We were deep in the trenches of launch mode, the kind where every waking moment is consumed by thoughts of success. Will people like what we’ve built? Penfriend v1 was nearly ready, our audience primed, and our marketing was in overdrive. The FoMO machine was in full swing—posts on LinkedIn were buzzing, emails flying out, each one more urgent than the last, all building up to launch day.

We’d engineered a full countdown of events, each one carefully choreographed to ramp up the anticipation. Every detail had been meticulously planned. Or so we thought.

It was during a routine call with the dev team—just a regular check-in, nothing special—when the world suddenly shifted beneath us. I was chatting with our lead developer, going over some minor bugs that needed fixing, when I casually mentioned the launch date. “Just making sure everything’s on track for next week,” I said, not thinking much of it.

There was a pause on the other end of the line. A long pause. The kind of pause that makes your heart skip a beat.

“Next week?” the lead developer finally asked, his voice laced with confusion.

“Yeah, the launch,” I replied, a knot beginning to form in my stomach. “Next Friday. You know, the big day.”

Another silence. This time, it was more like the calm before a storm.

“We didn’t know,” he said, his voice flat.

I felt my blood run cold as the weight of his words hit me. My mind raced, trying to process what I’d just heard. How could this have happened? How could we, the founders, have missed something so crucial?

The room seemed to shrink, the air growing heavy with the realization of what we’d done—or rather, what we hadn’t done. We had failed to communicate the most critical piece of information to the people who mattered most.

With just 11 days to go, I scrambled to find the words, but all I could manage was a feeble, “You’re kidding, right?”

But there was no joke here. This was real. This was a nightmare unfolding in broad daylight.

Panic set in. I immediately called the other two founders, both of whom were in London, hundreds of miles away but somehow still close enough to feel the dread that was now coursing through me. The phone rang, once, twice, then a hurried “Hello?” on the other end.

“Hey,” I said, trying to keep my voice steady. “I think we screwed up. We, err, we didn’t tell the developers we want to launch next week…”

The silence on the other end was deafening. I could almost hear their minds whirring, trying to grasp the enormity of what I’d just said.

Finally, one of them spoke, his voice tinged with disbelief. “So, we’ve been hyping this launch to everyone, and the dev team doesn’t even know?”

“Yup, pretty much,” I replied.

And so began the scramble. A mad dash to re-align everything that had so carefully been put in place. The launch date had to be pushed back—no question about it. We tore apart our marketing plan, redoing a big chunk of it, crafting new messaging that would make sense given the delay. Every piece of content had to be rechecked, re-timed, re-sent.

But the most important step? Making sure the dev team knew the new date. This time, we weren’t taking any chances. We looped them in on every single detail, over-communicating to the point where they probably wished we’d stop reminding them.

In the end, we managed to pull it off. The launch was successful, the product well-received, and our audience knew every bit of the hiccup. So now, I can tell this story almost without any changes to my heart rate.

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Picture this: You’re a marketer, and you just landed the holy grail of thought leadership—a partnership with the Elon Musk of your industry (except this one doesn’t tweet about cryptocurrency at 3 AM… usually).

We’ll call him “Jack”–a titan of tech, a sultan of SaaS, a prophet of profit margins. This guy could post a picture of his breakfast and accidentally start three unicorn startups.

Our co-branded content series was so hot it needed its own fire extinguisher. Engagement rates were through the roof. Our lead magnet turned into an actual magnet. Even our competitors were hate-sharing our posts, which, let’s be honest, is the B2B equivalent of going viral.

I was already practicing my humble-brag for the next marketing conference. “Oh, this little campaign? It just tripled our pipeline, no biggie.”

Then, faster than you can say “purgatory,” it all went to hell.

Midway through our campaign, Jack decided to do a live-streamed AMA. Perfect, we thought. What could possibly go wrong?

Everything. Everything could go wrong.

It started innocently enough. He shared his morning routine (apparently, unicorn tears are great in coffee), his favorite productivity hacks (time travel was mentioned), and then… the panic ensued:

“What’s your take on the future of AI in SaaS?”

Now, keep in mind, our product was AI-adjacent.

Jack cleared his throat and dropped this wisdom bomb: “AI in SaaS? It’s like putting racing stripes on a horse. Sure, it looks cool, but at the end of the day, you’re still just dealing with a horse.”

You could almost hear the collective gasp of every SaaS marketer watching. Our Slack channel erupted like a popcorn machine filled with firecrackers.

