Crossing the Cliff: A Founder’s Story About the Series B No One Tells You About
Daniel had just closed his Series A when he called me. “Hey,” he said, “I think we’re ready to go raise our B. Revenue’s climbing, the product’s stable, and we’ve got four enterprise logos now. I just need to polish the deck.” I could hear the energy in his voice. That special kind of optimism you get when a startup finally feels like it’s working. We set a time to meet the next day. He came in with clean slides, a revenue chart that curved the right way, and a pitch he’d been practicing for weeks. Halfway through, I stopped him. “Daniel,” I said, “This is a solid update. But let me ask you something. If I gave this deck to a junior partner at a VC firm, could they walk into Monday’s partner meeting and pitch it without you?” He paused. “Well… maybe not with the same energy, but I think the fundamentals are there.” “That’s not what I asked.” He looked down. And that’s when I knew: Daniel wasn’t ready.
The Cliff Most Founders Don’t See Coming
I’ve seen this moment dozens of times. Founders thinking Series B is just another funding round—a bigger ask, a nicer deck, maybe a new haircut and some updated Gartner stats. But Series B isn’t just more money. It’s a new level of scrutiny. A different kind of story. A leap across what I call the post-A cliff. It’s where the story changes—from potential to proof. From a great idea to a repeatable, defensible business.
“What’s Your Moat?”
I asked Daniel, “Let’s say I’m your investor. Convince me—right now, in one sentence—why someone can’t just build what you’ve built and outspend you.” He started talking. And talking. He told me about their engineering talent, their roadmap, their integration strategy, their customer relationships. Three minutes later, he stopped. I nodded. “That’s smart,” I said. “But I’ll tell you what the investor just heard: You don’t have a moat you can name.” He didn’t push back. Because he knew.
How to Actually Get Ready for a Series B
A Sales and Marketing MVP
We spend years building a product MVP. But by Series B, investors want to see a go-to-market MVP—a small, efficient, functioning growth machine. Can you: – Generate leads without depending on the founder? – Explain your sales process, conversion rates, CAC, and payback? – Prove that your message lands and scales? – Do you have a well mapped buyers’ journey? – Validate that your pricing is optimized? Daniel couldn’t answer those cleanly. So we helped him build the playbook.
Fluency Across the Buyer Stack
Daniel’s deck had one message. It was clever, sharp, and well-designed. But it treated every buyer like the same person. “Who makes the decision in your sales process?” I asked. He listed a VP, a Director of Ops, and someone from IT security. “Great. Now—does your story work for all three of them?” Silence. We rewrote the message for each persona: – VPs+ got the business case, focused on strategic/competitive advantages in embrace of the product – Directors got the workflow, headcount and budget narrative – Security got the risk and compliance pitch – Staff & managers got the CYA message
Evidence, Not Optimism
Investors don’t need you to inspire them at Series B. They need you to de-risk them. That means: – Cohort-level retention metrics – Conversion rates by channel – Churn explanations (and what fixed them) – AI-enabled efficiencies that reduce actual cost, not just headcount hypotheticals Daniel had vision. What he lacked was empirical confidence. Data that says: this works. And here’s how.
A Moat in One Breath
I told Daniel, “Your moat isn’t a story you explain. It’s a punchline. A headline. Something they repeat.” If you can’t say it in one breath, they won’t say it at all.
The Outcome
It took six weeks. We rebuilt the deck. Rewrote the narrative. Built out persona messaging. Added funnel metrics. And distilled his moat into one brutal, undeniable slide.
He walked into his first Series B pitch.
Ten days later, they offered terms.
Not because the market changed.
But because his story did.
Final Thought: Build the Story Before You Raise the Money
If you’re nearing your Series B, don’t start with the investor list.
Start with this question:
Can someone else tell your story—clearly, convincingly, and concisely—without you in the room?
If not, you’re not ready.
At The Artesian Network, we help founders craft that story. Not just for slides—but for scale.
Need help crossing the cliff?
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About me: https://www.jonathanwbuckley.com
About The Artesian Network: https://www.artesiannetwork.com