Episode 1

How CMOs Go Wrong Talking To Their Boards About AI… And How To Get It Right

Joe Sawyer, CMO of Flashpoint, joins Erica to share his experience and advice for how CMOs can talk with their Boards about their AI initiatives and their ROI.

You'll hear about:

  • How getting the AI dialogue right with your Board can help you overcome some of the problematic ways that CMOs have communicated with Boards in the past
  • Anticipating the questions your Board will ask about your AI initiatives
  • How Joe narrowed down from 20+ potential AI use cases to the few to differentially invest in that would have profound value
  • Why CMOs should avoid name-dropping consultants and tools, since that reinforces the perception of marketing as a function focused on activity rather than outcomes
  • How Joe approached a presentation on AI in GTM to a group of PE portfolio company CEOs
  • How to embrace "productive disappointment"
  • What actually moves a team from AI-curious to AI-operational
  • A maturity model for assessing a potential new hire's fluency with AI

Some quotes:

  • "We tried to look at things through a different view, which was not just what are all the things we could be doing, but what would our board value most?"
  • "Take a step back and say, 'What are boards talking about with respect to AI when the CMO is not in the room?' Generally, I would argue they're talking about enterprise value and what's the impact of AI on the company's enterprise value. When you show up as the CMO, they're looking at the levers you control that positively impact the way AI can influence the company's enterprise value."
  • " CMOs can be high-fiving each other over their use cases, but boards are worried about enterprise value… and survival."

Bonus Playlist:

Joe is not only a seasoned CMO, he's a seasoned DJ! He's created a companion playlist on Spotify.

CMO's Essential Summer Playlist

AI disruption and board expectations getting you down? Ten songs to restore perspective, lower your blood pressure, and remind you that not every problem requires a framework

00:00 Show Intro and Theme

00:37 Meet Joe Sawyer

01:25 Fun Fact DJ Dreams

03:07 AI Journey to CEO Summit

05:21 Inbound Conversion Win

06:28 MQL Experiment Lessons

08:15 What CEOs Asked

09:08 What Boards Want

10:20 Inside vs Outside Voice

13:18 Board Perceptions and Budget

15:26 AI as CMO Opportunity

16:36 Driving Team Adoption

19:23 AI Maturity Framework

21:00 Hiring and AI Work Samples

23:07 Best Day Interview Question

24:33 Wrap Up and Outro

The Get is here to drive smart decisions around recruiting and leadership in B2B SaaS marketing. We explore the trends, tribulations, and triumphs of today’s top marketing leaders in B2B SaaS.

This season’s theme is focused on how AI is reshaping the CMO role: how you lead, how you hire, and how you get hired."

The Get’s host is Erica Seidel, who runs The Connective Good, an executive search practice with a hyper-focus on recruiting CMOs and VPs of Marketing, especially in B2B SaaS.

If you are looking to hire a CMO or VP of Marketing of the ‘make money’ variety, rather than the ‘make it pretty’ variety, contact Erica at erica@theconnectivegood.com. You can also follow Erica on LinkedIn or sign up for her newsletter at TheConnectiveGood.com.

The Get is produced by the team at Simpler Media Productions



This podcast uses the following third-party services for analysis:

OP3 - https://op3.dev/privacy
Transcript
Speaker:

Welcome to The Get, the podcast that's all about recruiting and

Speaker:

leadership in B2B SaaS marketing.

Speaker:

I'm your host, Erica Seidel.

Speaker:

This season, we're looking at how AI is reframing and reinventing the CMO role.

Speaker:

We will look at this from the perspective of recruiting, career

Speaker:

management, and leadership in the role.

Speaker:

Today, our focus is all about AI, marketing leadership, and the board.

Speaker:

How should you, as a CMO, talk to your board about AI?

Speaker:

How can you frame your reporting so that it's not just about what tools you're

Speaker:

using, but about actual impact and alignment with board-level priorities?

Speaker:

My guest today is Joe Sawyer.

Speaker:

Joe is CMO at Flashpoint, the leading company focused on

Speaker:

threat data and intelligence.

Speaker:

Flashpoint helps businesses and governments to confront

Speaker:

security and risk challenges and improve operational resilience.

Speaker:

Joe

Speaker:

previously held CMO roles at Mirakl and ReliaQuest.

Speaker:

He also has held marketing leadership roles for a bunch of companies in the

Speaker:

health tech space, and earlier in his career, he was a Forrester analyst.

Speaker:

I always learn from talking with Joe, and you will learn

Speaker:

from this conversation as well.

Speaker:

Joe, welcome to the show.

