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How Sprout Social builds revenue marketing around segmentation (with Hailey McDonald, VP of Revenue Marketing)

44m 18s

How Sprout Social builds revenue marketing around segmentation (with Hailey McDonald, VP of Revenue Marketing)

This episode explores the evolving landscape of B2B marketing, focusing on strategic revenue growth and the role of AI. Haley McDonald, VP of Revenue Marketing at Sprout Social, discusses the growing demand and complexity of revenue marketing roles, emphasizing that success lies in deep segmentation—dividing audiences by behavior, verticals, and use cases—rather than broad, one-size-fits-all campaigns. She highlights how alignment across sales, marketing, and product is essential to avoid fragmented efforts and leaky funnels. Marketing success is measured not just in leads or pipeline, but in Net Revenue Retention (NRR), ensuring long-term customer value. The episode also examines how AI and new platforms like Optimizely and Webflow are reshaping operations, with Webflow enabling AI-optimized website visibility and Optimizely offering AI agents to automate marketing tasks. A key insight is that effective revenue marketing requires strategic leadership—balancing execution with executive-level influence—and that organizational design, such as a campaign team or chief of staff, is vital for coordination. Finally, the discussion touches on the urgent need for marketers to stay agile with technology, recognizing that while AI-powered tools offer promise, responsible adoption and deep internal alignment are critical for sustainable growth. The narrative underscores that modern B2B marketing is not just about volume, but about precision, strategy, and long-term customer outcomes.

