One of marketing’s most important things is protecting the time and energy we’re asking of our audience
— Lindsay O'Brien, Head of Marketing, Pragmatico
Lindsay O’Brien, Head of Marketing at Pragmatico, shares her marketing journey, insights on B2B marketing beliefs, the role of AI in marketing, community and relationship building, and the importance of content strategy and distribution. The conversation delves into the core themes of content marketing strategy, respectful marketing, protecting marketing investments, human expertise in marketing, budget and creativity in marketing, the future of marketing and AI, and practical implementation of AI in marketing. The discussion emphasizes the importance of clear content goals, audience respect, protecting marketers’ time and energy, the value of human expertise, the impact of budget constraints on creativity, and reshaping marketing organizations based on AI and buyer behavior.
Takeaways
Chloe Addis (00:45)
Welcome back to B2B Marketers Off the Record. I’m delighted to be joined this week by Lindsay O’Brien, Head of Marketing at Pragmatico. So welcome Lindsay, can you please give a little introduction to yourself?
Lindsay O’Brien (01:01)
Yeah, absolutely. Well, thank you for having me. So, like you said, Lindsay O’Brien, and I’ve been in marketing, gosh, for over 14 years now. held just about every role in marketing, whether or not my job title said so or not. I’ve been very much a marketing generalist, started out in content marketing, moved over to product marketing, demand gen, and now
Head of marketing, and it’s been an absolute blast. And I work at Pragmatico. We help companies get actual measurable business value out of their AI investments by providing adoption and transformation services and a platform that can actually help you understand your usage and proficiency and really upskill your team for this new generation that we find ourselves in.
Chloe Addis (01:57)
Yeah,
that’s amazing. And exactly one of the reasons why I invited you on the podcast to talk about AI, I suppose in general, how it’s affecting marketing, because I love following your posts on LinkedIn and kind of in various communities. I know that you’re involved in and talk a lot about AI, such as exit five and different places across that where a lot of marketers hang out. But it is just really valuable kind of.
Practical information on AI which I think is kind of you know the topic and an absolutely changing the landscape of marketing at the moment So super excited to dig into a couple of these things but before we do I know you kind of said a little bit there about like Whether you’ve been in marketing and not named as such but kind of you know Had it had a career a good career so far But how did you how did you get into marketing in the initial instance?
Lindsay O’Brien (02:52)
Yeah,
it was by accident, I think like most marketers. I don’t
Chloe Addis (02:55)
What?
Lindsay O’Brien (02:58)
I don’t know if I’ve actually met someone who went to school for marketing and ended up in marketing,
Chloe Addis (03:02)
You
Lindsay O’Brien (03:04)
which I think is kind of how everyone’s just creative in that way and just found
Chloe Addis (03:09)
You
Lindsay O’Brien (03:09)
themselves here. So I have always really loved math and being creative, 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 just
you don’t color in the lines there. You whatever needs to be done, someone, someone needs
Chloe Addis (03:48)
Yeah.
Lindsay O’Brien (03:51)
to take on. And I I had cross paths with our one of our co-founders, CMO, and they needed some help with sales decks, one pagers. And as I got more involved in that, I started working with our design team. So I started learning Adobe Creative Cloud and just how to actually format all of this content that I was creating. And
Ended up really being adopted by that CMO and and moved over into content marketing. And I was there for six years and I absolutely loved it.
Chloe Addis (04:25)
Wow.
Lindsay O’Brien (04:25)
I but again, I was doing much more than just content marketing. So yes, I was owning the content calendar and social, but also PR and some marketing ops and analyst relations. So
got to really test out what I really like to do there and it was great and I still keep in touch with that team because I had such a good time.
Chloe Addis (04:49)
that’s great. And it’s so good really hearing. mean, loads of people be able to relate to that way you kind of finding your feet and kind of a first role and doing lots of different pieces that kind of make up the puzzle overall. But there’s also normally someone there as a kind of mentor figure is like, I like that. I want I want you in my team.
Lindsay O’Brien (05:08)
Yes. Yeah. Yeah. Yeah. It’s
those people that give you a chance when you
Chloe Addis (05:17)
Yeah.
Lindsay O’Brien (05:17)
haven’t necessarily proven that you can do it yet, but they believe in you. And Christina, who was that first person, just absolutely incredible and loved working with her.
Chloe Addis (05:32)
yeah, perfect. Yeah, no, like I said, I think a lot of people can kind of, will be able to relate to that 100%. I don’t think anyone, like a lot of people have started out in some roles and like yourself actually, some more technical
Lindsay O’Brien (05:49)
yeah.
Chloe Addis (05:50)
things and kind of been interested in a certain subject area and then been like actually.
I kind of like the translation of it and explaining
Lindsay O’Brien (05:57)
Yeah.
Chloe Addis (05:58)
that to others and then marketing sort of that natural evolution.
Lindsay O’Brien (06:01)
Yeah. Yeah.
Chloe Addis (06:04)
So what is one belief about B2B marketing that you have changed your mind on in the last 12 months?
