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December 12, 2024 26 mins

In this episode of The Get, we highlight key insights from this season of The Get, which is all about the race to reduce risk in CMO recruiting. Host Erica Seidel and her guests delve into the intricacies of how CEOs and CMOs at B2B SaaS companies can make more-informed decisions before saying yes to each other.

Whether you’re hiring a CMO or looking to step into a new CMO role, you will learn a lot from these takeaways, which range from the practical to the provocative.

We discuss the challenges, fears, and risks that CEOs and investors faces when recruiting a CMO. For instance, they often worry about hiring CMOs who either misalign with the company’s growth stage or struggle to get to the right blend of short-term wins and longer-term impact. We discuss how to mitigate those risks, such as by co-creating the roles and managing expectations about timelines for marketing results.

Then we turn to the candidate side: What risks and red flags do CMO candidates perceive when evaluating CMO roles, and how can candidates reduce these risks? We discuss red flags such as unclear product-market fit, inadequate resources, and misaligned leadership dynamics. We cover several practical strategies for ensuring a good match and getting off to a successful start in a new CMO role.

A huge thank you to the guests this season:



00:00 Introduction to The Get

00:52 Understanding the High Stakes of the CMO Role

03:37 De-risking CMO Recruiting

07:53 Red Flags for CMO Candidates

10:16 Mitigating Risks as a CMO Candidate

18:53 Maximizing Success in a New CMO Role

23:26 Conclusion and Final Thoughts


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 The Race to Reduce Risk in CMO Recruiting. 

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

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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Welcome to The Get.

(00:01):
I'm your host, Erica Seidel.
I spend my days recruiting CMOsand VPs of Marketing in B2B SaaS.
I'm all about placing themake-money marketing leaders,
not the make-it-pretty ones.
This season is thesixth season of The Get.
We've been focusing on the raceto reduce risk when it comes to a
match between a company and a CMO.

(00:23):
How can you find out what you need tofind out before saying yes so that you
can make smart decisions that stick?
Whether you're hiring a CMO, orlooking to step into the role
yourself, you will learn a lotfrom this season's conversations.
The takeaways range from thepractical to the provocative.
Today, I'll summarize some key insights.

(00:44):
As you listen, make a note of topics thatseem particularly compelling so that you
can listen to those episodes separately.
Let's get started.
We'll look first from the perspectiveof the CEO or the investor for
a company that's hiring a CMO.
If this is you, you know thatthe CMO role is high stakes.
Marketing is often centralto a company's growth plan.

(01:06):
Often, CMO roles are "revenuerescue missions," in the words of
my guest, CMO Melissa Sargeant.
The challenge is that marketing is one ofthe least understood executive functions.
This came up in my conversation with PeterMahoney, Chief Commercial Officer of GoTo.
We called his episode What CEOsFear Most When Hiring CMOs.

(01:28):
He discussed how everyone at theC-level thinks they understand
marketing, but at the same timefears that they don't understand it.
That's a lot to unpack.
Part of it is that CEOs fear that thenew CMO won't connect with what the
actual problems are to be solved andwhat their role should be focused on.
You could worry about hiringthe CMO who focuses too much on

(01:50):
flashy campaigns and not enoughon delivering measurable results.
You could also worry that a marketingleader will overspend in general or fail
to adapt to your company's growth stage.
Another worry is just notknowing what you really need.
Maybe you've made hiring mistakesbefore, like hiring a demand
generation expert, when what youreally needed was someone more T-shaped

(02:13):
with more strategic background.
One thing's for sure, CMOs don't failfor lack of effort or lack of talent.
They fail, when they do, because oflack of clear role design, and they fail
because expectations are not aligned,especially for how long things will take.
James Lamberti, who's Head of Go-to-Marketfor the investment firm Georgian,

(02:34):
discussed this on the episode calledTop Threats to CMO Success and How
CEOs and CMOs Can Tackle Them Together.
This is a common issue for technicalfounders, first-time technical
founders, new day, new strategy.
It's a reset button on marketing, andI will often try to break through with
a technical founder by explaining whenyou reset your marketing strategy,

(02:55):
it's the same thing as if youfully reset your product strategy.
You would never just go into yourproduct team from an R&D perspective
and shred the two or three quarterproduct roadmap because you're putting
your entire dev team back to zero.
Marketing actually works more likeproduct than it does like sales.

