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Courageous Marketing: The B2B Marketer's Playbook for Career Success · Sales Pipeline Radio

• 0:16
  Matt Heinz: All right.
• 0:16
  Welcome to another episode of Sales Pipeline Radio.
• 0:19
  I'm your host, Matt Heinz.
• 0:20
  So excited to have you here as we round out May and head into June already.
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• 1:02
  Super excited to have today our guest.
• 1:04
  He is former CMO, and now chief evangelist for Gong, Udi Ledergor.
• 1:08
  Udi, thanks so much for joining us today.
• 1:10
  Udi Ledergor: Thanks for having me, Matt.
• 1:11
  I'm excited to be here.
• 1:13
  Matt Heinz: I feel like there's so many things we could talk about, but so
• 1:15
  much of it is in this book, Courageous Marketing that you published a month.
• 1:19
  I got my copy show off.
• 1:20
  You've all got a copy.
• 1:21
  I mean, hopefully if you don't have a copy, like go
• 1:23
  get a copy of this right now.
• 1:24
  I've got a few behind me.
• 1:25
  You might be able to see.
• 1:25
  I'm sure you, well, you do have a few.
• 1:27
  We got a whole row there.
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  Not surprising.
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  I'll tell you what, there's a lot of books that I need to read, in my
• 1:32
  job that are nonfiction, but this is one that was just a joy to read
• 1:36
  because of the topic, because of the approach that you took on it.
• 1:39
  And I think I would argue that this could be part of your beach
• 1:43
  reading list for summer 2025.
• 1:46
  Like there's a lot of business books.
• 1:47
  I would not say take to the beach, right?
• 1:49
  Because like it is not beach reading.
• 1:50
  I think this is one, and I'm not just saying that, but Udi what, I mean you've
• 1:54
  been in, you've been marketing leadership, investor advisor for a long time.
• 1:58
  Why this book?
• 1:59
  Why this topic?
• 2:01
  Udi Ledergor: You know, Matt, for the last 20 years I've been doing
• 2:04
  B2B marketing and in the last nine years I've been doing that at Gong.
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  For the first almost seven years, I was CMO at Gong and I kept going on podcasts
• 2:13
  not as wonderful as yours, but others, I've been speaking at conferences and I've
• 2:17
  been sharing how we did things to succeed as well as we've been doing at Gong.
• 2:21
  And lots of people tell me, Udi, you've gotta write a book.
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  It's so practical.
• 2:24
  It's so programmatic.
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  You just tell people tactically what they need to do.
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  And I used to joke like, when would I ever get time to write a book?
• 2:32
  And then two years ago, I transitioned into my current role as Chief
• 2:35
  Evangelist and suddenly I had the time to sit down and write a book.
• 2:39
  So I decided while it's all fresh and I'm still in touch with all the
• 2:42
  people who made the magic happen, I'm gonna sit down and write a book.
• 2:45
  And that's what I did in the last 18 months.
• 2:47
  And then last month, the book came out.
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  Courageous Marketing became an instant bestseller in half a dozen categories
• 2:54
  on Amazon, which is super exciting and thousands of people are already reading
• 2:58
  it on the beach while mowing the lawn, on vacation, on business trips, it's designed
• 3:02
  to be read on a coast to coast flight.
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  So between San Francisco and New York, it only takes four and a half hours to read.
• 3:08
  You can finish this.
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  On any short flight,
• 3:11
  Matt Heinz: Unless you're flying into Newark, you might finish
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  it before you even take off.
• 3:14
  Udi Ledergor: Before you even take off.
• 3:16
  Matt Heinz: Yeah.
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  So this, there's a couple angles of this book I wanna be
• 3:20
  able to talk about for folks.
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  First is sort of the marketing playbook component, and the second
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  is the career success component.
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  Boy I feel like it's becoming a harder and harder time to be a marketer in a more
• 3:31
  and more exciting time to be a marketer.
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  As the field is flooded with information, flooded with noise.
