There are so many CMOs I've talked to who say, I wish I had known X before

taking my role, or I wish I had been told the real truth about Y way earlier.

And there are, meanwhile, so many CEOs and investors who are

unhappy with the performance or the tenure of their last CMO.

What if we had better tools to reduce risk on both sides?

This season is the sixth season of The Get.

We are going to focus on the race to reduce risk when it comes to a

match between a company and a CMO.

How can you find out what you need to find out before saying yes, so that

you can move forward wholeheartedly?

This need to mitigate risk, it's always been the case, of course,

it's always been important, but it just feels more pressing lately.

If we haven't met yet, welcome!

I'm your host, Erica Seidel.

I spend my days recruiting CMOs and VPs of marketing in B2B SaaS.

My tagline is, I place the make- money marketing leaders,

not the make-it-pretty ones.

With my role, I have a front row seat to the trends, tribulations, and triumphs of

today's top marketing leaders in B2B SaaS.

And now with The Get, you do, too.

The Get is designed to drive smart decisions around recruiting and

leadership in B2B SaaS marketing.

Today, let's look at what the best CMOs find out before saying yes to a job.

If you're hiring, it's going to help you to be ready for the information that

some of your top candidates will ask for.

And, you'll see what they see as risky so that you can

position your role effectively.

If you're looking to get hired, it will help you use the limited time in the

recruiting process to your best advantage.

You'll hear from me, and then I'll bring on my guest, Andrea Kayal.

She will share her perspective as a CMO and now a CRO.

I'm also really excited to talk with her about something controversial - whether

it's a risk for CMOs to report to CROs.

So let's get started.

During the recruiting processes that you'll see, time and access

in general are so limited.

In an interview, time is really especially precious.

The best candidates will plan ahead and know what they're going to be looking

for and in roughly what sequence.

They'll have an idea of what to ask about directly in an interview with the CEO,

and what to ask for in other meetings.

And they'll know where they need to become a sleuth to find out things on their own.

I often ask candidates what their top three criteria are for accepting a job?

They talk about different things.

Information about the health of the business, the product, the marketing

impact so far, the culture, the upside opportunity, the relationships with the

investors, a lot of different things.

But one thing's for sure, the best candidates are very

intentional about their criteria.

Here's just a smattering of some of the best questions I've

heard CMO candidates ask lately.

One is, how long did it take to get to the number of customers the company has now?

How do you know you have product market fit?

What competitors worry you the most?

What is the organization's view on marketing?

It's definition of marketing?

What's working well with marketing and what's not?

What are the funnel metrics?

What are you measuring in general with marketing?

What is your retention rate?

What was a question that came up at the last board meeting that

marketing struggled to answer?

What does the sales cycle look like in terms of timing and

in terms of pipeline coverage?

What's the relationship with investors like?

What does the cap table look like?

And also culture questions.

Some of these questions I coach people to ask actually, and they include

things like what would happen here that doesn't happen somewhere else?

Or what surprised you about the culture when you joined?

And what do you value to the detriment of other things?

When a candidate asks questions, they're really demonstrating their altitude,

and with that, they're signaling how they are likely to tackle the role.

Now, let's go beyond questions to other things that good CMO candidates do.

They provide something to react to - some slides, perhaps, that talk about the

structure of their role, what is in scope, what's not, how they measure things.

And in this way, they're taking control of the interview.

It helps them to educate the CEO, especially if the CEO is somebody who

doesn't understand marketing too well.

They ask for product demos.

Usually these are product marketing people, people who have come up through

the product marketing ranks that do this.

But this could be a great way to see the product in action.

They get backdoor references on the hiring leader.

One CEO client I had, he proactively, actually, offered references of

people who had worked with him before to talk to candidates.

They ask for an in-person meeting.

On the hiring side, this can actually help you close a deal because if a candidate

is in multiple recruiting processes, they can feel more of a kinship to

the company that they meet in person.

Of course, some people have different perspectives on this.

I have a client who said she cared more about her CMO connecting via Zoom since

that was going to be 90 percent of the way he would be interacting with people.

Another thing that people do is they ask to talk to investors.

They ask to talk to customers or they just go ahead and do it.

And, of course, they tap the recruiter for their knowledge and guidance.

There's a whole art to that that we could talk about another time.

And I think the gold standard for de-risking from a candidate

side is to start fractionally.

Gold standard on both sides actually.

It's a great way to try before you buy.

It's just not always practical to do.

So of course, there's a lot to find out.

The trick here, if you're the candidate, is to not seem like you

have an endless array of questions.

Otherwise, it looks like you're sort of expensive to work with

and can't make a decision.