Lindsay O’Brien (06:12)
Yeah, this is a good one. So I for a very long time, and I I still struggle with this a bit, having marketing actually own a number. You know, we we moved from the MQL, which I’m so thankful for. I don’t think measuring marketing on the number of leads that we bring in is the best use of our time. It can absolutely be a leading indicator, but not the end goal.
Chloe Addis (06:41)
Yeah,
yeah.
Lindsay O’Brien (06:44)
but also putting marketing like having a revenue number or a pipeline number is difficult as well because we’re not in those conversations.
Chloe Addis (06:54)
Yeah.
Lindsay O’Brien (06:55)
So it it takes an immense amount of trust, knowing
Chloe Addis (06:59)
Mm.
Lindsay O’Brien (07:00)
that the company has hired really great sa sales counterparts for you to be able to raise your hand and say, Yes, I I agree to a pipeline number.
Chloe Addis (07:10)
Yeah.
Lindsay O’Brien (07:11)
And some
I’m very fortunate in my current role, but I I think we all have some horror stories of sales and
Chloe Addis (07:17)
You
Lindsay O’Brien (07:18)
marketing just competing against each other for attribution. And that’s absolutely not where I want to be. And where what I did to overcome this challenge in my current role is create this spreadsheet where we can basically plug in all of the campaigns that we anticipate running.
we plug in those different life cycle stages that we think they’ll come in. So for example, if they go to a webinar, maybe we count them as a marketing engaged lead, just to
Chloe Addis (07:51)
Okay.
Lindsay O’Brien (07:52)
have little checkpoints on
Chloe Addis (07:54)
Yeah.
Lindsay O’Brien (07:55)
how engaged they actually are with us. And we can estimate how many days they might be in that life cycle stage. So
Chloe Addis (08:03)
Mm-hmm.
Lindsay O’Brien (08:04)
for all of these campaigns, we can now say, okay, we think it’ll take this long.
For a cold lead to convert to a closed one deal. And this is our conversion rate at every stage. So if we run all of these campaigns, this is how much this is how many meet meetings we should be able to get in which month. This is how much pipeline we should be able to generate in which month and how much closed one revenue. And
Chloe Addis (08:28)
Mm-hmm.
Lindsay O’Brien (08:28)
that it’s really set up as this baseline of what we expect and what we’re targeting.
But it also allows us the flexibility to say, okay, if we’re not hitting our pipeline numbers with this, if there’s something that we can assist with sales to, you know, closed loss revivals, for example, something
Chloe Addis (08:48)
Yeah.
Lindsay O’Brien (08:49)
that’s going to be more of a pipeline acceleration, but not necessarily marketing originated, I I want to make sure we can shift our attention there instead of just saying, well, I need to focus on my originated number or my marketing source number because.
Chloe Addis (09:04)
Mm-hmm.
Lindsay O’Brien (09:05)
this is this is how I get paid. And
Chloe Addis (09:08)
Yeah.
Lindsay O’Brien (09:08)
and that’s where I think it gets dangerous for
Chloe Addis (09:13)
Yeah.
Lindsay O’Brien (09:13)
the company to to put so much weight on that. So that’s something that I I’ve shifted my my perspective on based on the type of team that I I’m working with and that trust
Chloe Addis (09:27)
Mm-hmm.
Lindsay O’Brien (09:28)
that’s built and also understanding that we’re all just aiming for the same goal. And
If marketing sourced is not how we’re going to get there, let’s let’s be able to be agile.
Chloe Addis (09:42)
Yeah, there’s so many different things in that. I think what you’re saying again, super relatable, like so many teams and know, sales and marketing teams trying to work together are gonna be facing this same type of thing. Like your work, it’s the alignment of those goals, isn’t it? And really the outcome. So instead of saying, I wanna be focused on number of MQLs, which is like you said, perfectly acceptable part of marketing.
Lindsay O’Brien (10:10)
Yes.
Chloe Addis (10:10)
If
you’re optimising just purely for that, you’re optimising against a number that isn’t necessarily translating.
Lindsay O’Brien (10:17)
Uh-huh.
Chloe Addis (10:17)
So to bring it all back sounds perfect, like, you know, it sounds very pragmatic, like the approach and, you know, you’ve got a spreadsheet with all of the numbers in it. And as long as you’re kind of tracking along there, then you know how you got there. But also exactly as you said, that it can show you the gaps, the holes and okay, we…
that month, it didn’t quite align, but then there was lots of close lost or we, know, people that didn’t respond, et cetera, to what we thought they were going to. So where can we help optimize that in the funnel and help out? It’s a really, I really value that type of thinking because it’s very simple. Like it’s
Lindsay O’Brien (10:58)
Mm-hmm.
Chloe Addis (10:59)
clear. And we often as marketers overcomplicate things so much that doesn’t need to be overcomplicated.
Lindsay O’Brien (11:08)
Yeah.
I think we over
Chloe Addis (11:09)
but I
Lindsay O’Brien (11:10)
we the we tried to fix just focusing on the lead number, but
Chloe Addis (11:15)
Yeah.
Lindsay O’Brien (11:16)
over focusing on marketing sourced revenue and pipeline.
Chloe Addis (11:20)
Yes, yeah, yeah, yeah.