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  Harder and harder to break through, but I think more exciting, more fun,
• 3:41
  more fulfilling to be in a role to sort of build and earn that attention.
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  What have you learned in your career and in your time at Gong that sort
• 3:50
  of feeds into the playbook that marketers need to follow today?
• 3:54
  Udi Ledergor: Right.
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  So I love how you divided the, the two main topics.
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  You know, the first two thirds of the book are things that people
• 4:00
  who have been following me and Gong would expect to find there.
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  So, I talk about timeless lessons in building brand, in building
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  content, in creating a product category or in creating magical event
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  experiences, all these things and more.
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  And people are telling me when they're reading the book that they think that
• 4:19
  these things are so important to reiterate now when people are using and abusing AI.
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  For things that it's good for, but also for things that it should not be used for.
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  Like having a sharp point of view on something.
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  AI can't do that yet because it's only averaging the things
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  that are already out there.
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  So if your content is not landing and you're using AI to create tons of it,
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  maybe that's why, because AI can come with that sharp point of view yet.
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  So that's, that's kind of the first part of the book.
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  And then the second part is things that I haven't talked about a lot publicly
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  but I thought would be an amazing opportunity to put some down in the book.
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  And I honestly co-wrote a lot of those chapters with not only
• 4:56
  my former team members, folks like Devin Reed and Chris Orlob.
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  Um, Vince Chan, Sheena Badani.
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  And many others.
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  But also I interviewed other CMOs and sales leaders like Ryan
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  Longfield, who's now at Shopify and was the longtime CRO at Gong.
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  We practically co-wrote the chapter on how sales and marketing should align together,
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  and I think those lessons are timeless because they talk about the human side
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  of marketing and how to navigate your career from finding the right company
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  identifying whether your CEO is gonna give you the flexibility and wiggle room
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  that you need to be creative in marketing.
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  How to build a courageous team to do their best work while working with you,
• 5:36
  and how to work with sales to produce the business outcomes that your company needs.
• 5:42
  Matt Heinz: So much to unpack there.
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  Talking today on Sales Pipeline Radio with Udi Ledergor.
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  He's the Chief Evangelist at Gong, author of the amazing book Courageous Marketing.
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  Excuse me, so many marketers are fixated on clicks and likes focused
• 5:57
  on impressions and form fills.
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  You talk a lot about experiences.
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  Experiences isn't always something you can immediately track.
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  It isn't something that you necessarily always have on a dashboard, but I
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  think it's becoming more and more important in the marketing playbook,
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  in the go to market playbook today.
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  Why do you think experiences are so important?
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  Udi Ledergor: Experiences are a phenomenal way of creating a memory link between what
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  your brand stands for and being valuable.
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  And so how does this work?
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  By now I assume most of our listeners and viewers have heard about the 95/5
• 6:33
  rule, which suggests that only about 5% of your audience are in market.
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  You can argue about the number.
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  It could be 7% or 9% in your market.
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  Nobody cares.
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  It's a small percentage of market.
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  Otherwise, everybody would be buying everything from you now,
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  and you'd have no pipeline for next quarter, but that's not the case.
• 6:48
  Right?
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  So most marketers would agree, there's only a small percentage of my market
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  right now in market, but how do I create and nurture relationship with them
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  so that when the 95% not currently in market do move into the buying zone?
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  It could be in six months, could be in 12 months, could be in 24 months.
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  How do I make sure I'm the first name that they think of?
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  Mm-hmm.
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  And the way to do that is to create memory links that connect what you stand
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  for with what they might need in the future and keep that relationship going
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  until they're finally in the buying zone.
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  Now, experiences are an amazing way of doing that.
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  Standing out and being valuable when others are trying to just hard sell all
• 7:28
  the time is an amazing way of doing that.
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  And so here are three very tactical tips to how to create those experiments
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  and relationships and experiences in a way that builds those memory links.
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  So.
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  I'd say number one preemptively budget your marketing
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  experiences and experiments.
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  And here's how I always do this with my CFO and CEO.
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  I say, look, there's two things you need to know.
