#149: Marketing Leadership | 16 Lessons I Wish I Knew As First Time B2B Marketing Leader
from The Dave Gerhardt Show (from Exit Five)
37m 18s
Exit Five Live webinars, powered by Zoom, are achieving high engagement with over 2,000 registrants and hundreds of hours of watch time through meticulous preparation and seamless production. The success stems from a structured process involving up to seven hours per session for topic selection, planning, and execution—all managed through Zoom’s integrated platform. Behind this, a core lesson emerges: marketing leaders must evolve from individual contributors to strategic leaders. This shift requires mastering three key areas: managing up (aligning with CEO priorities around revenue and story), managing down (driving team innovation beyond incremental changes), and managing around (aligning with sales, product, finance, and operations). A powerful strategy includes a clear two-word positioning, such as “conversational marketing,” to unify messaging across the organization. Leaders must also think long-term, allocating time to future experiments and avoiding reliance on short-term tactics. Bold, cross-functional experiments—like shifting team focus to new channels—have proven more effective than small optimizations. Alignment with sales teams is essential, driven by shared revenue goals and performance metrics. Marketing leaders should leverage tools like AI and personalization platforms (e.g., CustomerIO) to create human-centered, impactful campaigns. Ultimately, marketing is not just about tactics—it’s a craft requiring creativity, strategic vision, and collaboration across the entire organization.
Hey, it's Dave. So zoom webinars and events has made our recent exit five live sessions way
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to start. Check it out. It's convertiv.com/exit5. That's convertiv.com/exit5 and you can also see the
link in the show notes. So I want to share these lessons about going from marketing manager to
CMO because I made the jump from marketing manager to CMO over a course of five years,
which is a really accelerated time period and I made a ton of mistakes along the way.
I'm able to call them mistakes now because I have the wisdom of time and so I can look back and
see some of those things. So today I thought it'd be fun with this group to share some of the
lessons that I wish I had knew then because what I learned the hard way is it's a very different job
from being a good marketer so marketing manager Dave to actually being a good marketing leader.
Those are two very different things. We're going to go really fast today because we only have 30 minutes.
I'm going to give you a lot of things. I'm going to talk through a lot. I have listened to presentations.
I've watched a lot of presentations. I don't expect you to hang on every word that I say but I think
that you'll get one or two maybe new ideas or things that will help you get unstuck or maybe this
will just feel like therapy to you in your current role. So that's kind of how I like to look at
these things. I think there's 15 lessons that I'm going to go through. If you get one or two new
things today I'll be really happy about that. So like I mentioned before there's a huge difference
between being a marketing individual contributor and a marketing leader and making the jump from
good marketer to good marketing leader is really about understanding that being a marketing leader
is about yes having that marketing expertise but also you need to add in the marketing management
skills and there's really three kind of buckets of things that we're going to talk through today.
So one of them is managing up. I think it's so important for the marketing leader to have a great
relationship with the CEO and managing up to your boss. We're going to talk about managing down.
That is all about hiring and having a great team coaching them to be successful and helping you
to do the best job you can do you can be as a marketing leader. And then the third piece of this
is managing around. It's very tough to be a successful marketing leader without being able to
influence and manage change across the entire org from product to sale to customer success,
the finance to ops. You have to be able to work with all those teams because as you know marketing
touches all those departments. And so we've broken this talk up into those those three sections.
I do want to give you a little bit of a warning. If you were expecting a lot of data or science
or fact-based research in this deck. I hate to spoil it for you but that's not what I'm coming
from. This is all based on my limited experience in B2B marketing. And so there might be things
that you disagree with. There might be things that wish that I had like some proof and all I can
give you is my experience. And this is a basically my rant and lessons based on those things. So
first thing let's talk about managing up. The number one thing is you have to understand
what the CEO cares about. I see so many times marketers. We get so far in the weeds with the CEO
and we're sharing with her all of the 50 to 100 things that marketing is doing because we want to
show her how much we're doing and how important marketing is. And based on what I've seen in the
companies that I work with today, most of that stuff doesn't matter. When you're talking with the
CEO, there's really two things that that CEO cares about. And in no particular order, it's usually
those two things. It's revenue and it's the story. And so when you're trying to manage up,
it's very hard. You have so many things going on and you only have 30 minutes a week or 30 minutes
every other week with the CEO, right? If you're lucky, I would try to focus all of my updates and my
communication about these two things. In the story, meaning positioning messaging, kind of the overall
arc narrative of the company, that's always going to be a work in progress, but it might not be
something that you're actively working on in that meeting. And so if you're not focusing on
the story in that conversation, I typically like to focus on revenue, right? The things that
directly relate to building and growing pipeline. And I found that when you think of it like this,
you kind of remove some of the stress on your plate because you only have so much time, like let's
focus on the one or two big things that are actually going to move the needle. And for most CEOs,
just simplify how you think about the things they care about, they care about revenue, and they
care about the story. Number two is you have to be able to show your work and you need to try to
master internal communication. One of the top complaints that I've seen and I've felt and I still
see this today is the other teams inside of the company, they don't know what marketing is doing.
