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"Marketing to marketers is the dream job, but it makes everything that much more high stakes." – Jacqueline
In this Hot Seat episode, Jacqueline sits down with Jason, CMO at Customer.io, to ask a simple question: what would it actually take to make martech cool again? Drawing on stints at Dropbox, BetterCloud, and Microsoft, he unpacks how brand storytelling, design, and experience can turn forgettable software into something people genuinely want to be around, and why so many teams lost that plot after the early cloud-era glory days.
From Bob Ross livestreams to "Raiders of the Lost Lifecycle," this is a playbook for injecting swagger back into marketing without sacrificing pipeline, rigor, or credibility.
Timestamps
00:25 – First Martech tools, Mixpanel obsession, and Jason's weekly grilled cheese ritual
06:30 – Shaping brand storytelling: experience at Dropbox, BetterCloud, Microsoft
11:43 – What made early Salesforce so magnetic and why Martech lost its spark
16:40 – Making Martech cool again: inside Customer.io's Bob Ross, Hot Ones, and Raiders of the Lost Lifecycle concepts and playful brand identity
20:00 – What modern marketers actually want from live experiences
25:55 – Can mascots, memes, and influencers bring consumer fandom dynamics to Martech?
Sponsor
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Creators and Guests
What is Making Sense of Martech?
Unfiltered takes on the biggest shifts in marketing technology. We spotlight what matters, who's leading (or lagging), and what's next. In Martech, clarity is power — and we're here to deliver it.
00;00;06;09 - 00;00;15;03
Unknown
Welcome to the Making Sense of MarTech podcast, where we interview leaders and put them in the hot seat. I'm Jaclyn Friedman, founder of monarch and global head of advisory for the MarTech weekly.
00;00;15;03 - 00;00;19;03
Unknown
Let's dive in and meet Jason Lyman, the Chief marketing officer of customer
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Unknown
IO.
00;00;19;14 - 00;00;20;26
Unknown
A little bit about him.
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Unknown
He has over a decade of SAS marketing leadership at Dropbox, Better Cloud, and Microsoft.
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Unknown
He now
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Unknown
leads the customer IO team, and he's focused on strategic customer centric growth across both products. LED and enterprise sales motions. And I I've done that in my past. It is not easy. It's a very hard thing to deal with. So thank you. Welcome to the podcast.
00;00;41;12 - 00;00;47;17
Unknown
Of course. So to start us off, we'll begin with a few very quick questions to kind of rapid fire get to know you.
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Unknown
What was your first martech tool you ever used?
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Unknown
Yeah.
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Unknown
that as the
00;01;47;16 - 00;01;52;19
Unknown
Nice. I love that answer. Because, truthfully, if you can't present and
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Unknown
outline, describe what you're wanting to accomplish, you've already failed marketing one on one. So
00;01;57;12 - 00;02;04;19
Unknown
it's unusual, but I like it. What is one martech brand right now that's living rent free in your head?
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Unknown
I just, I can't I can't kind of stop thinking about. I thought it really kind of elevated the experience that they offered to their
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Unknown
experience and, and, and kind of how the brand augmented the product experience was something that really stood out to me.
00;02;31;29 - 00;02;34;20
Unknown
I think it definitely changed my perceptions around the brand.
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Unknown
So now I kind of think about Mixpanel as being more sophisticated than maybe some of the other analytics tools out there.
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Unknown
Hello. Okay. Good to know. And this one is a little bit spicier because we're going to delve into it later. But who is the Marc Benioff of this era.
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Unknown
and kind of defining how marketing and sales works. And so,
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Unknown
I think she was the one that kind of came top of mind for me first.
00;03;20;11 - 00;03;24;19
Unknown
Yeah. She's a great one. Would love an intro.
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Unknown
If there was one marketing myth you wish CEOs would retire. What is it?
00;03;35;01 - 00;03;39;04
Unknown
email is still one of the most effective marketing channels that marketers use today.
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Unknown
I wholeheartedly agree.
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Unknown
And this is a question we ask everyone. Who is someone you admire, whether it's professional or personal.
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Unknown
Also to I feel like he understands what what makes him unique and was really committed to honing that competitive advantage. So, you know, he's known for,
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Unknown
you know, being a long range shooter, but you know, his his routine, his investment in repetition, you know, his and his ability to understand that and then add these elements like moving without the ball
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Unknown
just really stood, stands out to me as someone who is thinking about kind of the role they can play more holistically.