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  One, whatever's working for us in creating pipeline and demand gen right now is
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  going to stop working at a certain point.
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  I don't know if that's next week or next quarter or next year.
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  Mm-hmm.
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  But everything that's working now is going to stop working.
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  We need to constantly be experimenting with new things that we're not doing yet.
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  Some of them are gonna be duds, some of them are gonna look promising.
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  We need to budget for that.
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  So they say, okay, that makes sense.
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  What's the second thing?
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  I say, here's the second thing.
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  We're usually doing the budgeting exercise, say in October November,
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  preparing for next year's budget.
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  But here's the thing, there's gonna be things that, opportunities that
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  present themselves in the middle of next year that we'll wanna do.
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  But I don't know about them now because they haven't been announced yet.
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  This could be a big event that happens next October that might only be
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  announced in April if we don't put aside some budget for these things now.
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  I'm never gonna be able to capitalize and monetize on those opportunities.
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  So that's the second reason why we need to preemptively budget
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  for these marketing experience.
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  And even the most data-driven, cynical, CFO or CEO will see the
• 8:53
  light in those two arguments.
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  So that's one really practical tip.
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  The second one is different is better than better.
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  Mm-hmm.
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  You don't wanna play the game that everyone is playing by
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  trying to outspend them, because as a startup you can't do that.
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  All you can hope to do is be different and by being different, you're
• 9:11
  already leading in your own space.
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  Gong did that when we looked at hundreds of B2B websites back in
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  2018 or 2019 when we wanted to roll out our first visual identity.
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  And back then everyone was using the same palette of what one of my team
• 9:26
  members called the Series A blues.
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  And they pair beautifully with whites and grays, but that's what everyone was using.
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  So Gong decided not to find a better blue than everyone was using, but to
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  go in a completely different direction.
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  And we chose fuschia pink and purple, and a drooling bulldog as a mascot.
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  And guess what?
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  That earned us a lot of attention with very little budget.
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  So that's the second thing.
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  And then the third thing is really to provide continuous and consistent value
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  in your content marketing, in your event experiences, in your thought leadership,
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  in your swag, and everything that you're doing to create those memory links so
• 10:02
  that in 18 months when John Smith is finally moving from the no buy zone to
• 10:07
  the buy zone, Acme, Inc. or whatever your company is, is the first name that
• 10:11
  he thinks of when he's ready to buy.
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  Matt Heinz: I love that you've differentiated sort of budgeting for
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  courageous marketing and creating a culture for courageous marketing.
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  I will never forget years ago, working with a company that told me that
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  internally there was something that they knew of as reputation capital,
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  and what that meant, what that literally meant was you don't wanna be
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  associated with a project that fails.
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  Think about that.
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  Think about what that does to innovation.
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  Think about what that does to courage.
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  Think about what does, to letting anybody try something that is not by the book.
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  And you could imagine how well that company did over time, but
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  Udi Ledergor: That's such a terrible idea.
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  Matt Heinz: Well, of course it is, right?
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  But like, I think, but it's not, but not everyone understands it sort
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  of inherently, like this culture of courage or this cult-, like I've just
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  in the past, like culture of failure.
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  Accepting and encouraging failure as part of the process.
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  That is not a common thing.
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  How do you create a culture and a team that accepts and
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  rewards courage in that format?
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  Udi Ledergor: Right?
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  So let's talk about that.
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  'cause I think it's, it's one of the most important.
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  And one of my favorite chapters of the book, I'll be honest is how to create a
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  courageous team that does their best work.
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  And this was a discovery process for me in hindsight, when I interviewed
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  half a dozen of my team members and saw all these themes and stories
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  bubbling up, they finally formed a picture and a framework that I could
• 11:37
  not have put into words earlier.
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  So let's say two things about this.
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  One, exactly what you said.
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  If you create a culture where people are afraid to take risks, if they never
• 11:48
  want to be associated with failure, you're creating a culture where
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  everyone is always playing it safe.
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  And guess what?