They know that the marketing team is busy and everyone is stressed and there's a lot of things
going on, but they are not really sure how the things that you're doing actually fit into the
company goals. And so you need to make it your job to hammer this into the company and every time
you get the opportunity to present or to share an update about marketing, you need to relate this
back to how it fits into your company goals. I learned this the hard way in my early days at Drift,
we had something on Fridays called Show and Tell where every team would present what they worked on
and as one of the earlier employees at the company, I was the only person doing marketing at the time.
There's 10 other people at the table, they're all engineers and designers, people who had really
cool, tangible things to show what they presented. And I remember my first week on the job, they're like,
all right, let's let's go over to Dave and what did you work on this week, Dave? And I was like,
I wrote a blog post and that was like the most humbling experience because nobody, it was just
dead silent. Nobody cared, nobody understood why. And that was like my opportunity to have some
eat some humble pie because what I learned was they actually have no idea, the blog post is just
a tactic, right? Instead, next week, I needed to come back and I actually gave them a whole presentation,
I said, hold on, last week, I kind of threw up on myself and just said that I was writing a blog post.
But really, let me tell you why, right? So here, we're writing this blog post, we wrote this article
this week and here's why, right? Our goal right now is to build an audience. We're trying to go our
website traffic. The way we're going to do that is to regain the content. We think if we can do this,
then we're going to be able to eventually generate this many trials a month. And if we can do that,
you have to be able to show them, you have to be able to paint the picture like that. And so I think
it's a safer mindset, safer mindset to operate from if you can assume that nobody has any idea
about how what you're doing impacts the company. Another thing that we did in the early days that
drift and even into year three and four of the company that I was there at least was there was a
meeting called Monday Metrics where each team leader marketing sales, customer success, product,
ops, they would present, what is that part of the company working on this week? And so if I just
got up in front of 300 people in the company and I said, hey, this week we're doing two webinars and
we got these nurture emails going out like nobody's going to have any idea what we're doing. So I
always took this as an opportunity to share like, hey, as a reminder, here's what our goal is for
this month or for this quarter, right? And then talk about that. So every opportunity you have to
relate what you're doing back to the broader company goals and how marketing fits into that puzzle,
that's the mindset that you want to operate from. So there's also kind of three, I would call them
day-to-day week-to-week rhythms and routines that I really liked as a marketing leader to just keep
everybody in the loop with what marketing is working on. So number one is Slack, right? Everybody's
in Slack, there's a marketing channel in Slack. One of the things that I like to do is to encourage
the team to share like work and progress updates in the Slack channel. So typically we only like to
share things when they're done or fully baked or perfect.
I like to push the team to share screenshots of videos, of articles, of a screenshot of an email from a customer who you tested a new message with, like the more you can show your work in Slack, doesn't even have to be perfect.
But then you have this channel where there's just kind of always marketing is always is always shipping stuff and you're sharing those updates directly in Slack and anybody can hop in and see what marketing is working on.
The other thing I like to do proactively and I've been at two companies now where we started this proactively and I saw the rest of the kind of leaders across the company rally and do the same thing is just sharing weekly, monthly and quarterly recaps about what marketing is working on.
So this would be like a five minute kind of loom video with a deck and say it have three to five slides and it's like here's what marketing got done this week and here's what working on next week and then you can extend that out here's what marketing got done this month and what we're working on here's what marketing got done last month and here's
what we're working on this month same thing for the quarter the more you can not just share what you're working on so hey you got to do that share what you're working on but be related back to and here's where that fits in our goals for this month and I like to do that at the end of the week.