Speaker:

Thanks, Erica.

Speaker:

It's great to be here and to have two Forrester alums coming together.

Speaker:

You can always expect a strong discussion.

Speaker:

Yes, yes, I know.

Speaker:

We weren't there at the same time, I don't think, but- similar DNA.

Speaker:

The DNA goes deep, yeah.

Speaker:

Yes, absolutely.

Speaker:

So why don't we start with introductions.

Speaker:

Can you amplify my introduction and maybe share a fun fact about you

Speaker:

that would never appear on LinkedIn?

Speaker:

Sure.

Speaker:

I thought, in terms of introduction, you covered all the bases.

Speaker:

What I might add is I've probably taken an atypical path to the CMO seat coming as I

Speaker:

did through the world of industry analysts and then, some roles in sales and product.

Speaker:

So I got both the more strategic view, but the sense of looking at marketing

Speaker:

from other functions and seeing marketing at its best, and marketing

Speaker:

when it's creating challenges for other functions, or when it's not optimal.

Speaker:

That's been my story as I've focused on marketing-centered leadership roles where

Speaker:

these organizations, each of the ones that you named, Miracle,  ReliaQuest, they had

Speaker:

a really strong from to, where they were trying to get from one stage of growth or

Speaker:

one stage of their category to the next, and that's the kind of journey that an

Speaker:

ex-analyst can't help himself but love.

Speaker:

Yeah.

Speaker:

As far as a non-LinkedIn kind of personal, fact, I think, in my next

Speaker:

life, I'd like to come back as a DJ.

Speaker:

Over the years I've-- I'm super passionate about music.

Speaker:

Over the years I've acquired this broad, deep, sort of encyclopedic

Speaker:

knowledge of everything from the standard to the very unusual, and I

Speaker:

just love putting this stuff together.

Speaker:

So if you ever have a party and your DJ gets sick or something, you

Speaker:

can feel free to give me a call, and I can probably step right in.

Speaker:

That's awesome.

Speaker:

I can imagine that.

Speaker:

Yeah, you spinning the tunes.

Speaker:

This is good.

Speaker:

I wonder if your tastes are just as eclectic or more eclectic than mine,

Speaker:

'cause there's such a range of stuff.

Speaker:

Very eclectic.

Speaker:

Many decades, many genres.

Speaker:

Awesome.

Speaker:

I love how you've had different roles beyond marketing, because I think

Speaker:

that the strongest marketers are ones that can get out of marketing.

Speaker:

Hmm

Speaker:

You know, go sit in sales for a while, sit in product for a while,

Speaker:

and then come back to marketing.

Speaker:

I think that's really great experience from the people I've talked with.

Speaker:

Let's just jump into this.

Speaker:

You recently were the only CMO at a CEO summit of a major PE firm, invited to

Speaker:

talk about what you're doing with AI.

Speaker:

So you're kind of a poster child for the portfolio, evidently.

Speaker:

When you told me about this, I thought, "Oh, wow, I think a lot of people would

Speaker:

be curious to know about that journey."

Speaker:

What was the AI journey that led up to that presentation, and

Speaker:

what was that conversation like?

Speaker:

Can you bring us up to speed on the background there and the talk

Speaker:

that you gave at this CEO summit?

Speaker:

Yeah, absolutely.

Speaker:

I'll tell you a little bit about the journey that led up to that room.

Speaker:

About a year ago, we probably looked like most marketing

Speaker:

organizations when it comes to AI.

Speaker:

A lot of experimentation going on with the team, whether it was content

Speaker:

generation, product marketing, content creation, ideation of creative campaigns.

Speaker:

We were doing lots of things across the team, and that was great.

Speaker:

It was taking place at a time where I found that the noise within the industry

Speaker:

around AI was just becoming deafening and actually often quite distracting.

Speaker:

I remember, if you think back a year, I remember posts from CMOs

Speaker:

at the time saying, you know, product marketing is dead, content

Speaker:

marketing is dead, CMOs are toast.

Speaker:

Or on the reverse, we've bought these tools, we've hired these consultants, and

Speaker:

this is all well and good and probably very natural for a major transformation,

Speaker:

but it made me disoriented and I wanted to get our team back to a very clear

Speaker:

focus of how are we were gonna proceed.

Speaker:

Because we were never going to be doing the most things nor spending

Speaker:

the most money, so it became about how do we get the strongest focus.

Speaker:

So I got my team together at the time and we looked at-- We tried to

Speaker:

look at things through a different view, which was not just what are

Speaker:

all the things we should be doing, but what would our board value most?