00;05;03;27 - 00;05;05;04
Unknown
And then finally, I just
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admire how he leads the team. You know, he does it with joy and humility and confidence.
00;05;29;24 - 00;05;37;01
Unknown
I love that answer. And this is a special one. Because we have to ask. Last but not least, I hear you have a very, very
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Unknown
long held tradition. So, what is this week's grilled cheese recipe? And what day of the
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Unknown
week you do it?
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Unknown
Nothing beats a grilled cheese. And then the addition. Sometimes. But tomato soup.
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Unknown
It's perfect.
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Unknown
Exactly. All right, let's dive in to
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Unknown
the topic we're going to be talking about. But first let's let's hear a little bit about your experience. Dropbox. Better cloud Microsoft. Like
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Unknown
how did those shape how you see brand storytelling and how that applies as a philosophy today to.
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Unknown
I love that.
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Unknown
It's a
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Unknown
very hard.
00;08;39;09 - 00;08;40;07
Unknown
An amazing.
00;09;50;13 - 00;09;56;12
Unknown
Love. It makes a lot of sense. So I first used customer SEO in 2018 with a client.
00;09;56;12 - 00;10;00;11
Unknown
I'm curious, how did you first discover customer IO and then ultimately, how did,
00;10;00;11 - 00;10;02;22
Unknown
about the brand drew you into the role of CMO?
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companies
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Unknown
Oh,
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Unknown
wow.
00;11;16;00 - 00;11;24;03
Unknown
For sure. And speaking of how we really figure out how to get marketers interested and not just customer, but
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Unknown
a platform in general. I initially reached out to you a couple months ago because I appreciated what your team was doing and reshaping the
00;11;31;12 - 00;11;35;26
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narrative for what we typically see as very, very boring webinars and,
00;11;35;26 - 00;11;37;05
Unknown
know, vendor events.
00;11;37;08 - 00;11;40;02
Unknown
the first time. And, I mean, it's in the best way remind me of the
00;11;40;02 - 00;11;43;15
Unknown
early 20 teens where Salesforce had
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Unknown
market, they had the swagger, they had Dreamforce parties, they had golden hoodies, which were such an honor. And lovable mascots like Einstein, my personal favorite. And it made B2B and just really marketing a vendor.
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Unknown
Cool.
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Unknown
And what do you think made Salesforce so magnetic? And if we apply that to just martech in general, like how did we lose that spark culturally?
00;13;51;20 - 00;14;02;24
Unknown
Yeah. I think to your point, if you adopt B2C practices. And also B2C should learn from B2B too. There's so many components that it's really not that different. Yes, you have different needs requirements, but at the same time,
00;14;02;24 - 00;14;08;07
Unknown
we're marketing to people. But you have to remember, of course, those accounts on the B2B side and there's a little bit more to it.
00;14;08;07 - 00;14;08;23
Unknown
But
00;14;08;23 - 00;14;09;11
Unknown
I agree that
00;14;09;11 - 00;14;16;13
Unknown
we kind of went in the exact opposite. And so are there any companies right now in the martech space that you think are channeling
00;14;16;13 - 00;14;18;28
Unknown
the Zeit geist, the energy of the 20 teens?
00;14;24;15 - 00;14;35;14
Unknown
best that I could kind of come up with is, I would say, not again. Traditionally thought of as a martech solution, but, I mean, I know we use it every day in our marketing team, and and so that example would be Figma.
00;14;35;14 - 00;14;37;06
Unknown
I think that they've done some
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Unknown
I definitely agree with you. And I would say also maybe Canva. In that same kind of vein. They bring a very similar energy in the best way possible.
00;15;35;26 - 00;15;47;10
Unknown
design for companies. You know, I guess the, the, the fact that they value that means that it's maybe easier for them to understand the impact of brand investments. And so maybe that's why they're on the kind of
00;15;47;10 - 00;15;51;27
Unknown
bleeding edge of that. But I think it's a lesson that, you know, we all can all can learn from,
00;15;51;27 - 00;15;55;10
Unknown
we think about our own kind of marketing strategies and approaches.
00;15;55;10 - 00;16;01;03
Unknown
Exactly. And also recognizing its value without needing the performance metrics in the same capacity.
00;16;01;04 - 00;16;20;03
Unknown
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00;16;38;19 - 00;16;40;10
Unknown
And now back to the hotseat.