The end of the month and the end of the quarter just really simple.
The other thing that I always kind of took seriously inside of the company is presenting I think anytime you have the opportunity to grab the mic and get on on stage or on zoom or whatever the format is and present and talk about marketing take that opportunity because one of my favorite ways to think about this is from Christopher Lockhead who's an amazing author and I realized we didn't have a disservice by spelling his name wrong here in the in this deck.
But he always thinks about marketing is the leadership department and I totally agree if you're in marketing right you're probably and should be the best communicators inside the company like please use that opportunity to present and take any opportunity you can to grab the mic and share what marketing is working on as you can.
Number three is you need a story more than anything else you need a story but it's not just a story you need a story that can become your strategy I love this quote from Seth Godin this was from an AMA that he did an online genius is a slack community that somebody asked him hey what's the difference between B2C and B2B marketing and I think this perfectly kind of captures all of it he said the secret is understanding that the people buying from you are still people but one big difference is that they're spending somebody else's money.
The job is to give them a story that they can tell their boss if you can't tell them a story and the only story then the only story available to tell them is either number one.
I bought the product that we bought at my last job right or number two I bought the cheaper one because nobody's going to get fired from their job for buying the product that they've used before or buying the cheaper one.
So this is the opportunity from marketing perspective is to give especially in B2B marketing is to give these people the people are trying to sell to a story that they can take back to their boss.
For me as a marketer coming up in my career I think HubSpot did an amazing example of this where there was probably five years before I even had the opportunity to buy HubSpot as a customer.
But I was you know religiously following their blog and going to their webinars and going to their events and they made me get smarter at my job in marketing.
And so when it came to buying a tool like HubSpot you're like look sure maybe there's features that HubSpot has and Marquetto doesn't or whatever you don't you don't have to play the feature war because we're already in the conversation
and this company has become an expert to me and made me smarter in my job and so the way that I like to think about this now is just like I call it two word positioning which is HubSpot was inbound marketing.
Gainsight was customer success drift was conversational marketing and this is really powerful because when you simplify the story to two words inside of the whole company a drift from the product team to sales to finance right everybody had this frame like what we're building is conversational marketing.
For we need a marketing strategy that positions us as the leader in conversational marketing the product team needs to be delivering products and features and building a roadmap that helps us deliver on this vision of being the leaders in conversational marketing.
The sales team has to be able to sell and educate people on why conversational marketing is a better way to do things and so.
So many companies of story it's too complex nobody can repeat the company's tagline or they're worried about the home page headline is like what's more important is this idea of like what do you want to be known for HubSpot was inbound marketing Gainsight was customer success drift conversation marketing.
You can call this a category you can call us whatever you want I think the simplest way that I like to think about is what do you want to be known for and from a B2B marketing opportunity standpoint I think the best strategy that you can have.
Is to position your company as an expert and as a leader in that space and so for Gainsight that means how do we educate people on customer success how do we make customer success pros get smarter about their job and I think.
This lens itself really nicely to figure out like hey what should our content strategy be what is our product marketing strategy need to be you can boil this all the way down to.
The two word positioning and ultimately this is only going to happen in a healthy and effective marketing team if you have a strong relationship with the CEO I think one of the things that I credit a lot of our marketing success to drift was.
Being really close and involved with with David the CEO we collaborated so much on the marketing strategy and the story we were always texting and riffing on this and I think it has to be that level of relationship between the marketing leader and the founder CEO in order to really execute on this.
Fourth thing is you have to be able to articulate your marketing strategy this is something that drives me nuts because I see we default right into the tactics and the channels and I see a lot of marketing leaders or marketing teams who aren't really sure what the actual marketing strategy is and this is this might seem obvious but this is worth like double clicking and pausing on this for what you're doing at your company you have to be able to say like what do we think that are.
Marketing motion is this like how are we going to generate revenue as a company is this sales led is it ABM is a product assisted is a product led that really matters and you can really tell when a company is kind of half in and half out of one of these strategies.
I don't believe that there's a perfect one and I actually think you can be successful with with any of these approaches but it's about being being committed to this as a team especially as a leadership team.
