CMOs Unscripted, Season 2, Episode 02: Technical Storytelling in the Age of AI: Why CMOs Must Embrace the Tools or Get Left Behind
33m 24s
Jason McClellan, a five-time CMO, discusses the art and science of category creation and repositioning in tech marketing. He emphasizes that most tech companies must create and own a category to stand out against giants like Oracle, which are far larger. Drawing from his engineering and product background, including leading Adobe’s Creative Cloud transformation and DataStax’s pivot to an enterprise AI platform, he highlights that this process is chaotic and challenging, not the smooth narrative often portrayed in case studies. Key to success is driving alignment across product, sales, and finance, and maintaining confidence in the chosen positioning despite internal resistance, even from CEOs. He advises marketers to prioritize speed and market feedback over perfect strategies, using a "fake it till you make it" mindset, especially as AI rapidly reshapes the landscape. In 2026, AI tools enable marketers to conduct daily primary research, generate copy, and deploy webpages far faster, but true AI experts are scarce. McClellan urges marketers to proactively experiment with AI tools and lead their companies through adoption, rather than risk being replaced. He notes that workflows remain inefficient due to tool-switching, but the potential for innovation is immense, making AI both an exciting opportunity and a disruptive force requiring continuous adaptation.
In my mind, for most tech companies, you have to create and own a category
because you have to be different. If you want to go after Oracle or whatever,
they're a thousand times your size. So you've got to be, I don't know,
5,000 times better than them if you think you're going to try to beat them.
Or you carve out a niche and say, no, Oracle sucks at X and we're the world leader at X.
And you've got to be confident doing that or else you're never going to win.
What does it take to help companies like Adobe, Heroku, DataStax, Domino Data Lab,
not just compete, but create entire categories? Well, on today's CMOs Unscripted,
Jason McClellan joins me, five-time CMO,
he's going to be talking about the art and the science of repositioning and the role of AI
in modern marketing and why technical storytelling, I love this part,
might just be the most underrated superhuman power in B2B. I'm Lisa Martin. Welcome to CMOs
Unscripted. Jason, it's great to have you. Thank you so much for joining us today.
Thanks for having me, Lisa. So excited to be here.
Yeah. So I mentioned five-time CMO, you've helped shape marketing at some of the most
innovative companies in tech. We're talking, I mentioned Adobe, but also Salesforce,
and I love that your career sits at this intersection. I don't know, maybe it's a
roundabout or a traffic circle of strategy and technology and storytelling, because mine does
too. Tell the audience a little bit more about you and some of the things that you're taking
away as leading marketing for five different companies so far. Yeah. So I started my career
as an engineer, a software developer, you know, back in the early dot-com boom and all of that,
loved doing that transition into product. And so then I was over in product for a while over at
Adobe, helped them build what ultimately became Adobe's marketing cloud. So acquired Omniture and
Day CMS and a number of other companies and helped Adobe become an enterprise company and sell
enterprise software. And in that role, I was offered the ability to come run and build and
start their creative cloud business. And so taking that from, it wasn't even an idea, it was a bunch
of experiments that we'd ran. Some of that stuff took off. We decided to go all in on subscription.
We needed somebody to run that. And I helped lead that, ultimately leading the Americas team.
And it ended up when I left there, I had a billion dollar revenue accountability, had a team of like,
I don't know, a hundred some people, helped Adobe go through their transformation all the way from
like beginning to end. And so that was, that was a really cool job. Like, I mean, life-changing and
just formative to my career. And it's helped me so much in all these other jobs that I've had,
you know, this sort of intersection, as you say, of like technical capabilities and like going
through a big transformation, seeing how rocky it is and how unsure it is. You know, it's funny,
there was a Harvard business,
review article written about my team and the transformation we went through at Adobe.
And the article makes it sound really easy, right? Like, I love the article, you know,
it's like David Woodwani, who's the GM of that business. David Woodwani was like looking out
his window, pondering the future and Adobe did blah, blah, blah. And I was like, that's not at
all how it went. I'm sure David pondered out his window, but, but that's not, other than that,
I was like, it was, it was chaos. But we got through it and you learn a lot. You just get
a lot of confidence.
Going through an experience like that. So happy to share that with your audience.
I love that. And I agree. There's so much, it's like orchestrated chaos, or sometimes it's not
orchestrated, but you've had some great opportunities to help companies reposition and create
categories. And I think that's a dream of a lot of marketers. What pulls you in when you see
opportunities like that to, to reposition, to create new categories and to lead them?