(03:17):
The returns on it are two,three, four quarters out.
And so that is a huge area where if youdon't pull that out of the conversation
effectively, that can come back to bereally painful because every quarter
we're gonna switch strategy and marketing,and then you can never get anywhere.
And eventually you're out thedoor in four to six quarters.

(03:37):
So, how can you de-risk CMO recruiting?
First, clarify your needs ahead of time.
Co-create the role withcandidates, learning as you go.
The best CMOs are also ChiefMarketing Education Officers.
Ask them to teach you.
One of my clients asks candidates thingslike, how should I think about ABM?
And asks for them to educate her.

(04:00):
Next, make sure you have a structuredframework to vet candidates, and
reduce risk by considering a trialperiod, like having someone work
on a fractional or advisory basisbefore making a permanent hire.
Beyond interviewing, acknowledgethat the CMO role is on a different
time horizon for producingvalue than some other functions.

(04:21):
Their value is not just this year, butin years two, three, four, and beyond.
This means that CMOs have to embracethe duality of being asked to produce
both short-term and longer-term value.
Norman Guadagno, former CMO of Mimecast,discussed this in his episode called, What
Veteran CMOs Know That First-Timers Don't.
Fundamentally, I think the CMO has toembrace the duality of no matter what, or

(04:50):
at least most of the time, you're going tobe asked to produce something short-term.
Just the way business works.
And what you have to be able to dois explain, yes, I can do X, Y, Z.
But you also have to beright, clear, upfront.
There's a set of other thingsthat are going to take longer.

(05:12):
And I want to make sure I laythem out right from the start.
And I give you my best estimateon how long this will take.
Oftentimes, and we can't avoidthis discussion, it'll be brand.
"I want to build a big brand."
"Let's make the brand better."
Awesome!
We all love that.

(05:33):
But it doesn't happen overnight.
Everyone knows that,but doesn't know that.
You know it intellectually, but everyexecutive, CEOs included, are under
pressure from someone else to get resultsfaster, especially in today's climate.
You have to start to thinkabout, there's not one timeline

(05:54):
that you want to talk about.
You want to talk about the timelinefor things that will happen in months
and quarters, and the timeline forthings that will happen in quarters and
years, and how do you balance those?
And how do you know that, I understandthat it's going to take a while.
And this is something I've experiencedmultiple times in my career.

(06:18):
I have had the discussion with boards,with other executives, where I say,
this is the thing we're going to do.
We'll talk about brand.
We're going to invest in brand building.
It's going to take threequarters, four quarters, whatever
numbers I put on the board.
And then I also say, we need tohave it be sustained investment.

(06:40):
If you lose your patience in twoquarters and want to pull the investment,
we shouldn't do it at all becausethen it's just wasted investment.
That then shows you as a goodeconomic business decision maker.
Also, look for CMOs who use collaboration,education, and communication
as their not-so-secret weapons.

(07:02):
Tracy Eiler, who's CMO atOpen Sesame, discussed this.
As marketers, we end ourselves up inbusinesses where we have to do loads
and loads of internal marketing andcommunicating and not only about
what we're going to do, but whatwe're not and why we made a decision
to do thing A versus thing B.
In fact, right now we're working ona website redesign and we're using a

(07:25):
very much iterative kind of testingapproach to decide where we land on
fundamental things like our homepage.
And, you know, I'm using thatmantra that we are continuously
testing because of this constantopinion that we keep getting back.
So that for me is a scenario that Ithink we all should expect that there's

(07:46):
going to be lots of opinions aboutwhat we should and shouldn't be doing.
And we need to be the ones thatare going to provide clarity on
how we're making decisions and why.
Now, let's look at all of thisfrom the perspective of a CMO who
is considering joining a company.
If this is you, there are somered flags that you would be
wise to be on the lookout for.
I discussed this topic in detailwith Melissa Sargeant, who is CMO

(08:09):
at Lumaverse now, in our episodeon Avoiding Red Flags and Decision
Making Flaws in CMO Recruiting.
One red flag is that the companyused to have product market
fit, but doesn't anymore.
It can also be a red flag if the companyis pitching a strategic CMO role, but they
really see marketing as a lead factory.