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  When everyone's playing it safe, you're never gonna drive innovation.
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  You're not gonna do anything creative, you're never gonna stand out.
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  You're just going to play it safe and follow those dreaded best practices,
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  which in reality are boring practices because by the time anything becomes
• 12:08
  a best practice, everyone is doing it.
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  So you are guaranteed at best, the ordinary results that
• 12:14
  everyone else is getting.
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  You're never gonna create anything extraordinary.
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  So if we all agree that to create something extraordinary, which is
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  what most of us say we wanna do, we also have to do extraordinary things.
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  And that means risk failure and actually, promote it and encourage it.
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  So that's one thing.
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  The second thing is, okay, so how do you actually do this?
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  How do you create this culture?
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  And here's a really overly simplified version of it.
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  There's lots more in the book.
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  And not only in my book, I would highly recommend Adam Grant's book "Think
• 12:41
  Again" to anyone who wants to learn more about creating this culture.
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  He wrote about winning teams at NASA and other great organizations
• 12:49
  and how they created this culture.
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  But here are the two main points from that chapter.
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  What you want to create is psychological safety where your
• 12:57
  team members feel safe to fail.
• 13:00
  They know that if they drive an experiment and take risks and things,
• 13:05
  inevitably will not always work out.
• 13:08
  They will not be fired for doing that.
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  They will be celebrated for the learning, for the initiative, for the risk taking,
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  and it's that culture of psychological safety that allows people to come
• 13:19
  out of their shell and go beyond the best practices and do amazing things.
• 13:24
  Now, theoretically, that could lead to people going rogue and doing experiments
• 13:29
  for the sake of experiments and not always tied to the business goals.
• 13:32
  So you do have to counterbalance that with something else that Adam
• 13:35
  Grant calls process accountability.
• 13:38
  In the simplest of terms, the way I could describe this is everyone needs to
• 13:42
  be rowing towards the same North Star.
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  So if we know that we have a certain amount of pipeline to create
• 13:48
  this quarter, that is the goal.
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  And we're gonna create a process accountability around achieving that goal.
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  But within everyone's realm, in social media and in events and in content,
• 14:00
  everyone can do whatever they need to.
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  Use whatever means and take risks and drive experiments to get to that goal.
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  And that's where the psychological safety meets the process accountability.
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  If you can create those two things working in harmony, you would be
• 14:15
  amazed at what your team can do.
• 14:17
  Matt Heinz: So important and just so easier said than done and so rare
• 14:21
  I think, in organizations today.
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  I think last topic I want to cover with you, Udi.
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  We've talked about courageous marketing.
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  We've talked about courageous teams.
• 14:29
  Let's talk about courageous careers because this is a, this book was written
• 14:32
  as a playbook for how to do better marketing, but I love that it really
• 14:36
  covers this as a function of career success for people listening, whether
• 14:40
  they're beginning of their careers, mid career, wherever they're at, what does
• 14:44
  a courageous career mean and what are some things people can do to sort of
• 14:48
  lean into that concept a little more?
• 14:51
  Udi Ledergor: I think courageous career means that you lean into
• 14:56
  your strength and you focus on them.
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  And this is again, a counterintuitive, I think, mistake or false assumption
• 15:04
  lots of people have, which are, oh, I've gotta work on my weaknesses because
• 15:07
  maybe I'm a super creative person, but I don't know enough about data.
• 15:11
  So I'm gonna take all these data courses and try and get better at that.
• 15:14
  I'm not saying don't do that, but you're probably never gonna be
• 15:17
  the best data person if you're already inherently weak at that.
• 15:21
  But if you continue to sharpen your creativity skills, which you're
• 15:24
  passionate about and you're already good at, and everyone's telling
• 15:27
  you what a creative person you are, that's where you can actually shine.
• 15:30
  Yeah.
• 15:30
  And so not accepting that you have to change dramatically to succeed,
• 15:35
  but actually taking what you're good at and finding an opportunity to let
• 15:38
  those skills shine, sharpen them, and use them in everywhere you can.