Yeah, so one of the things I look for when I look for jobs,
well, there's a couple of things when I look for a job in general, I look for, is it a team that I
believe in? Right? Like who else is sitting around the table? You know, have they worked together
before? Have they, you know, found success before? Are they, are they better than me?
You know, like, are they going to help, you know, pull me up? Like, are they willing to make big
bets? And then I look at like, what's that market space? Like, is there an opportunity to do
something different? Like, um, the ADD part of me is I can't just come in and run like demand gym.
Right. Or product marketing. Like, if you're like, I've got a run rate business and I need
somebody to come in and just like, you know, help us with like product marketing, demand gym,
probably somebody else. I'm like, um, I describe myself like a Husky, you know, where it's like,
if I don't get enough exercise, I'll make my own exercise by tearing up the couch. Um, I'll look
for disruption if there's not enough. Um, and so I look for like, well, does a company want to try
to do something new? Right. And if you look at like some of the companies, you know, that I worked for,
that was exactly it. Like if we take data stacks, we can go into data stacks a little bit more in a
bit. Um, we take data stacks. So data stacks have been around for 13 years. It was the Cassandra
company. So enterprise big data, right. Cassandra, the database behind like Netflix and the app store
and all that kind of stuff. Uh, their thesis was, you know, two and a half years ago, right before
I joined, they said, Hey, AI is coming out. We've got a pivot. That's a new growth vector. Let's go.
That was exciting to me. Right. You know, coming in and saying,
how do I take this 13 year old big data enterprise motion data based company,
totally create a new, uh, category around, you know, enterprise AI platform, uh, help them become
seen as an AI platform. So, and then like build out the whole thing, right. The motion and the
team and the, how do we get from here to there? Super, super exciting to me. Right. Where it's
just like, okay, there's something new, no idea how we're going to get there, but there's the
wherewithal and the willing to invest and whatnot to like actually get from here to there. A lot of
fun, a lot of mess. Um, but ultimately a lot of fun, right? You feel at the end of it, you're like,
wow, I did something. So that's cool. Something transformative, like truly transformative. But
you also, from what I understand, you did something similar at Heroku. You actually
helped define the modern app development space before a lot of people even knew what it was.
So what's it like as a marketer, you've talked about your engineering background,
but to create that category from scratch, you talked about the culture that's needed,
but, but what's it like as a marketer coming in and helping lead that creation?
It's, um, I think for, I think one of the things that's underappreciated is it's really hard.
Yeah. And, you know, now that I've done it five times, uh, I feel like I have a lot of opinions
and a lot of scar tissue, uh, on, on that, but I think a lot of first timer, early CMOs or VPs of
marketing come in and say, well, the company hired me for this. I'm just going to come in and start
doing it. And then you run into at every company I've been at, whether it's, you know, a $40
billion company or a $20 million company. And I'm like, well, I've done it five times. And I'm like,
you run into a lot of the same issues. Uh, how do I drive alignment across product, uh, sales
finance around? Like, what do we want to call ourselves? Yeah. In my mind, for most tech
companies, you have to create and own a category because you have to be different, right? Uh,
there's like, if you, if you want to go after, I don't know, um, if you want to go after Oracle
or whatever, they're a thousand times your size at least. Right. And so you've got to be, I don't
think you're going to be able to beat them if you think you're going to try to beat them or you carve
out a niche and say, no, Oracle sucks at X and we're the world leader at X. Yeah. Right. And you
gotta be confident doing that or else you're, you're never going to win. And so most companies,
you have to go out and create differentiation, you know, and like be super clear on your
positioning. Uh, and you're like, yeah, yeah, no crap. Right. Like that's my job as a marketer.
Then you come into the company and nobody wants to be put in a box, right? Like I've run into
this at every single company where it's like, well, we could do everything, you know, we can help
everybody.
We can do this and we could do that and we could do this or we picked a position and you know,
uh, Verizon came in and said, they'd give us a million dollars if we did something else,
we should go do that. That's the actual struggle. Like how do you get alignment and how do you get
buy-in and how do you maintain that buy-in to say, guys, like we've got to be confident in
our thing and it will change over time. Like that's fine. Right. But time to market is more
important. Like you've got to be clear, you've got to be fast. And then you listen to the market
and you make changes, but nobody's looking for a thing that does everything.