00;16;40;10 - 00;16;50;01
Unknown
All right, so the whole point of this conversation is about making martech cool again. And I have been genuinely very impressed with what your
00;16;50;01 - 00;16;57;12
Unknown
team has been doing. You originally got me excited with the Bob Ross webinar, because who doesn't love a really fun cultural throwback?
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Unknown
It's already been impersonated a few times. I've seen,
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Unknown
which is obviously
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Unknown
huge kudos to the team who built it.
00;17;02;08 - 00;17;10;09
Unknown
You've also had fun panels like Hot Ones. Admittedly, I was, I participated and I love heat, so I did very well.
00;17;10;09 - 00;17;19;05
Unknown
No one else did. But also recently, Raiders of the Lost Life Cycle, like your your team is really breaking the mold and, like, having fun.
00;17;19;07 - 00;17;20;07
Unknown
And I'm
00;17;20;07 - 00;17;25;16
Unknown
curious, like, what is the strategy behind injecting that that playfulness that
00;17;25;16 - 00;17;29;25
Unknown
just a little bit different into the brand experience? But also, does this reflect the company culture
00;17;29;25 - 00;17;30;16
Unknown
as well?
00;19;32;14 - 00;19;43;11
Unknown
I definitely agree, and I think a lot of companies could take note, and. And, I mean, they already kind of are, but really move beyond the sales pitch. Webinar. No one wants it.
00;19;43;11 - 00;19;47;10
Unknown
No one wants to even do it when you're on the inside.
00;19;47;10 - 00;19;50;06
Unknown
And so, of course, your team's been doing really
00;19;50;06 - 00;19;53;19
Unknown
fascinating and playful creative events.
00;19;53;19 - 00;20;01;07
Unknown
I guess from these events in general, just activations in person. Like, what are you learning that today's customers really want?
00;21;08;01 - 00;21;10;23
Unknown
Agreed. And something I
00;21;10;23 - 00;21;19;01
Unknown
am envious of. Folks on vendor side is you get to market to marketers like that is the dream job. Because
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Unknown
they know what is and isn't working, and they understand the the strategy, the playbook. So that just means it's like that much more high stakes.
00;21;26;22 - 00;21;37;29
Unknown
And how do you structure your team to keep things both creative without losing speed or scale, but also keep it interesting to probably the most difficult audience?
00;23;41;06 - 00;23;51;26
Unknown
I love that. And as we've been talking about all these different types of events and ways to engage, do you think overall for the greater industry, that more vendors should host
00;23;51;26 - 00;23;55;00
Unknown
conferences, festivals, themed user experiences or
00;23;55;00 - 00;23;59;12
Unknown
activations and events? The answer or is it a larger, broader conversation?
00;25;09;00 - 00;25;12;27
Unknown
justify, investments in these conferences or
00;25;19;12 - 00;25;37;21
Unknown
Yeah. The breaking through the noise is so difficult when there's. There's over 15,000 martech vendors in the entire space. And that's technically a contraction compared to last year in terms of the number of companies that went away. Granted, new companies came on board. Thank you, Scott Brinker, for the information. But at the same time, that's a lot
00;25;37;21 - 00;25;43;09
Unknown
of things to wade through, both as a customer, as an audience, as a marketer.
00;25;43;11 - 00;25;47;21
Unknown
And so I'm curious, like we've alluded to what Salesforce they did as a
00;25;47;21 - 00;25;53;13
Unknown
playbook. Do we think mascots, maybe memes now influencers, since they're newer concepts
00;25;53;13 - 00;25;55;25
Unknown
compared to what we were at 15 years ago? Let's be honest,
00;25;55;25 - 00;25;59;09
Unknown
do you think those things would potentially help martech borrow,
00;25;59;09 - 00;26;02;19
Unknown
that kind of funds? Like Geist of consumer fandom dynamics.
00;27;20;28 - 00;27;29;18
Unknown
For sure. I, I'll just say take that magic quadrant and Forrester wave. I think if we're
00;27;29;18 - 00;27;38;02
Unknown
talking about what it used to be like, that was probably the singular, most helpful, boring metric. And I think there's a lot more to it now.
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Unknown
Well,
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Unknown
thank you so much for coming on. We ask everyone at the very end who is someone else we should have on the podcast.
00;28;12;03 - 00;28;18;03
Unknown
Well, I'll take you up on that offer. Thank you so much, Jason, for being here. Where can folks find you?
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Unknown
Awesome.
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Unknown
I.