The first time I sat across from a fund manager, I didn’t know what a capital call was.
I’m not proud of that. But I’m not ashamed of it either, because that moment of genuine ignorance — the slight pause, the careful nod, the frantic Googling under the table — is the origin story of everything PipelineRoad became in the fund management space.
We didn’t enter this market with a plan. We entered it with a client who happened to be building software for GPs and LPs, and who needed positioning help badly enough to overlook the fact that we couldn’t tell a limited partnership agreement from a lease.
That first engagement almost killed us. And it turned out to be the best thing that ever happened to the business.
The Problem With Knowing Too Much
Here’s something nobody tells you about domain expertise: it can make you blind.
When you’ve spent twenty years in an industry, you stop seeing the things that confuse newcomers. You stop questioning the jargon, the workflows, the assumptions baked into every product description. You write copy that makes perfect sense to other insiders and completely mystifies the 80% of prospects who are still learning.
I’ve seen this play out dozens of times now. A SaaS company in financial services hires a marketing agency staffed with former financial services people. The agency produces content that reads like a regulatory filing. The website sounds like it was written for the people who already use the product, not the people who should.
The content is technically accurate. It’s also completely unpersuasive.
Because persuasion requires empathy with the uninitiated. And empathy with the uninitiated is very hard when you’ve forgotten what it’s like to be uninitiated.
Week One: The Crash Course
When we signed that first fund management client, Bruno and I gave ourselves two weeks to become conversant. Not expert — conversant. Enough to ask intelligent questions and not embarrass ourselves.
I spent the first week reading everything I could find. Industry reports from Preqin. Blog posts from fund administrators. LinkedIn posts from GPs complaining about their tech stack. Podcast episodes where fund managers talked about operations. I read the Investopedia entries for about forty terms I should have already known.
By Friday, I had a notebook full of definitions, a rough mental model of the fund lifecycle, and a growing suspicion that most software companies in this space were terrible at explaining what they did.
That suspicion turned out to be worth more than an MBA in finance.
The Interview Phase
The second week, I started talking to people. Not pitching. Talking.
I called three fund administrators who had no connection to our client. I found them on LinkedIn, explained that I was trying to understand their world, and asked if they’d give me thirty minutes. Two of them said yes. One of them gave me ninety minutes and seemed almost relieved that someone from outside the industry was asking basic questions.
“Nobody ever asks me to explain what I actually do,” he said. “They either already know or they don’t care.”
Those conversations were worth more than all the reading combined. Not because the information was different, but because I heard how practitioners actually talked about their problems. The words they used. The frustrations they led with. The features they cared about versus the ones vendors kept pushing.
I learned that fund managers hate the word “solution.” I learned that they care about audit trails more than dashboards. I learned that the relationship between a GP and their fund administrator is weirdly intimate and deeply trust-dependent, like a marriage where one partner handles all the money.
None of this was in the industry reports.
The Outsider Advantage
About three months into that first engagement, something unexpected started happening. Our client’s CEO began forwarding our positioning work to his investors. Not because we’d produced anything technically groundbreaking, but because we’d managed to explain his product in a way that non-technical LPs could understand.
“This is the first time someone has described what we do and my mother could follow it,” he told me on a call. He was half-joking. But only half.
That’s the outsider advantage. When you don’t come from the industry, you can’t hide behind jargon. You’re forced to find the simple truth underneath the complexity. And that simple truth is usually what sells.
The insiders skip it because it feels too basic. They assume everyone knows. But in B2B SaaS, especially in vertical markets like fund management, the buyer is often someone two or three levels removed from the daily operations. They need the simple version. They need someone to connect the software to a business outcome they care about without requiring a glossary.
We became very good at building that bridge. Not despite our ignorance, but because of it.
The Research Framework
After that first engagement, we formalized what had been an improvised crash course into an actual process. Every time we take on a client in an unfamiliar vertical, we run the same playbook.
Week one: immersion reading. Industry reports, competitor websites, customer reviews on G2 and Capterra, relevant subreddits, LinkedIn discourse. I’m looking for patterns — the recurring complaints, the shared vocabulary, the unspoken assumptions.
Week two: practitioner interviews. At least three conversations with people who aren’t our client. People who use tools like our client’s product, or who chose a competitor, or who decided to build something in-house. These conversations reveal the emotional landscape that no amount of reading can surface.
Week three: competitive teardown. I go through every competitor’s website, pricing page, demo video, and case study. I map their positioning on a simple grid: who are they for, what problem do they solve, how do they talk about it. The gaps in that grid become our client’s opportunity.
Week four: first draft positioning. By now, we know enough to be dangerous. Not expert. Dangerous. Which is exactly where you want to be when you’re writing a homepage or a pitch deck, because dangerous means you’re still asking “wait, why?” about things the experts stopped questioning years ago.
What We Got Wrong
I don’t want to romanticize this. Being an outsider also means you make mistakes that insiders would never make.
Early on, I wrote a blog post for that first client that confused GP and LP in a way that was, to anyone in the industry, roughly equivalent to confusing a doctor with a patient. Our client caught it before it went live, but the email he sent was the kind of polite that’s actually furious.
Another time, we proposed a campaign angle that referenced a regulatory change I’d misunderstood. I’d read about it in a news article and assumed I knew enough. I didn’t. The compliance team flagged it within an hour.
These mistakes taught me something important about the outsider approach: it only works if you’re genuinely humble about what you don’t know. The moment you start pretending expertise you don’t have, you lose both the outsider advantage and the insider trust. You become the worst of both worlds — someone who doesn’t know the details and doesn’t know they don’t know.
So we built in checkpoints. Every piece of content goes through a subject matter review with the client before publication. Every campaign concept gets a “sanity check” call. We never publish in a vertical without someone from that vertical reading it first.
The creative instinct comes from us. The accuracy verification comes from them. It works.
The Fund Management Play
Fast forward two years, and fund management software became one of our strongest verticals. Not because we became fund management experts — we didn’t. But because we became expert at translating fund management complexity into clear, compelling marketing.
We now work with four companies in the space. Each one came to us after seeing what we’d done for another. The referrals happened not because we spoke the industry’s language perfectly, but because we spoke the buyer’s language. Which is a different thing entirely.
The fund managers at these companies sometimes look at me sideways when I ask a question that reveals how much I still don’t know about waterfall calculations or carried interest mechanics. But they keep hiring us. Because the content converts. The positioning resonates. The landing pages generate demos.
And I think it’s because every time I sit down to write about fund management software, I’m still channeling that version of myself in the first meeting — the one who didn’t know what a capital call was, who had to fight through the jargon to find the meaning underneath.
That confusion isn’t a bug. It’s the product.
The Broader Lesson
Every agency I know claims to specialize. And most of them mean they’ve done three projects in a vertical and updated their website to say “we serve financial services.”
Real specialization in an unfamiliar market requires something counterintuitive: you have to be willing to be bad at it first. To ask dumb questions. To get corrected. To spend your first month feeling like a fraud and your second month feeling like you’re finally catching up.
But if you can survive that discomfort, you develop something the insiders can’t replicate. A beginner’s eyes with a practitioner’s craft. The ability to see what’s confusing from the outside while knowing how to fix it from the inside.
I’ve built my whole career on being willing to not know things. It’s less glamorous than expertise. But it might be more valuable.
Because the market doesn’t need another expert talking to experts. It needs someone who can make the complex feel obvious. And that’s a job for outsiders.