Right. Like that's not a Google search, you know, like I want the platform that does everything,
uh, says no. And people have jobs to be done. And so you have to figure out which of those jobs do
I think I can credibly do better than anybody else. How do I put a wrapper around that? That's
your category name. That's punchy. That's like, yeah, that, that captures the problem that I have.
And now you go build a whole machine around that. Right. And you, I mean, there's going to be lots
of bumps and scrapes around like messaging and landing pages, sales enablement, all that kind
of stuff. Um, but your job as a marketing leader is you've got to maintain the connection with
product and the CEO and the CRO to stay the course. Right. But if you allow yourself to get knocked
around or like you will never be successful. And the thing that ultimately wins is if you're
starting to get results. Right. And that's where, you know, I've worked at, um, it's funny, uh, at
my current company data stacks, uh, just acquired by IBM. When we first started doing our repositioning,
you know, like Chet, uh, the CEO.
I was like, oh, I hate it. Right. You know, literally it's like, I hate it, but it was
kind of like, well, we're going to run with it because it's working and it ultimately did work.
Right. And resulted in an exit. Um, but you run into that a lot, right. Where it's like,
even your boss, you know, like strong feelings and opinions. Um, but you've got to establish a
relationship, which is like, I've got to go do my thing. The thing that we should all care about is
what is our cap to LTV? Are we growing, you know, like what are the, what are the, the sort of
metametrics for marketing? Uh,
uh, everyone has an opinion, right. Oh yeah. And verbatim, blah, blah, blah. And it's like,
I'm happy to be wrong. And that was one of the things I learned at Adobe is,
I've got a ton of opinions and half of them are wrong, right?
Let's actually go take it out to market,
see what actually happens.
What do our customers and prospects do?
And be like, that's the one that wins, even if I hate it.
Exactly.
You've got to have a management team that's okay
with like a high ego, but willing to let go, right?
And say, okay, as long as it's working,
I'm happy to run with it.
And that's hard.
Do you think though, a couple of things that you mentioned,
you talked about alignment,
which I think is absolutely critical.
You also mentioned the word confidence a number of times.
Do you think where most CMOs get it wrong
when they're trying to achieve category creation
is because they don't have that alignment
or they don't have that confidence to go to the CEO
and say, you don't like this, we do, it's working.
We're not going to reposition.
We're going to reinforce this existing narrative.
What if most folks kind of go the wrong direction?
Yeah, this is one of the things that I would encourage
all CMOs or VPs of marketing to do.
Take advantage.
Take advantage of your network.
Because I have found that most CMOs are super open.
Anybody who's done this more than two or three times
has got the exact same scar tissue.
Yeah.
And so they're more than happy to grab a coffee or a beer
or a glass of wine or whatever and say,
yeah, I ran into that problem.
Here's what I did.
The other thing is, again, like I've been lucky enough
that I've worked at some world-class companies
like Adobe and Salesforce who are universally known
for being successful at this.
Being on the inside of the machine,
you really see how messy it actually is.
Oh, sure.
Right?
And once you realize, oh, if the world-class people
have no idea what the hell they're doing,
then it's okay, right?
To say like, nobody knows how this is going to shake out.
My job is to be smart and fast on my feet, right?
My job is to go set up systems where my team can listen
and learn, make quick iterations,
hire a bunch of scrappy people,
and go make those pivots that are necessary or whatever.
My job isn't to be like, oh my gosh, I know more about this
and I know exactly how to position this thing.
I know how to position this thing better than anybody else.
Nobody knows that, right?
Or even if you did know that,
that process would take two years and by then, who cares?
Yeah, exactly.
Right?
And so you just like, it's an overused statement,
but I do think it a lot,
the whole fake it till you make it, right?
Which is like, nobody knows.
And especially now in the world of AI,
where I mean, the verbiage is changing every month.
Oh my gosh, yes.
You're trying to go through your traditional ICP definition
and positioning definition,
and you're like, it's changing like 30% a month.
How do I do that?
Yeah.
And you're like, just create like a rough skeleton
that's kind of good enough
and everything else can evolve around that.
Yeah.
So hopefully that's helpful, but yeah.
Yeah, absolutely.
We talked about, you know, time to market
and as marketers, we know that that's a really,
that's a really valuable metric
because you also talked about differentiation,
which is, it's key.
You have to differentiate today.
To your point earlier, we don't want to,
nobody wants to fit in one little box.
However, to deliver what the customers want,
it's incredibly important to be able
to help shape customer perception.
Now we're in this AI,
AI era, ChatGPT is only three years old.