You have to have a very clearly defined go to market motion because so much of what you're going to do from a marketing standpoint is dictated by what this motion is right the tactics and channels required in a sales led.
Revenue function are going to be much different than product led and if you can't articulate that and think about your your marketing strategy from that lens it's going to be very hard to be successful.
The other thing that's really important here and I don't mean this to be like 101 level stuff but I'm just like I wanted to hammer this home here because I still see it all the time is like which segments are you going to sell to having that very clearly defined ideal customer profile really matters.
I've been able to do the best work with the marketing team inside of a company when that ICP was really clear when we're trying to be everything to everyone is when things get a little bit mushy and I see this a lot inside of B2B SaaS companies is going to take one average theory on what your strategy should be and you peanut butter it across all of these channels.
You got to focus and as the marketing leader you have to have a strong opinion about what your marketing strategy should look like and the whole organization has to be aligned on those things you can't have marketing thinking it's one thing sales thinking it's another product thinking it's another.
And I really think that it's your job as the marketing leader to be the one to drive that alignment you're not going to be able to solve it all by yourself.
But you need to be the one who's raising your hand and like if nobody's solving it inside the company then make that your job be the one to get the right people in the in the meeting and make those conversations happen.
I think you also have to have a view on the market and so you can't just do this in a vacuum because someone presented it in you know in a virtual event or whatever but look take a look around and see what your competitors and what's happening with related companies in your industry.
What is their approach to go to market what are the gaps and opportunities to you for you to fill.
And I also think you have to be able to have a point of view on what good marketing looks like one of the reasons that I got along so well with David the CEO I drift and Ben the CEO I privy was we spend so much time both them were like I want to do marketing like this I love how this company does it I want us to do it that way and that for me as a marketing leader is amazing when you have a CEO that can at least articulate.
Here's what I think good looks like and so just make sure that you have a perspective whether that is slack or maybe it's drift or maybe it's attentive or clarity or gong or whoever trying to unpack somebody else's marketing strategy and take lessons from that and be like hey we want to do.
We want to do we want to do marketing like this even at drift we took so much inspiration from companies who are not B to B companies David was almost religious about saying like I want us to feel like a consumer brand and that was great because that gave us a guard real.
For figuring out what types of things in marketing did we want to go do and execute on.
Hey, it's Dave today's episode is brought to you by optimizely if you want to know what AI agents can actually do for a marketing team optimizely is where I'd point you to right now for a real example last month we ran an ex of five live session where a bunch of our members showed off their best AI agent use cases
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Fifth one is forget acronyms.
Use your brain and you have to figure out how to grow
by using this thing inside of your head.
I didn't go to school for B2B marketing.
I know many of you didn't either.
You go on LinkedIn or you go to an event
and all you see is these acronyms, MQL, SAL, PQL, whatever.
I'm not saying these are not important,
but ultimately we get obsessed with what we think
are B2B marketing, acronyms, and jargon, and benchmarks,
and all that type of stuff.
One of the reasons why I had a couple of wins early in my career
was honestly I didn't know that much about B2B marketing.
I was able to look at it and I got the freedom to do this
from David, who's a CEO, a drift, to be like, look,
I don't care about those benchmarks.
I don't care about those acronyms in the jargon.
Just use your brain.
At the end of the day, there's only three ways
really to grow a business.
You can get more customers.
You can get those customers to pay more when they come in
and you can get them to come back more often.
Just don't obsess over what you see on LinkedIn
and in other forums.
Just use your brain, operate from first principles.
B2B marketing is not that different
than any other, then growing any other type of business.
So focus on these core things.
Don't obsess over all the jargon-y nonsense stuff
that gets put out in the world.
It's not that complicated.
We like to over-complicate it
because it just makes for more content to go and create.
Sixth thing is you have to be able to think short-term
and long-term, and damn, if this is probably like the number one
thing that I wish I understood earlier,
short-term thinking-dave versus short- and long-term thinking-dave.
And it's really hard, right?
Because you're under a lot of pressure.
You got to hit the number this quarter, especially right now.
I know it's Q4 in a tight economy.
You're having a hard enough time to hit the number today.
It's very hard to think about what you're going to be doing
next June.
But I promise you that the lesson I learned the hard way was
in June, you're going to be like, damn, we're 20% behind.