Transcription

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Hey, it's me Dave. Today's episode is brought to you by Optimizely. Look, I hear about AI agents every single day on the internet, in the X5 community. But it's confusing. It's a little bit overwhelming, which platform should I be using? Which agents are actually worth building? How do I even set this up? There's a lot of noise out there. It's kind of hard to tell what's actually going to make the job easier versus what just can be another thing to manage. Or is this just a cool little thing some guy wrote about on LinkedIn? Well, Optimizely's agent platform is built specifically for B2B marketers. You can build your own agents or pull from a directory of 50 plus pre-built ones made just for marketing use cases all in one place. This is really smart. They also just launch virtual teammates. These are digital members of the team that can learn over time and can join meetings, complete tasks, support campaigns, and keep your whole website optimized. Humans, that's us, of course. We still get the final say over these robots, but this seems really useful. This is worth leaning into right now, right? Agents have so much potential and using AI in a platform like Optimizely for the stuff that eats your week. So you can get more time for the strategic thinking and actual fun parts of your job on into that. Let's make marketing about the craft of marketing. Again, I think there's something there. So go and check out Optimizely right now. See how their AI agents can help you with your B2B marketing operations. They purposely built this for B2B marketing. This is really cool. Optimizely.com/exit5. That's Optimizely.com/exit5. Go and check out their agents. Hey, it's me, Dave. Today's episode is brought to you by Webflow. Webflow is a website platform for the agentic web built for modern marketing teams to build fully custom sites that perform in AI search. No developer needed your website isn't just your homepage anymore. It's actually the first thing an AI agent is going to read about your company and from there decide whether or not to recommend you to a potential customer before a demo before a sales call before anyone on your team even knows that buyer exists, which means if your site isn't structured to show up in AI search, you're not in the buying conversation. It's as simple as that. Webflow is the platform marketing teams used to fix that. You can build a fully custom site without a developer, optimize it for AI search, govern your content and actually see how agents are reading and interpreting it all in one place. Make your website your biggest growth engine right now with Webflow. Check them out at Webflow.com/4/exit5. That's Webflow.com/FOR/exit5. You're listening to the Dave Gararcho. 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% 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. Enjoy my conversation with Haley McDonald. Seems like this role, which you are, your 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 this role of a demand gen leader. This is you. Why is this role so hard to find? Yeah. I mean, I think there's a lot of people, the man done isn't new. It's been the favorite child. They think I'd especially be to be tech for a while. I do think right now, there's a lot of pressure on hiring this role because ultimately, your responsibility to attach all of marketing's activity into some sort of revenue generating machine, right? Like, ultimately, for the most part, if you're in B2B tech or B2B marketing, you're there to like sell a service or sell a product. You're not there to just have fun in games. And so it's the serious business 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. Well, 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. And I have to do it from a place of authenticity and also a place that connects onto the product side as well, right? Like as ultimately you want your you want to get great customers. You want to get great customers that say 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 like 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? Like that's my bread and butter. That's what I do every day. Okay. So we're going to get into that your big in segmentation apparently from my prep doc. We're going to get into that. But let just set the lay of the land for the Sprout social marketing or 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 their 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. Yeah. Yeah. So we 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 in the CMO where we have the 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 this chief of staff when you do get that privilege. Yeah. Yeah. Well, that's why I wanted to ask like I don't have familiarity with that you haven't had it before. So what is that the team like what is this office of the CMO? Is that like a does each company have a group? Each team have a department like what does it even mean? I don't understand. Yeah. So I actually had a similar setup. I met my last company too at Miracle where we had we're 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 what's like if we get into a room and we don't have a facilitator it's a mess. So we have we have someone that helps them 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 is over. It's like everyone has their whole spiel. Yeah. It's like our chief of staff 80 like chiefs 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 idea 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 you've been there for you know I think you joined in the spring ish LinkedIn says five months. What's been your big task? It 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 you know another part if I had to talk about revenue marketing in general at a higher level I think a lot of it is around like helping your marketing team street man around how people buy and that you know both like you want to create a good experience for your customers but you also like want your activities to make sense control your like cost of operating all of that and so sprout actually has been you know we're 15 year old companies 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 but we've been a sales led organization for a really long time so you are an individual practitioner even and you would like 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 like move up market and also 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 when do 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. I mean just really honestly sales led growth motion gets really expensive particularly when you're you know like what you're serving such a broad market. Yeah can you break that down like why what is a sales led growth motion mean versus another motion and then why does it get expensive. Yeah 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 you're customer service person like your accounting vacuative reaches out bold your hand tells you everything that you possibly need to know it's a very concierge experience which feels good that's fun right like that super great that side not everybody wants to buy like that number one like some people just want to interact. Look I'll say it for me annoying as shit I'm sorry I understand this is the dichotomy of marketing where like I'm allowed to have both thoughts but I wrote about this This is their day. It's like, and we don't even do this. Someone is asking like the price. price of our community, whatever, and I was like, oh, we don't, 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, you're going to get a concierge. I'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, you know, 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. In 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 in so many organizations, so many startups start up like that. Even 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. So 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 going to punch me in the face that they hear me say segmentation one more time on my team about my company. But it's like this is why segmentation is so important for us so that we're we can really drive effectiveness to our marketing rather than just kind of have a one size fits all, which gets a little unwieldy and isn't effective to 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 VP of marketing a tech metric. They have a very specific ICP is 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. And just last week I do a podcast with Katie who's runs marketing at survey monkey and she's more similar to you, which is like, well, we have enterprise customers. We have small business customers and it's like, okay, well, what are you showing 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 tech this? How do you build the marketing strategy here? What are you doing? Yeah. So I like to describe this like 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 personalized 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. Sales is thinking about segmentation in different ways. Product is thinking about it in another way. It is where I see like, I mean, efficiency go to die basically when everyone is thinking 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. And it can be done in a lot of different ways. Sometimes you'll see it show up in verticals. Sometimes you'll see it as like business types. I generally try to lead that conversation around how, 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 throw 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 for like, you know, like e-commerce sort of things. And that's the use case that they're really getting out of us. And so they use, you know, A, B, and C product or solution, whereas like, if you look at a technology organization, like, you know, NB2B, they use social for an entirely different reason. And they might be using it more. It was like a publishing mechanism, reporting, listening, analytics. And so they use more often our products, you know, D-E-N-F or something like that. And that sort of alignment, like where you're looking at this, there's a little here. If you can get your, your segments on your kind of, when 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 and what is the priority, like, which one are we selling more of to who? Okay. And so does this, is this like one on one, the point is 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. It'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 one or one. 