Lindsay O’Brien (11:22)
And they’re just we just need to find a balance and we don’t have to go to the extremes. Like
Chloe Addis (11:26)
Yeah.
Lindsay O’Brien (11:27)
and treating marketing and sales as a true team and go to market function, that’s where
That’s where the magic happens. It just we have to get out of this attribution war that we w we try to get out of it and it just keeps pulling us back in.
Chloe Addis (11:47)
Yeah, yeah. And it’s understandable, isn’t it? Like at the end of the day, we are part of that, like that revenue team and you want to be able to say, that we were, we were involved in this, this number and how many like that were passed to sales, that converted. But it is really difficult, as you say, like, you know, you’ve got the, the leads at the beginning of their journey and you’ve nurtured and whatever else you’ve done that you want to.
and the need to explain and demonstrate the marketing influence, but then you’ve handed that across and you’ve got no control over the rest of that conversation or the rest of that cycle.
Lindsay O’Brien (12:25)
Yeah, it’s it’s very
tricky. It’s a high trust situation and that’s why it’s been so difficult.
Chloe Addis (12:34)
Yeah,
yeah, but yeah, there’s a lot to be said, I guess, for for trust in that in that relationship. But no, fantastic, fantastic answer. And I think a lot more people should be focusing on that area of like bringing sales and marketing teams together on the same page, which you sound like you’ve quite literally done on the same spreadsheet.
Lindsay O’Brien (12:55)
Yeah. Yeah. That’s
a good point. Yeah. I’m n I have not thought of it that way, but yes, that’s kind of our our source of truth, at least as we are we’re a fairly new company. We
Chloe Addis (13:05)
Yeah.
Lindsay O’Brien (13:08)
are still figuring out what our days and cycle and the conversion rates are. So we had to start somewhere. There had to be a baseline or a target to figure out what we anticipate and then
As we go through this quarter, we’ll update those numbers as we
Chloe Addis (13:28)
Yeah,
Lindsay O’Brien (13:29)
see things change.
Chloe Addis (13:30)
yeah, it’s very logical. It’s a very calculated approach, which is and then, you know, as time moves forward and you can adopt and change and optimize.
Lindsay O’Brien (13:42)
Yeah.
Chloe Addis (13:43)
Yeah, it sounds clear. It’s very, very clear. I love this. Like the foresight on it as well as going to be able to use that as a document that you can look back on and say, well, we changed it when that happened. So.
Lindsay O’Brien (13:56)
Yeah.
Chloe Addis (13:57)
Yeah, sounds perfect. So what shift are you seeing in how B2B buyers are behaving right now?
Lindsay O’Brien (14:06)
Think that word of mouth has ever been more important. I there’s so much information there you can go just about anywhere for information. And it but it’s really hard to figure out what’s what’s true and what is just content creation from those companies that are showing up.
Chloe Addis (14:32)
Yeah.
Lindsay O’Brien (14:34)
And
I think a lot of people are turning more to their own communities and networks to
Chloe Addis (14:40)
Mm-hmm.
Lindsay O’Brien (14:40)
understand what what people like them are actually doing and where their time should be focused. Because with the amount of information there’s there’s so many rabbit holes that you can go down that you’re you’re like I and by the end of it, you just don’t know what what is true, where you should be focused, what’s the right solution for you. And I
I’m just seeing more and more people go directly to a peer and just have that conversation about I’m having this problem, how are you solving it?
Chloe Addis (15:17)
Yeah, absolutely. I think that’s, it’s also really interesting from some coming from somebody who works closely with AI and adopting it and kind of getting it within the organisations and within the fabric of how people work to
Lindsay O’Brien (15:36)
Mm-hmm.
Chloe Addis (15:37)
recognise the other side of it. And I think that that does come up in conversations a lot is kind of, and even just in working.
And being a marketer yourself to be like, okay, well, what content are we developing? hang on. That’s the same. Like, you know, it’s, it’s AI has been the great leveler of everyone having the
Lindsay O’Brien (15:57)
Yes.
Chloe Addis (15:57)
same content and the contribution to.
Lindsay O’Brien (16:01)
Everyone
everyone can produce the content and and
Chloe Addis (16:04)
Mm, yeah.
Lindsay O’Brien (16:07)
case studies are great, review sites are great, but nothing beats getting on the phone, seeing someone at an event, and
Chloe Addis (16:15)
Mm-hmm.
Lindsay O’Brien (16:16)
having their peer say, This is the challenge we were trying to solve and this is what we did, and having
Chloe Addis (16:22)
Yeah.
Lindsay O’Brien (16:23)
your company be that the part of that conversation. There’s nothing more valuable.
Chloe Addis (16:30)
Yeah. Social proof, isn’t it? It does come back as I’m kind of finding having a lot of these, these conversations, it comes back to kind of these more traditional marketing values. They’ve kind of resurfaced again in the last kind of, I suppose, as the adoption of AI has come up in these last kind of couple of years, it’s all just getting more and more prominent that it’s like trust relationships. Like you said, the social proof, but in ways that are
kind of expressed directly, if you know what mean.