My mom just got on ChatGPT recently.
I was so proud.
That's awesome.
She calls it Zach TPS,
but I know what she's talking about.
Hilarious.
Yeah.
We're seeing AI transform marketing every day.
I mean, every episode we do have CMOs and scripted,
we're now in season two,
market research, message testing, content creation.
But what are you seeing as it's moving so fast,
can't put the toothpaste back in the tube.
What's different about how you're seeing it?
How you're seeing AI applied in marketing today in 2026?
Yeah, it's a weird, I mean, I'm having this conversation,
I don't know, eight times a day.
Yeah.
Right, because we're at this weird place
and I'm lucky enough that I'm old enough
that I've gone through this a couple of times.
Like when web first came out, when mobile first came out.
I mean, this is, AI is happening, I don't know,
probably it feels like 10 times faster.
It does, doesn't it?
Yes, it's a huge wave.
Yeah, like those took like three years
and this is like in a year it's already transformed things.
I guess it's three times faster.
Yeah.
And so the conversation that comes up every day
is companies are looking for marketers and engineers
and product and salespeople who are AI experts.
Yeah.
The reality is that doesn't exist.
Right.
Right, or if it does exist,
those people probably work at OpenAI or Anthropic
or something like that, right?
Yeah.
And so there's a lot of expectation,
and you see this, right?
Like Amazon just laid off like 14,000 people yesterday.
Yes.
And so there's this expectation coming from the top
that's like, hey, I can get rid of
90% of my people and all I need are world-class AI experts
who already have AI playbooks.
99.9% like time, like that doesn't exist.
It doesn't, right.
I think what these companies really need
and what marketers really need to be is,
am I passionate about AI?
Am I figuring out the tools and the patterns?
Am I willing to experiment and adopt?
And am I willing to be the leader in my company
even though I'm figuring it out?
Yeah.
I would say that if you're a marketer,
you have to do that or else somebody's gonna do that for you.
Absolutely.
Right.
You have to be the one that says,
hey, I'm gonna go figure out Claude and Anthropic
and how do I merge these things, whatever to do,
like world-class market research in a day, right?
Because if you're not doing that,
then your CEO is gonna say,
ah, I've got some person on LinkedIn
saying how they did this.
I wanna go hire that person, right?
Even if you're like, well,
the formula is gonna change in a month.
It's gonna change, right?
I mean, I'm super excited by the AI tools.
We started adopting inside of DataStax maybe nine months ago,
at this point.
And the ability to do primary research on a daily basis
of just social listening with all of our competitors,
what are we seeing in their news cycle, their social cycle,
webpage changes, semi-daily summaries,
along with like copy suggestions, right?
Of sort of themes that stand out, you know,
based on our themes, like what do you think I should do?
Then I can easily go back and forth with these tools,
create brand new copy,
and then using things like Lovable or vZero,
like grab our templates, build and deploy,
deploy my own webpages on my own, right?
So as a CMO, I'm like, I don't know, 10 times faster.
- Oh yeah, yeah.
- I don't know how that scales, right?
So I love the tools.
I love the ability for fast iteration.
I have no idea how it scales, right?
But what I need as a CMO is I need a team of people who say,
hey, I'm the head of creative,
and I'm figuring this out from a creative standpoint,
or I'm the head of editorial,
and I'm figuring this out from a content standpoint.
You know, it's like, oh, I need partners who are like,
well, what does this mean?
Like, you've got five people on your team,
kind of who does what.
- Right.
- But if you're like, I don't wanna change,
you know, I wanna keep doing things the way I did it before,
it's like, I don't have that option.
- No, none of us has that option, really.
- So yeah, I mean, you know, it's amazingly exciting.
And like some of the companies I'm advising,
there's so much innovation happening in this space right now.
There's so many companies that are trying to say,
okay, like, how do I productize this?
- Yeah.
- Right, because like, I love it,
but I'm still, I call it swivel chairing, right?
It's like, I move over from like ChatGPT over to Claw,
then I go over to Lovable
to do something, then I'll go over to Canva
and do something.
And I'm kind of like doing a lot of this, right?
Which is, and again, like it's at least 10 times faster
than the previous workflow.
- Yeah.
- But it's still like, I don't know, 99% inefficient.
Right, because I'm jumping from tool to tool.
- Right.
- And so like, that's gonna be amazing.
- You're orchestrating all these things.
- Yeah, like amazing to see how that, you know,
plays out over the next couple of years.
