Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
There are so many CMOs I've talked towho say, I wish I had known X before
(00:04):
taking my role, or I wish I had beentold the real truth about Y way earlier.
And there are, meanwhile, somany CEOs and investors who are
unhappy with the performance orthe tenure of their last CMO.
What if we had better toolsto reduce risk on both sides?
This season is thesixth season of The Get.
(00:25):
We are going to focus on the raceto reduce risk when it comes to a
match between a company and a CMO.
How can you find out what you need tofind out before saying yes, so that
you can move forward wholeheartedly?
This need to mitigate risk, it'salways been the case, of course,
it's always been important, but itjust feels more pressing lately.
(00:45):
If we haven't met yet, welcome!
I'm your host, Erica Seidel.
I spend my days recruiting CMOsand VPs of marketing in B2B SaaS.
My tagline is, I place themake- money marketing leaders,
not the make-it-pretty ones.
With my role, I have a front row seat tothe trends, tribulations, and triumphs of
today's top marketing leaders in B2B SaaS.
(01:08):
And now with The Get, you do, too.
The Get is designed to drive smartdecisions around recruiting and
leadership in B2B SaaS marketing.
Today, let's look at what the best CMOsfind out before saying yes to a job.
If you're hiring, it's going to helpyou to be ready for the information that
some of your top candidates will ask for.
(01:29):
And, you'll see what theysee as risky so that you can
position your role effectively.
If you're looking to get hired, it willhelp you use the limited time in the
recruiting process to your best advantage.
You'll hear from me, and then I'llbring on my guest, Andrea Kayal.
She will share her perspectiveas a CMO and now a CRO.
I'm also really excited to talk with herabout something controversial - whether
(01:52):
it's a risk for CMOs to report to CROs.
So let's get started.
During the recruiting processesthat you'll see, time and access
in general are so limited.
In an interview, time isreally especially precious.
The best candidates will plan ahead andknow what they're going to be looking
for and in roughly what sequence.
(02:13):
They'll have an idea of what to ask aboutdirectly in an interview with the CEO,
and what to ask for in other meetings.
And they'll know where they need to becomea sleuth to find out things on their own.
I often ask candidates what their topthree criteria are for accepting a job?
They talk about different things.
Information about the health of thebusiness, the product, the marketing
(02:33):
impact so far, the culture, the upsideopportunity, 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 ofsome of the best questions I've
heard CMO candidates ask lately.
One is, how long did it take to get to thenumber of customers the company has now?
(02:57):
How do you know youhave product market fit?
What competitors worry you the most?
What is the organization'sview on marketing?
It's definition of marketing?
What's working well withmarketing and what's not?
What are the funnel metrics?
What are you measuring ingeneral with marketing?
What is your retention rate?
What was a question that came upat the last board meeting that
(03:18):
marketing struggled to answer?
What does the sales cycle looklike in terms of timing and
in terms of pipeline coverage?
What's the relationshipwith investors like?
What does the cap table look like?
And also culture questions.
Some of these questions I coach peopleto ask actually, and they include
things like what would happen herethat doesn't happen somewhere else?
(03:39):
Or what surprised you aboutthe culture when you joined?
And what do you value to thedetriment of other things?
When a candidate asks questions, they'rereally demonstrating their altitude,
and with that, they're signaling howthey are likely to tackle the role.
Now, let's go beyond questions to otherthings that good CMO candidates do.
(04:00):
They provide something to react to - someslides, 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 takingcontrol 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.
(04:22):
Usually these are product marketingpeople, people who have come up through
the product marketing ranks that do this.
But this could be a great wayto see the product in action.
They get backdoor referenceson the hiring leader.
One CEO client I had, he proactively,actually, offered references of
people who had worked with himbefore to talk to candidates.
They ask for an in-person meeting.
(04:43):
On the hiring side, this can actually helpyou 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 havedifferent perspectives on this.
I have a client who said she cared moreabout her CMO connecting via Zoom since
that was going to be 90 percent of theway he would be interacting with people.
(05:07):
Another thing that people do isthey ask to talk to investors.
They ask to talk to customersor they just go ahead and do it.
And, of course, they tap the recruiterfor their knowledge and guidance.
There's a whole art to that thatwe could talk about another time.
And I think the gold standardfor de-risking from a candidate
side is to start fractionally.
Gold standard on both sides actually.