Speaker:

How do we go back to the overall function and articulate a way forward that is

Speaker:

gonna be truly aligned so that we keep our cycles as focused as possible?

Speaker:

So, while we identified just shy of twenty use cases across product, corporate, and

Speaker:

revenue marketing that we felt could have truly profound value on the team, we also

Speaker:

came back saying the one place that we are going to differentially invest and

Speaker:

lean into is anything related to pipeline creation and pipeline acceleration.

Speaker:

Because at the end of the day, while AI is changing so much, our goals don't change.

Speaker:

That was where we really segmented the major areas of focus.

Speaker:

Then transitioning to the choices we made that led to that day in the room,

Speaker:

we also looked at what are the parts of the funnel that are most broken where

Speaker:

AI can help us solve problems that have never really had a perfect solution?

Speaker:

And that was inbound conversion.

Speaker:

At Flashpoint, the inbounds are about thirty percent of the net new business

Speaker:

pipeline of the entire company.

Speaker:

And while we were doing an okay job handling them, that was also probably

Speaker:

where we had the most inefficiency or lack of clarity in terms of

Speaker:

account ownership, account routing, follow-through, and advancement from

Speaker:

the stages that came from there.

Speaker:

So we decided to focus AI there first, and within about a quarter and a half

Speaker:

of a pilot focused on smoothing out that stage of the conversion cycle, we were

Speaker:

able to increase the conversion rate of our inbounds, the thirty percent of new

Speaker:

business pipeline, by eighty-nine percent.

Speaker:

And that had an overall positive pipeline impact of about six million, both in

Speaker:

sourced and influenced pipeline as a result of taking the inbound and what

Speaker:

ultimately, we can talk more about this, what ultimately was a change management

Speaker:

project first that also happened to be enabled by AI and also required

Speaker:

some new tooling and some workflows.

Speaker:

So that was part one.

Speaker:

Part two, which in some ways to me is the more interesting challenge

Speaker:

right now, is what we also tried with AI that didn't work, or that didn't

Speaker:

work yet in support of Pipe Create.

Speaker:

Once we start to see initial momentum on inbound conversions, we targeted

Speaker:

the next jump ball or the next thing that wasn't working well with a lot

Speaker:

of upside, which were engaged MQL.

Speaker:

People who do a bunch of things and through the intent that they demonstrate

Speaker:

would normally pop up on the radar screen of BDRs and reps for follow-up.

Speaker:

There we had a much bigger problem where only thirty-nine percent of

Speaker:

these people were ever getting followed up on, and usually the follow-up was

Speaker:

pretty… was not very robust, right?

Speaker:

But on the promising side, if we could get past that, they would convert at

Speaker:

three times the rate of the urgents.

Speaker:

So we actually, on that one, tried a much more, like a hard cut over to

Speaker:

AI, and we said, "Let's do all of this through AI." 'Cause speed to lead,

Speaker:

someone like that is never going to be the first priority of either a seller

Speaker:

or BDR, so let's let AI go for it.

Speaker:

The AI did a really good job of solving on the speed to lead front,

Speaker:

so we saw increased open rates.

Speaker:

We saw people engaging more, but they just didn't convert like we hoped.

Speaker:

We had a bit of a, I'd say, a productive disappointment there in Q1.

Speaker:

Q2 has been about a pilot that's focused on human in the loop, where we're

Speaker:

leveraging both AI and BDR together to do the things that they do best

Speaker:

to drive those incremental meetings.

Speaker:

Long story short, it was that journey from intention to win that

Speaker:

actually was very productive for the business and kind of a next frontier

Speaker:

that we're still figuring out.

Speaker:

That's what I focused on in the room that day.

Speaker:

That's great.

Speaker:

Thank you for sharing.

Speaker:

I love that.

Speaker:

Two things stick with me from that.

Speaker:

One is the kind of focus on focus as opposed to getting like, "Oh

Speaker:

my God, everything's changing so fast, and there's all these things

Speaker:

we could do." So I like that.

Speaker:

Also, I like how you're talking about productive disappointment.

Speaker:

That's cool.

Speaker:

I wonder, when you were doing this talk among the CEOs, where

Speaker:

were they leaning in the most?

Speaker:

Where did they get bored?

Speaker:

Were there any unexpected questions that came up in that meeting that you

Speaker:

think would be instructive for other CMOs going into similar situations?

Speaker:

Yeah, I think naturally where they leaned in and were asking questions was around

Speaker:

how relevant is this to me and my company?

Speaker:

Like, let me understand better your previous go-to-market model.