Lindsay O’Brien (17:02)
Yeah, it’s the fashion. Everything comes style eventually if you just wait long enough. But
yeah, I think everyone’s just kind of craving that what does the actual human think? How are you solving the problem?
Chloe Addis (17:16)
Yeah. Yeah.
Lindsay O’Brien (17:18)
And not to say that people aren’t using AI and traditional
Chloe Addis (17:22)
Mm.
Lindsay O’Brien (17:23)
search to find some answers for themselves.
Chloe Addis (17:26)
Yeah.
Lindsay O’Brien (17:31)
But when it comes to the final decision, maybe they’ve shortlisted some some different solutions or vendors. But in the end, if your company comes up from a trusted network, you’re in.
Chloe Addis (17:46)
Yeah, 100%. So what is a strategic bet you think more marketing leaders will need to make over the next couple of years?
Lindsay O’Brien (17:57)
Yeah, I think it goes with the word of mouth. I in person. that’s how I think we will truly combat this all of the content, all of the AI search and everything that we’re we’re consuming, it’s going to bring us back to connecting with each other, which I love.
I think that’s that’s the whole point of marketing is to actually make those connections. And I know for us specifically, we’re looking at a lot of different speaking engagements and sponsoring events, but not necessarily with a booth, but more like getting creative with different on-site activations, whether that’s a a networking opportunity or an activity.
Just something again that we bring people together because we we’ve kind of strayed from that with our all of the digital opportunities. And now I’m I’m really loving that we’re bringing it back to just being humans together.
Chloe Addis (19:06)
Yeah, it’s the community piece as well, isn’t it? It’s having that, but in a way that, I mean, a lot of brands, big and small, especially from my side of the technology, B2B side, struggle with creating their own community. But I don’t necessarily think that it has to be, like you don’t necessarily have to have that kind of ownership of it, but being present in…
communities exist, like we’ve mentioned before,
Lindsay O’Brien (19:37)
Mm-hmm.
Chloe Addis (19:38)
know, ones that you just have to be present in them and kind of contributing in that way.
Lindsay O’Brien (19:45)
Yeah.
And I and just going back to the word of mouth, like
Chloe Addis (19:50)
Okay.
Lindsay O’Brien (19:51)
finding those communities for yourself.
Chloe Addis (19:54)
Yeah.
Lindsay O’Brien (19:54)
And then if you’re marketing to those communities, like finding ways to partner with them so you can get more access and at least an understanding of who you’re actually marketing to is just so valuable.
Chloe Addis (20:09)
Yeah, absolutely. Especially, like you said, it’s the ones that are trusted and they kind of stand out for themselves, don’t they? And people naturally will fall across and come upon them. Yeah,
Lindsay O’Brien (20:23)
Yeah.
Chloe Addis (20:24)
so that’s, yeah, definitely a key part of the strategy now in that way that kind of…
will be, I mean, the whole awareness piece is becoming, you know, goes hand in hand with word of mouth, but it’s almost throughout the funnel, isn’t it, like having that influence of relationships throughout.
Lindsay O’Brien (20:45)
Yeah, communities have just become a another channel for us
Chloe Addis (20:48)
Yeah.
Lindsay O’Brien (20:48)
to find that really persona dense population that you’re looking for. So if you can find a community that has your ICP, even better. Because that if you can get into that trusted network and get people
Chloe Addis (21:03)
Yeah.
Lindsay O’Brien (21:04)
trusting you and talking about you, that’s the the same as if you were at an event or an in-person.
activity or activation that’s just as valuable.
Chloe Addis (21:17)
Yeah, 100%. I think that’s again, it comes back to the to these age old principles of be where they are at, you know, like be where they’re kind of consuming looking for that
information,
Lindsay O’Brien (21:28)
Yeah.
Chloe Addis (21:29)
but they’re going to be receptive to it as well because they’re in that right environment. It’s extremely valuable. So what do you think? So this is about kind of we’ve been talking a lot about what we think where the focus should be. But what do you think the marketers are?
currently still doing or have kind of just repeated just because it’s part of the practice that you think actually we should no longer be doing.
Lindsay O’Brien (21:56)
Yeah, so coming from content marketing, I and maybe I’m biased, but the I I really believe if you don’t have content, you can’t possibly have any marketing going on because they just go hand in hand.
Chloe Addis (22:12)
Yeah.
Lindsay O’Brien (22:12)
But I think where we’ve we sometimes forget is a content strategy.
is nothing without a distribution strategy. So
Chloe Addis (22:22)
Yeah.
Lindsay O’Brien (22:23)
if we don’t have an idea of how this content is going to not only get to the people that we need to read it or skip it, because let’s be honest, no one’s no one’s
Chloe Addis (22:30)
Mm-hmm. Yeah.
Lindsay O’Brien (22:34)
reading your full report. They’re looking at the highlights and the headlines. But it it’s also just as important to make sure that it’s crawlable, scannable from AI and search. It needs to be discoverable.
So and if that means that one piece of that is gated, so
Chloe Addis (22:54)
Mm-hmm.
Lindsay O’Brien (22:54)
be it. I I I’m really pushing toward nothing being gated unless it absolutely has to be. But how do we repurpose that content to different formats and different channels where it can’t be discovered? So
Chloe Addis (23:11)
Mm-hmm.