- I think my favorite thing about marketing is
that it's a blend of art and science.
It's a balance and that balance shifts, but you know,
all the noise about AI.
I do iHeartRadio twice a week
and I get to talk to a consumer audience.
And most consumers are terrified of AI,
especially depending on your generation, your industry.
I have a nephew who's an actor in Hollywood
and is terrified of it for good reason.
But there's also a lot of noise
about it replacing creativity.
But I see it as an amplifier of creativity.
What do you see in practice?
And how can we as marketers help get that message
out there to more folks to be able to embrace it?
It's hard when you hear noise from, you know,
companies like Meta and AWS slashing jobs.
It's hard to compete with that.
But I think we have a sense of obligation there.
- Yeah, yeah.
I mean, it's definitely a tale of two cities, right?
Which is, I agree that I love it
and embrace it as like a force magnifier, right?
Which is, if you think about yourself as like, you know,
the pilot in a cockpit or the quarterback of a team
or, you know, sort of the orchestra leader or whatever,
sort of leading an orchestra,
you are now empowered to do so much more, right?
And so if you think about it like that, you're like, okay,
like now I don't have to do the menial stuff
that would take hours and hours of my time or whatever.
I've got these tools that are, you know,
can go grab a bunch of stuff and synthesize it for me.
And then I just have to direct it.
Incredibly freeing.
- Yes. - I love that.
That said, there are a lot of menial jobs, right?
And so, and that's like the combo
of the companies are trying to figure out like, well,
okay, does that mean I don't need as big of a content team?
Does that mean I don't need as big of a creative team?
And again, like I wasn't quite old enough
that I was in market back when like, you know, Photoshop
and sort of digital tools like first came out,
but I did work at Adobe early on.
And that was one of the things that Adobe, right?
Is like original photographers were anti-Photoshop
because they were like, no, you have to be in a dark room
and you have to do it this way.
And this is the way it's been done.
And so I'm sure there were tons of jobs that were displaced.
- Yeah. - Right?
Because it's like, well, I don't need that anymore.
- I now have a tool. - Yeah.
And so you kind of look at the societal way
and you're like, okay, well, it's good
because you're moving society forward.
And it's bad because those are real people
and real jobs who have to figure out the path forward.
I don't know how that plays out.
But my only recommendation is like you,
there's one side of the fence to be on, right?
And that side of the fence is like, it's coming for you.
And so you've got to own it and, you know, position yourself.
This is where you have to do category creation
for yourself, right?
Like position yourself
as like I am the leader in this area
and here's what I've done and here's what I can show you.
It's going to change.
can't tell you this is a playbook, you know, but I can tell you that I'm smart enough to figure it
out. I'm on top of it and you need that at your company. Yes. And so whether you're creative or
content or, you know, a web developer, whatever you are, like you just got to grab ahold of it
and run. Yeah. Um, I do feel, I feel really bad for, um, new college grads. Like I don't have a
good answer. I don't have an answer for that because it is like somebody has to go learn the
skills somewhere and they would usually start on those like sort of more mundane jobs. And now that
people are outsourcing that, I don't know how that plays out, you know? And I have a lot of kids that
I advise and talk to and they're kind of going through this and like, well, here's what I would
do. I would go look for like experiments and side projects and things to try to say like,
oh, I've used this and I built this, go work for free for a coffee shop or whatever and help them
do their social. And like, you know, you just use Claude and lovable for all of it or whatever.
Right. It's just kind of like, you're doing it. Like nobody cares whether you're a
paid or not, but you actually have like real work that you can show.
And that's, that's so the proof in the pudding is so key. Cause you mentioned, you know, it's coming,
it's not coming, it's here and it's just accelerating. So those of us that the fake
it till you make it kind of syndrome is people need to, to embrace it, I think, and go, okay,
it's here. How can I leverage this to tune up my skills? So, because if I don't, there's going to
be somebody else right behind me in my rear view mirror who is going to embrace the AI technology
and the emerging tech.
trends and will be more valuable than I will be. I still think, though, there's that the emotional
element. I did an iHeartRadio report on Aisha Gabon, who was a UK AI reporter, and they actually
did this program recently and it was called Will AI Take My Job? And at the very end of this hour
long segment on like UK's Channel 4, the presenter said, I'm not real. My likeness, my gestures,
everything is AI generated. And so people were like, what? And so we talked about that on the
radio. And I thought, you know, one of the things so AI can read the news, but can it understand it?