Speaker:

Let me see if I can compare it to the way we do things, and then as

Speaker:

a result, what steps would we take next to move forward with this?

Speaker:

Where they didn't go, I'd say almost like an opposite to conversations that

Speaker:

I would have with other CMOs, which makes sense, is I didn't really get

Speaker:

asked about which vendors did you use?

Speaker:

What parts of the solution were people versus what parts were tooling?

Speaker:

So the how they didn't really care a whole lot about.

Speaker:

They cared more about what could we do, what are the next steps, and what

Speaker:

kinds of outcomes could we expect?

Speaker:

Yeah, the business context and the outcomes.

Speaker:

Okay.

Speaker:

Yep.

Speaker:

Great.

Speaker:

I did, in a previous season of The Get, you're familiar with this, I did this

Speaker:

whole series on how CMOs and boards should interact and how CMOs can get on

Speaker:

boards and what boards are looking for.

Speaker:

My next question is around that with a focus on AI.

Speaker:

In your view, what are boards looking for from marketing leaders when

Speaker:

it comes to AI and AI adoption?

Speaker:

Can you hit that head-on?

Speaker:

Yeah, absolutely.

Speaker:

To answer that, it helps to actually take a step back and say, what are

Speaker:

boards talking about with respect to AI when the CMO is not in the room?

Speaker:

Generally, I would argue they're talking about enterprise value

Speaker:

and what's the impact of AI on the company's enterprise value.

Speaker:

When you show up as the CMO, they're looking at you, putting on the helmet and

Speaker:

looking at you through the lens of what are the levers that this person controls

Speaker:

that positively impact the way AI can influence the company's enterprise value.

Speaker:

So if you're, you know, in your marketing, your main levers are going

Speaker:

to be growth, EBITDA to some extent, and then, areas of risk or what are

Speaker:

things that more holistically that a CMO might see first that no one else

Speaker:

sees that they should know as they're either, feeling particularly robust

Speaker:

and happy or insecure in a given day about the impact of AI on the business.

Speaker:

Okay.

Speaker:

Yeah.

Speaker:

That's great.

Speaker:

Thank you.

Speaker:

How do you think this is different?

Speaker:

You've suggested it a little bit so far.

Speaker:

How is it different from the way marketing leaders, who are not thinking

Speaker:

about it this way are thinking and talking about what they're doing?

Speaker:

We talked before about how CMOs can be high-fiving each other

Speaker:

over these use cases, but boards are worried about survival.

Speaker:

Can you more specifically contrast what you think CMOs should be doing with

Speaker:

boards versus the errors of the ways when bringing AI initiatives to the board?

Speaker:

Yeah, I think there's some disconnect that's generally related

Speaker:

to contact switching, right?

Speaker:

Here in the CMO profession, change is happening so quickly, the role is

Speaker:

already so challenging that there are lots of positive networks and dialogues

Speaker:

forming around like what are you doing?

Speaker:

What's the activity?

Speaker:

What are the use cases?

Speaker:

What are the vendors?

Speaker:

Are they good or are they bad?

Speaker:

And this is also bigger than the CMO role, which I think anybody in any kind

Speaker:

of C-level role right now is always afraid of falling behind and wanting to show

Speaker:

that they're staying ahead of things.

Speaker:

So how do you do that?

Speaker:

You do that by keeping the best grasp you can on all of these things that are

Speaker:

going on that you could be implementing.

Speaker:

So when I go to CMO dinners or in CMO networking events, it's very beneficial

Speaker:

in that context, but people will generally talk about, we bought Profound, we

Speaker:

bought Qualified, we looked at Brand Light, we did these things or I've-- you

Speaker:

know, we've got these agentic workflows that are gonna understand from GEO what

Speaker:

we need to optimize and then produce the content and post the content.

Speaker:

These are important and it's helpful for CMOs to talk about this with other CMOs.

Speaker:

But I think it reminds me a little bit of when that kind of dialogue is shared with

Speaker:

the board, I think we start to get into some of the problematic ways that CMOs

Speaker:

have communicated with boards in the past.

Speaker:

There's a… I think having young children, I always have top of mind

Speaker:

the notion of an inside voice in the marketing profession and an outside voice.

Speaker:

So, what are the things that matter and have value, but they are relevant within

Speaker:

the context of a marketing or maybe, at its broadest level, a go-to-market team

Speaker:

versus ensuring that you're translating those things back to the board.

Speaker:

A few months ago, I was in a super productive CMO dinner.

