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May 30, 2025 18 mins

This week's show is entitled, "Courageous Marketing: The B2B Marketer's Playbook for Career Success" and my guest is Udi Ledergor, Chief Evangelist at Gong.

Tune in to...

  1. Learn how to create memorable brand experiences and why they are crucial for lasting customer connections.
  2. Understand the balance of providing psychological safety and process accountability to inspire innovative marketing teams.
  3. Discover how to shape a courageous career by aligning your strengths with the right opportunities and roles.

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Matt Heinz (00:16):
All right.
Welcome to another episodeof Sales Pipeline Radio.
I'm your host, Matt Heinz.
So excited to have you here as we roundout May and head into June already.
For those of you that are joining liveon LinkedIn or YouTube, thank you very
much for making us part of your day,part of your business day, your week.
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(00:36):
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today feel free to throw that in.
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And thank you as always for doing that.
If you're listening or watching ondemand thank you for downloading and
subscribing over 260,000 downloadsnow for Sales Pipeline Radio.
If you wanna access any of thiscontent, current, past, and

(00:58):
future you can always find it.
Sales Pipeline Radio dot com.
Super excited to have today our guest.
He is former CMO, and now chiefevangelist for Gong, Udi Ledergor.
Udi, thanks so much for joining us today.

Udi Ledergor (01:10):
Thanks for having me, Matt.
I'm excited to be here.

Matt Heinz (01:13):
I feel like there's so many things we could talk about, but so
much of it is in this book, CourageousMarketing that you published a month.
I got my copy show off.
You've all got a copy.
I mean, hopefully if youdon't have a copy, like go
get a copy of this right now.
I've got a few behind me.
You might be able to see.
I'm sure you, well, you do have a few.
We got a whole row there.
Not surprising.
I'll tell you what, there's a lotof books that I need to read, in my
job that are nonfiction, but thisis one that was just a joy to read

(01:36):
because of the topic, because ofthe approach that you took on it.
And I think I would argue thatthis could be part of your beach
reading list for summer 2025.
Like there's a lot of business books.
I would not say take to the beach, right?
Because like it is not beach reading.
I think this is one, and I'm not justsaying that, but Udi what, I mean you've
been in, you've been marketing leadership,investor advisor for a long time.

(01:58):
Why this book?
Why this topic?

Udi Ledergor (02:01):
You know, Matt, for the last 20 years I've been doing
B2B marketing and in the last nineyears I've been doing that at Gong.
For the first almost seven years, I wasCMO at Gong and I kept going on podcasts
not as wonderful as yours, but others,I've been speaking at conferences and I've
been sharing how we did things to succeedas well as we've been doing at Gong.
And lots of people tell me,Udi, you've gotta write a book.

(02:23):
It's so practical.
It's so programmatic.
You just tell people tacticallywhat they need to do.
And I used to joke like, when wouldI ever get time to write a book?
And then two years ago, I transitionedinto my current role as Chief
Evangelist and suddenly I had thetime to sit down and write a book.
So I decided while it's all freshand I'm still in touch with all the
people who made the magic happen,I'm gonna sit down and write a book.

(02:45):
And that's what I didin the last 18 months.
And then last month, the book came out.
Courageous Marketing became an instantbestseller in half a dozen categories
on Amazon, which is super exciting andthousands of people are already reading
it on the beach while mowing the lawn, onvacation, on business trips, it's designed
to be read on a coast to coast flight.
So between San Francisco and New York, itonly takes four and a half hours to read.

(03:08):
You can finish this.
On any short flight,

Matt Heinz (03:11):
Unless you're flying into Newark, you might finish
it before you even take off.

Udi Ledergor (03:14):
Before you even take off.

Matt Heinz (03:16):
Yeah.
So this, there's a coupleangles of this book I wanna be
able to talk about for folks.
First is sort of the marketingplaybook component, and the second
is the career success component.
Boy I feel like it's becoming a harderand harder time to be a marketer in a more
and more exciting time to be a marketer.
As the field is flooded withinformation, flooded with noise.

(03:38):
Harder and harder to break through,but I think more exciting, more fun,
more fulfilling to be in a role tosort of build and earn that attention.
What have you learned in your careerand in your time at Gong that sort
of feeds into the playbook thatmarketers need to follow today?

Udi Ledergor (03:54):
Right.
So I love how you dividedthe, the two main topics.
You know, the first two thirds ofthe book are things that people
who have been following me andGong would expect to find there.
So, I talk about timeless lessonsin building brand, in building
content, in creating a productcategory or in creating magical event
experiences, all these things and more.