Where's the emotional element? You've done, you've spent a lot of time, Jason, in your career
marketing really technical products built by developers for developers. So you speak their
language. And I think that emotional element, isn't it still key to earning their trust?
Yeah, there's, I think there's, I don't know, a couple facets of
this. It's a really good point. I appreciate you bringing it up. Maybe five, eight years ago,
something like that, when marketing first started becoming way more scientific, there was a really
big push where all these startup companies, like all they cared about was like CAC to LTV and, you
know, sort of acquisition costs. And they just wanted marketers to be scientists. And I mean,
even still, there's marketers who are not good at the data side. And it's like, okay, you're,
you're really like a Luddite, you know, it's like, you gotta catch up.
Like, that's where the world's going. But they were missing the heart, which is, yeah, I can go
pump out more ads and somebody else at a faster rate or whatever. And I could drive click through
and go freaking nuts at that. But who is my company? Yeah. Right? Like, how do I tell that
story? Like, what do my customers really care about? Like, who are they as people? And how do
I combine all that to say, like, hey, you've got hopes and dreams. My company can help you meet
those hopes and dreams. And here's how. And then I'll go back that up by like, real story,
real stories and content, blah, blah, blah, that actually like show how you like get from here to
there. But that's marketing's job. Right? And that's even happening in AI, which is like AI is
really great at pulling together market research and summarizing and synthesizing and coming up
with like, you know, content. But if that's all you did and said, Oh, I just have AI do all that
you're going to sound exactly like every other company. Right? Right. And that was one of the
funniest things. Like when we first started going through our AI pivot, I would look at our
competitors websites. And you know, I would look at our competitors websites, and I would look at
them and I would put something up like, I don't know, you know, vector, blah, blah, blah, or, you
know, rag, blah, blah, blah, like AI terms. And like, within days, like it would show up on our
competitors website. And I don't know if they were like watching or if everybody was speaking the
same language. But literally, it was like, I don't know, every two weeks, all of our websites would
look the same. And so we were always trying to stay ahead. Like one of the things I think we're
really good at a data stacks is like, you know, the whole like social community listening of going,
what are the future topics, the future being like,
a month from now, and future topics, and how do we get out there and rank for that stuff and get
that stuff on, you know, Twitter and whatnot, ahead of anybody else? Yes, the people were like,
wow, this company really understands this, you know, better than, you know, some of the other
companies that were out there. But point being that it was like, if you were a customer, you
look at that, you're like, everybody says the exact same thing. And it was funny, because you
would go I mean, even like Salesforce, and snowflake, and you know, Twilio companies that
have like nothing to do, they all look exactly the same. Right? Yeah, they're
like, you know, rag agents, multimodal rag agents, blah, blah, blah, AI, blah, blah, blah. And you're
like, they're fundamentally different companies, right? But they sound exactly the same. And so
that's what you miss out. And that's the job of a marketer is to say, like, hey, I'm the chief
storyteller. Yeah, right. Like, I go out there and I go, okay, like, now, where's the magic? Like,
what do we do that nobody else can do? And how do we crisply get that out there in a way that's
compelling that people are like, wow, I need that. Right? I mean, I'm fortunate, again,
like, you know, working at Salesforce and Adobe, like two companies that were amazing at that.
Yeah. And so it's, it's drilled into me, you know, this idea of like, anybody can buy an ad,
right? Anybody? Yeah. Oh, yeah. API, blah, blah, blah. Yeah. But why are you cool? Right? How can
I make you cool? You know, it's just, um, I got a passion for that. I can tell. So do I think that
the the storytelling element, it's still who appeals to who we are as people. And even with the AI
acceleration, we're still people, hopefully, at the end of the day. And so using, being able to
leverage these tools to learn, to grow, to become better at our jobs, to be able to understand our
audiences better so that they can understand, oh, I get why they're different. They, all these look
the same. This one's different. And I can see why. Um, I think there's a lot of potential there, but
to your point earlier, it's, it's a nebulous time. It's the biggest wave we've ever seen. And it's
happening so quickly that it, we don't often have time to take a breath because there's going to be
a competitor in a rear view mirror who's, who's maybe more agile, maybe more culturally willing
to adapt. Um, so it's, it's an interesting time that I think will, uh, just continue to evolve.