What can we do? And you're just going to keep chasing this game
of short-term tactics where the easiest way to hit your number
is to have invested in that channel last year.
And I've made this mistake two or three times now,
because I'm sharing it because hopefully you don't.
A really simple framework is like, if you're--
you need to audit and look at all the things that you're doing.
And if you're not spending at least 30% of your time, budget,
people, resources on the future, you're
going to be in a tough spot.
I wish that I did a better job of having new channels ready.
And so when you know the plan jumps 30% in Q2 of next year,
you can't wake up that quarter and figure out
what new channel is going to get you there.
You've got to be able to be testing and learning
and scaling up some of those channels behind the scenes now.
And so you've got to be able to think at least 70% of your time
in budget and resources is spent on hitting the number today.
But you have to remember that a big portion of this 30%
at least has to be about laying the foundation for the future.
Something that I've seen lately that I really
think it's great is from Chris Walker and Refine Labs.
They're talking about this concept of revenue R&D, which
is a little bit more advanced than my 7030 framework.
But I think it's a great way to like--
they give you a framework to think about like running experiments
now, looking for positive signals, finding ways
to scale those things and get them repeatable.
And then when you need that new channel in Q2, Q3 of next year,
you're not having to learn from zero.
You're like, oh, this is great.
We were testing this channel for three to six months.
Now we needed to start contributing 500K in pipeline.
Like, let's go scale that up.
You can make the case of the CFO to get 50 grand,
100 grand, or whatever you need to go out and do that,
as opposed to having to learn and scale in the same quarter.
It's very challenging to do that.
And ideally, you have some portion of the team
or everybody's job.
You have time and budget carved out so people can do this.
It's like about managing down.
So we talked about managing up.
Let's talk about managing down.
You have to be able to push your team
past incremental thinking.
One of the lessons that I learned is,
it's so often default to like, if you're behind on pipeline,
you're trying to figure out how to grow pipeline.
We default to these tiny optimizations and updates.
Like, let's redo the email nurture flow.
Or hey, how many times does this happen inside of your company?
So I was like, oh, that's a great idea.
Let's add it to the email nurture flow.
I promise you that that is not going to be the thing
that is going to make that big leap for your company.
Typically, that's going to come from figuring out a new channel,
figuring out a different segment and different ICP
to go after.
I actually just saw this yesterday
as we were putting the finishing touches
on this presentation from--
this is from Gontop Martin.
Gontop Nicus, who is the SVP of marketing at Auth0.
And he posted, I just want to read this really quickly.
Years ago, Auth0 stopped growing in pipeline.
We'd the change with the marketing team
was doing for six months to get us back on track.
It was a hard decision, but required bold decisions.
He basically said they had 40 people on the marketing team.
They took 20 of those people and focused them
on four kind of key buckets and experiments.
They stopped their day-to-day jobs.
They built four pods inside of marketing
and they worked cross-functionally.
One group focused on the website and AB testing.
One group focused on increasing top of funnel traffic.
The other group focused on finding alternatives
to talk to sales, whether that be chatbots
or other kind of mid funnel offers.
And then the fourth group took big bets
by really changing the sign up flow.
This is a perfect example of what I mean when I talk about
avoid incremental thinking.
This is something that's very hard to do
because it requires change and having hard conversations
with people inside of the company
and being okay with missing your goals for a quarter.
But this is what it takes to get out of a hole.
And so if you're in a revenue hole right now,
I promise you that the solution
is not going to be more nurture emails,
more website optimizations.
It's going to be bigger thinking like this.
And you have to have the guts to be able to blow up
the marketing team and change what everyone's doing
for three to six months to get out of the hole.
As a result, off zero went from 20 million to 40 million.
Couple of years later, they had a six and a half billion dollar
exit to Octim.
I'm not saying that was directly because of this.
But I just think it's a perfect example
of what I mean when I talk about avoiding incremental thinking,
especially as the marketing leader.
It's your job to be able to think like this
and be okay with taking big swings.
Number eight, please you got to be able to think hard about offers.
Dan Kennedy, one of my favorite direct response marketers,
salespeople, copywriters of all time.
He worked on proactive Walmart and QuickBooks.
He says you're marketing needs to have an offer
that tells your ideal prospects exactly what to do
and why they want to do it right now.
It should be irresistible, time sensitive
and give them transformative value.
