something that will be revenue generating, but also in a way where you hope that, again, you're going to get happy long-term customers as well.
17:02and the other side of it is like i mean like not to dig on any other marketers out there or whatever but i also i would say there's not a lot of organization doing this there's many more organizations out there that are plainly kind of doing the one size fits all thing or probably more often are in that situation where every different department is thinking about segmentation differently and so at the end of the day like sure things might come together especially if the market is pulling you forward, but there are so many leaky, you know, we were talking about leaky funnel. It's like the ultimate leaky funnel.
17:36There's just stuff coming out of all different holes in your business when you're not aligned to something like that. So how does this play out for all of the channels, right? So you run, you run demand gen revenue marketing at this company. How do you figure out where to spend the budget? How do you figure out which channels to invest on. Especially today, I like to say that everything works. You could certainly talk to a marketer or listen to enough episodes of this podcast and they have an example of something works. I think one of the challenges is not in figuring out what to do. It's like what to say yes to and what to say no to.
18:10It's like less of an innovation problem, especially as you get to your scale. So how have you figured out which plays you're going to run? It's too much. It's too much for my little brand. That's why I run a tiny little business. Yeah, it's a lot. Well, it looks overwhelming when you kind of see it in a chart like that. And you're like, wait, that's effectively, you know, it's so many different like holes that you're filling on that sort of chart that I showed. But ultimately, if you can decide the prioritization around your segments, and that is normally like an exercise that happens oftentimes driven by the revenue team and the product team and like a planning exercise where it's like you're someone in your organization needs to figure out where you think the most revenue is going to come from out of those segments.
18:55So let's just let's keep them let's talk about them as a verticals to make it easy. So let's say you have retail, travel, media and entertainment, so on and so forth. Right. And you decide like someone in your organization decides like based on modeling or based on best guests or whatever. we think we could talk about that later too as far as like the signals that should inform that in my opinion but like however that's prioritized they like great we think that 30 percent of our revenue is going to come from retail and therefore we know it'll be attached to these solutions that they use we think 20 percent of it's going to come from media and entertainment 10 percent from travel right and that gives you a pretty direct ability to understand how you should spend how you should invest.
19:38So I normally kind of am taking those sorts of percentages and then cross multiplying them against like total revenue targets. And generally you're getting those split. That's a lot of, this is where it gets like really math heavy because you'll typically get those split out by like region. I'll typically get them split out, you know, in all the different ways that matter to like your sales organization, but you can start determining like, all right, our campaign for retail needs to essentially funnel down to these products and it needs to generate this amount of revenue and back that out to pipeline based on your model compared to, right?
20:13And maybe that's our tier one compared to travel, which was only 10%, which maybe is our tier three. I got you. So you're splitting, like if you and me are on a whiteboard right now, you're building this plan by the different verticals or segments that you're calling them. So retail is a core persona. You're going to have a pipeline target for retail. You're going to sign reps have quota, then you're going to have all the marketing channels and plays. Some of that cascades and like hits the whole Sprout Social brand, but you're like trying to drive specific pipeline in a segment, right? Am I understanding that right?
20:45That's right. And then you were kind of asking about like, how does that then get down in the channels? Oh, yeah. Wait, can I interrupt? And one layer on there like that I've always thought is interesting is how teams have this setup because it's like, do you have a digital team that just run that runs ads just for retail? Or, you know, do you have specialists doing across all, and then how does product marketing fit, and then content. That's kind of like the layers that I'm interested in as you give me that answer. Hey, it's Dave. Today's episode is brought to you by Optimizely. If you want to know what AI agents can actually do for a marketing team, Optimizely is where I'd point you to right now for a real example.
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23:00Everything CGM does gets tracked, measured and improved over time. That means more pipeline for you. And this works because they were started by an actual former VP of marketing who really gets this space that you work in in B2B. So visit compoundgrowthmarketing.com slash exit five to see how they can help you meet your 2027 revenue goals. That's compoundgrowthmarketing.com slash exit five. The org design around this is like, that's the interesting thing. I think that I feel pretty passionately that you can like design your org how you feel is necessary, like just whatever works for your team.
23:36Like some organizations are very, very like solutions marketing forward, right? And they have a product marketer that is on a particular segment. And then they have everyone that like falls in suits to that. We're not like that. Like we even have like, I know we've kind of been talking about demand gen. In general, like our demand gen really is actually split across a couple of teams. Like we have customer marketing, which also does some of our demand generation within lifecycle marketing. We have the digital function on my team and on my partner's team that runs brand experience and field. They have like events and field.