So again, an art to this.

So the net is, there's lots of things to de risk for both parties,

and there's a compressed time frame in recruiting, as we know.

And it takes intentionality and some finesse to manage the process the best.

In the end, both sides will also always be making a leap.

Now, let's bring on another perspective on this topic.

So andrea i'm really excited to welcome you to The Get.

I am excited to talk with you about this topic of kind of everything a SaaS CMO

should know before they say yes To a job and how they should find that out.

The reason I picked you as a person to talk to was I remember

I was taking this Pavilion class.

I think it was a CMO school and you did a session and it was great.

And you said, "I have a whole worksheet that I fill out

before I say yes to a job."

And I thought that was so cool.

I thought, oh, I want to see her worksheet.

I want to, I want to hear more about this.

And so I am thrilled to have you.

Just so our guests know, you have been a CMO multiple times,

and a CRO multiple times.

Now you're a CRO at Help Scout.

So this is going to be great.

We're going to talk about the whole, you know, CMO versus CRO.

And marketing leaders reporting to CROs.

But also, you know, this topic of what to find out before saying yes to, to a role.

I think it's really cool that you were on the board of Help

Scout before you became CRO.

It's like the ultimate try before you buy.

So, let's first talk about being a CRO.

You're a CRO, you've been a CMO, and this whole theme is about reducing risk.

So I'll just come out and say it.

Some CMOs, VPs of Marketing, whatever, they recoil, they would like puke

at the idea of reporting to a CRO.

Yet, this is kind of a trend that you know, that we see in SaaS.

And so I'm wondering, what do you see as the benefits of it?

You know, how do you react to somebody who says too much risk,

you know, if I report to a CRO, I'm just going to become a lead factory.

I'm going to become nothing more.

What do you say?

And what's the pitch for a CMO to work for CRO?

And, and If you have time to also talk about this, like when should a CEO

consider having marketing report to the CRO rather than the CEO directly?

Actually, I'll start there, Erica, because I think that's primarily one of

the things to, I don't know, evaluate prior to you taking a role as a CMO

to reporting into the CRO is why does the CRO exist in the first place?

And what has the CRO aligned with the CEO on as the value that

they're going to drive or the leverage they're going to give them?

In that, you know, in that particular company, because every company is nuanced.

So, I would say first, the benefit of a CRO in an organization, at least as far

as my experience has kind of illuminated is that what I noticed the CEO doing

frequently was kind of like going to his C-level counterparts by function

and, you know, asking for numbers.

Or we were like reporting up you know, particularly siloed metrics.

And it wasn't that I didn't have great sales and marketing alignment with my

sales peer or great sales and customer success alignment with my CCO peer.

We were aligned, but that there was no one deliberator of the actual

singular number that the CEO cares about was like, is our revenue on track?

So there's new revenue, which is usually what the sales and marketing

leaders are responsible for, primarily.

And then there's like the retained revenue, which the CCO is responsible for.

And so, in that way, if you have three very senior people reporting on these

things, I felt like there was always like a gap in the strategy around

where to put resources because sales and marketing efficiency is one of the

things that like help your valuation.

I said, well, one person should probably be the deciding capital

allocator among all the teams in terms of like where the money is

best spent to generate the revenue.

So I think that's the value of the CRO.

Now, if I'm a CMO and I'm thinking like, okay, can I make an impact

here under a CRO who's responsible for the revenue strategy?

I would say this is a great opportunity to come in and partner with what the

leader that has the responsibility to the CEO for that one revenue strategy

versus like three competing viewpoints on like what markets we should go after.

You should be evaluating, obviously your relationship with the CRO

and where their strengths are, but usually, and this is the trend I'm

hoping to bork, it's a sales leader.

And in my opinion, hiring a CMO to support the revenue leader is like critical

because they don't have that skill set.

And in my opinion, not to discredit my, my sales counterparts, marketing is

sort of like the more multi-dimensional-

Yeah.

-harder, if you will?

Like role to solve for because there's content marketing, product

marketing, brand marketing, creative, design, PR, like demand gen, events.

There's like twelve disciplines to marketing and there's

like one dimension to sales.

And so like, if I'm a CRO, now my background is marketing.

I have a great VP of Marketing because I still need all that stuff done.

But I still really want a strong marketing leader because it's

such a hard thing to wield.

So, I can stay focused on the sales side of the organization and

my sales leaders and a strong VP of Marketing or CMO is capable of running

point on all the marketing stuff.

But ultimately my job is to take all that information and

then go to the CEO with it.

Mm hmm.