(04:15):
And people are telling me when they'rereading the book that they think that
these things are so important to reiteratenow when people are using and abusing AI.
For things that it's good for, but alsofor things that it should not be used for.
Like having a sharp pointof view on something.
AI can't do that yet becauseit's only averaging the things
that are already out there.
So if your content is not landing andyou're using AI to create tons of it,

(04:38):
maybe that's why, because AI can comewith that sharp point of view yet.
So that's, that's kind ofthe first part of the book.
And then the second part is things thatI haven't talked about a lot publicly
but I thought would be an amazingopportunity to put some down in the book.
And I honestly co-wrote a lotof those chapters with not only
my former team members, folkslike Devin Reed and Chris Orlob.

(05:00):
Um, Vince Chan, Sheena Badani.
And many others.
But also I interviewed otherCMOs and sales leaders like Ryan
Longfield, who's now at Shopifyand was the longtime CRO at Gong.
We practically co-wrote the chapter on howsales and marketing should align together,
and I think those lessons are timelessbecause they talk about the human side

(05:21):
of marketing and how to navigate yourcareer from finding the right company
identifying whether your CEO is gonnagive you the flexibility and wiggle room
that you need to be creative in marketing.
How to build a courageous team to dotheir best work while working with you,
and how to work with sales to produce thebusiness outcomes that your company needs.

Matt Heinz (05:42):
So much to unpack there.
Talking today on Sales PipelineRadio with Udi Ledergor.
He's the Chief Evangelist at Gong, authorof the amazing book Courageous Marketing.
Excuse me, so many marketers arefixated on clicks and likes focused
on impressions and form fills.
You talk a lot about experiences.
Experiences isn't always somethingyou can immediately track.

(06:05):
It isn't something that you necessarilyalways have on a dashboard, but I
think it's becoming more and moreimportant in the marketing playbook,
in the go to market playbook today.
Why do you think experiencesare so important?

Udi Ledergor (06:17):
Experiences are a phenomenal way of creating a memory link between what
your brand stands for and being valuable.
And so how does this work?
By now I assume most of our listenersand viewers have heard about the 95/5
rule, which suggests that only about5% of your audience are in market.
You can argue about the number.

(06:37):
It could be 7% or 9% in your market.
Nobody cares.
It's a small percentage of market.
Otherwise, everybody would bebuying everything from you now,
and you'd have no pipeline for nextquarter, but that's not the case.
Right?
So most marketers would agree, there'sonly a small percentage of my market
right now in market, but how do I createand nurture relationship with them
so that when the 95% not currently inmarket do move into the buying zone?

(07:02):
It could be in six months, could bein 12 months, could be in 24 months.
How do I make sure I'm thefirst name that they think of?
Mm-hmm.
And the way to do that is to creatememory links that connect what you stand
for with what they might need in thefuture and keep that relationship going
until they're finally in the buying zone.
Now, experiences are anamazing way of doing that.

(07:23):
Standing out and being valuable whenothers are trying to just hard sell all
the time is an amazing way of doing that.
And so here are three very tacticaltips to how to create those experiments
and relationships and experiences ina way that builds those memory links.
So.
I'd say number one preemptivelybudget your marketing

(07:44):
experiences and experiments.
And here's how I always dothis with my CFO and CEO.
I say, look, there's twothings you need to know.
One, whatever's working for us in creatingpipeline and demand gen right now is
going to stop working at a certain point.
I don't know if that's next weekor next quarter or next year.
Mm-hmm.
But everything that's workingnow is going to stop working.

(08:04):
We need to constantly be experimentingwith new things that we're not doing yet.
Some of them are gonna be duds, someof them are gonna look promising.
We need to budget for that.
So they say, okay, that makes sense.
What's the second thing?
I say, here's the second thing.
We're usually doing the budgetingexercise, say in October November,
preparing for next year's budget.
But here's the thing, there's gonnabe things that, opportunities that

(08:26):
present themselves in the middleof next year that we'll wanna do.
But I don't know about them now becausethey haven't been announced yet.
This could be a big event that happensnext October that might only be
announced in April if we don't putaside some budget for these things now.
I'm never gonna be able to capitalizeand monetize on those opportunities.
So that's the second reason whywe need to preemptively budget

(08:47):
for these marketing experience.
And even the most data-driven,cynical, CFO or CEO will see the
light in those two arguments.
So that's one really practical tip.
The second one is differentis better than better.
Mm-hmm.
You don't wanna play the gamethat everyone is playing by
trying to outspend them, becauseas a startup you can't do that.