24:08And so really demand generation is everywhere. And the thing that kind of drives what gets activated is our campaigns team, which does sit on my team. and they are taking any like our goals, our prioritization. And then with all of their partners around the team, they're having a conversation of like, okay, we're doing a retail campaign or we're doing a travel and hospitality campaign. How might we, how can we best go engage those people? Is it at events? Like how do retail marketers, like where are they if we're selling to retail marketers or maybe we're selling to people in HR and retail, whatever.
24:41Tell me more about this campaigns team. I like this idea, obviously not new. Some guy who hates me, I mean, Lou will listen to this podcast. Like, how does this guy not know what a campaigns team is? What does a good campaigns person do? What does that look like on a team? So when this is like such a marketer thing, like it depends. I mean, that could be the whole podcast. We could do no guests. It's just, I don't know. Depends. Listen and join me for the next episode on It Depends. You need to start a new podcast. Yeah, it depends. It depends. Yeah, I think like, so I have a very selfish perspective having like campaigns on the revenue team.
25:14But when you attach it to revenue marketing, I kind of view them as like the quarterbacks, really. I make this joke all the time with the team. Like I need to stop the sports analogies and the sports. But they're kind of the quarterbacks, right? Like they're bringing that strategy down from the office, right? And they're pulling it down and working with all of their partners to design like what a campaign should look like that's ultimately going to attach back into that goal. So they really lean on their partners, like let's say in field for like, what does that experience feel like? And what is the event strategy?
25:45Right. But we know that when we market to X segment, we need a lot of events for when we market to this other segment, we need digital on point. And so we have to have digital channel experts. Well, I think, but it's almost like I've been in companies where there is not the like campaigns layer. And so certainly, cause I'm kind of the other side of this is like, well, couldn't you just have a revenue marketing manager and their job is to interface with the field, the digital, the whatever. Totally. But the hard part about that is like, those people also have other things. And then it's like this weird ownership and responsibility too.
26:17It's almost like the same, the same concept of like, why does the marketing org have a chief of staff? The campaigns manager owns the like goal and then the delivery might be working with different teams? Question mark period. Yeah. I mean, like, that's how I think about it for sure. It's like, there's, they're wrangling everything and bringing everything together harmoniously. And like, look, if we're being really honest, when I've had campaign assumptions like this, there's generally some sort of like, there's something that no one is owning. There's always like one thing, right? And it's like, who's going to do this?
26:50And like, a lot of times your campaign managers have a more kind of broad set of skills and demand generation and they pick it up. So like, oh, I'll do the webinars. I'll be the one that runs webinars or like I'll be the one that handles our kind of like sponsorships with media organizations or something like that. Like they're sometimes a little bit of a catch all. Okay. Understood. How do you talk about success and measurement and reporting? I'm not trying to ask you like, how do you measure marketing? Because that's another like it depends thing. But there's a little bit of an art and science and being the revenue marketer in that not all this stuff is directly attributable to we did X, we sent this email and this thing happened.
27:26Any lessons you've learned as to like making, you know, making sure you're making the right bets and investment, you know, not everything is direct response. I just love to hear your philosophy on how you would guide someone listening to this, a peer of yours or someone similar in your shoes. How do we talk about the strategy of revenue? How do we talk Talk about marketing's impact on the funnel. Well, I'll tell you what I've got right. And then I'll tell you what I've got wrong. And I'm still like learning. I've done this enough cycles and done it enough rhythms that I've learned over time. And it really feels strongly that like I modeled back from like the farthest thing from a marketing, a marketing metrics that I can, you know, so I'm not like, like, I don't.
28:10Yes, we still use MQLs where I am today. you know, and like things like that. But when I'm thinking about modeling back, I actually want to be thinking all the way from NRR. Like, I also don't like modeling from pipeline because we can go man with after a pipeline. Like if you've been in marketing long enough, you know, you can go make it up. Model back from NRR. Again, the point of your organization is that you want happy customers that are staying with you as long as possible and spending more money over time, right? And so model back from that. Is that true though? Can you make up, I think you could make up leads.