(05:27):
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 thecandidate, is to not seem like you
have an endless array of questions.
Otherwise, it looks like you'resort of expensive to work with
and can't make a decision.
So again, an art to this.
So the net is, there's lots ofthings to de risk for both parties,
(05:51):
and there's a compressed timeframe in recruiting, as we know.
And it takes intentionality and somefinesse to manage the process the best.
In the end, both sides willalso always be making a leap.
Now, let's bring on anotherperspective on this topic.
So andrea i'm really excitedto welcome you to The Get.
(06:11):
I am excited to talk with you about thistopic of kind of everything a SaaS CMO
should know before they say yes To ajob and how they should find that out.
The reason I picked you as aperson to talk to was I remember
I was taking this Pavilion class.
I think it was a CMO school andyou did a session and it was great.
And you said, "I have a wholeworksheet that I fill out
(06:34):
before I say yes to a job."
And I thought that was so cool.
I thought, oh, I wantto 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, youhave 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 thewhole, you know, CMO versus CRO.
(06:56):
And marketing leaders reporting to CROs.
But also, you know, this topic of what tofind out before saying yes to, to a role.
I think it's really cool thatyou 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.
(07:18):
You're a CRO, you've been a CMO, andthis 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 thatyou know, that we see in SaaS.
And so I'm wondering, what doyou see as the benefits of it?
(07:40):
You know, how do you react tosomebody who says too much risk,
you know, if I report to a CRO, I'mjust going to become a lead factory.
I'm going to become nothing more.
What do you say?
And what's the pitch fora CMO to work for CRO?
And, and If you have time to also talkabout this, like when should a CEO
consider having marketing report tothe CRO rather than the CEO directly?
(08:02):
Actually, I'll start there, Erica,because I think that's primarily one of
the things to, I don't know, evaluateprior to you taking a role as a CMO
to reporting into the CRO is why doesthe CRO exist in the first place?
And what has the CRO alignedwith the CEO on as the value that
they're going to drive or theleverage they're going to give them?
In that, you know, in that particularcompany, because every company is nuanced.
(08:25):
So, I would say first, the benefit of aCRO in an organization, at least as far
as my experience has kind of illuminatedis that what I noticed the CEO doing
frequently was kind of like going tohis C-level counterparts by function
and, you know, asking for numbers.
Or we were like reporting up youknow, particularly siloed metrics.
And it wasn't that I didn't have greatsales and marketing alignment with my
(08:48):
sales peer or great sales and customersuccess alignment with my CCO peer.
We were aligned, but that there wasno one deliberator of the actual
singular number that the CEO caresabout was like, is our revenue on track?
So there's new revenue, which isusually what the sales and marketing
leaders are responsible for, primarily.
And then there's like the retainedrevenue, which the CCO is responsible for.
(09:11):
And so, in that way, if you have threevery senior people reporting on these
things, I felt like there was alwayslike a gap in the strategy around
where to put resources because salesand marketing efficiency is one of the
things that like help your valuation.
I said, well, one person shouldprobably be the deciding capital
allocator among all the teams interms of like where the money is
(09:32):
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 thinkinglike, okay, can I make an impact
here under a CRO who's responsiblefor the revenue strategy?
I would say this is a great opportunityto come in and partner with what the
leader that has the responsibility tothe CEO for that one revenue strategy
(09:53):
versus like three competing viewpointson like what markets we should go after.
You should be evaluating, obviouslyyour relationship with the CRO
and where their strengths are, butusually, and this is the trend I'm
hoping to bork, it's a sales leader.
And in my opinion, hiring a CMO to supportthe revenue leader is like critical
because they don't have that skill set.
(10:14):
And in my opinion, not to discreditmy, my sales counterparts, marketing is
sort of like the more multi-dimensional-
Yeah.
-harder, if you will?
Like role to solve for becausethere's content marketing, product
marketing, brand marketing, creative,design, PR, like demand gen, events.
There's like twelve disciplinesto marketing and there's
(10:36):
like one dimension to sales.
And so like, if I'm a CRO, nowmy background is marketing.
I have a great VP of Marketing becauseI still need all that stuff done.
But I still really want a strongmarketing leader because it's
such a hard thing to wield.
So, I can stay focused on thesales side of the organization and
my sales leaders and a strong VP ofMarketing or CMO is capable of running
(10:59):
point on all the marketing stuff.