Speaker:

A great room full of CMOs, but like, "What is the business value?" was the

Speaker:

last question that the group discussed.

Speaker:

Before that, it was all favorite consultants, favorite

Speaker:

vendors, things of that nature.

Speaker:

So I think that's where the major opportunity is for CMOs to make sure that

Speaker:

we're separating the things that we need to keep us, ourselves feeling like we're

Speaker:

ahead of the curve as professionals, the things that we're trying so that

Speaker:

we're trying to keep our organizations ahead of the curve, and then going

Speaker:

back to again, what does the board care about when you're not in the room?

Speaker:

And then how does that influence your outside voice for when you walk into it?

Speaker:

I like this idea of an inside voice and an outside voice.

Speaker:

It's kind of like you have to be a big context switcher.

Speaker:

Or, it's almost like code switching.

Speaker:

Your marketing versus business talk.

Speaker:

I think that's the biggest challenge that people have, especially when

Speaker:

they're taking their first CMO role, that they've been used to reporting to CMOs,

Speaker:

and so they talk in marketing speak.

Speaker:

And then when they go and interview with a CEO or board member, investor, whatever,

Speaker:

the conversation is very, very different.

Speaker:

And so developing that inside versus outside voice, very early,

Speaker:

early and often, is a good idea.

Speaker:

Yeah.

Speaker:

Interesting.

Speaker:

So Joe, any other advice for CMOs who need help communicating

Speaker:

impact with AI to their boards?

Speaker:

Yeah, I think there's one other topic that's really important to surface, which

Speaker:

is what is your board's preconception about the impact of AI on marketing?

Speaker:

This is another thing that comes up.

Speaker:

You hear all kinds of crazy stories when you get together in rooms full of

Speaker:

CMOs about, boards who have a latent opinion that AI is a big, replacement

Speaker:

and cost takeout vehicle for marketing, or is it more of a force multiplier?

Speaker:

Even if it's not coming up, even if it's not part of the time you're

Speaker:

allocated in a board meeting, I believe it's really important to force the

Speaker:

conversation through your point of view and make that argument and embed it

Speaker:

in other reporting that you're doing.

Speaker:

A few months back, as part of talking about the marketing plan overall for the

Speaker:

year, the way I grounded it was, given our target growth rate for 2026, given

Speaker:

the investment levels that we're looking at in order to get there, consulting

Speaker:

benchmarks from other similar companies and PEs like ours, AI is going to serve

Speaker:

for us in 2026 as a lever for de-risking plan and for force multiplication.

Speaker:

Others may have that opportunity, I think maybe more in the VC space,

Speaker:

you might get proactively asked to opine on the future of AI and how it

Speaker:

transforms the marketing organization.

Speaker:

But I strongly recommend making sure that you either state it explicitly or find out

Speaker:

explicitly so that it's not coming to you indirectly through feedback on initiatives

Speaker:

and feedback on other investments because there is a perception there.

Speaker:

Gotta find out what it is.

Speaker:

That's interesting.

Speaker:

So it's like, the board is thinking about something that they might

Speaker:

not be asking about, but if they're thinking so much about that, it

Speaker:

could come out sideways in how they react to what you're talking about.

Speaker:

Yeah.

Speaker:

There's one story, a CMO I know whose CFO had run a bunch of budgeting for

Speaker:

2026 through ChatGPT and who came back pushing as to why the marketing org

Speaker:

couldn't cut 30% out of their budget because, look, ChatGPT said that all

Speaker:

these different changes were possible.

Speaker:

So, you know, there's no safe bet in life, but it is best to try to

Speaker:

get ahead of that and shape the organization's belief to how you see

Speaker:

it fitting in and what you think is the appropriate outcome of AI in marketing.

Speaker:

Yeah.

Speaker:

I'm wondering, like we talked about before, CMOs have traditionally sometimes

Speaker:

struggled to articulate the business impact of their work at a board level,

Speaker:

at a CEO level, just aside from AI.

Speaker:

Yeah

Speaker:

Do you think the ability to talk about AI in the way that you're talking about

Speaker:

it today gives an opportunity for CMOs who have struggled in the past to leapfrog

Speaker:

forward and actually, I don't know, claim a bigger, I hate to say, seat at

Speaker:

the table, but kind of leapfrog their impact because they finally get it right?

Speaker:

Or do you think that we'll see more CMOs who have struggled on the

Speaker:

business side just also struggle when AI is brought into the mix?

Speaker:

Yeah, I absolutely think it's a huge opportunity for CMOs to

Speaker:

kind of reset the dialogue or the position they have with the board.