They offer right that a marketing is about the offer.
And then in B2B marketing,
our offers are typically like start your free trial,
request to personalize demo or contact sales, right?
Who wants to do any of those things?
Like maybe the urgent people who are like so hot to buy
and they want to do this right now,
but that's not going to be the majority of the people
that are aware of your company.
And so you've really got to push hard
and try to come up with more middle of the funnel offers
that address the selfish benefit of what is in it for me
as your ideal customer.
So for example, we love to kind of shit on webinars
in B2B marketing, but is the webinar bad?
No, it's just typically that we've kind of gotten used
the webinar being a code word for like a boring one hour
presentation, right?
What if the webinar offer was like,
hey, you want to become a better rapper?
Well, we have Jay-Z on this webinar
and he's going to teach you how to write legendary lyrics
in an hour Zoom call, right?
Is the webinar bad?
No, that's an amazing offer.
The webinar is not the problem that is the offer.
You've got to be able to think about that.
I think Privy's done a great job of this.
They sell to small e-commerce businesses.
So here's a session that would actually be useful.
Hey, steal this expert-approved playbook
to have your best Black Friday Cyber Monday ever.
That's coming up in 30 days.
And that's a great offer for somebody to actually,
like, should I spend an hour in my time
or watch the recording?
Should I actually spend my time on that?
So number nine, you have to have the keys
to create momentum on your own.
So often today, the biggest spikes that you create
in marketing are going to be based on these big launches
that you do on your own.
You don't need to wait for a gardener
or far sort of write about you.
And I actually believe you don't even need to wait
for the product team to deliver some big stuff.
You can be your own publisher as a marketing team today
through content, through channels like this.
Virtual event is a great one, podcasting.
You have the tools to be your own publisher
and create your own launches and momentum.
One thing that we did at Drift
was we had monthly marketing launches.
We called them marketable moments.
They were on the calendar, no matter what was going on.
The first Tuesday of every month,
we were doing a marketable moment.
It wasn't a blog post.
It wasn't just a webinar, it was something bigger.
It pushed us to come up with a big launch,
something that we can do on our own
to get more people talking about us
or give us an excuse to go back out
and talk to potential customers and potential buyers.
And that really allowed us to create our own momentum.
And then when you do get ammo and stuff
from the product team, it makes it even more powerful.
The same way I also believe like you have your own channels,
you don't have to wait, like I said,
you don't have to wait for a gardener to validate you
to be your own publisher today.
Look at what metadata has done, for example,
with their podcast and their efforts on social and content here today.
you can be your own publisher.
So think like that.
Don't think that you have to rely
on these other people to write about you
in order to get the word out.
You have all the tools that you need today
as a marketing team.
Number 10 is you have to get comfortable
making bets without perfect data.
If you wait around to get perfect data,
it's gonna be too late.
And rarely are you gonna have that perfect set of data.
We love marketing attribution.
Marketing attribution does not tell you,
does not tell you what to go and do next.
You still have to make a bet on where you're gonna go
and spend your time and spend your money.
So I like to think of marketing strategy
as portfolio management.
It's never gonna be perfect.
You're never gonna have all the data.
You have to be able to act and make decisions
and knowing that ultimately you're placing bets
in that you're hoping things that work out.
Too often earlier in my career,
I was paralyzed without perfect data
and not able to make decisions.
I think now almost I have the opposite problem
which I make really quick decisions without the data.
Be somewhere in the middle.
Be okay with making decisions without all the data.
Number 11 is your job is to get the job done.
And this was the biggest shift for me
as an individual contributor to marketing manager.
If you are the marketing leader
and you're trying to do all the things yourself,
you are never going to survive
and you're also your team is gonna hate you.
So you have to be able to change your mindset
from like it's not your job to do it.
It's your job to get the job done.
And that can mean through people, through programs.
I can tell you that your CEO, your boss, whoever that is,
they don't care if you spend that money on an agency
or if you hire people or if you spend it on programs.
They want you to hit the goal.
And so once you can like free yourself of thinking like,
well, I gotta show them that we did this all in house.
Doesn't matter.
Use your budget and use your programs to your advantage.
Your job is to get the job done.
Not do it all yourself personally.
Somewhat related to this is when you're talking about hiring
you have to be able to test into the job
or at least do a part of it internally
before hiring externally.
