
Lindsay O'Brien
Head of Marketing at Pragmatico, an AI-native company helping mid-market organizations adopt AI
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Sep 7, 2026
S01E15 - Lindsay O'Brien, Pragmatico - B2B Marketers: Off The Record
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2:48speaker_1HOST
But how did you how did you get into marketing in the initial instance?

Lindsay O'BrienGUEST
I think marketers, I don't know if I've actually met someone who went to school for marketing and ended up in marketing, which I think is kind of how everyone's just creative in that way and just found themselves here.

Lindsay O'BrienGUEST
And I feel like marketing kind of serves both of those those pieces of me and why it's fit really well but out of college my first job was at a series a startup and i was hired as a technical writer so i sat with our developers and engineers who were building these e-commerce apps and websites for big retailers and very much in startup fashion, you don't color in the lines there.

Lindsay O'BrienGUEST
And I had crossed paths with one of our co-founders, CMO, and they needed some help with sales decks, one-pagers.
33 MINS LATER
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37:29speaker_1HOST
yeah 100% and before I leave you thank you so much you've answered all my questions beautifully but how so from your role in and what you do around AI is there any kind of final thoughts i know this is a bit of a broad question but around kind of how people are implementing ai whether it's maybe like a kind of number one practical golden rule that you follow or anything like that is there anything that you can share with me
Why Onboarding at an AI-Native Company Broke Her Definition of Fast with Lindsay O'Brien
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But if there was any judgment of like, are you using this thoughtfully? Are you using it efficiently?

Lindsay O'BrienGUEST
So I'll say one on a personal level, the way that you can show that your AI forward is just amazing.

Lindsay O'BrienGUEST
posting about it, writing about it, showing your thought leadership about it, because there's so many people talking about AI.

Lindsay O'BrienGUEST
If you can give really tangible examples to point to, it doesn't matter how many impressions or likes you get.

Lindsay O'BrienGUEST
It's about showing your thought process and being able to indicate that to the people you're interviewing with.
9 MINS LATER

Mark KillensHOST
so for being like the head of marketing like what are like your couple favorite most productive whatever like how are we gonna frame it in your mind, use cases that you're seeing right now that are helping you as a head of marketing?