Damage control mode engaged.

We had two choices: distance ourselves faster than a politician from a scandal, or double down harder than a blackjack player with rent due.

As we scrambled to spin this “unique perspective” (read: potential career suicide), I learned a valuable lesson:

Influencers are like fireworks. Exciting, attention-grabbing, and occasionally, they blow up in your face.

Always, always have a crisis management plan. And maybe a time machine.

Because in B2B SaaS, sometimes the real thought leadership is knowing when to keep your thoughts to yourself.

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Creating your first SaaS startup from scratch means running headfirst into a ton of first-time challenges. Here’s a story about one of those, ahem, fun little surprises.

As part of the sales and marketing team, I used to joke that my job was to bring in so many users that the product would strain under the pressure, while the dev team’s job was to keep it from crashing. Well, one day, that joke got a little too real.

I had just closed a few big deals with new customers—huge accounts, not your average users. These folks were about to push our system to its absolute limits, with hundreds of people all logging in at once. Just to be safe, I checked in with the dev team to make sure we could handle the load. “Yep, we’re good!” they said. So, feeling confident, I pressed ahead.

Then the day arrived. The usage spiked, and before long, I started hearing some… nervous murmurs around the office. It turned out that the load was way higher than we’d anticipated.

Let’s just say the dev team had a very intense 15 minutes figuring out how to keep the whole thing from falling apart. Meanwhile, I was in the hot seat, keeping our new customers calm and reassured while we scrambled behind the scenes.

Luckily, the team jumped on it fast, and we resolved the issue before it could spiral out of control. After that brief, heart-pounding moment, everything ran smoothly. It was a close call, but we pulled through, and it’s a lesson I’ll never forget.

No matter how confident you are, you always need contingency plans for the unexpected. After that, we made sure to run tougher stress tests before launching anything new and had better scaling solutions ready. It’s all about staying one step ahead and planning for surprises.

P.S. And yes, I still firmly believe that marketing’s job is to push the system to its limits and see just what it can really handle. 😉

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Well, everybody’s sharing their nightmares from the past, but I want to open up about my current nightmare. It’s the procurement process.

The deal is sealed with the champion and the leadership. It was a long process (took 3 months), a lot of loops to jump through, including testing some pieces of data in the platform.

We’re good to go 🚀 Yay!

But wait: you’ll have to meet our privacy team, then the procurement team, and then finance.

OK, it’s a significant deal, should not be that bad: we’re SOC2 compliant, GDPR compliant, have a Security portal, and whatnot. This should take 2-3 weeks—and we’re good.

Well, 2 months in—we’re still jumping privacy loops, including having to re-explain the solution and what was sold to the legal team.

Somebody, wake me up, please!

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Let me fire up my time machine and briefly take you to the peaceful years of pre-recession marketing. Back then, I was in digital marketing, and LinkedIn Ads campaigns were running like a well-oiled machine.

Every quarter, the business was hitting new highs. The sales team was closing deals left and right, and the CEO was happily approving budgets without a second glance.

We all knew the playbook: invest heavily in LinkedIn Ads, build that brand presence, and let the leads roll in. It was almost too easy.

Then the recession hit.

Suddenly, the free-flowing budgets turned into drips. Sales cycles stretched from weeks to months, and the once-eager B2B buyers became elusive.

As the company tightened its belt, the questions started rolling in. The kind of questions you dread as a marketer, the ones that keep you up at night.

The CEO called me into his office one afternoon, the worry lines on his face deeper than I’d ever seen. He leaned forward, hands clasped, and asked the question I’d been avoiding: “What exactly are we getting from these LinkedIn campaigns?”

My stomach dropped. Sure, we’d been spending millions on LinkedIn Ads, but in the good times, nobody cared to ask about attribution. The business was booming, so who cared where the leads were coming from? But now, every dollar was under scrutiny, and I was suddenly being asked to justify a budget line that looked more like a black hole than a gold mine.

So, I did what any good marketer would do: I dug into the data. Hours turned into days as I sifted through reports, metrics, and analytics dashboards. Finally, the cold, hard truth emerged—only 10 leads had come directly from clicking on our LinkedIn Ads in the last quarter. And the kicker? Not a single one had turned into revenue.

My heart sank. There was no way to sugarcoat this. I had to face the music and present the findings to the CEO. The decision was swift and brutal: we were cutting off LinkedIn Ads entirely.