(09:08):
All you can hope to do is be differentand by being different, you're
already leading in your own space.
Gong did that when we looked athundreds of B2B websites back in
2018 or 2019 when we wanted toroll out our first visual identity.
And back then everyone was using thesame palette of what one of my team
members called the Series A blues.
And they pair beautifully with whites andgrays, but that's what everyone was using.

(09:32):
So Gong decided not to find a betterblue than everyone was using, but to
go in a completely different direction.
And we chose fuschia pink and purple,and a drooling bulldog as a mascot.
And guess what?
That earned us a lot of attentionwith very little budget.
So that's the second thing.
And then the third thing is really toprovide continuous and consistent value

(09:53):
in your content marketing, in your eventexperiences, in your thought leadership,
in your swag, and everything that you'redoing to create those memory links so
that in 18 months when John Smith isfinally moving from the no buy zone to
the buy zone, Acme, Inc. or whateveryour company is, is the first name that
he thinks of when he's ready to buy.

Matt Heinz (10:14):
I love that you've differentiated sort of budgeting for
courageous marketing and creatinga culture for courageous marketing.
I will never forget years ago, workingwith a company that told me that
internally there was something thatthey knew of as reputation capital,
and what that meant, what thatliterally meant was you don't wanna be
associated with a project that fails.

(10:37):
Think about that.
Think about what that does to innovation.
Think about what that does to courage.
Think about what does, to letting anybodytry something that is not by the book.
And you could imagine how wellthat company did over time, but

Udi Ledergor (10:51):
That's such a terrible idea.

Matt Heinz (10:52):
Well, of course it is, right?
But like, I think, but it's not,but not everyone understands it sort
of inherently, like this culture ofcourage or this cult-, like I've just
in the past, like culture of failure.
Accepting and encouragingfailure as part of the process.
That is not a common thing.
How do you create a cultureand a team that accepts and

(11:14):
rewards courage in that format?

Udi Ledergor (11:17):
Right?
So let's talk about that.
'cause I think it's, it'sone of the most important.
And one of my favorite chapters of thebook, I'll be honest is how to create a
courageous team that does their best work.
And this was a discovery process forme in hindsight, when I interviewed
half a dozen of my team members andsaw all these themes and stories
bubbling up, they finally formed apicture and a framework that I could

(11:37):
not have put into words earlier.
So let's say two things about this.
One, exactly what you said.
If you create a culture where peopleare afraid to take risks, if they never
want to be associated with failure,you're creating a culture where
everyone is always playing it safe.
And guess what?
When everyone's playing it safe,you're never gonna drive innovation.
You're not gonna do anything creative,you're never gonna stand out.

(12:00):
You're just going to play it safe andfollow those dreaded best practices,
which in reality are boring practicesbecause by the time anything becomes
a best practice, everyone is doing it.
So you are guaranteed at best,the ordinary results that
everyone else is getting.
You're never gonna createanything extraordinary.
So if we all agree that to createsomething extraordinary, which is

(12:20):
what most of us say we wanna do, wealso have to do extraordinary things.
And that means risk failure andactually, promote it and encourage it.
So that's one thing.
The second thing is, okay, sohow do you actually do this?
How do you create this culture?
And here's a really overlysimplified version of it.
There's lots more in the book.
And not only in my book, I would highlyrecommend Adam Grant's book "Think

(12:41):
Again" to anyone who wants to learnmore about creating this culture.
He wrote about winning teams atNASA and other great organizations
and how they created this culture.
But here are the two mainpoints from that chapter.
What you want to create ispsychological safety where your
team members feel safe to fail.
They know that if they drive anexperiment and take risks and things,

(13:05):
inevitably will not always work out.
They will not be fired for doing that.
They will be celebrated for the learning,for the initiative, for the risk taking,
and it's that culture of psychologicalsafety that allows people to come
out of their shell and go beyond thebest practices and do amazing things.
Now, theoretically, that could lead topeople going rogue and doing experiments

(13:29):
for the sake of experiments and notalways tied to the business goals.
So you do have to counterbalancethat with something else that Adam
Grant calls process accountability.
In the simplest of terms, the way Icould describe this is everyone needs to
be rowing towards the same North Star.
So if we know that we have acertain amount of pipeline to create
this quarter, that is the goal.

(13:51):
And we're gonna create a processaccountability around achieving that goal.
But within everyone's realm, in socialmedia and in events and in content,
everyone can do whatever they need to.
Use whatever means and take risks anddrive experiments to get to that goal.
And that's where the psychologicalsafety meets the process accountability.