But ultimately my job is totake all that information and
then go to the CEO with it.
Mm hmm.
And I think when I talk to people, I'mstarting to ask them, you know, I've got
these people come to me, "I'm lookingfor a job, I'm looking for a job."
And one of the qualifying questions I askthem is, are you okay working for a CRO?
Because this is a bit of a trend.
I just want to know, are you, youknow, allergic to it a priori?
(11:20):
And what I'm starting to hearis, "Oh, it depends on the CRO."
And I think if it's somebody likeyou, who's come from marketing,
that's very different than somebodywho was a sales leader yesterday and
only has led, you know, five personsales team or something like that.
Exactly.
There, there's a lot of, I think theapprehension marketers have is to
report into a sales leader who reallydoesn't get marketing at all and can't
(11:41):
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 becausethe person is a big factor in that.
So I'd love to see more marketingleaders move over to CRO because I
do think that like, there's no reasonthat that shouldn't be the case.
Like a revenue strategy isn'tonly able to be determined by
(12:02):
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 MarketOfficer at one point because, knowing the
market and how to read the business andwhere 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 deeperjob than just, you know, that one thing.
(12:24):
Interesting.
Yeah.
God, I could talk to you aboutthat 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 marketingleadership role reports, what do
you see as like the top two or threethings for a CMO, Head of Marketing,
whatever it's called, to find outbefore saying yes to that role?
Like, is it this whole worksheet of,you know, thirty things, or do you
(12:47):
have a couple, you know, top, youknow, 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 isa signal to me of product market fit.
Certainly like, you know, you could getthis, you could cut different segments of
(13:09):
those sales so that the gross retentionof maybe smaller customers is crappy
and larger ones is really great orwhatever, however you want to cut it.
But you really want to get anunderstanding of whether or not the
ideal customer for that businessis retaining with their dollars.
There's a logo retention andthen there's a dollar retention.
I would look at gross retention, gross retention of absolute logos.
The dollar amount is important, butif you bring on a company, you want
(13:32):
to see that the company is able toretain that segment at about 90%.
90% is like a healthy number, I wouldsay, for some small companies who
are focused on small business, likemaybe that number is around 80% just
because naturally small businesses goout of business sooner than others.
But let's just say like yourmedium to enterprise size
company, you want it to be at 90%.
(13:52):
And the reason this is so important fora marketer assessing a job is because
for all commercial teams, I would saysales, marketing, and let's just say
customer success, if the gross retentionis suffering below 90%, that is a problem
that the product team needs to solve.
And the VCs and the CEO, veryapprehensive to spend more at the top
of the funnel generating more leadsand more pipeline and more revenue if
(14:16):
they know it's leaking out the bottom.
So that's definitely the questionI would ask, you know, that's
far and away the most important.
The second thing to look at, if I were amarketing leader joining an organization
is probably the close rate percentage.
Because the worse the sales team is atclosing deals, the harder the job is
(14:39):
for the marketing leaders because youare covering what their quotas are.
So if their close rate is 25%, thenyou need to be covering, you know, you
need 4x the pipeline to cover that.
If they close at 20%, just fivepoints less, you need five times
the pipeline to cover that.
And what happens is, as that close ratechanges, the budget you need to support
(15:03):
that organization also needs to increase.
And sometimes that's not clear to thecompany that it's not, it's nothing
that I can do to solve for this.
Every time the close rategoes down, the budget for the
marketing team needs to go up.
So, you know, those are probablylike, I think the top two
that I would be digging into.
That's great.
All right.
And, you know, and I find asI talk to marketing leaders, I
(15:25):
always ask, you know, what are yourcriteria for saying yes to a job?
And many have a kind of structure for it.
You know, I, I like yours as, asvery, 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 theirprocess of due diligence.
And what, what tips do you have for, fora CMO to do that process of due diligence?
(15:50):
And how do you, I am very curious,curious about how you balance
efficiency and thoroughness?
Because if you ask every single lastquestion, you know, you're going to
exhaust the CEO and the whole teamand the recruiter and everything.
Yeah, and so I think the, you mentionedthis at the beginning, there is a list of
questions that I have, which are basicallywritten in the order of importance to me.
(16:14):
And at the very top of the listis this gross retention, like
the customer health metrics.
The second is people.
I do mention this because likeyour relationship either with
the CRO or the CEO is everything,mostly just for your mental health.