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. And the other side of it is like, I mean, like not to dig on any of their marketers out there or whatever. But I also, I would say that 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. There'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? Do you figure out which channels to invest on, especially today, like I like to say that everything works, everything you could, you know, you could certainly talk to a marketer if you are listening enough episode of this podcast and they have an example of something works. I think one of the challenges is not in, it's not in figuring out what to do. It's like what to say yes to and what to say no to. It's like less of an innovation problem, especially as you get to your scale. So how do you, how have you figured out which plays you're going to run? It's too much. It's too much for my little brands. Why 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. But they showed, 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 and the instant figure out where you think the most revenue is going to come from out of those segments. So let's just, let's keep them, let's talk about them as a verticals to making 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 guess or whatever we think, we could talk about that later into 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% 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% of it going to come from media and entertainment, 10% from travel, right? And that gives you a pretty direct ability to understand how you should spend, how you should invest. So 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. You'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? Tier one. Yeah. 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 in place. Some of that cascades and hits the whole Sprout Social brand. But you're trying to drive specific pipeline in a segment. Am I understanding that right? That's right. And then you were asking about how does that then get down in the channels? Oh yeah, wait. And can I interrupt? And one layer on there that I've always thought is interesting is how teams have this set up. Because it's like, do you have a digital team that just run that runs ads just for retail or 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 me, Dave. This episode is sponsored by Zoom webinars. Zoom webinars lets you host polished, engaging webinars that actually drive pipeline. We recently switched to Zoom webinars for exit five live. I don't know if you've seen this. It's been everywhere. I think our conversations about webinars, everyone's talking about webinars right now. Let's do great webinars. That's what we're talking about, right? I've been super happy since we moved over to Zoom. Just really the high quality. It just, some of it feels different. Our webinars feel professional and polished. Our media team shout out to Marissa and Rhea. They've been putting a ton of work in behind the scenes to get this thing right. And it really helps us run these exit five live sessions. And put on a performance. This is not a webinar. It actually feels like our performance and the results have been there. Our attendees and our teams have been really happy. The platform gives you everything you need to run a real event from branded registration built in promotional tools, live engagement features and post event follow-up that helps you convert attendees into pipeline. That's the difference between hosting a meeting and running a great event. If you're a BDB marketer with a webinar program that needs a reboot or you're thinking about building one, you should go and check out Zoom webinars, right? You know Zoom, but go and check out the webinar product. And come to one of our upcoming exit five live sessions every other Friday. It's two Fridays a month. You can see it in action. Check them out, check our sessions out. I think it really gives a good example of what you can do. Go and check them out zoom.com/exit5. That's zoom.com/exit5. Hey, it's Dave. This episode is brought to you by compound growth marketing. They're a full funneled, demand-gen agency. Look, I personally hired them twice. I think I was the very first customer before I was even a thought leader just when I was a VP of marketing. A real marketer back in the day, right? CGM was one of the best agencies that I've ever hired. I think that's because they understand the job. The founder John came from this background, knows what it's like, knows the life of a marketing leader. And they help high growth, cyber security and enterprise software companies show up earlier in the buying journey where potential customers are forming opinions about which product to use. They offer the combination of AEO, modern paid advertising strategy and a dedicated go-to-market engineering team. Everything CGM does gets tracked, measured and improved over time. That means more pipeline for you. And this works because they were started by a former VP of marketing. Like I said, John, he really gets this space. I think that matters. By the way, for B2B tech companies, CGM has a special offer for people who listen to this podcast. You can get two free sessions focus on media planning to learn what channels are driving the best ROI. How much you should be investing in demand, capture, versus creation and how to invest up funnel effectively. Hey, this is a really smart offer. So go check it out, compoundgrowthmarketing.com/exit5. Go check this out, get some free help. That's compoundgrowthmarketing.com/exit5. Bye-bye. - 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. Like, 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 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, engine 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 in field. They have like events in field. And so really demand generation is everywhere. And the thing that kind of drives what gets activated is our campaign's 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 do we, how fun we best go and engage those people? Is it out of 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. - Tell me more about this campaign's team. I like this idea. Obviously not new. Some guy who hates me, Lewis and this bloggers were like, "How does this guy not know what a campaign's team is?" What does a good campaign's 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 guess. 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 campaign's on the revenue team, but when you attach it to revenue marketing, I kind of view them as like the quarterbacks. Really, I make this, I make this joke all the time with the team like I need to stop the sports analogies and the sports and 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 does the event strategy, right? But we know that when we market 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 expert. I think, but it's almost like I've been in companies where there is not the like campaigns layer. And so certainly because 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 to it's almost like the same concept of like why does the marketing org have a chief of staff, that campaigns manager owns the like goal and then the delivery might be working with different teams? - Uh-huh, question mark period. - Yeah, I mean, like that's how I think about it for sure. It's like there's, there they're wrangling everything and bringing everything together harmoniously. And like, look, if we're being really honest, when I've had campaigns functions 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 gonna do this? And 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 they're like, 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 there's 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? 