How Sprout Social builds revenue marketing around segmentation (with Hailey McDonald, VP of Revenue Marketing)
44m 18s
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.
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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.
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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.
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[Music]
Podcast Summary
Key Points:
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.
Webflow enables marketers to build fully custom websites optimized for AI search, ensuring visibility in AI-driven buyer journeys before traditional sales engagement.
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.
Effective segmentation—based on buyer behavior, use cases, and verticals—allows marketers to tailor messaging, budget, and channel investments to specific customer groups.
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.
Organizational structures like a Chief of Staff or campaign team are critical for cross-functional coordination and strategic execution in large marketing teams.
AI and emerging tech platforms are transforming marketing automation and tech stacks, requiring marketers to balance innovation with responsible, sustainable adoption.
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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