Lindsay O’Brien (23:12)
that’s that’s something where you know whenever you
Either an early marketer at a company, first marketer, or you just have someone who’s, you know, lived through the 2000s and gating was everything. Like
Chloe Addis (23:27)
Yeah.
Lindsay O’Brien (23:28)
sales obviously wants the leads, but
Chloe Addis (23:30)
Mm-hmm.
Lindsay O’Brien (23:31)
if people don’t get the value before they give their information, they’re either going to give you fake information or they’re just gonna say, forget it. I don’t, I don’t actually care that much.
Chloe Addis (23:45)
Absolutely. mean, everything has its place, doesn’t it? know, it depends what the goal of that specific part of the marketing is. And like you said, kind of making sure that it is available and readable, or like they’ve already got that trust built up before you’re asking for something else. Exactly that. Do you think in terms of, I mean, from your background as content marketing, is there a rule of
as to how, as to like before you even create a piece of content, to what, you know, knowing what you’re going to achieve from it, how much you’re going to get out of it. Do you have anything that kind of guides that for you?
Lindsay O’Brien (24:28)
Yeah, I think it’s whenever I I always like to put together a content brief before
Chloe Addis (24:35)
Mm-hmm.
Lindsay O’Brien (24:36)
anything that outlines, you know, the who it’s for, like why they should care and what they’re getting out of it. And if you can’t answer what they get out of it or if you’re getting more out of it than they are, it’s probably not w worth it. Like we all
Chloe Addis (24:53)
Hehehehehe
Lindsay O’Brien (24:54)
know the buyer’s guides, the ultimate buyer guides.
Chloe Addis (24:57)
with
you.
Lindsay O’Brien (24:58)
That were really just it promotional pieces. It wasn’t even in disguise. It w it was always
Chloe Addis (25:01)
Yep.
Lindsay O’Brien (25:05)
your solution was best and here’s why. And those served their purpose for a time. But
Chloe Addis (25:12)
Mm-hmm.
Lindsay O’Brien (25:12)
I think those and the other pay to play third party reports where you get your your business
Chloe Addis (25:19)
Yeah.
Lindsay O’Brien (25:19)
in a in a in a report, it those only go so far now. So it’s just I think
One of marketing’s most important things is protecting the time and energy we’re asking of our audience.
Chloe Addis (25:38)
Mm-hmm.
Lindsay O’Brien (25:38)
We need to be respectful of that because people it they have so much to do at work. And then they also have lives. If
Chloe Addis (25:47)
Yeah.
Lindsay O’Brien (25:47)
if we can’t justify why they should spend that time with us, then we shouldn’t be doing it.
Chloe Addis (25:54)
Yeah, that’s like so important, isn’t it? It’s the value exchange of what we’re putting
Lindsay O’Brien (26:00)
Yeah.
Chloe Addis (26:00)
in and giving out as to what we’re expecting from them. If we’re helping them with a bit of research, then that needs to be at a level of, well, we’re giving it to you to provide, to start a relationship.
again, that’s kind of all coming back to developing the trust and adding that in there. that’s a really great rule of thumb as to that’s the underlying piece, remembering what you’re giving and why they should want to read it,
And on the wider…
subject of it being content that drives everything. And we were like, yeah, completely agree with that too.
Lindsay O’Brien (26:41)
Yeah, I you the you
physically, digitally cannot have marketing
Chloe Addis (26:48)
Wee.
Lindsay O’Brien (26:49)
without content. So it it’s just thinking through how that content actually gets to the person and
Chloe Addis (26:58)
Mm-hmm.
Lindsay O’Brien (26:59)
how you can articulate that message in multiple formats and channels so that
Chloe Addis (27:05)
Yeah.
Lindsay O’Brien (27:06)
it’s it’s always
resonating and and reaching them in in a similar way, even if it’s a different format.
Chloe Addis (27:15)
Yeah, a hundred percent. think that, and that goes back to what you were saying about these ultimate guides and they have become a lot more, you know, there’s, there’s a lot more comparison available. So you can’t just say, well, we’re the best. So obviously by our thing, like it’s going to be, you know, there’s a, there’s, it is a bit more open and honest and truthful because it’s more visible and searchable by AI, but therefore, you know, hopefully that, that, contributes to the.
sifting out and finding real information, building trust, et cetera.
Lindsay O’Brien (27:46)
Mm-hmm.
Chloe Addis (27:47)
All goes hand in hand in the end, doesn’t it?
Lindsay O’Brien (27:50)
That’s right.
Chloe Addis (27:50)
So what type of investment would you think marketers should be protecting right now if budgets are tightened?
Lindsay O’Brien (27:59)
So
it might be not what people would think. At least I I would say headcount and learning and development. So
Chloe Addis (28:07)
Okay.
Lindsay O’Brien (28:10)
with with AI, we know teams are not as big. We don’t need
Chloe Addis (28:15)
Mm-hmm.