(14:12):
If you can create those two thingsworking in harmony, you would be
amazed at what your team can do.

Matt Heinz (14:17):
So important and just so easier said than done and so rare
I think, in organizations today.
I think last topic I wantto cover with you, Udi.
We've talked about courageous marketing.
We've talked about courageous teams.
Let's talk about courageous careersbecause this is a, this book was written
as a playbook for how to do bettermarketing, but I love that it really
covers this as a function of careersuccess for people listening, whether

(14:40):
they're beginning of their careers, midcareer, wherever they're at, what does
a courageous career mean and what aresome things people can do to sort of
lean into that concept a little more?

Udi Ledergor (14:51):
I think courageous career means that you lean into
your strength and you focus on them.
And this is again, a counterintuitive,I think, mistake or false assumption
lots of people have, which are, oh,I've gotta work on my weaknesses because
maybe I'm a super creative person,but I don't know enough about data.
So I'm gonna take all these datacourses and try and get better at that.

(15:14):
I'm not saying don't do that, butyou're probably never gonna be
the best data person if you'realready inherently weak at that.
But if you continue to sharpen yourcreativity skills, which you're
passionate about and you're alreadygood at, and everyone's telling
you what a creative person you are,that's where you can actually shine.
Yeah.
And so not accepting that you haveto change dramatically to succeed,

(15:35):
but actually taking what you're goodat and finding an opportunity to let
those skills shine, sharpen them,and use them in everywhere you can.
That's one way of creatinga courageous career.
Now, I talk in the book abouttwo paths of getting there.
One of them is correctly choosingthe company, the CEO, and the role
where they will let you shine.
And I have frameworks for how to do thatand how to check the culture on Glassdoor

(15:59):
and how to check the product market fit onG2 and how to ask your friends who might
be using the product or potential users ofthe product to find a lot of the pitfalls.
'Cause here's one very common one,Matt, when every marketer I know has
stepped into a company without productmarket fit and ended up having to
leave the company pegged as a failure.
When it was not even her fault.

(16:19):
Mm-hmm.
Because the company had noway of succeeding because they
don't have product market fit.
But of course, marketing gets, uh, getsblamed for that because you didn't create
pipeline and you didn't create sales.
And nobody knows about us.
Of course, nobody knows about us.
Like we don't have a single happy customerwho's getting value from the customer.
I can't scale that.
Right.
But so that's one path.
And then the second one that Italk about extensively in the book

(16:41):
is how to create your own roles.
So you might not do this from yourvery first role, but once you get
into an organization and see whereyour skills are most helpful, not only
did I build my career that way, but abunch of other people I spoke to like
Tricia Gellman and Carilu Dietrich andother great stars in the CMO world,
they built and charted their own path.

(17:02):
Based on what they were passionateabout and where they saw a problem
that they were excited to solve, andthey built the whole role around that.
And, you know, in my humble example,I've stepped into product management
roles and then marketing leadershiproles and now evangelism roles that I
created all of them from scratch, and Inever stepped into someone else's role
and continued what they were doing.

(17:24):
I always was excited abouta problem that I saw.
I wanted to solve it, andI created a role around it.
Even while I was working at a companyand I saw a domain that was being
neglected, I made the businesscase for, we need someone to solve
that, working on that full time.
And once the CEO said,yeah, Udi, you're right.
Then I said, well, I've gotthe perfect guy for you.
Here's how I want to transition frommy current role and how I'm gonna do

(17:45):
that without dropping any balls, andI want move on and solve that problem.
And so that's another great way ofbuilding your own career that from
my personal experience, can come witha lot of satisfaction and gratitude
because you're really working on themost exciting things and you're using
your favorite skills to do that.

Matt Heinz (18:02):
Well, I'll tell you that the passion, optimism, and
energy you've heard over the last18 minutes with Udi is in this book.
I highly encourage you to check this out.
It really is a very quick read.
It's a very fun read.
I think you'll learn a lot from it.
Udi, thank you again so much for joiningus on Sales Pipeline Radio today.

Udi Ledergor (18:17):
Thank you so much for having me, Matt, and I'd love to
hear the listeners take on the book.

Matt Heinz (18:21):
Yeah, would love, Hey, throw those into the comments.
We'll make sure Udi sees those.
If you like the book, give it agood review on Amazon as well.
That certainly helps spreadthe word to more marketers.
Have a great weekend.
Thanks so much for joining us.
We'll see you next weekon Sales Pipeline Radio.
Take care.
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