Courageous Marketing: The B2B Marketer's Playbook for Career Success

By Udi Ledergor

**#1 Bestseller in Marketing & Sales**

Take the Boring Out of B2B Marketing

Courageous Marketing is your guide to grabbing att

• Language: English
• Publisher: Actionable Ideas Press
• Release date: Apr 10, 2025
• ISBN: 9798992178425

Book preview

Often, in the real world, it’s not the smart that get ahead but the bold.

—Robert Kiyosaki

Jerry Maguire isn’t the only one demanding, Show me the money!

Every board of directors, CEO, revenue and finance leader is pleading with marketing teams to do the same. Marketing doesn’t exist to win creative awards or provide jobs (although those are helpful byproducts). Marketing—especially business-to-business (B2B) marketing—exists for one main reason. And if you get that one thing right, it’s like having career insurance.

Great marketing makes sales easier. It’s that simple. Show them the money and everything becomes infinitely less complicated. At its best, marketing is a force multiplier, fueling the well-oiled sales machine. So why does it fail so often?

Look at most B2B brands and you’ll find yourself yawning at a swamp of mediocrity: boring stock images, bland color palettes, and messaging that sounds like an AI regurgitation. After studying hundreds of B2B brands, speaking with dozens of Chief Marketing Officers (CMOs)—several of whom I’ve interviewed for this book—and serving as the CMO of Gong from 2016 to 2023, I’ve discovered a few common reasons why marketing efforts tank.

From playing it safe through death by committee and lack of product-market fit (PMF), to ignoring the long-term game, there are different reasons why marketing fails.

You might have brilliant ideas for taking your company from zero to hundreds of millions in revenue in a few years (like we did at Gong). But if you play it too safe or subject your ideas to death by committee, you’ll never realize your full potential or your company’s.

Cows kill more people than sharks every year¹. (I’m surprised cows kill any sharks at all! goes the old joke). Death by committee will kill far more marketing efforts this year than all the cows and sharks ever could. When you try to please everyone, you get caught in the cycle of never-ending opinions. That’s not a place of action or innovation. But if you’ve got a great PMF and can make bold long-term plays while speaking up and taking a stand, you’ve got a solid recipe for recurring marketing success.

We’ll discuss ways to overcome common obstacles, when to speak up, and how to present crazy ideas to create remarkable marketing. You’ll discover frameworks for succeeding in everything from brand building, through content marketing and event experiences, to unlocking your full career potential while building a high-performing team.

More importantly, you’ll uncover what courageous marketers do to create careers they are passionate about while building iconic brands.

You’ll gain practical insights and actionable strategies from the brightest minds in marketing, such as Dave Gerhardt, Carilu Dietrich, Tricia Gellman, Anthony Kennada, Michelle Taite, and Andrew Davies. These leaders helped build iconic brands like Salesforce, Drift, Atlassian, Box, Intuit Mailchimp, and Gainsight. They generously shared their experiences, lessons, and frameworks for success with me.

Through interviews with brilliant operators I collaborated with on building Gong, such as Ryan Longfield, Russell Banzon, Sheena Badani, Devin Reed, Chris Orlob, Jonathan Costet, and Vince Chan, you’ll see what’s possible when marketers dare to be courageous and work well with sales.

At the time of writing this book, I’m the Chief Evangelist at Gong, which employs well over 1,000 professionals globally and is still growing rapidly. While most of my experience and lessons are from the B2B startup and scale-up space, many of them are valuable and applicable to other company types and stages.

From building and leading marketing teams at highly successful companies, advising dozens of others, serving as a board member and angel investor, and mentoring hundreds of startup founders and marketers, I’ve learned that the marketing world is rapidly changing.

Most startups don’t get a seemingly overnight success story like we’ve built at Gong. Believe me, I get it. In fact, I’ve been there. I know most B2B marketing sucks. And that’s why I’ve combined what I’ve learned from my decades-long marketing career into this book. I hope it inspires other marketers to create visionary, courageous marketing that truly moves the needle.

The purpose of this book is to help you create a movement of raving fans around your brand and grow a successful business by engaging prospects, customers, and employees. I know from experience that courageous marketing leads to predictably scaling demand generation and brand awareness while responsibly running creative experiments.

I’ve discovered strategies, tactics, and secrets of finding your courage as a marketer, creating an iconic brand, grabbing mindshare in a noisy market, and appearing to be much further ahead than where your company’s really at. This makes prospects believe they’re buying from an established brand, which makes sales and marketing a lot less challenging.

Whether you’re a startup founder figuring out your first marketing hire, a CEO setting goals for your marketing team, or a marketer aspiring to transform from meh to wow! you’re in the right place. This book will help you find the courage to take action on those seemingly hair-brained ideas that could command the attention your company deserves.

Are you ready to create an iconic brand for your company? Become the talk of your industry for effective marketing? Earn a seat at the management table for showing them the money? Then have the courage to read on!

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¹ Jade Eckardt, Fact Check: Do Cows Kill More Humans Than Sharks?, Surfer, July 24, 2024, https://www.surfer.com/news/cows-kill-more-humans-sharks.

Boldness be my friend.

—William Shakespeare

Your neck is on the line, read the email from my CEO.

It all started a couple of weeks earlier, on a frosty San Francisco night in October 2020. I was the CMO at Gong, an early-stage startup helping sales teams close more business by capturing insights from their customer conversations.

My CEO, Amit Bendov, who was based out of Israel, traveled into the city. We met for drinks at a trendy rooftop bar. As our second round arrived, I took my shot with one of my crazy ideas.