'Cause that's another like, it depends thing. But there's a little bit of an art and science being the revenue marketer in that not all this stuff is directly attributable to. We did X, we sent to this email and this thing happened. Any lessons you've learned as to like making sure you're making the right bets and investment, 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 about marketing's impact on the funnel? - Well, I'll tell you what I've got right and then I'll tell you when I've got wrong and I'm still learning. (laughing) I've done this enough cycles and done it enough for them that I've learned over time and it really feels strongly that like, I modeled back from like the farthest thing from a marketing, unmarketing metrics that I can, you know? So I'm not like, I don't, yes, 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 manuals 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 for 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 can make up leads. I 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, 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 exactly to 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. And if you couple them as meetings, you could juice the pipeline number that way. And sales is still-- - VDRs are incentivized off of pipeline too, right? Like, a either 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 land. - 100%. - 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 got paid out more if it was like not marketing sourced, right? And so it's like things like that, you could start to unpack and realize like, oh, it's actually driving the behavior here, or I've been in a company where they really wanted to do cross cell, but it was nobody. Nobody owned that. Nobody had a number. Nobody had a strategy. So it's like, well, we sure we're 25% behind on our cross-cell plans. It's like, yeah, but who owns that? Well, and that's so full circle. Why go to NRR too? Like when you can. Look, it's an evolution. Yeah. And while you answer this, can you tell me how does marketing drive NRR? Isn't that going to be down to 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 create, I can manufacture leads. And then we can put pressure on VDRs and then simplify 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, or regardless of like their likelihood to turn in 12 months is like 90%. You can still put pressure on sales to do that. And 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 or 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. Like 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, you'll 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 like rate of 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. And I think that is such a hot topic right now on marketing, but it's like signals. So like you can engineer what I just talked about and all of this stuff is like to 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 run campaigns on these sort of segments. And we've learned we've made our bets on like we're going to make that this is our tier one. We'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 would 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 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 fall into my system to be able to kind of build smarter. Oh, that's super interesting because I think so often the marketers brain goes to more, more, more, more, more, more, more, more new leads, more meetings, more of 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. It'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 with 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. 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 lock step. 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. I 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, what we hit the marketing goals? I did my job. We grew traffic. We grew this for that. But if you want to be a CMO of 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, like, my job is to influence. It's like, oh, product's not my job. 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. Love marketing. Love doing all of the different roles that I've been in. But 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. You're better or worse. I like, but I don't know, I'll remember, 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. Like, 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, somewhere the 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? Are 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 generated AI really hit the market. So I was in such a sweet spot to have an incredible exposure to that. Really, my CEO at the time was from like workforce transformation backgrounds. So like, early days, I was in to 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 do we think about our organizational structure and our like, we call that our workforce DNA? Like, how many full-time employees do you have versus Flex? Where does AI have been there and done that? It's not old news. Definitely how it mastered it. But like, my personal take on like what's actually keeping me up is less about like how we're augmenting are 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 marketing automation platforms, AVM 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 are able to develop something that we've never been able to do before. And so when you're at an organization that already hasn't 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 on to 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 are this is a just a kind of trend or, you know, like, is going to is fleeting and is going to be gone in a couple years or change and how much should we be acting on now? Like, should we go vibe code or 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 talk 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 hired an agency, hired this guy that they know and they, you know, and it once someone does it and like kind of half works. And 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 sprouts 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, I 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 a company that just started off two years ago that's been able to build AI first and has been able to do things and come up with processes and just in a way that 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 and 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 and 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 like to send I take a screenshot like when we're recording the pod part of my system as I take a screenshot and I'm like kind of live taking notes as this is going on so 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. I was in this like she's firing just like hang up on her no no no tell Alison I'm on it. Please don't apologize. I mean 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 an AMX lounge somewhere on the road? Where are you? I'm not cool enough to be in an AMX lounge. I'm in the Alaska lounge Seattle girl. But yes, I'm in the lounge. I'm on the road all month. I can't wait to see you guys next week at drive. But yeah, I'm heading to Boston right now, you're old stomping down so I'll say hello. What are you doing there? Web flow. Going to Web flow. All right. Okay, good. There you go. So another example. We're about the website or like higher vendor and use them to run the website, right? I know. Web flows like please feel about don't go just go by and go to your site. Anyway, no, no, no. 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 I can't even remember what it was, but I'm not going to be there on everything all in on exit side drive this year. And also just like quick flood is that so much of what I was talking about today in regards to segmentation, both like that kind of granular level as well as I use think about it across PLG and enterprise. My workshop is on after 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. Hey, I'm going to let you go get out of here on the Alaska safe travels to Boston. Thanks. I'm busy today, man. You right now I got a prep call with Cara 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. Hey, thanks for listening to this podcast. If you like this episode, you know what? I'm not even going to ask you to subscribe and leave a review because I don't really care about that. I have something better for you. We've built the number one private community for B2B marketers at exit five and you can go and check that out. Instead of leaving a rating and a review, go check it out right now on our website exitfive.com. Our mission at exit five is to help you grow your career in B2B marketing and there's no better place to do that than with us at exit five. There's nearly 5,000 members now in our community. People are in there posting every day asking questions about things like marketing, planning, ideas, inspiration, asking questions and getting feedback from your peers, building your own network of marketers who are doing the same thing you are so you can have a peer group or maybe just venting about your boss when you need to get in there and get something off your chest. It's 100% free to join for seven days so you can go and check it out, risk-free and then there's a small annual fee to pay if you want to become a member for the year. Go check it out, learn more, exitfive.com and I will see you over there in the community. [Music]