I think I look back at every hiring mistake
that I've made in the past.
And it's because we didn't kind of already have that role
tested and proven before we went and hired for it.
So in the early days of drift, I was ahead of marketing.
We wanted to do more events.
Our first move was not what I wanted to be
but the CEO said, no sir.
We wanted to go and test events as a channel.
He wasn't like, yeah, go hire an event person
and go test events.
He was like, nope, you're gonna go,
you figure out events for us.
So you go run three events this quarter,
figure out what works, what doesn't,
what might work for our audience.
Then you'll actually know what good looks like
and you can model this and scale this
and then we can go hire somebody.
And I just think that that was such an important lesson
and you can do this.
So maybe that means, hey, you think partner marketing
could be a channel for you.
You have a great product marketing person.
Maybe she could take on partner marketing
as, you know, 20% of her job for this quarter
and then you can go and figure out
like how you're gonna scale that
and what good looks like to hire that person full time.
Number 13, you have to make hiring your job
not a side project.
And so obviously you've read every business article ever
and they talk about people are everything.
I had read it too, but I didn't feel it really
until I was able to go to my second company
where I was running marketing, which is privy.
And so at drift, we had an amazing team,
but I've made a lot of mistakes
and spent a lot of unnecessary time
and budget to get there.
And that was because I was only spending 25% of my time
on hiring and building the team.
Or I thought, well, we're not hiring anybody right now
and so I don't need to be going and hiring build pipeline.
But the same way you build sales pipeline,
you don't just go and get it when you need it,
you get it before you need it.
And the last piece of this is managing around.
This seems so obvious, but you have to find a way
to get on the same page as sales.
Like revenue is really the only thing
the company cares about.
So the CEO cares about the board cares about.
So if you're in marketing and you're in sales
and those two teams are not in the same page
and something is fundamentally broken.
And I think one of the biggest challenges
in the B2B SaaS world is that sales and marketing
and other teams are not aligned.
And it's not for any other reason
than like how those teams are actually gold.
And so I'm going to try to flip through this a little bit.
But too often the reason that those teams
are struggling and have problems with each other
is not because of some creative problem.
It's because fundamentally they have different comp plans.
Sales is getting comped in one way.
Marketing is getting comped in another.
And those things don't add up.
You have to understand the incentives
that drive the organization.
And you should push the CEO or others
to be like, look, I want sales and marketing
to be measured the same way.
Obviously there's different inputs there.
But you have to create a culture
where everyone, the team leaders on the revenue function
are measured on revenue.
Not some random metrics inside of each team.
And so if it's not working like that inside of your company,
again, be the one to drive the change and fix it.
It's going to make your life much easier.
Or else, I think so often this is the root cause.
But we don't want to go and address this
because it has so many other issues related to it.
But this is often the root cause of so many sales
and marketing revenue challenges.
When those two teams work together, life is so much easier.
I promise you.
Somewhat related to this is understanding finance and ops.
Number 15 is your job is to be the marketing leader.
Don't become finance and ops.
And I know it's a common narrative.
You got to understand finance.
You got to understand ops.
Totally agree.
You have to understand those things.
But don't become those things.
Make best friends with those two teams.
I think you need to look at those at finance and ops
the same way as you look at sales, which are collaborators.
Those are partners with you.
Treat marketing as a business function.
And so at drift, two of my most valuable colleagues
were VP of ops and VP of finance, right?
My job is not finance.
You don't want me building the model.
Earlier, my career, I thought I had to be the one to do that.
Later in my career, I realized, oh no, we're all working
on this together.
These are my business partners.
Treat them like that.
Collaborate on revenue together.
Sales, ops, finance, marketing, product, CS.
Should all be collaborating on these things together.
Marketing drives revenue, but marketing
can't possibly own revenue solo.
You have to be able to work with everybody.
OK, that was a lot.
I tried to jam in basically 10 years of my career
into a 35-minute presentation.
I hope you got at least one new thing out of that.
If you liked anything that I talked about,
you will love what we do in the exit five community.
Go and check out exit five.com.
Hey, it's me Dave.
Today's episode is brought to you by CustomerIO.
They're one of our longest running sponsors.
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So you can reach the right people with the right message
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What we love about CustomerIO
is that they have a great team of marketers
who really care about the craft.