And I think when I talk to people, I'm starting to ask them, you know, I've got

these people come to me, "I'm looking for a job, I'm looking for a job."

And one of the qualifying questions I ask them is, are you okay working for a CRO?

Because this is a bit of a trend.

I just want to know, are you, you know, allergic to it a priori?

And what I'm starting to hear is, "Oh, it depends on the CRO."

And I think if it's somebody like you, who's come from marketing,

that's very different than somebody who was a sales leader yesterday and

only has led, you know, five person sales team or something like that.

Exactly.

There, there's a lot of, I think the apprehension marketers have is to

report into a sales leader who really doesn't get marketing at all and can't

appreciate the value or the impact.

And that would be a red flag.

So that's why I think there's a, there's a nuanced answer there.

Where just like, it depends truly because the person is a big factor in that.

So I'd love to see more marketing leaders move over to CRO because I

do think that like, there's no reason that that shouldn't be the case.

Like a revenue strategy isn't only able to be determined by

somebody who grew up in sales.

In a lot of cases, I think even like, you know, Latane from 6sense, she had

called herself like a Chief Market Officer at one point because, knowing the

market and how to read the business and where to go is the job, not necessarily

like, oh, I'm here just to drive leads.

Mm hmm.

Like I said, it's a more, it's a deeper job than just, you know, that one thing.

Interesting.

Yeah.

God, I could talk to you about that topic all day long, but let's,

let's focus on other aspects of, of this, you know, risk management.

So, no matter where the marketing leadership role reports, what do

you see as like the top two or three things for a CMO, Head of Marketing,

whatever it's called, to find out before saying yes to that role?

Like, is it this whole worksheet of, you know, thirty things, or do you

have a couple, you know, top, you know, the Andrea Kayal top things?

Yeah, I have a very, very top.

It like eclipses the others by probably, by a very large margin which is gross

retention and that gross retention is a signal to me of product market fit.

Certainly like, you know, you could get this, you could cut different segments of

those sales so that the gross retention of maybe smaller customers is crappy

and larger ones is really great or whatever, however you want to cut it.

But you really want to get an understanding of whether or not the

ideal customer for that business is retaining with their dollars.

There's a logo retention and then there's a dollar retention.

I would look at gross retention , gross retention of absolute logos.

The dollar amount is important, but if you bring on a company, you want

to see that the company is able to retain that segment at about 90%.

90% is like a healthy number, I would say, for some small companies who

are focused on small business, like maybe that number is around 80% just

because naturally small businesses go out of business sooner than others.

But let's just say like your medium to enterprise size

company, you want it to be at 90%.

And the reason this is so important for a marketer assessing a job is because

for all commercial teams, I would say sales, marketing, and let's just say

customer success, if the gross retention is suffering below 90%, that is a problem

that the product team needs to solve.

And the VCs and the CEO, very apprehensive to spend more at the top

of the funnel generating more leads and more pipeline and more revenue if

they know it's leaking out the bottom.

So that's definitely the question I would ask, you know, that's

far and away the most important.

The second thing to look at, if I were a marketing leader joining an organization

is probably the close rate percentage.

Because the worse the sales team is at closing deals, the harder the job is

for the marketing leaders because you are covering what their quotas are.

So if their close rate is 25%, then you need to be covering, you know, you

need 4x the pipeline to cover that.

If they close at 20%, just five points less, you need five times

the pipeline to cover that.

And what happens is, as that close rate changes, the budget you need to support

that organization also needs to increase.

And sometimes that's not clear to the company that it's not, it's nothing

that I can do to solve for this.

Every time the close rate goes down, the budget for the

marketing team needs to go up.

So, you know, those are probably like, I think the top two

that I would be digging into.

That's great.

All right.

And, you know, and I find as I talk to marketing leaders, I

always ask, you know, what are your criteria for saying yes to a job?

And many have a kind of structure for it.

You know, I, I like yours as, as very, you know, quantitative metrics.

Sometimes people are talking about, oh, I love culture and good people

and good product and, and, you know , good market, big tam, et cetera.

There's a lot of different things.

So everybody has their process of due diligence.

And what, what tips do you have for, for a CMO to do that process of due diligence?

And how do you, I am very curious, curious about how you balance

efficiency and thoroughness?

Because if you ask every single last question, you know, you're going to

exhaust the CEO and the whole team and the recruiter and everything.

Yeah, and so I think the, you mentioned this at the beginning, there is a list of

questions that I have, which are basically written in the order of importance to me.

And at the very top of the list is this gross retention, like

the customer health metrics.

The second is people.

I do mention this because like your relationship either with

the CRO or the CEO is everything, mostly just for your mental health.