And you're going to hold on because we're like in a formula one car and it's going around a,
a, a chicane at crazy speeds. Yeah. I mean, it's super fun, you know, thinking, thinking
about that, like, you know, we realized, I don't know, it was probably a year ago at this point
that our audience was no longer using Google. Um, and then it was one of those like obvious things
because I was like, I'm no longer using Google, you know? And so I was like, of course our audience
isn't because I'm like, well, chat TVT at that time was way better than Google. I mean, Google's
caught up with Gemini now. Yes. Um, and so I'm going back into Google. And so then we started
investing. Yeah. And so then we, we started investing heavily in LLM optimization,
uh, geo or whatever you want to call it. The term's not, not solidified. Um, and for a long
time we ranked as number one for almost every term versus, I mean, monster competitors like
Mongo and whatnot, because they just, they just weren't doing it. And so it was just like, uh,
it was kind of like a low hanging fruit of, you know, go out and put like, you know, robots.txt
and, you know, go off and, you know, like see the couple of Reddit forums and whatever. And I mean,
literally within like weeks we were capturing almost a hundred percent of the traffic because
it's like, we were the only ones showing up. Oh, that's awesome. I mean, now like,
everybody's doing it right. And everybody's like figuring that kind of stuff out. But the point
being like, it's super fun. And so if I were in the market, um, one of the things I'm most excited,
actually I am in the market because we got acquired by IBM. So I'm figuring out what's next.
Um, I would look at that as an opportunity because it's resetting the table. Yeah. Right. If you look
at sort of the way things have been the last 10 years, there's a hierarchy and there's experts
and you know, there's a social expert and a man, gen expert and blah, blah, blah. Uh, very few AI
can look at it as like, Oh, it's scary because things are changing. Or you can look at it as
like, Oh, this is my opportunity to get ahead. Right. Like I can go find this new crazy thing
or whatever that other people don't know about or don't know how to do or whatever. And I can
figure it out whether you're brand new in the market or whether you've been working for 30
years. Like it doesn't really matter. Uh, and same, like if you're a developer, if you're a
salesperson, uh, for every role or whatever, I think it's pretty cool because it's resetting
the table. Yes. And so I love that. I guess it depends on your mindset. It does.
It does because I think of it as massive opportunity. I'm an, I'm an optimist like
through and through and I see opportunity there. But my last few questions for your kind of rapid
fire questions as we're in this era of AI, this new wave, that's just only getting bigger and
bigger. What is one marketing buzzword that you think just has got to go away? What are we moving
away from? Yeah. Um, I don't know if I have a particular buzzword. I've always been kind of
anti buzzword, right? Like, you know,
ABM, it's like, well, no, this is what we've always done. Right. Yeah. MQL. And then you get
into this weird conversation. So I guess, I don't know, maybe I'm the wrong person to ask that
because I've always been kind of anti buzzword in general, which is like, what do you really want to
do? Well, you want to be unique and differentiated and the buzzwords to your points earlier just
makes everybody sound the same. But I, for me, it's MQL. I think the MQL is dead. I think it's
all about marketing qualified, um, attribution and things like that, that we're learning from our CMOs.
Um, but you never know, but we always have to have buzzwords. Everybody knows that we've got to have
those three letter acronyms that, that mean something.
When I was at NASA, an EVA was an extravehicular activity.
That's a spacewalk.
When I got into tech and HP, an EVA was an enterprise virtual array.
I've never heard that second one.
Yeah.
So it was funny.
So anyway, last question for you.
What's one underrated skill that you think every CMO, especially in today's accelerated environment, needs to have?
I would say your ability to create credible relationships with your C-suite peers.
Yes.
This is where I see so many CMOs just undermine themselves.
And I get it, right?
Because you're like, hey, I'm the expert.
I've been doing this for 20 whatever years or 10 years or whatever.
I'm the CMO.
Why is the product person like, you know, sort of on my back all the time about like messaging and positioning?
Or why is the salesperson second guessing, whatever, whatever?
That's just the reality of the job.
Right.
And so sort of putting yourself in a hole or whatever and saying like, no, no, no.
I'm just not going to.
I'm not going to talk to you or I'm going to go kind of do my own thing.
Like, it's just not going to work.
No.
And people are very different.
Right.
You know, like typically the people who run product are very different than the people who run marketing.
Right.
The people who run sales are very different.
And so your ability to really understand their world and create a relationship.
And going back to the MQL thing.
In my best jobs, I had 100 percent alignment with sales.
Yep.
Right.
Which is like, I'm not trying to create leads.
You're not trying to create leads.
Right.
What we're trying to do is win.