(08:30):
Another thing to look out for is asituation where you won't actually have
the resources and authority to succeed.
This can sometimes be the casewhen the head of marketing reports
to the CRO, which is a topic wecovered in several of the episodes.
Another red flag to look out for, that thecompany won't really be ready for change.
That innovation is needed butnot wanted, in other words.

(08:53):
Relatedly, it's a red flag ifthe CEO has overly optimistic
expectations of what marketing canachieve in a certain time frame.
Obviously, there's a lot to considerbefore you say yes to a role.
Part of evaluating a position entailstuning into your own appetite for risk.
Realize that your perception of riskchanges as you evolve in your career.

(09:14):
I talked with Norman Guadagno about this.
Norman has led marketing many times,including most recently at Mimecast.
We talked about what we called anarc of caution in career progression.
What that means, as a marketingleader, you could go through stages
with your relationship with risk.
Early on in your career, you could bevery open minded and gung ho to take

(09:35):
on big challenges, even with risk.
You just don't recognizethe risk in a situation.
Then, as you get more marketingleadership experience, you're increasingly
able to recognize risky situations.
Over time, you'll be able toidentify more warts in a situation,
so your risk profile peaks.
Then, you may right size your risk ifyou diversify your career by contributing

(09:58):
to different boards, for instance, orif you take on a non-marketing role.
So think about where youare on your arc of caution.
Okay, we've looked at the risksthat CEOs and investors perceive
and how to mitigate those.
And we've looked at the risksthat CMO candidates can notice.
Now, let's finish by looking at waysthat you as a CMO candidate can mitigate

(10:21):
risk before saying yes to a role.
First, look inward when you're atthe start of a career transition.
What are your non negotiables?
Maybe you need to report to a CEO andwon't consider reporting to a CRO.
Maybe you need clear evidenceof product market fit.
Next, define what my guest JamesLamberti calls your ideal CEO profile

(10:42):
and how to add value to that person.
Also, do your due diligence ona company's culture, leadership
team, and strategic priorities.
The best CMOs have frameworksfor doing this, like Tracy Eiler,
who has a rapid pressure testingplaybook that we talked about.
You'll come up with your own.
Analyze the growth metrics.
Consider calling up people whohave worked for the CEO before.

(11:04):
Ask for a product demo to evaluatethe company's go-to-market maturity.
The first episode this season wascalled Everything a Good SaaS CMO Should
Find Out Before Saying Yes to a Job.
I interviewed Andrea Kayal, CROat HelpScout and a former CMO.
Andrea talked about some ofthe key things she looks for.
Here's a clip:

(11:25):
If the gross retention is sufferingbelow 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
they know it's leaking out the bottom.
So that's definitely thequestion I would ask, that's
far and away the most important.

(11:46):
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
for the marketing leaders because youare covering what their quotas are.

(12:08):
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
that organization also needs to increase.

(12:28):
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, those are probably I think thetop two that I would be digging into.
Another good perspective on what toask when doing your due diligence comes
from Melissa Sargeant, multi-time CMOnow running marketing for Lumaverse.

(12:51):
She shared a couple of key questions sheuses to suss out organizational dynamics.
So the areas I really like to digdeep into are the dynamics around how
that executive team works together.
I will usually start at a higherlevel and ask about how does

(13:11):
strategy get developed here?
And often people will say something like,we do OKRs, or we do the V2MOM framework.
Great.
I love frameworks.
How do you get there?
What happens before that comes on paper?
Oh, we go on an offsite.
Fantastic.

(13:31):
What does that offsite look like?
Do you, Ms.
CEO, come to that meeting withdocumentation that you've put
together in terms of your goals andhere's how you see the strategy?
Do you have each of your executiveteam members come prepared with
a presentation or a talk trackon what they see the strategy is?

(13:56):
How does that happen?
It's very telling about the dynamics ofthat organization because what I've seen
is some very top-down structures wherethe CEO, or maybe it's a founder CEO,
very common, certainly in my space, isthe visionary in the company and they're

(14:18):
the person that's looking around corners.
So they have a very clear view of whatthey think that strategy should be.
Or perhaps it's a more mature organizationand all the key stakeholders, all the
key executives come with what they think.
They've done their research and they'vegotten their feedback from customers

(14:39):
and they come to the table with that.
How that process happens and thediscussions that happen around it
is incredible insight on how thatteam works together on a daily
basis and what you can expect tosee in your executive team meetings.
Because in those meetings, my viewis that everyone should be talking.