Podcast Summary

Key Points:

  1. Optimizely’s AI agent platform is specifically designed for B2B marketers, offering customizable agents and pre-built marketing tools to automate tasks and optimize campaigns.
  2. Webflow enables marketers to build fully custom websites optimized for AI search, ensuring visibility in AI-driven buyer journeys before traditional sales engagement.
  3. Revenue marketing is a high-demand, complex role in B2B, requiring strategic segmentation and alignment across sales, marketing, and product to drive predictable, scalable revenue.
  4. Effective segmentation—based on buyer behavior, use cases, and verticals—allows marketers to tailor messaging, budget, and channel investments to specific customer groups.
  5. Success in revenue marketing should be measured by modeling back to Net Revenue Retention (NRR), not just pipeline or leads, to ensure long-term customer value and alignment with product health.
  6. Organizational structures like a Chief of Staff or campaign team are critical for cross-functional coordination and strategic execution in large marketing teams.
  7. AI and emerging tech platforms are transforming marketing automation and tech stacks, requiring marketers to balance innovation with responsible, sustainable adoption.
  8. A clear, data-driven strategy combining segmentation, customer insights, and revenue metrics is essential for modern B2B marketing success.

Summary:

This episode explores the evolving landscape of B2B marketing, focusing on strategic revenue growth and the role of AI. Haley McDonald, VP of Revenue Marketing at Sprout Social, discusses the growing demand and complexity of revenue marketing roles, emphasizing that success lies in deep segmentation—dividing audiences by behavior, verticals, and use cases—rather than broad, one-size-fits-all campaigns. She highlights how alignment across sales, marketing, and product is essential to avoid fragmented efforts and leaky funnels.

Marketing success is measured not just in leads or pipeline, but in Net Revenue Retention (NRR), ensuring long-term customer value. The episode also examines how AI and new platforms like Optimizely and Webflow are reshaping operations, with Webflow enabling AI-optimized website visibility and Optimizely offering AI agents to automate marketing tasks. A key insight is that effective revenue marketing requires strategic leadership—balancing execution with executive-level influence—and that organizational design, such as a campaign team or chief of staff, is vital for coordination.

Finally, the discussion touches on the urgent need for marketers to stay agile with technology, recognizing that while AI-powered tools offer promise, responsible adoption and deep internal alignment are critical for sustainable growth. The narrative underscores that modern B2B marketing is not just about volume, but about precision, strategy, and long-term customer outcomes.

FAQs

Optimizely's AI agent platform is specifically built for B2B marketers. It allows users to build custom agents or use pre-built ones for marketing use cases, and includes virtual teammates that can learn over time, join meetings, complete tasks, and support campaigns.

Webflow enables marketing teams to build fully custom websites that are optimized for AI search. AI agents can now read and interpret the website content, potentially recommending a company to potential customers before a sales call, making the website a key growth engine.

The role is hard to hire for because it requires balancing revenue generation with authentic, human-centered marketing. It demands a deep understanding of how marketing, sales, and product teams connect to drive predictable, long-term customer growth.

Segmentation helps align marketing, sales, and product teams by defining clear customer profiles and purchase behaviors. This ensures marketing activities are targeted, efficient, and directly tied to revenue goals, avoiding a one-size-fits-all approach.

The campaign's team acts as strategists and quarterbacks, translating revenue goals into actionable plans. They coordinate across functions like digital, events, and field marketing to design effective campaigns tailored to specific customer segments.

Measuring from Net Revenue Retention (NRR) focuses on long-term customer value and loyalty. It provides a clearer picture of true marketing impact by tracing success back to happy, retained customers, which is the ultimate goal of sustainable growth.

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