28:44I think pipeline is tough to make up. If you - You pressure sales hard enough. You say, hey, make these leads into pipeline and they go make it up. Okay. Not saying that sales are bad guys. It's just like there's enough pressure and people do things, right? Okay. No, no. My mind went to, so my mind went to, yeah, you're wrong because you can't just make pipeline happen because sales has to create opportunities. But what you're saying is actually that even a more gangster move was like, no, actually there are levers you could probably pull internally to like incentivize the wrong types of meetings.
29:12And if you book them as meetings, you could choose the pipeline number that way. And sales is still... BDRs are incentivized off of pipeline too, right? Like AEs are incentivized off of revenue, but like it goes wrong that way. And it's not because anyone's trying to be a bad guy. It's just like how human psychology works and everyone's just trying to like pay their rent. You know what I mean? 100%. I think this is such an underrated, like one of the things, and I'm learning this in building my own company now, Dan and I talk a lot about this, but as a lesson, I wish I had known when I was running marketing was how important incentives are for driving behavior, not just on your team, but also in understanding the other, like I had a sales leader that I worked with and the CEO, the comp plan was all messed up in that we were literally fundamentally misaligned to never be on the same team because they didn't, they got, they got paid out more if it was like not marketing sourced.
30:03Right. And so it's like things like that, you, you, you start to unpack and realize like, oh, what's actually driving the behavior here? Or I've been at a company where they really wanted to do cross-sell, but it was nobody owned that. Nobody had a number. Nobody had a strategy. So it was just like, well, we sure we're 25%, you know, behind on our cross-sell plans. It's like, yeah, but who owns that? So. Well, and that's so like full circle. Why go to NRR too? Like when you can, like, look, it's an evolution. Yeah. And while you answer this, can you tell me how, how does marketing drive NRR, right?
30:33Isn't that going to be down to like product usage, expansion, retention? What role does marketing play there? I don't understand. That's a great question. It helps me answer this. And that's why I model back from NRR because like ultimately, like, okay, I just said, right, I can, I can manufacture leads and then we can put pressure on BDRs and incentivize them to create pipeline. And then we can put pressure on sales and incentivize them to sell to literally whoever, right? Regardless of whether they're in your ICP or not, regardless of like their likelihood to churn in 12 months is like 90%. You can still put pressure on sales to do that.
31:08And then it just gets kicked down to your poor, your poor CSM, right? Like that account goes over. And like, that's why NRR is the true definition of success. And if you can model back to like the people that you are marketing to are the people that are most likely the ones to be happy and successful with your organization long-term, like we are the start of the chain. Product, obviously, it's like a big circle, right? And product has to like build for those groups too. But that's why. Yeah. It's like all about expectation settings on the way in, right? Yeah. So that's what I've gotten right as far as like measuring marketing goes.
31:44Like, look, if you can model back from NRR or like if you're not there yet and you're like modeling off of leads today or pipeline today, at least start with revenue, right? And try to get your way to NRR. But like, if you can do that, you're already on the right track and then kind of model that all the way backward? Am I engaging the customers that are going to be the highest likely to stay with me? What I have not aced and what I'm working on as a marketer myself today, and also it's attached to why I was like so invested and interested and also going to sprout. As you said, I've only been here five months.
32:15And I think that is such a hot topic right now in marketing, but it's like signals. So like you can engineer what I just talked about and all of this stuff is like, so be fair, it's a little bit of like building spreadsheets and ivory towers. You can do that all day long. But if you're not then also layering on and paying attention to the signals that are telling you which of your segments you should be prioritizing where and when, then it's literally just a spreadsheet and it all goes to hell. And so I've kind of seen that play out in the last couple of years when I've run campaigns on these sort of segments and we've learned, we've made our bets on like, Like we're going to make the, this is our tier one.
32:55We're going to make the most revenue out of this segment. And then at the end of the day, 90 % of that pipeline falls out at stage two. And it's like, what? What did we just do? And we actually were not listening to or ignoring all the signals in the market that told us your product is, you might be on the short list, but you're not winning any deals because your product fell behind. Or this segment right now is suffering and they're never going to get budget approved because like they're just suffering in the market. And so those are the sort of signals now that I'm trying to like pull into my system to be able to kind of build smarter.
33:29Oh, that's super interesting because I think so often the marketer's brain goes to more, more, more, more, more, more, more new leads, more meetings, more this. But what you're saying is actually the root cause of this might be, hey, we're going after the wrong persona or we have the right persona. However, especially in your case, right, 16-year-old company, the market has a perception about our product that we need to go change. And so the deals are not going to close until we make this investment in the product. So this is a great example of where like a real demand gen revenue leader doesn't just drive net new.