Speaker:

'Cause the good news is the stuff that you and I are talking about on a podcast

Speaker:

about CMOs is equally true of CROs.

Speaker:

It's equally true of a lot of other functions, where I think any executive

Speaker:

right now is trying to get their arms around how to talk about AI.

Speaker:

If the CMO is the first one there, or always brings that mindset, they're

Speaker:

very likely gonna differentiate themselves within the executive team.

Speaker:

And by the way, be helpful and more ingrained with the

Speaker:

other go-to-market leaders.

Speaker:

Yeah.

Speaker:

That's great.

Speaker:

You talked earlier about change management, and if I heard you right,

Speaker:

like AI-driven change management.

Speaker:

So I'm wondering if you can talk about your journey with your team

Speaker:

and what actually moves a team from AI curious to AI operational?

Speaker:

What specific things have you done to drive AI adoption on

Speaker:

your team where you need to?

Speaker:

Does that even make sense as a question when some things are

Speaker:

more bottom-up than top-down?

Speaker:

'Cause that question kind of assumes a top-downness.

Speaker:

And I know that's a bunch

Speaker:

Yeah.

Speaker:

all at once, so I'll let you just, you know, chew on that.

Speaker:

Well, you know, I mean, leaders gotta lead, right?

Speaker:

There's a lot of noise and FOMO that kind of drives the culture of

Speaker:

marketing organizations or just people who are professionals and see what's

Speaker:

going on in the space around them.

Speaker:

A lot of people in our space have very vocal, leaned in founders who

Speaker:

are also mandating their expectations for AI in the organization.

Speaker:

So recognizing that listeners are gonna have a lot of different contexts.

Speaker:

From my perspective, the best ways to do it are to set the vision and the roadmap.

Speaker:

When I mentioned that offsite we had last year, actually the major

Speaker:

deliverable from my team's perspective was a vision document and a roadmap.

Speaker:

We're gonna go AI first.

Speaker:

These are our 18 most important use cases.

Speaker:

This is where we're going to invest and these are the expectations going forward.

Speaker:

And then around the edges of that, it's still required because CMOs need their

Speaker:

leadership to also have that same degree of care and attention to making sure that

Speaker:

we're taking things as far as we can.

Speaker:

I'd say a year ago, it was more about a mix of evangelization and arm twisting.

Speaker:

I think now this year where I've focused on more is talking about

Speaker:

outcomes with team members.

Speaker:

Wouldn't it be cool if we could have a predictive dashboard that took BDR

Speaker:

activity and leading indicators on our gen MQLs and forecast out a monthly

Speaker:

landing with a quarter in advance?

Speaker:

And then the second would be professional relevance, particularly

Speaker:

with more junior team members because, which is completely true, right?

Speaker:

It's an opportunity for people if they're able to come up with

Speaker:

something that no one knew enough to ask them to do, to distinguish

Speaker:

themselves not only like at Flashpoint but in their career beyond that.

Speaker:

We see people who are leaping forward in their careers as

Speaker:

a result of being proactive.

Speaker:

I think there's no perfect, but that's how I've addressed it over the last year.

Speaker:

I was talking to another CMO who said to their team, "Oh, you just got a

Speaker:

promotion. You're no longer a writer, you're an editor." And that's just

Speaker:

a good way of thinking about it.

Speaker:

Was there a moment where you realized somebody wasn't on

Speaker:

board and needed to not, I don't know, come along for the ride?

Speaker:

Were you able to get like 100% sufficient adoption on your team?

Speaker:

I'd say n-not at first, no.

Speaker:

It was hard coming out of the roadmap exercise, it was harder.

Speaker:

There were folks who I don't think necessarily resisted, but were

Speaker:

still-- Again, it seems like the Stone Ages at this point, right?

Speaker:

Didn't fully see it, or we have so much going on, or, why do

Speaker:

we need to prioritize this?

Speaker:

I will say that after really, like pushing there, within a few months

Speaker:

later, my biggest resistor had AI native in his LinkedIn profile headline.

Speaker:

So I think, uh, saw that as a badge of honor that we ultimately got there

Speaker:

Yeah.

Speaker:

Yeah.

Speaker:

So let's do an exercise here.

Speaker:

I wanna ask you to put on your former Forrester hat, and I would love

Speaker:

your take on building a model on the fly, like a framework for assessing

Speaker:

AI maturity, whatever you call it, maturity, fluency, impact in a CMO.

Speaker:

What would that look like?

Speaker:

Maybe it's a maturity model of sorts.

Speaker:

Can you talk about that?