Lindsay O’Brien (28:16)
as many people to do the same amount of work. but we also need to make sure we’re always upskilling and we’re learning.
so that the quality of work stays the same even if we have fewer people. And
Chloe Addis (28:31)
Mm-hmm.
Lindsay O’Brien (28:33)
w you know, all of the headlines that we’re seeing of all of these AI-specific layoffs, I don’t totally buy. I think there’s in some cases I’m sure that that’s somewhat true.
Chloe Addis (28:50)
Yeah.
Lindsay O’Brien (28:51)
But you’re not replacing an entire function with AI agents.
Chloe Addis (28:55)
Yeah.
Lindsay O’Brien (28:56)
The the people with the expertise
Chloe Addis (28:59)
Mm-hmm.
Lindsay O’Brien (29:01)
are what make everything really powerful and impactful. And think about marketing. You know, if you have someone who’s had years of experience in marketing and you give them AI, they’re unstoppable. But if you give someone
Who it has never been in marketing, whether they’re just coming into the workforce or they’re coming from a different function, and you give them AI, we’ve talked about like that level set that AI is able, you know, everyone can kind of participate in other functions, but that doesn’t make them an expert in it. So
Chloe Addis (29:38)
Mm-hmm.
Lindsay O’Brien (29:39)
keeping that expertise and the creativity for the human.
Chloe Addis (29:45)
Mm-hmm.
Lindsay O’Brien (29:45)
And then empowering them with AI and you know, who who knows what other tools are going to come out and in the next five to ten years, but
Chloe Addis (29:55)
Yeah.
Lindsay O’Brien (29:56)
continuing that learning while maintaining the expertise is where I think we really need to focus.
Chloe Addis (30:03)
Yeah, that’s, that is really interesting.
There’s a, there’s a content person for a reason that specializes and has their expertise. so it’s like efficiencies will have been made, but like you said, you’re, you’re, really investing in those people. But I think your point of it’s not just protect the people, it’s protect the people and their future with the learning and development. to
Lindsay O’Brien (30:26)
Yeah. Yeah.
Chloe Addis (30:28)
that point, you don’t know what’s going to happen.
We don’t really know what’s going to happen next year. AI is, and all technology, suppose, is developing so quickly that, yeah, we don’t know what kind of skills we’re going to have to have, but
Lindsay O’Brien (30:43)
No, no.
Chloe Addis (30:44)
you kind of are relying a little bit on that expertise and experience that, okay, whatever changes, we’ll all sort of be able to adapt as long as we’ve got the time and focus to be able to relearn and be agile and…
Lindsay O’Brien (30:59)
Yeah.
Chloe Addis (31:00)
and that kind of thing.
Lindsay O’Brien (31:01)
Yeah, we have to keep the curiosity and wanting to learn more because I do foresee you know, as we continue down this path and we need fewer people, you the specialization, you’ll always need
someone specialized for certain things, but
Chloe Addis (31:21)
Yeah.
Lindsay O’Brien (31:22)
that doesn’t mean you’ll necessarily have them in-house. Like they might be
Chloe Addis (31:25)
Mm.
Lindsay O’Brien (31:25)
a contractor instead. So I I think there’s still room for everyone. It’s just some people, if you’re in-house, will specifically need to learn
how to do multiple functions or at least lead multiple functions. And maybe
Chloe Addis (31:42)
Mm-hmm.
Lindsay O’Brien (31:43)
you have a contractor who comes in with that deep expertise and experience to do something. Like for me, that’s paid ads. Like d you don’t want me I I can generally give you a strategy, but you don’t want me bidding on certain things. I I will need that expertise. so that’s
Yeah,
so I d I don’t think I I don’t want to scare people and say, you know,
Chloe Addis (32:10)
Amen.
Lindsay O’Brien (32:10)
fewer people on a team and, you know, limited jobs. we are seeing some of that right now, but my hope is if we can all keep our curiosity and keep learning and companies continue investing in their people, that that will be that will eventually even out.
Chloe Addis (32:30)
Yeah. it’s a core part of marketing, isn’t it? I think it’s like that curiosity, the creativity, the ability to have an idea and test it as long as it’s pragmatic and thought through and, and it has a place.
Lindsay O’Brien (32:47)
Yeah.
Chloe Addis (32:47)
and it’s, then it’s kind of what, what remains like core part of, being able to reach your market and understand is that things change and we adapt with that. And, you know, we’re kind of.
in a lot of businesses, marketing is the most agile function to kind of go out and test things and be talking to the audience, because that’s what’s informing the product or service at the end of the day.
Lindsay O’Brien (33:14)
Yeah, absolutely.
Chloe Addis (33:17)
So what is one thing you wish you could change about marketing if you could?
Lindsay O’Brien (33:22)
If I could change anything, I would make it so budget was not a thing and you can run all of the creative experiments without
Chloe Addis (33:32)
you
Lindsay O’Brien (33:33)
having to worry if you’re blowing your budget. I think there’s also a special kind of creativity with having those restraints and guardrails
Chloe Addis (33:43)
Mm-hmm.
Lindsay O’Brien (33:44)
of saying, okay, well, this is all I’ve got
Chloe Addis (33:46)
Mm-hmm.