(15:04):
And some organizations, if you see or ifyou hear, it seems like there's one person
who talks the most and others are justlistening and maybe asking a question.
That's something you want to understand abit more about because if everybody really
has a strategic seat at that table, howthat process happens is really critical.

(15:31):
The part two of that that I willask them is, how do you disagree?
You get lots of differentresponses to that.
In a healthy working environment,there is a level of disagreement that's
necessary to move the company forward.
It can be done in a respectful andprofessional way, but it should be a red

(15:56):
flag for candidates if they see thoseinteractions, and if you feel like you
get into these spirited discussions andthen you go away from that meeting, and
if you have to spend the next two weeksrepairing your relationship with your
colleagues, it's probably not a healthyorganization that celebrates and wants

(16:19):
those diverse voices at the table.
Next, treat the interviewprocess as a two way dialogue.
Sometimes, candidates don't realize thatthey can help the recruiter and the CEO
to shape the search and the outcome.
By coming prepared with specificframeworks and questions, you can
position yourself as a strategic partnerrather than a transactional hire.

(16:41):
Beyond simply positioning yourself for therole, the recruiting period is a good time
for starting to align expectations theway you will do when you are in the seat.
James Lamberti, the veteran CMOwho's currently at Georgian,
shared how he has collaborated withCEOs to jointly figure out a fit.
I always try to, in the earlystages of the interview process,

(17:03):
start to probe the CEO and be like,for example, starting with the ICP
definition, who are you selling to?
Please tell me all you can about thespecifics of who you're selling to,
and what I'm trying to understandis how well defined is the ICP?
And does this CEO founder truly understandhow important it is to have a specific,

(17:24):
quantifiable description of the ICP,and how focused and quantifiable is it?
The more clear that is as amarketer, of course, frankly, the
easier it is for you to add value.
'Cause if you're coming into acompany that's like I know my sales
addressable market in the next twelve totwenty-four months, it's $350 million.

(17:45):
It's in these geographies.
It's this type of persona.
It's this pain point that I'm solving for.
These technologies are present as a clueor signal from an intent perspective.
All those details are so valuable for youbecause you can now be laser focused on
doing what you do as a marketer, which isdrawing a circle around that market from

(18:07):
how you do your targeting, your demandgen, your brand building, your messaging,
your event selection, all of that.
And throughout the process, realizedthat it often takes a village
to make a smart career decision.
I talked about this with TracyEiler, CMO at Open Sesame.
Our session is called CMOSecrets to Maximize Recruiter
and Network Relationships.

(18:28):
Tracy shares her roadmap forstaying in touch with her network
in an almost programmatic way.
She talks about the importanceof a personal board of advisors.
People that you can share job leads with,swap ideas with, get advice from, etc.
From my standpoint, one of the best linesof questioning I get from candidates is
simply, how do I line up with the spec?

(18:48):
What are the concerns that thecompany has about my candidacy?
Now, once you're in the role, yourrisk mitigation strategy does not end.
It continues.
How can you increasethe chances of success?
First, realize that yourjob is not just marketing.
Peter Mahoney, Chief CommercialOfficer at GoTo, makes the point
that fifty percent of the CMO rolehas nothing to do with marketing.

(19:12):
The first time you're a CMO, youmay not realize this, that only
half of your job is marketing.
The other half is being part ofthe executive team and leading
the business, and that requiresa different set of skills.
One thing Peter recommends, if you needto, call up a friend in finance and
have them walk you through the P&L.
They'll be happy to do it.
Next, realize that change may takelonger than you think it will take,

(19:35):
depending on a company's appetite for it.
First-time CMOs may be overly optimisticabout how long it takes to implement
change, so they may fall into the trapof over promising and under delivering.
Beware that, and manage up aroundexpectations and timeframes for results.
For instance, if you're doinga big rebrand, tread carefully,
communicate thoroughly, and set clearexpectations of how long it'll take.