Speaker:

Yeah.

Speaker:

This is an intriguing question.

Speaker:

I'm not sure I ever fully take that hat off, Erica, so I may already have it.

Speaker:

I don't know about you.

Speaker:

The way I think about it is actually based on the kinds of interactions I've had.

Speaker:

I told you about that dinner where business value was the last thing.

Speaker:

Of course, there are many other breakfasts and dinners like it.

Speaker:

So I think the best way for me to assess maturity is to ask a very,

Speaker:

very simple question, very open-ended.

Speaker:

So what are you doing with AI?

Speaker:

Stop, silence, and see what answer you get over the next minute or so.

Speaker:

So a level one of maturity, very common, is you'll probably get a

Speaker:

tool or a consultant, or many tools.

Speaker:

We bought Qualified, we bought Profound.

Speaker:

I went to this event.

Speaker:

Level two, you might get use cases, even like Agentic, even very exciting

Speaker:

use cases, but use cases nonetheless.

Speaker:

Right now I'm focused on using it, for an agentic workflow that automatically

Speaker:

publishes content to improve our GEO.

Speaker:

Level three would be you get an outcome from the start.

Speaker:

I still find that quite rare, where someone may immediately go to our

Speaker:

major priority with AI is to grow our bookings number by twenty percent

Speaker:

by renovating our pricing model or to increase our conversion rates by

Speaker:

fifty percent because we have this really broken stage in the process.

Speaker:

So simple question, open-ended, pause, and then see where people's heads go first.

Speaker:

That kind of says a bit about where they're at most of

Speaker:

their day when it comes to AI.

Speaker:

Are you interviewing like that for your team?

Speaker:

I know we're talking about more CMO level, but when you meet people

Speaker:

for potential fits on your team, are you taking that approach?

Speaker:

Yeah, very much so because if I think back a few years, remember

Speaker:

when intent was like a new thing, and so you'd ask people, you'd ask CMO,

Speaker:

"Oh, what are you doing with intent?

Speaker:

How are you targeting that kind of demand?" They'd

Speaker:

say, "Oh, I bought 6sense."

Speaker:

But years later, and I love 6sense, but most people still hadn't done a

Speaker:

whole lot with it, or you'd find it might be sitting on a shelf somewhere.

Speaker:

So I ask very open-ended questions to understand what people are

Speaker:

doing with it that's beyond the tool or the check the box.

Speaker:

For most people on my team, to be honest, I would be looking more for a

Speaker:

level two because it's someone whose job responsibility would be primarily--

Speaker:

we would give the direction and outcome, and they would be figuring

Speaker:

out the best way to get there.

Speaker:

Got it.

Speaker:

Got it.

Speaker:

I'm wondering, just as an aside, do you think we're still gonna have resumes

Speaker:

when marketers are looking for jobs?

Speaker:

Or do you think it's gonna be some kinda, "Oh, let me show

Speaker:

you my AI workflows directly?"

Speaker:

it's an interesting question.

Speaker:

Where I thought you were gonna go with that is whether people will just

Speaker:

diligence through LLMs and that versus LinkedIn becomes the place people go

Speaker:

because it could be a more holistic view.

Speaker:

That's one direction.

Speaker:

And then show me what you built would certainly be a very focused and,

Speaker:

depending on the role, would be a pretty provocative way to interview.

Speaker:

Yeah.

Speaker:

For a future in which the doing isn't the virtue anymore, it's the being

Speaker:

able to manage agents and manage workflows to be able to do at scale.

Speaker:

Right.

Speaker:

Right.

Speaker:

If you were advising a CMO on how to interview like that, would you advise

Speaker:

them to ask and catch somebody unawares?

Speaker:

Or would you advise them to ask a candidate, " Let's chat about

Speaker:

this in a few days and you show me what you're doing with AI"?

Speaker:

It could vary in an interview cycle, but I'll give you an example.

Speaker:

For product marketing roles, I've always asked, no matter the level, always ask

Speaker:

candidates to deliver something as part of the late-stage interview process of look

Speaker:

at these sources, give us a one-pager.

Speaker:

How would you message this?

Speaker:

How would you do this thing?

Speaker:

The way to do that now would be to see how they used AI in order to generate

Speaker:

the deliverable, and did they generate an AI slop deliverable or one that

Speaker:

actually shows a marriage of the best of their own analytical perspective and

Speaker:

insight along with what the broader net that AI can allow them to cast.

Speaker:

Okay.

Speaker:

I know we're running out of time, so I'm gonna ask you my final question, which

Speaker:

I ask everybody on The Get, and that's related to what we've been talking about.