They just get marketing and understand
our audience, Molly, Rosie, and the team
bring something creative every time that we work together
at our exit five event in Austin.
They handed out cowboy boots in our newsletter.
They shared an AI prompt cookbook.
And at Drive last month, they were giving out Airbnb gift cards
in AirPods.
They believe marketing is a craft
that takes creativity, thought, and taste.
And no, AI can't do this part for you.
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Podcast Summary
Key Points:
Exit Five Live webinars, powered by Zoom, deliver high engagement with over 2,000 registrants and hundreds of hours of watch time through rigorous prep and seamless production.
Marketing leaders must shift from tactical execution to strategic leadership by focusing on revenue, storytelling, and cross-functional alignment across sales, product, and operations.
A clear, two-word positioning (like “conversational marketing”) helps unify the company’s narrative and guides content, product, and sales strategies.
Marketing leaders should prioritize long-term strategy—allocating 30% of time and budget to future experimentation—over short-term tactics to ensure sustainable growth.
Incremental improvements (e.g., email tweaks) are insufficient; breakthrough growth comes from bold, cross-functional experiments and realigning team efforts.
Strong alignment between marketing and sales is critical, driven by shared incentives and revenue-focused metrics, not siloed performance.
Marketing leaders must act as strategic enablers, using tools like AI and content to build momentum independently and make data-informed bets without waiting for perfect data.
Marketing is a craft requiring creativity and human touch; tools like CustomerIO enable personalization while preserving authenticity and marketing integrity.
Summary:
Exit Five Live webinars, powered by Zoom, are achieving high engagement with over 2,000 registrants and hundreds of hours of watch time through meticulous preparation and seamless production. The success stems from a structured process involving up to seven hours per session for topic selection, planning, and execution—all managed through Zoom’s integrated platform. Behind this, a core lesson emerges: marketing leaders must evolve from individual contributors to strategic leaders.
This shift requires mastering three key areas: managing up (aligning with CEO priorities around revenue and story), managing down (driving team innovation beyond incremental changes), and managing around (aligning with sales, product, finance, and operations). A powerful strategy includes a clear two-word positioning, such as “conversational marketing,” to unify messaging across the organization. Leaders must also think long-term, allocating time to future experiments and avoiding reliance on short-term tactics.
Bold, cross-functional experiments—like shifting team focus to new channels—have proven more effective than small optimizations. Alignment with sales teams is essential, driven by shared revenue goals and performance metrics. , CustomerIO) to create human-centered, impactful campaigns.
Ultimately, marketing is not just about tactics—it’s a craft requiring creativity, strategic vision, and collaboration across the entire organization.
FAQs
Exit Five Live webinars stand out due to extensive preparation—up to seven hours per session—covering topic selection, prep calls, and run-of-show planning. They leverage Zoom’s production studio for seamless, high-quality live broadcasts with clean transitions, clear audio, and video, resulting in high engagement with nearly 2,000 registrants and hundreds of hours of watch time.
Zoom Webinars and Events centralizes all aspects of a webinar—from registration and email campaigns to polls and analytics—into one platform. This streamlines the entire workflow, making it easier to plan, execute, and analyze every live session, allowing teams to run cycles every two weeks efficiently.
A successful B2B marketing strategy includes a clear go-to-market motion (like sales-led, ABM, or product-led), a well-defined ideal customer profile (ICP), a compelling two-word positioning story (e.g., 'conversational marketing'), and alignment across departments like sales, product, and finance to drive unified revenue growth.
Storytelling helps buyers justify their purchase decisions to their own bosses. In B2B, customers need a narrative that shows how a product improves their business—like HubSpot’s 'inbound marketing' story—so they can confidently recommend it to others, turning marketing into a trusted, repeatable conversation.
Marketing leaders should allocate at least 70% of their time and budget to immediate goals while reserving 30% for future initiatives like testing new channels or running experiments. This ensures sustainable growth, allowing teams to scale proven strategies without being reactive to quarterly pressures.
Marketers should take bold, strategic actions—like reorganizing teams into focused pods or launching new channels—instead of making small optimizations. For example, Auth0 grew pipeline from $20M to $40M by shifting 20 of 40 marketing staff to key experiments, proving that big bets can lead to significant results.
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