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Jerome Stewart

Jerome Stewart

Marketing executive and author; CMO (formerly VP, Head of Marketing) at AI analytics company Conviva, previously VP Marketing at Dynatrace and head of cloud marketing at Splunk.

Sep 14, 2026

10:15
Can you share about a time when you realized that your way of leading or living no longer met the demands of your work and life and growth was needed, like personal growth was needed?
10:24
That's a good question and a tough reflection because I think inherent to the question is just a recognition.
10:31
Again, as I said, sometimes despite all planning and hope and expectation, things don't work out exactly as I have wanted them to.
10:43
I'd say actually right now, 2026 is a really good example of that.
10:50
And again, this is a little bit cliche.
10:52
I think a lot of people are thinking and working through what AI means for them at work and elsewhere.
11:00
And in my case, I've been embracing artificial intelligence to help augment my skills and my team skills for several years.

12 MINS LATER

22:42
How did you pivot in this situation and turn around and actually embrace it?
BenHOST
7:11
Going and doing this transition and relying so heavily on AI, where were the cracks? Where did they start to form? Where did you notice that? And how did you start to maybe shore up some of those deficiencies using that system?
7:25
There's a few cracks that I'm noticing.
7:28
I think we're all noticing several of them.
7:30
And in some cases, proactively shoring them up, as you say.
7:34
But in other cases, I think it's still a work in progress.
7:37
Great example would be content saturation.
7:40
If I ask myself or I ask you or any of the listeners, how many emails are you receiving? how many LinkedIn outreach requests are you receiving? And how many of those do you think are AI generated? And then if we were to ask this question again in three months, I think the numbers are going to change and they're going to increase, their percentages are going to increase.

12 MINS LATER

BenHOST
19:39
For marketing leaders who are building their team, building out their tech stack, how should they be setting this up? What should they keep in mind? What should their human AI split look like? What would your advice be as marketers are trying to adapt to this new system? And honestly, this new way of performing marketing activities and ultimately achieving our marketing goals?
MattHOST
2:50
Give us a chronological look at the last couple years of AI and then the miracle of 2026.
2:56
Yeah, so what was it, Darius, when ChatGPT came out? It was 2023, right? Yep, 2023.
3:02
So let's just start the time clock there.
3:05
For me, those first two years up until December of 2025, so just this past December, I was digging in and I was using AI as an assistant to help round out my skills.
3:17
And I was kind of astonished.
3:19
I would say a 2x, maybe pushing 3x productivity improvement for me and my teams.
3:25
I mark 2025 to 2026, that transition as a new massive milestone.

6 MINS LATER

MattHOST
9:56
So what do you do if you're 21 in college and looking at going to law school, Jerome? Or what do you do if you just graduated with a marketing degree? What do you do if you're studying to be an engineer?
4:06
Give us a chronological look at the last couple of years of AI and then the miracle of 2026.
4:12
Yeah, so what was it, Darius, when ChatGPT came out? It was 2023, right? Yep, yeah, 2023.
4:19
So let's just start the time clock there.
4:21
For me, those first two years up until December of 2025, so just this past December, I was digging in and I was using AI as an assistant to help round out my skills.
4:33
And I was kind of astonished.
4:35
I would say a 2X, maybe pushing 3X productivity improvement for me and my teams.
4:42
I mark 2025 to 2026, that transition as a new massive milestone.

6 MINS LATER

11:13
So what do you do if you're 21 in college and looking at going to law school, Jerome, or what do you do if you just graduated with a marketing degree? What do you do if you're studying to be an engineer?

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