At first, everything seemed fine. We trimmed the fat, shifted budgets, and tightened our belts. But then, something strange happened. A few months after we killed the campaigns, the company’s results started to nosedive. Website traffic plummeted. Inbound leads dried up. Even our brand search volume—a metric that had been steadily climbing for years—started to tank.

It didn’t take long to connect the dots. People might not have been clicking on our LinkedIn Ads, but they were definitely seeing them. The ads were doing their job in the background, building brand awareness, driving interest, and keeping us top of mind for when decision-makers were ready to buy.

Without those ads, it was like we’d turned off the lights in the middle of a crowded room. Nobody was paying attention to us anymore.

The lesson was painful but clear: not everything that counts can be counted. Attribution is messy, imperfect, and often misleading. Sometimes, the real value of a marketing campaign isn’t in the clicks or the direct leads, but in the brand presence it builds, the trust it fosters, and the long game it plays.

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​This could have been my best campaign. We came up with the theme, created a set of nice landing pages, ran paid ads, and even found an old article on the blog with decent traffic that we revamped according to the new messaging.

The results were mind-blowing: the revamped article started ranking on Google like crazy. At some point, it was generating over 20,000 clicks monthly. We had hundreds of conversions associated with this article and the campaign in general.

The thing was… it all happened outside the attribution window. Our practice was to look at the campaign data in 90 days after launch and then report on its success or failure.

Our data over the first 90 days had shown it was a failure.

Then, a month later, traffic started growing. In six months after the campaign launch, the campaign was steadily generating dozens of thousands of visits per month. All organic, no paid. I tried to bring it up, showing the spike in traffic and new users to the management and the analytics team—all I got was “Okay, curious, but the campaign is over already.“

There’s a silver lining to it though—I have some very good numbers to put up on my LinkedIn bio. Who cares if it happened 90 or 180 days after—it happened, and that’s the most important thing, isn’t it?

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It was a surprisingly bright Fall day – the air crisp, the leaves just beginning to turn. Nathan, my coworker and I were cheerfully chatting about an upcoming webinar campaign.

As marketers—more specifically, content and lifecycle marketers—much of our conversation revolved around the best way to leverage email as a promotional channel for the campaign. We wanted to be bold, and laugh in the face of typical email conventions.

Now, the funny thing is, as a Head of Lifecycle, you’d think I’d be all for proper segmentation—but as marketers who love to fail fast, Nathan and I sometimes choose to live dangerously.

So, we created a cleverly crafted and wittily written email campaign that would impress even the most fickle of writers.

All that was left to do was launch it.

With the thrill of two giddy marketers who truly thought we had struck gold with our campaign, we decided to broaden our segmentation. “What would happen if we widened the audience? Say, to one million recipients?”

I looked at the audience data, shrugged my shoulders, and said, “Never try, never know!”

What I probably should have said is, “F**k around and find out.” Because find out, we did.

Unbeknownst to us, we had a people-reach limit from our email service provider.

So, imagine our surprise when we receive messages from the CEO, the founder, and other leaders in our company, letting us know of a $40k charge for exceeding said limit. $40k. For an email campaign. Ouch!

We panicked.

With sweat rolling down our backs, tears gathering in our eyes, heart rates pumping like an old-school Bugs Bunny clip, we knew we had not only f***ed around, but were about to really find out just how much we could mess up.

Hastily written, panic-induced Slack messages were sent; apology notes begging and pleading for mercy were sent off, and a tear-stained email to our email service provider rep was dispatched.

And you know what happened?

Drumroll… The world didn’t end. We didn’t lose our jobs. Our audience wasn’t upset.

• Our leadership was totally understanding, and knew we recognized our mistake.
• Our phenomenal email service provider rep helped us swiftly deal with the overcharge, waiving his magic wand and making it disappear.
• We immediately paused the campaign, optimized, and carefully QA’d.

And we were able to compile a robust process for email sends that would help guide others in leveraging email thoughtfully.

The email campaign performed well—exceeding our expectations, and somehow managing not to totally implode our spam rate 😂 But that isn’t the point.

The real lesson learned? It’s not taking risks, failing fast, or wanting to try new things that will hold you back—it’s missing the opportunity to learn from your mistakes. There’s no growth without failing.

Oh, and it never hurts to be humbled—even people who know what they’re doing can make mistakes.

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