It has nothing to do with howsmart they are, but like, can
you wake up every day and getmotivated to work with this person?
Very important.
And I check Glassdoor for that.
(16:35):
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 withthe CEO or the CRO, you know, you
kind of need to investigate that.
So I would say, you don't want toexhaust the other side in the process.
But one of them, one of the asksI had when I joined Teampay was
(16:56):
basically, I put the questions ina spreadsheet and I just said, hey,
can I work with the CFO on this?
Mostly because they're a thought partnerto you just as much as the CEO is.
At Help Scout, it's a CFO, theCEO, and myself, and we manage
the different business units.
I manage the commercial.
Nick, the CEO, manages the productand engineering organization, and
Shawna manages the business functions.
That's, like, FP and legal, et cetera.
(17:18):
And so working with someone like a CFOor COO upon, like, even even joining
the, the company shows you like whatthat relationship would be like.
So, I did send the whole list over.
And I did say like, thisis part of my diligence.
I think it's important.
The article I have, it just saysinterview companies with the same
(17:39):
rigor they're using to interview you.
And frankly, that spreadsheet isvery well received in the, let's just
call it dozen times I've had to kindof like run a process in my career.
When I've used it, it shows thecompany that you have a very good
handle on the things that are goingto make you successful in the role
and they're very appreciative of that.
Because they too don't want tohire somebody who isn't a fit.
(18:02):
And one other thing I'll mention,like, I'm saying this, knowing that
sometimes you just need to take a jobbecause you need one and like, that's,
you know, certainly understandable.
But in the event that you have theopportunity to evaluate a job, I
would say, don't be shy in youknow, 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
(18:23):
Market Officier, which I think is great.
But I also think a way ofthinking about the CMO role as
Chief Marketing Education Officer.
Within a company, you know, they'reeducating about what the role is, and
a lot of companies, you know, the CEOis just not a marketing expert, and the
investors are not marketing experts.
And so part of the process of them doingthe recruiting is them learning from CMOs.
(18:45):
And so if a CMO just shows up andsays, okay, okay, let me answer
your questions, those questionsmight not be the right ones.
It's like, you're almost kind of guidingthe interview process, you know, with
your framework of, of what you want tofill in and figure out for yourself.
You said it exactly right.
It's like, well, they'regoing to interview you and
they have a set of questions.
(19:06):
Like, are you more of a brand marketeror a, you know, a performance marketer?
Right?
Like you, you come up in oneof those two paths, generally.
Either you grew up writing commsfor product marketing or content
marketing or your performance marketer.
Like, are you good at figuringout 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 companywhere your type is going to most benefit
(19:31):
them and that's how you become successful.
So like if you don't run a processand you get there and you find out
that they have ten reps and only fiveof them are getting over 50% of quota.
You've already joined an organizationwhere you know the uphill battle
will be on performance marketing.
Again, it's just really like a giveand take there, but I, I highly
(19:52):
recommend really scrutinizingthe business before you say yes.
Yeah, I love that.
And we'll include a linkto your article on LinkedIn.
Yeah, in the show notes.
Cause I think that'llbe, that'll be great.
So, you have this worksheetand, and you've shared it before.
Have you ever in any of your roles thatyou've been in, seen a CEO bristle about,
(20:13):
you know, over a particular question?
Or, you know, has that person eversaid like, "Oh, you know, you're asking
this, ooh, that's a little sensitive?"
You know, it's like a partnershipand, and you're saying, look, I'm
going to give you everything I havein this company, everything I have
to like make this company successful.
I need you to show me where I canbest give you leverage to do the
(20:34):
thing it is you're asking me for.
And if you're telling, and sothe bristle question usually
comes around gross retention.
It's the first one.
It's the most annoying because forCEOs, because that's their baby.
They can't stand that somebodyisn't loving their baby, right?
And thinking it's cute and likewanting to use it all the time.
And, you know, so gross retention usuallyreveals kind of where there might be
(20:57):
some, I don't know, weakness in, youknow, in, in the product market fit.
But I think approaching it in theway 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 goingto need to do all this stuff to grow.
(21:18):
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, wellthen why are you paying me?
You know?
At my level, like at, again, notnecessarily me, but like at a C level, C
levels have to be giving the CEO leverage.
They have to be able to offload stuff toyou that they just cannot do on their own.
(21:39):
And you have to be able tolevel that up and show impact.
And if they can't simply just revealto you where those problems are?