Speaker:

Can you share an interview question that you ask when you're hiring that

Speaker:

you find particularly revealing?

Speaker:

It does not have to be about AI.

Speaker:

Yeah, sure.

Speaker:

I guess everyone has their question, right?

Speaker:

I love that this is one of the ones that The Get focuses on.

Speaker:

In my case, and independent of AI, marketers are so broad generally in

Speaker:

their skill set and so polished in the way they present themselves that

Speaker:

I find that you can have an hour-long conversation and still struggle to

Speaker:

figure out who's in front of you and how they're gonna fit with the job at hand.

Speaker:

So the question that I love most is, think back on the last year of your

Speaker:

job and think about the best day that you've had during that entire year,

Speaker:

and tell me about what happened.

Speaker:

What did you do, how did you feel, and why?

Speaker:

Why did you have these reactions?

Speaker:

And then just pause.

Speaker:

There is a version of that too, if time allows, to focus on what

Speaker:

did your worst day look like?

Speaker:

But the reason why I like these questions is you learn where people really get their

Speaker:

energy from and where their minds go first when presented with a broad skill set.

Speaker:

Is it the day that they delivered something very important, or

Speaker:

they hit a number, or they had a breakthrough in their heads?

Speaker:

Or if they're a revenue marketer, was it on the field side or

Speaker:

was it on the demand gen side?

Speaker:

And how do they handle highs and lows along the way?

Speaker:

So I find that you can learn a lot about many different dimensions of

Speaker:

someone through that question about their best day or their worst days.

Speaker:

And then, as a bonus, people often smile or they pause when they're asked, and I

Speaker:

feel like they go to a different place.

Speaker:

You get a different side of the candidate that you're talking to.

Speaker:

I like that.

Speaker:

Thank you so much for sharing.

Speaker:

This has been great chatting with you.

Speaker:

You're so compact with how you talk about things and you're so quotable.

Speaker:

This is a great lens into you, how you've been fulfilling the

Speaker:

role of the CMO in recent months.

Speaker:

So thank you so much for sharing.

Speaker:

It's my pleasure.

Speaker:

And there's so much going on with AI that if it's at all helpful to narrow

Speaker:

things down or make sense of what's going on out there, it's time well spent.

Speaker:

So thanks so much, Erica.

Speaker:

Wonderful.

Speaker:

That was Joe Sawyer, Chief Marketing Officer at Flashpoint.

Speaker:

Now that you've heard from Joe, think about how you will

Speaker:

navigate your next conversation with your board or CEO about AI.

Speaker:

Does the way you're talking about AI align with what your

Speaker:

board needs to hear from you?

Speaker:

Thanks for listening to The Get.

Speaker:

I'm your host, Erica Seidel.

Speaker:

The Get is here to drive smart decisions around recruiting and

Speaker:

leadership in B2B SaaS marketing.

Speaker:

We explore the trends, tribulations, and triumphs of today's top

Speaker:

marketing leaders in B2B SaaS.

Speaker:

For more about The Get, visit TheGetPodcast.com.

Speaker:

If you like The Get, please share it, and please leave a review.

Speaker:

To learn more about my executive search practice, which focuses on recruiting the

Speaker:

make-money marketing leaders rather than the make-it-pretty ones, follow me on

Speaker:

LinkedIn or visit TheConnectiveGood.com.

Speaker:

The Get is produced by Evo Terra and the team at Simpler Media Productions.

About the Podcast

Show artwork for The Get: Finding And Keeping The Best Marketing Leaders in B2B SaaS
The Get: Finding And Keeping The Best Marketing Leaders in B2B SaaS
Your inspiration from the best marketing leaders in B2B SaaS today... from hiring, getting hired, leading, organizing, and more!

About your host

Profile picture for Erica Seidel

Erica Seidel

Erica Seidel recruits the marketing leaders of the 'make money' variety – not the 'make it pretty' variety. As the Founder of The Connective Good, a boutique executive search firm, she is retained to recruit CMOs and VPs in marketing, growth, product marketing, demand generation, marketing operations, and corporate marketing. She also hosts The Get podcast. Previously, she led Forrester Research's global peer-to-peer executive education businesses for CMOs and digital marketing executives of Fortune 500 companies. Erica has an MBA in Marketing from Wharton, and a BA in International Relations from Brown. One of her favorite jobs ever was serving as the Brown Bear mascot.

You can find her on LinkedIn at https://www.linkedin.com/in/ericaseidel/, or on her website/blog at www.theconnectivegood.com.