So I’ve been thinking about how to elevate our brand in a big way that would set us apart from the competition.

I’m listening. He lowered his drink.

You know how big consumer brands take over the Super Bowl commercial breaks? I treaded carefully.

Sure. He furrowed his brow. But those spots cost millions of dollars—our entire annual marketing budget!

Turns out we can buy regional media where our target audience is, I grinned, at a fraction of the cost of the national spot.

I love it! Amit raised his drink as his face shifted from puzzled to mischievous. We’re having dinner with our CFO tomorrow night, let’s twist his arm there and get him on board.

Our glasses clinked as we toasted our plan.

The next day, we approached Tim, our predictably skeptical CFO.

Amit led the charge with enthusiasm. Udi got us a great deal on a Super Bowl commercial!

Naturally, Tim had a list of questions, but we answered each one with the confidence that comes with extensive preparation. We were both surprised when he didn’t put up much of a fight after seeing how excited Amit and I were about elevating our brand in such a substantial way. We assured him that the investment would be minimal because we intended to buy a regional spot and develop a marketing campaign around the well-placed ad.

The next step would be going before the company’s board of directors to ask for their approval. You probably know that Super Bowl commercials are a battlefield of marketing creativity usually reserved for business-to-consumer (B2C) brands. Few business-to-business (B2B) brands have made the risky investment in the big game, and for good reason. It’s difficult to target the right audience, not to mention measuring the performance of the steep investment.

Many board members consider this a form of vanity marketing that can’t be financially justified. So I had to be careful about the way I positioned it. I explained that this was a long-term brand play and that we were not expecting to see any short-term moving of the needle.

Amit emailed our board: Udi and I believe it can make an impact … and will help elevate the company’s profile. If it does not make an impact, we will not repeat it in the following year. It is worth trying.

One after another, the board members responded with hesitant approval. The last one signed off his email, If we did not have Udi and I did not have confidence in him, I would say let’s not do it but that’s not the case.

Amit forwarded me the board approval thread with his succinct take on it: Basically, your neck is on the line. Good luck.

Challenge accepted.

Not taking lightly the board’s trust and budget, I set out to build an entire digital campaign to support this 30 seconds of very expensive airtime. We started one week before the game and we continued it a full week after the game.

My biggest hurdle was producing an effective commercial on a modest budget. When I asked a fellow CMO who’d produced several Super Bowl commercials to recommend a creative agency, he laughed me off. He didn’t know anyone who could work with my tiny budget. I ended up trusting a small video production agency. They had never created anything at that scale, but I’d had positive experiences with them on smaller projects.

With scarce resources, I had to be very creative. Working through multiple COVID-related restrictions, we filmed a single actor at a furniture store over the weekend. The commercial had a somber humor to it, appropriate for the pandemic times.

We used a shooting style called forced perspective, which made the actor portraying a VP of Sales appear tiny in what looked like a giant, empty office. Remember the movie Honey, I Shrunk the Kids? It’s kind of like that.

Borrowing a trick I’d used in email and social media campaigns, the first four seconds of the commercial featured a close-up shot of a VP of Sales nameplate on a desk, aimed at keeping our target audience glued to their seats instead of filling their Doritos bowls during halftime.

We shot the commercial in December, right before the winter holidays, giving ourselves January for editing and signing off, just before the Super Bowl deadline in early February. We barely made it.

Getting More Bang for Our Buck

We kept our commercial a surprise until game day. I was one of the first to share it on LinkedIn on the morning of Super Bowl Sunday 2021. Now, if I had paid attention to best practices, I would have held off sharing until Monday. But I would have lost invaluable momentum.

Conventional wisdom says that Sunday is a terrible time to share something on a business network. But I discovered through this experience that Sunday works just as well as weekdays, if not better—as long as you’ve got something exciting to share. And we did.

It completely blew up on LinkedIn. People couldn’t stop commenting. There were over a thousand engagements, and hundreds of comment and shares. People were going wild about it. If you haven’t already seen it, you can watch the commercial online by going to this link or scanning the QR code below:

bit.ly/gongcommercial

On Sunday and Monday, we got hundreds of thousands of views online once our employee advocacy campaign kicked into high gear. Hundreds of employees, whom we affectionately refer to as Gongsters, shared the commercial on their personal LinkedIn profiles.

To encourage our followers to share it with their networks and increase the buzz, we gave out free swag—200 special-edition Gong Super Bowl t-shirts. One of them has our mascot, Bruno the bulldog, in a football helmet (a role he landed after auditioning among seven other bulldogs). The other one has the helmet on the front and the back says, Closer.

We posted the commercial on LinkedIn and promised, If you share this and tag Gong, Vince from my team will send you a special edition Super Bowl t-shirt. Within a few short hours, hundreds of fans shared our commercial. By 11 a.m., the t-shirts were gone. My team ordered several hundred more t-shirts to keep the momentum going.

We also contacted our top 10 influencer-partners who shared with their social networks on Monday morning, giving us another huge audience. Our LinkedIn followers, mostly sales professionals, were bursting with pride. They couldn’t believe they were being featured in a commercial during the most-watched game of the year.

What could have been a quickly forgotten 30 seconds of fame turned into our company setting a new

Reviews for Courageous Marketing

[Yoav · Rating: 5 out of 5 stars]

Both actionable and inspiring book, a must read for both seasones and new marketers who look for sharpening their sense of boldness and courageousness.