• 15:42
  That's one way of creating a courageous career.
• 15:44
  Now, I talk in the book about two paths of getting there.
• 15:47
  One of them is correctly choosing the company, the CEO, and the role
• 15:52
  where they will let you shine.
• 15:54
  And I have frameworks for how to do that and how to check the culture on Glassdoor
• 15:59
  and how to check the product market fit on G2 and how to ask your friends who might
• 16:03
  be using the product or potential users of the product to find a lot of the pitfalls.
• 16:08
  'Cause here's one very common one, Matt, when every marketer I know has
• 16:11
  stepped into a company without product market fit and ended up having to
• 16:15
  leave the company pegged as a failure.
• 16:18
  When it was not even her fault.
• 16:19
  Mm-hmm.
• 16:20
  Because the company had no way of succeeding because they
• 16:23
  don't have product market fit.
• 16:24
  But of course, marketing gets, uh, gets blamed for that because you didn't create
• 16:28
  pipeline and you didn't create sales.
• 16:30
  And nobody knows about us.
• 16:31
  Of course, nobody knows about us.
• 16:32
  Like we don't have a single happy customer who's getting value from the customer.
• 16:35
  I can't scale that.
• 16:36
  Right.
• 16:37
  But so that's one path.
• 16:38
  And then the second one that I talk about extensively in the book
• 16:41
  is how to create your own roles.
• 16:43
  So you might not do this from your very first role, but once you get
• 16:47
  into an organization and see where your skills are most helpful, not only
• 16:51
  did I build my career that way, but a bunch of other people I spoke to like
• 16:55
  Tricia Gellman and Carilu Dietrich and other great stars in the CMO world,
• 17:00
  they built and charted their own path.
• 17:02
  Based on what they were passionate about and where they saw a problem
• 17:06
  that they were excited to solve, and they built the whole role around that.
• 17:09
  And, you know, in my humble example, I've stepped into product management
• 17:14
  roles and then marketing leadership roles and now evangelism roles that I
• 17:18
  created all of them from scratch, and I never stepped into someone else's role
• 17:22
  and continued what they were doing.
• 17:24
  I always was excited about a problem that I saw.
• 17:27
  I wanted to solve it, and I created a role around it.
• 17:29
  Even while I was working at a company and I saw a domain that was being
• 17:32
  neglected, I made the business case for, we need someone to solve
• 17:36
  that, working on that full time.
• 17:37
  And once the CEO said, yeah, Udi, you're right.
• 17:39
  Then I said, well, I've got the perfect guy for you.
• 17:42
  Here's how I want to transition from my current role and how I'm gonna do
• 17:45
  that without dropping any balls, and I want move on and solve that problem.
• 17:50
  And so that's another great way of building your own career that from
• 17:53
  my personal experience, can come with a lot of satisfaction and gratitude
• 17:57
  because you're really working on the most exciting things and you're using
• 18:00
  your favorite skills to do that.
• 18:02
  Matt Heinz: Well, I'll tell you that the passion, optimism, and
• 18:04
  energy you've heard over the last 18 minutes with Udi is in this book.
• 18:07
  I highly encourage you to check this out.
• 18:09
  It really is a very quick read.
• 18:11
  It's a very fun read.
• 18:12
  I think you'll learn a lot from it.
• 18:13
  Udi, thank you again so much for joining us on Sales Pipeline Radio today.
• 18:17
  Udi Ledergor: Thank you so much for having me, Matt, and I'd love to
• 18:19
  hear the listeners take on the book.
• 18:21
  Matt Heinz: Yeah, would love, Hey, throw those into the comments.
• 18:24
  We'll make sure Udi sees those.
• 18:25
  If you like the book, give it a good review on Amazon as well.
• 18:28
  That certainly helps spread the word to more marketers.
• 18:31
  Have a great weekend.
• 18:32
  Thanks so much for joining us.
• 18:33
  We'll see you next week on Sales Pipeline Radio.
• 18:35
  Take care.