Red flag.
You have to be evaluating that as aninput to your decision making process.
Yeah, yeah.
I love that.
And certainly , as part of this, you'renot just throwing a spreadsheet at
them and saying, "Fill this out."
You know, there's, there's a certainamount of talking about why you're asking.
(22:05):
And I, I think that's, you know, youhave to do that artfully in an interview.
It's certainly an art.
But I think, yeah, I think the whyyou'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 myjob is to give you leverage because you
need help in these areas, like, let'sjust, let's talk about what those are.
(22:26):
The spreadsheet is really just anassessment to make sure that the things
that I have been successful in doing inthe past, I will be able to apply here.
If, for example, this is aenterprise level issue, right?
Like they're, they're having high, orlet's say high churn on the S and B side.
(22:46):
They want to go after enterprise, butmy experience is not aligned to that.
Like we need to know that now, you know?
So to your point, and about the themeof your podcasts, like it's just
de-risking on both sides is to makesure 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.
(23:08):
One is, just going back to this wholeCMO, CRO thing, because I know people
might say, Oh, I listened to Andreaand I see what she's saying about
one CRO, you know, kind of being overthe whole like growth number and the
whole, you know, like the number.
I wonder if those people would say, butI really like reporting to a CEO because
(23:33):
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 reallyhave a view, not just to sales
and customer success, but alsoproduct and finance, et cetera.
Also a great path, you know?
I think if you're a CMO, themessage is feel encouraged to move
into CRO because you're capable.
(23:54):
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 counterpartsto be very successful in the role.
You know, like to helpdrive that strategy.
So as a CRO, I think CMOsmake a great person for that.
And I think when the CEO hasone person very helpful to him.
(24:15):
However, in the event that in thatorganization, there's, you know, a sales
leader, really just responsible fornew business, and you're, you're one
input to that, which is to help generatepipeline, but there's all this other
stuff you really do need to connect withthe CEO on, like brand positioning, et
cetera, then absolutely I still thinkit's great to report into the CEO.
(24:35):
I would just want to make sure thatyou check in with the CEO to make sure
that they're still getting leveragefrom having the roles separated.
Yeah, yeah.
Okay.
Thank you for clarifying that.
And my final, final question for youis now that you're in a different
role and you hire, you know, you havea VP of Marketing reporting to you.
Do you have a favorite interviewquestion that you ask marketing
(24:58):
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 trackrecord of success and doing the role.
So that's kind of like table stakes.
So I'm asking a bunch of questions tomake sure that they're generally going
to be a fit for the needs we have.
But I just want to know that this personis nice and kind and compassionate
(25:22):
and like, you know, really caresabout the work they're doing.
So passion, curiosity, and grit.
I think some of the, whatdo you do in your free time?
Again, there's no evaluation orjudgment about what that thing is.
Say like, you know, do you liketo read books or something else?
The non work questions help me just betterunderstand who they are as an individual.
And if they bring an animal ontothe interview, even better.
(25:43):
We, I love people who bringtheir pets, you know, into
meetings and things like this.
I mean, it's sort of like a sillyanswer, but truly I am hiring for
the whole person and not just, youknow, a machine who maybe got lucky
on a ride with some company wherethey have that on their resume.
Truly it's about the, I don'twant to say the softer skills.
(26:04):
I don't think we're allowed to use thatanymore because they're not like soft.
They're still very important skills.
They're just the, the compassionateskills are really where I think
I ask more of my questions.
That's great.
Well, thank you so much.
This has been greatchatting with you, Andrea.
You too, Erica.
Thanks for having me.
That was Andrea Kayal, CROat Help Scout and former CMO.
(26:26):
Now, think about what questions aremost key for you to address when
you're in a recruiting process.
And how can you reduce riskas efficiently as possible?
Next time on The Get, you'll hearmore 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 smartdecisions around recruiting and
(26:47):
leadership in B2B SaaS marketing.
We explore the trends, tribulations,and triumphs of today's top
marketing leaders in B2B SaaS.
If you liked thisepisode, please share it.
For more about The Get,visit thegetpodcast.com.
And to learn more about my executivesearch practice, which focuses on
recruiting the make-money marketingleaders rather than the make-it-pretty
(27:08):
ones, follow me on LinkedIn orvisit theconnectivegood.com.
The Get is produced by Evo Terraof Simpler Media Productions.