34:06It's we have to influence change across the org. And so you need to be able to say, well, actually, the reason we're booking meetings, but the reason these deals aren't closing is because people are just shopping and they end up going with this other product. That's right. Right. And I have for that reason, it's like it's my part time job to be best friends with my product marketing leader, too. Right. It's just like in lockstep. And I mean, brand like everyone is involved. But like that product marketing relationship and intelligence and feedback loop is like probably the most important thing to like making my plans successful.
34:36I want to put a bow on that because I think the difference that whatever we just talked about in the last couple of minutes, that to me is the difference between a marketer and an executive. A marketer is someone who's going to execute on campaigns to hit the marketing goals and say, wait, we hit the marketing goals. I did my job. We grew traffic. We grew this or that. But if you want to be a CMO, a VP or an executive treated like an executive in marketing, the real ones that I've worked with, they treat the company as their job. Marketing is the thing they oversee. You know what I mean, Haley?
35:09Like my job is to influence. It's like, oh, product's not my job. No, no, no. My job is to like marketing is like the mouthpiece. We're the tip of this with sales, where you need to influence the thing we're selling. 100%. And that's actually, it's a funny, just like a personal reflection. It's an interesting place where I'm at. And kind of like the middle of my career is like, I feel so fortunate that I'm still close enough to like hands-on tools. Like I'm still hands-on tools some days, right? And like, that's the marketer. I love marketing. I love it. Love doing all of the different roles that I've been in.
35:44But now I'm in a world where I do kind of need to take those executive responsibilities. And so balancing between like how much time you spend on those sort of like strategic drivers versus like doing your craft is hard. Like that takes like mental energy from me every day to make the right call on that. I mean, your craft at this point, though, your craft is that that is your job. That's true. I think that's where it's going for better or worse. I like that. I don't know. I'll never, I think about that a lot. Like when you love something and you do the craft for so long, it's like, if you keep moving up, it changes.
36:19Like your day-to-day changes. And I kind of like have those career conversations with people on my team about that. Like, what do you want your day-to-day to look like in a couple of years? Because that very much will push you in a different direction. Yeah, who knows? Who knows? Speaking of that topic, give me Haley's take. not as a revenue marketer, just as you, someone with a bunch of experience in this field. How are we feeling about AI, the state of marketing as of us recording this September 2026? What's cool? What's real? What's overhyped? Where is marketing going? Are things changing as much as people say they are?
36:53Are they not? What's your pulse? Yeah, I mean, it's a great question. Everyone's talking about it. I was really lucky that I was in. So I was working for an organization that's in the AI workforce transformation space, like when generative AI really hit the market. So I was in such a sweet spot to have incredible exposure to that. I really, my CEO at the time was from like workforce transformation background. So like early days, I was into the using it, how do we augment the way that we work to do things better, faster, unlock capabilities that we didn't have before. How does that change how we think about our organizational structure and our like, we called it our workforce DNA.
37:36Like how many full-time employees do you have versus Flex versus AI? I've been there, done that. It's not old news. Definitely haven't mastered it. But like my personal take and like what's actually keeping me up is less about like how we're augmenting our like, you know, daily workflows. And for me, it's like how tech stacks are changing because of how AI has unlocked tech development. So like just our marketing automation platforms, ABM platforms, like all of these tools that we've been using for so long are changing overnight because new companies that are AI first are coming in and are able to develop something that we've never been able to do before.
38:16And so when you're at an organization that already has an established tech stack or is already has so much built on these like legacy systems. It's like, how do we as marketers, which are very tech dependent and heavy, how do we move ourselves forward in a responsible way? And we're not just like clinging onto some trend. And yeah, I'm losing a lot of hours of sleep on that these days. A lot of hours of sleep over like, are you keeping up enough with tech? And just like, how are we, what if this is a, just a kind of trend or, you know, like is gonna, is fleeting and is gonna be gone in a couple years or change.
38:52and how much should we be acting on now? Like, should we go vibe code our site? Like, should we go vibe code it? Like, what do we do? Like, that's just a big question. I don't know. Did you see, I'm not a big stocks market guy, but I am following like companies like Salesforce and HubSpot pretty closely, just as it's telling of like the marketing landscape and no one's ripping out Salesforce. And there's going to be like a couple of core. And we talked to so many execs. It's like, I don't know, the vibe coding stuff is cool, but I've talked to more people who've like, hire an agency, hire this guy that they know.