It has nothing to do with how smart they are, but like, can

you wake up every day and get motivated to work with this person?

Very important.

And I check Glassdoor for that.

Glassdoor is...

mixed reviews on Glassdoor.

'cause people just like, you know, really like complain about what the

issues are in their, their roles.

But you do, you can pick out trends.

Something's constantly coming up with the CEO or the CRO, you know, you

kind of need to investigate that.

So I would say, you don't want to exhaust the other side in the process.

But one of them, one of the asks I had when I joined Teampay was

basically, I put the questions in a spreadsheet and I just said, hey,

can I work with the CFO on this?

Mostly because they're a thought partner to you just as much as the CEO is.

At Help Scout, it's a CFO, the CEO, and myself, and we manage

the different business units.

I manage the commercial.

Nick, the CEO, manages the product and engineering organization, and

Shawna manages the business functions.

That's, like, FP and legal, et cetera.

And so working with someone like a CFO or COO upon, like, even even joining

the, the company shows you like what that relationship would be like.

So, I did send the whole list over.

And I did say like, this is part of my diligence.

I think it's important.

The article I have, it just says interview companies with the same

rigor they're using to interview you.

And frankly, that spreadsheet is very well received in the, let's just

call it dozen times I've had to kind of like run a process in my career.

When I've used it, it shows the company that you have a very good

handle on the things that are going to make you successful in the role

and they're very appreciative of that.

Because they too don't want to hire somebody who isn't a fit.

And one other thing I'll mention, like, I'm saying this, knowing that

sometimes you just need to take a job because you need one and like, that's,

you know, certainly understandable.

But in the event that you have the opportunity to evaluate a job, I

would say, don't be shy in you know, going to the mat with all

the questions that you have.

Yeah, that's great.

And I think that gets to this point of, you know, you talked about the Chief

Market Officier, which I think is great.

But I also think a way of thinking about the CMO role as

Chief Marketing Education Officer.

Within a company, you know, they're educating about what the role is, and

a lot of companies, you know, the CEO is just not a marketing expert, and the

investors are not marketing experts.

And so part of the process of them doing the recruiting is them learning from CMOs.

And so if a CMO just shows up and says, okay, okay, let me answer

your questions, those questions might not be the right ones.

It's like, you're almost kind of guiding the interview process, you know, with

your framework of, of what you want to fill in and figure out for yourself.

You said it exactly right.

It's like, well, they're going to interview you and

they have a set of questions.

Like, are you more of a brand marketer or a, you know, a performance marketer?

Right?

Like you, you come up in one of those two paths, generally.

Either you grew up writing comms for product marketing or content

marketing or your performance marketer.

Like, are you good at figuring out which ads you need to run

and those kinds of things.

But so they have questions for you.

They are looking for a type.

But you need to be looking for the company where your type is going to most benefit

them and that's how you become successful.

So like if you don't run a process and you get there and you find out

that they have ten reps and only five of them are getting over 50% of quota.

You've already joined an organization where you know the uphill battle

will be on performance marketing.

Again, it's just really like a give and take there, but I, I highly

recommend really scrutinizing the business before you say yes.

Yeah, I love that.

And we'll include a link to your article on LinkedIn.

Yeah, in the show notes.

Cause I think that'll be, that'll be great.

So, you have this worksheet and, and you've shared it before.

Have you ever in any of your roles that you've been in, seen a CEO bristle about,

you know, over a particular question?

Or, you know, has that person ever said like, "Oh, you know, you're asking

this, ooh, that's a little sensitive?"

You know, it's like a partnership and, and you're saying, look, I'm

going to give you everything I have in this company, everything I have

to like make this company successful.

I need you to show me where I can best give you leverage to do the

thing it is you're asking me for.

And if you're telling, and so the bristle question usually

comes around gross retention.

It's the first one.

It's the most annoying because for CEOs, because that's their baby.

They can't stand that somebody isn't loving their baby, right?

And thinking it's cute and like wanting to use it all the time.

And, you know, so gross retention usually reveals kind of where there might be

some, I don't know, weakness in, you know, in, in the product market fit.

But I think approaching it in the way I just mentioned, which is like,

I don't care what the answers are, but if your gross retention is 75%,

hire me in a year when you fix that.

Because I'm going to say, we're going to need to do all this stuff to grow.

And you're going to be like, wait, that money needs to go to the R&D team.

And I'm going to be like, well then why are you paying me?

You know?

At my level, like at, again, not necessarily me, but like at a C level, C

levels have to be giving the CEO leverage.

They have to be able to offload stuff to you that they just cannot do on their own.