(19:58):
Maybe you tell your CEO that sincebrand building is a longer term thing,
it's natural for them to start feelingantsy in a few months into the project.
Get to know the talent on your team, boththe people who are in their seats already,
and people who are interviewing with you.
Peter Mahoney shared a goodperspective about how to assess talent.
When I just took over this go-to-marketorganization, there was a lot of questions

(20:24):
about, well, what's he going to be like?
How is he going to be as a leader?
And I spent a lot of time tellingpeople that I like as a leader myself,
I like to start by understanding.
I like to dive into a lot of detailto understand what's going on.
So I'm going to ask a lot of questions.
I'm going to really try to understand,maybe peel back the onion, push on you

(20:45):
a little bit to really understand what'sgoing on within your particular domain.
And then I'm going to back off.
Ideally, I want to get to the pointwhere I give you a set of guardrails,
give you a goal, say this is what I wantyou to achieve for your particular area,
give you some guardrails, and thoseguardrails are things like these are the

(21:05):
behaviors that we accept, and this isthe way that we operate as a company,
this is how you need to communicate, etc.
But it's really important to be ableto have that beginning part, be able
to really dive down and understandthe specific domain, and that's one
of the things that I find some ofthe most effective executives can do.
Even if they're not an engineeringleader, as an example, should absolutely

(21:28):
be able to ask provocative questionsthat are at least logical questions.
It doesn't have to be abouta specific line of code.
You should be able to understandand question people to the level
that you understand what their levelof understanding is, how confident
they are, and whether they reallyhave a plan to achieve what they're
saying they're trying to achieve.

(21:50):
Next, in a new role, think about howyou can build a flywheel of credibility.
Gary Survis from Insight Partnerstalked with me about this.
We called our episode, Building YourFlywheel of Credibility: A Playbook
for New CMOs in PE-backed Companies.
Take your time initially tobuild an assessment of the org.
Identify and surface problems ratherthan sweep them under the rug.

(22:12):
In other words, diagnose, don't delude.
Be able to make swiftorganization decisions.
As Gary says, if you're not successfulbecause the people below you are
not strong, you have no one to blamebut yourself for not making the
changes you know you need to make.
Gary also encourages new CMOs to havea perspective on AI, including how to
organize their teams and define rolesdifferently for AI supported marketing.

(22:37):
I'm encouraging CMOs today to thinkabout whether they want to create a BG
or an AG organization, Before Generativeor After Generative organization.
If you choose to do the BGorganization, recognize that the
responsibilities are going to change,the roles are going to change.

(22:58):
Or, are you going to try to start movingyour organization to the way technology
is going to change the structure?
For that reason, I encourage them todo a little more forward thinking about
what people's roles are really goingto be, where you're going to need.
Do you need five creative people?
Do you need as many writers?

(23:19):
Do you need more editors?
What do you need based on howthis technology is moving?
You should have a point of view.
Taking a step back here.
A successful career, in my view,comes from three things - talent,
good luck, and good decision making.
Let's assume you're talented, andlet's assume luck is out of your hands.
The lever that you're leftwith is your decision making.

(23:41):
In the episode I did with MelissaSargeant, who's now leading marketing
at Lumaverse, we talked about the flawsin decision making that can get in
the way when hiring or getting hired.
For instance, trusting someone else'sdue diligence without doing your own.
Thinking that this situation isso much like another, so the same
playbook you used then will work now.
Or the same person who didthis job in another company

(24:03):
will succeed at your company.
Another flaw?
Falling in love with the companythat someone worked at, rather
than focusing on how they approachtheir role and their work style.
Remember, sometimes a company issuccessful because of someone's
contribution, and sometimes it'ssuccessful despite their contribution.
This all sounds very analytical.
The fact remains, there's only somuch de-risking you can do with a

(24:25):
hiring decision before taking a leap.
That's why your gut matters, too.
In my episode with Melissa, shesaid something that stuck with me.
"Your gut is your truth."
So if you feel a red flag, becurious and investigate it more.
Learn to recognize andinterrogate your gut.
Translate for it becauseit doesn't speak English.
I hope these insights from our guestshave given you actionable ideas for

(24:49):
your next big CMO recruiting decision.
Thanks for listening to The Get.
I'm your host, Erica Seidel.
The Get is here to drive smartdecisions 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 thisepisode, please share it.

(25:10):
For more about The Get,visit TheGetPodcast.com.
To learn more about my executive searchpractice, which focuses on recruiting the
make-money marketing leaders rather thanthe make-it-pretty-ones, follow me on
LinkedIn or visit TheConnectiveGood.com.
The Get is produced by Evo Terra andthe team at Simpler Media Productions.
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