Lindsay O’Brien (33:47)
and let’s figure out what I can do with this budget, but
was it would just be so incredible to say
Chloe Addis (33:53)
you
Lindsay O’Brien (33:54)
money is no object, let’s let’s go with whatever we can envision and imagine. And I that’s where that creativity comes back. And that’s where you you have to have those people in seat because they’re the ones with the unique and creative ideas. And
Chloe Addis (34:12)
Yeah.
Lindsay O’Brien (34:13)
it’s just synthesizing that right now of all
Chloe Addis (34:15)
You
Lindsay O’Brien (34:16)
all that it knows. So yeah, no budget. I just
Chloe Addis (34:20)
I love that answer. Nobody has said that and I think it’s the best.
Lindsay O’Brien (34:23)
Yeah. you know, those
the brand experiments that you just want to run that you’re like, I think this could be really cool. I don’t know
Chloe Addis (34:31)
Yeah. Yeah.
Lindsay O’Brien (34:34)
how we’ll measure it, and it’s kind of expensive. Th those
Chloe Addis (34:37)
Yeah.
Lindsay O’Brien (34:38)
would be the like can you imagine how fun it would be to be in that world and see all of those creative experiments running? Like as a consumer or the audience.
Chloe Addis (34:46)
Yeah, just run them because. Yeah.
Lindsay O’Brien (34:52)
how fun that would be to be marketed to without the worry of having to justify the ROI on the back end.
Chloe Addis (35:00)
Yeah,
for the love of marketing and for the joy
Lindsay O’Brien (35:04)
Yeah.
Chloe Addis (35:05)
of being able to set something up that’s reaching the right audience and that’s doing the right thing. Yeah.
Lindsay O’Brien (35:09)
Yeah, it just and maybe and
maybe it fails and you go, Okay, well that’s fine because budget isn’t a thing. Yeah.
Chloe Addis (35:15)
Because we’re doing what we love, it’s fine.
Perfect, that’s fantastic, fabulous answer. So yeah, that’s bringing us to kind of the end of the questions of the pod. And then we just kind of go on to who would you recommend that we try and get on the pod next?
Lindsay O’Brien (35:34)
Yeah. I think Colin Kendall comes to mind. He
Chloe Addis (35:40)
Okay.
Lindsay O’Brien (35:41)
is the CMO at S H and C S C and H, sorry. Too many letters.
Chloe Addis (35:48)
You
Lindsay O’Brien (35:51)
yeah, he’s he’s really great. He runs a a team, they’re doing a lot of cool things and he’s been there for a while.
Chloe Addis (36:00)
Okay.
Lindsay O’Brien (36:01)
can’t remember how many years, but you know, in this age it feels like everyone moves jobs every,
Chloe Addis (36:08)
Yeah.
Lindsay O’Brien (36:09)
you know, one to three years, depending on where
Chloe Addis (36:10)
Yeah.
Lindsay O’Brien (36:11)
you are. And he’s been there for a while and I I think he’s just doing really great stuff.
Chloe Addis (36:17)
cool, we love an industry vet and you know people that are kind of doing what they love in the in for the long term. Fantastic, I can’t wait to reach out to him and whether it’s for him or for whoever happens to be our next guest, what question do think we should ask them?
Lindsay O’Brien (36:40)
How
do you think you will reshape your marketing organization based on buyer behavior and AI in the next five years?
Chloe Addis (36:53)
That’s a good question, that really is a good question. And I’m sure one that many people are reassessing all the time, like five years is a long time, isn’t it? Like we’re saying.
Lindsay O’Brien (37:04)
And AI, yeah.
Chloe Addis (37:06)
Yeah, yeah.
Lindsay O’Brien (37:08)
I started just testing it out in 2023 and you know I would have never let it run as much as I let it run right now. And it’s just
Chloe Addis (37:20)
Yeah.
Lindsay O’Brien (37:20)
gotten so advanced over the the past three years that I I can’t imagine what the next five will look like.
Chloe Addis (37:29)
Yeah, 100%. And before I leave you, thank you so much. You’ve answered all my questions beautifully. But how, from your role in and what you do around AI, is there
Lindsay O’Brien (37:42)
Mm-hmm.
Chloe Addis (37:42)
any kind of final thoughts? I know this is a bit of a broader question, but around kind of how people are implementing AI, whether it is maybe like a kind of number one practical.
golden rule that you follow or anything like that? Is there anything that you can share
Lindsay O’Brien (37:58)
Yeah.
Chloe Addis (37:59)
with me?
Lindsay O’Brien (38:00)
I think for from an individual standpoint, it is really critical to if you haven’t started or you you’re not really sure where it could be most impactful, pick one workflow that you do that’s either
recurring regularly or that takes a lot of time and just outline those steps. What are all of the steps that you take to complete that? How long
Chloe Addis (38:33)
Mm-hmm.
Lindsay O’Brien (38:34)
does it take you? What are the tools that you use to do those tasks?
Chloe Addis (38:40)
Mm-hmm.
Lindsay O’Brien (38:41)
And then identify where AI could help you. Or if you’re if you’re really early, test AI out for every single step.
Chloe Addis (38:51)
Mm-hmm.