39:24And they, you know, and then when someone does it, and like kind of half works, it's like, I don't know, that's cool. Yes. Okay, cool. AI can like one shot the website. But like, maybe if you're like a two person startup with not a lot of risk with like a high tolerance for risk, like Sprout Social absolutely is not going to like vibe code a website and have some, you know, 22 year old on the team maintain it in their cloud code environment. That's just not realistic. No, 100%. Right. But that's the thing. is like in this space that we're in right now, like in general, like anyone that's kind of like in technology, yes, we are.
40:00I mean, I work here. I've got to say it. We're like the biggest and the best, right? We have like this great reputation and all of this stuff. And like, if there's going to be an RFP that goes out for a social intelligence platform, we're going to be in it. That's great. But like a company that just started off like two years ago, that's been able to build AI first and has been able to like do things and like come up with processes and like just in a way that like we would have to undo and then rebuild and we're big, we're like a cream ship and so things take long. It's like that balance that I'm like, how do big organizations move with that same level of agility as the up and comers?
40:40And like a lot of that for marketing swirls around like how you're leveraging technology. So right now that's really where I'm kind of trying to figure it out. I have tons of brilliant people on my team that know how to put AI to use in like the best, most responsible ways. And I'm like, so proud of them. And it's just like, you guys are off to the races learning all these things. Now, how do we think about that on the macro scale for like, how we drive our entire strategy and how we operate? Like that one's hard. Yeah. All right. I just got a ping from my team because I'd like to send, I take a screenshot, like when we're recording the pod part of my system is I take a screenshot and I'm like kind of live taking notes as this is going on.
41:19So it makes our post-production easier. And yeah, our team was like, great. Ask her when her slides are going to be ready for drive.
41:28Allison is like, she's fiery. Just like hang up on her. No, no, no. Tell Allison I'm on it. Please don't apologize. I am the number one culprit of this. If I were ever speaking at an event, you're certainly not getting my slides until the day before because I need the flight on the way there to like do them. Totally. No, I'll be sending them through. Where are you, by the way? You're on the road. Are you in the road right now? Are you in an Amex lounge somewhere on the road? Where are you? I'm not cool enough to be in an Amex lounge. I'm in the Alaska lounge, Seattle girl. But yes, I'm in the lounge.
41:57I'm on the road all month. I can't wait to see you guys next week. Yeah. At Drive. But yeah, I'm heading to Boston right now. You're old stomping ground. So I'll say hello. What are you doing there? Webflow. Going to Webflow. Oh, right. Okay, good. There you go. So another example. We're about the website or like hire a vendor and use them to run the website, right? I know. Webflow's like, please, for the love of God, don't just go vibe to your site. Yeah, go in there. I'm excited to see you guys. All right. And then you're coming our way. Are you going to be inbound, unbound also? I'm not. No, I had something else going on.
42:28I can't even remember what it was, but I'm not going to be there. Everything all in on X6 Drive this year. And also just like quick plug, is that so much of what I was talking about today in regards to segmentation, both like at that kind of granular level, as well as how you think about it across PLG and Enterprise, is what my workshop is on. That's right. So I'm super excited. Yeah, that's awesome. We're lucky to have you in our universe. Nice to get to hang out with you a little bit. Haley, I'm gonna let you go. Get out of here on the Alaska. Safe travels to Boston. Thanks. I'm busy today, man.
42:58I got you right now. I got a prep call with Kara Hardin after this. She's one of our keynote speakers. And then after this, I'm doing a podcast with Ross Simmons. So I'll look forward to give you a hug when I see it next week here in Vermont. Haley Rock. I'll talk to you soon. Thanks so much for having me. It's like such a privilege. Okay, bye-bye.
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#391 | Dave sits down with Hailey McDonald, VP of Revenue Marketing at Sprout Social, to talk about what revenue marketing looks like inside a 16-year-old social intelligence platform with 30,000 customers. Hailey explains why demand gen has become the hardest role to hire for in B2B. She shares her core framework, how she maps segments against solutions, and how that turns into budget, channel bets, and pipeline tiers by vertical. Dave and Hailey also get into what it takes to go from sales-led company to product-led growth, and what north star metric she uses instead of leads or pipeline. You’ll also hear how reading market signals keeps you from over-investing in a segment that's never going to close. Finally, the difference between a marketer and an executive, whether big companies can vibe-code their way to startup agility, and the truth about incentives.
Timestamps:
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