Like, how do we how do we break up, you know, divvy the work, division of labor between us, whatever, to actually be successful?
And how are we making sure we're talking every day about that?
Where I've been least successful was jobs where, you know, you got a head of sales.
He's like, I want 100 percent inbound from MQLs.
And we're going to talk about MQLs all the time.
You're like, if you're not closing them, it doesn't matter.
Right.
It doesn't really matter.
Like, this is a partnership and not like a service relationship.
Oh, I love that.
You should write a book, Jason.
You really should.
You have so much knowledge.
He's got GPT to help me, you know.
There you go.
Well, you've done such a great job and not only in your career, but on your time on this podcast, really helping define what modern marketing looks like.
It's changing from the things that you talked about in the beginning, like category creation, to the technical storytelling, to what we're now living with AI transformation.
You definitely should write a book because I feel like you're a living playbook.
But we thank you so much for sharing your insights, your experiences.
Where can folks go to follow you?
Yeah, the best place is probably LinkedIn.
I mean, that's that's where that's where people really are these days.
Excellent.
I agree.
Awesome.
We want to thank you again, Jason.
We want to thank you, the audience, for tuning in to season two of our Little Engine That Could podcast.
For more conversations like this, follow CMOs Unscripted.
If you haven't smashed that subscribe button on YouTube, do it because this is where the world's top marketing leaders go off script.
For Jason McClelland, I'm Lisa Martin.
We'll see you on the next pod.
We'll see you on the next pod.
Podcast Summary
Key Points:
Category creation is essential for tech companies to differentiate against larger competitors like Oracle, requiring confidence and a clear niche.
Jason McClellan’s career spans engineering, product, and marketing, including leading Adobe’s Creative Cloud transformation and repositioning DataStax for enterprise AI.
Successful repositioning demands alignment across product, sales, and finance, plus resilience to maintain course despite internal pushback, including from CEOs.
Marketing leaders must embrace experimentation and market feedback over rigid opinions, as time-to-market often beats perfection.
In the AI era, no true AI experts exist yet; marketers must lead by adopting tools, iterating quickly, and driving primary research and content creation, despite messy workflows.
AI accelerates marketing tasks (e.g., social listening, copy, webpages) by 10x, but scaling and tool orchestration remain inefficient and evolving.
Summary:
Jason McClellan, a five-time CMO, discusses the art and science of category creation and repositioning in tech marketing. He emphasizes that most tech companies must create and own a category to stand out against giants like Oracle, which are far larger. Drawing from his engineering and product background, including leading Adobe’s Creative Cloud transformation and DataStax’s pivot to an enterprise AI platform, he highlights that this process is chaotic and challenging, not the smooth narrative often portrayed in case studies.
Key to success is driving alignment across product, sales, and finance, and maintaining confidence in the chosen positioning despite internal resistance, even from CEOs. He advises marketers to prioritize speed and market feedback over perfect strategies, using a "fake it till you make it" mindset, especially as AI rapidly reshapes the landscape. In 2026, AI tools enable marketers to conduct daily primary research, generate copy, and deploy webpages far faster, but true AI experts are scarce.
McClellan urges marketers to proactively experiment with AI tools and lead their companies through adoption, rather than risk being replaced. He notes that workflows remain inefficient due to tool-switching, but the potential for innovation is immense, making AI both an exciting opportunity and a disruptive force requiring continuous adaptation.
FAQs
Most tech companies must create and own a category to be different, especially when competing against giants like Oracle. Instead of trying to beat them head-on, you carve out a niche where you can be the world leader, which requires confidence.
He looks for a team he believes in, where members are better than him and willing to make big bets. He also seeks a market space with an opportunity to do something different, avoiding run-rate roles like demand gen.
A major challenge is driving alignment across product, sales, and finance on positioning, as everyone wants to be everything. Maintaining buy-in and confidence in the chosen category is crucial, even when leaders have doubts.
CMOs should leverage their networks for advice, as most have similar scar tissue. They should embrace that no one knows how it will shake out, focus on fast iteration, and listen to market feedback rather than insisting on a perfect plan.
AI tools enable faster iteration, like daily primary research and quick copy creation, making marketers at least 10 times faster. However, true AI experts are rare, so marketers must be passionate, experimental, and willing to lead despite uncertainty.
They should be passionate about AI, figure out tools and patterns, and experiment. If they don't lead this adoption, the CEO might replace them with someone who appears to have AI playbooks, even though those don't truly exist.
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