Lindsay O’Brien (38:51)
And
It it’s not about the perfect prompt. If you’re looking for help prompting, ask AI itself, hey, this is my goal. Think think
Chloe Addis (38:59)
Yeah.
Lindsay O’Brien (39:00)
of it as if you’re writing a story: the who, what, when, where, why, how.
Chloe Addis (39:04)
Yeah.
Lindsay O’Brien (39:05)
Give AI as much context so it can help you write the prompt to complete that
Chloe Addis (39:10)
Mm-hmm.
Lindsay O’Brien (39:10)
task. And then as you get comfortable, then you can start.
with the integrations? What are the tools that are you’re using? Okay, let’s create those connectors between AI
Chloe Addis (39:20)
Yeah.
Lindsay O’Brien (39:21)
and those tools. Now can we automate any of these steps? Do I have to be a part of this step?
this is pretty low value. I could use my time somewhere else. So, from an individual standpoint, picking one workflow and just going all in on one is your best opportunity. If you’re looking for more of an organization-wide rollout
Chloe Addis (39:43)
Mm-hmm.
Lindsay O’Brien (39:44)
and strategy, having the leadership team be like the C-suite really drive this from the top.
Chloe Addis (39:54)
Mm-hmm.
Lindsay O’Brien (39:54)
People who see the leadership make this a priority, see them modeling it and tying it to actual business outcomes are going to be more likely to follow your lead. So if you’re in the C-suite, you should be the one making the impact. If you’re not part of that, who can you talk to to make this more of an organization-wide
Chloe Addis (40:19)
Mm-hmm.
Lindsay O’Brien (40:20)
initiative? Because
I especially from a marketing perspective, I don’t know of any company not asking marketers in the interview process how they’re using AI. And if your company’s completely banning it, you’re also you’re you’re going to have limited opportunities moving forward.
Chloe Addis (40:40)
Yeah, yeah, that’s true.
Lindsay O’Brien (40:42)
So it’s also looking out for yourself.
Chloe Addis (40:46)
Absolutely protecting, protecting that learning and development, it? And kind of growing that knowledge. Amazing, that was a really interesting answer. Thank you. And sorry for throwing it at you at the end.
Lindsay O’Brien (40:57)
Yeah.
Chloe Addis (40:58)
Thank you so much for coming on the pod. I’ve really enjoyed chatting to you. Can you tell everyone where they can find you?
Lindsay O’Brien (41:06)
Yeah, you can find me on LinkedIn. there are probably millions of Lindsay O’Brien’s, but if you look for Lindsay Kenders, K-E-N-D-E-R-S, that was my maiden name. So that’s where I’ll be.
Chloe Addis (41:20)
Fantastic,
amazing, thank you so much and we’ll
Lindsay O’Brien (41:23)
Yeah, thank you.
Chloe Addis (41:24)
take care, we’ll speak soon.
Lindsay O’Brien (41:25)
Thank you.
In this episode of B2B Marketers: Off The Record, Chloe Addis speaks with Lindsay O’Brien, Head of Marketing at Pragmatico, about how AI is reshaping marketing, why word of mouth and human connection are becoming increasingly important, and how marketing teams can balance commercial accountability with the freedom to focus on what will genuinely drive business growth.
Lindsay also shares a practical approach to AI adoption, arguing that the biggest opportunity isn’t simply using more AI tools, but identifying the right workflows, developing the skills of existing teams and using AI to amplify human expertise.
AI may make marketing faster and more efficient, but it also increases the importance of the things technology cannot easily replicate: expertise, creativity, judgement, trust and genuine human relationships.
As teams become leaner, marketers may need to broaden their capabilities while bringing in specialist expertise when required. The opportunity is not to replace experienced marketers with AI, but to give experienced, curious people the tools and development they need to become significantly more effective.
At the same time, marketers need to reconsider how they earn attention. When buyers can access almost unlimited content and information, simply producing more is not enough. Brands need to create something genuinely useful, distribute it effectively and become part of the trusted networks and communities buyers already rely upon.
For marketers wondering where to start with AI, Lindsay recommends choosing one recurring or time-consuming workflow and mapping it from beginning to end.
Break down every step, how long it takes and which tools are involved. Then test where AI can help. As confidence grows, look at connecting AI with the tools already being used and identify low-value steps that can be automated altogether.
At an organisational level, adoption needs to be driven from the top. When leaders visibly use AI, make it a priority and connect it to genuine business outcomes, employees are more likely to experiment and develop their own capabilities.
One of marketing’s responsibilities is to protect the time and attention it asks from its audience.
Whether creating content, running an event or developing a campaign, marketers should be able to answer a simple question: is what we’re asking the audience to give us worth what they receive in return?
That principle connects many of the themes throughout the conversation, from ungating useful content and investing in communities to using AI to improve marketing without sacrificing the human expertise and relationships that make it valuable.
Lindsay has spent 14 years as the first or early marketing hire at B2B companies, building from scratch and owning the full funnel — wearing every hat from content and product marketing to demand and RevOps. Outside of work, she has taught AI workshops for marketing and sales teams as well as parents and families learning to navigate it.
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