And you have to be able to level that up and show impact.

And if they can't simply just reveal to you where those problems are?

Red flag.

You have to be evaluating that as an input to your decision making process.

Yeah, yeah.

I love that.

And certainly , as part of this, you're not just throwing a spreadsheet at

them and saying, "Fill this out."

You know, there's, there's a certain amount of talking about why you're asking.

And I, I think that's, you know, you have to do that artfully in an interview.

It's certainly an art.

But I think, yeah, I think the why you're asking, and like, you know,

you sign an NDA anyway, it's not why, cause you're like going to go run to

a competitor and take another job.

It's like, you know if we agree that my job is to give you leverage because you

need help in these areas, like, let's just, let's talk about what those are.

The spreadsheet is really just an assessment to make sure that the things

that I have been successful in doing in the past, I will be able to apply here.

If, for example, this is a enterprise level issue, right?

Like they're, they're having high, or let's say high churn on the S and B side.

They want to go after enterprise, but my experience is not aligned to that.

Like we need to know that now, you know?

So to your point, and about the theme of your podcasts, like it's just

de-risking on both sides is to make sure that you feel confident to ask the

questions prior to going into the role.

Great, great.

I know we're getting towards the end.

I have two final questions for you.

One is, just going back to this whole CMO, CRO thing, because I know people

might say, Oh, I listened to Andrea and I see what she's saying about

one CRO, you know, kind of being over the whole like growth number and the

whole, you know, like the number.

I wonder if those people would say, but I really like reporting to a CEO because

marketing is not just more, you know, it's communications and it's, you know,

employment marketing and everything.

And I need to be able to really have a view, not just to sales

and customer success, but also product and finance, et cetera.

Also a great path, you know?

I think if you're a CMO, the message is feel encouraged to move

into CRO because you're capable.

You have all of the tools to do that.

And you probably have a little, actually more of, a wider lens than

maybe some of your sales counterparts to be very successful in the role.

You know, like to help drive that strategy.

So as a CRO, I think CMOs make a great person for that.

And I think when the CEO has one person very helpful to him.

However, in the event that in that organization, there's, you know, a sales

leader, really just responsible for new business, and you're, you're one

input to that, which is to help generate pipeline, but there's all this other

stuff you really do need to connect with the CEO on, like brand positioning, et

cetera, then absolutely I still think it's great to report into the CEO.

I would just want to make sure that you check in with the CEO to make sure

that they're still getting leverage from having the roles separated.

Yeah, yeah.

Okay.

Thank you for clarifying that.

And my final, final question for you is now that you're in a different

role and you hire, you know, you have a VP of Marketing reporting to you.

Do you have a favorite interview question that you ask marketing

leaders when you're interviewing them?

Like what do you do in your free time?

I actually don't ask work- I ask, like, I think, like, I want to make sure

that the VP of Marketing has a track record of success and doing the role.

So that's kind of like table stakes.

So I'm asking a bunch of questions to make sure that they're generally going

to be a fit for the needs we have.

But I just want to know that this person is nice and kind and compassionate

and like, you know, really cares about the work they're doing.

So passion, curiosity, and grit.

I think some of the, what do you do in your free time?

Again, there's no evaluation or judgment about what that thing is.

Say like, you know, do you like to read books or something else?

The non work questions help me just better understand who they are as an individual.

And if they bring an animal onto the interview, even better.

We, I love people who bring their pets, you know, into

meetings and things like this.

I mean, it's sort of like a silly answer, but truly I am hiring for

the whole person and not just, you know, a machine who maybe got lucky

on a ride with some company where they have that on their resume.

Truly it's about the, I don't want to say the softer skills.

I don't think we're allowed to use that anymore because they're not like soft.

They're still very important skills.

They're just the, the compassionate skills are really where I think

I ask more of my questions.

That's great.

Well, thank you so much.

This has been great chatting with you, Andrea.

You too, Erica.

Thanks for having me.

That was Andrea Kayal, CRO at Help Scout and former CMO.

Now, think about what questions are most key for you to address when

you're in a recruiting process.

And how can you reduce risk as efficiently as possible?

Next time on The Get, you'll hear more from me and from another guest.

Don't miss it.

Thanks for listening to The Get.

I'm your host, Erica Seidel.

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.

If you liked this episode, please share it.

For more about The Get, visit thegetpodcast.com.

And to learn more about my executive search practice, which focuses on

recruiting the make-money marketing leaders rather than the make-it-pretty

ones, follow me on LinkedIn or visit theconnectivegood.com.

The Get is produced by Evo Terra of Simpler Media Productions.