on a journey to PMF: the best outbound I've ever seen told me what i didn't want to hear

I hired a world-class GTM operator to test our best GTM hypotheses with the best-in-class outbound system for LinkedIn. What we learned and what next?

Hey everyone,

Sorry for the delay on this one. I wanted to get permission from the folks I referenced before shipping this one…

Last week, I got the results back from the most expensive experiment I’ve run at Journey. I hired one of the best GTM operators I could find, someone who builds outbound systems for a living, and gave him a simple brief: build the Porsche of go-to-market engines for Journey, and let’s see what happens.

The goal was to get to a repeatable, predictable playbook as quickly as possible for one of the several niche segments we honed in on during our customer deep dive prior to the experiments.

As a founder of a start-up that doesn’t have PMF, I’ve learned something that is hard to say:

For a pre-PMF company like Journey, ANY concrete outcome, either good or bad, from a go-to-market investment is extremely valuable. It’s a hard pill to swallow, but failure from a go-to-market investment is an important data point that helps you know where to STOP investing, where to STOP digging, and where to STOP being hopeful.

fun stuff (before we get into things…)

went to a family wedding in Fredericksburg this past weekend. it was 99 degrees, and we were in Texas hill country celebrating my wife’s cousin.

the boys had a great time… i was just surviving the heat.

a reminder on what we built

For commercial real estate investment funds, we wrote a Claude Code scraping tool that crawled every SEC Form D filing from the past two years. It pulled how much each fund raised, how many funds they managed, whether they were actively raising, whether they had a portal on their website, the number of downloadable PDFs on their site. Eight qualification criteria, all extracted automatically, all feeding hyper-personalized outreach that referenced each fund’s specific situation.

For industrial manufacturing, similar depth. Scanning for 3D renderings on company websites. Counting downloadable CAD files. Finding YouTube channels with webinars and referencing exact view counts in the messaging.

It was the best segmentation and personalization I’ve seen. Every message was crafted with a level of specificity that should’ve made the recipient stop and think, “wait — this person actually understands my business.”

It got nothing. Crickets. Hundreds of contacts, multiple segments.

is it just me and Journey?

I got some additional context from other companies to understand their GTM experience.

A recruiter reaching out to YC founders in Europe with pre-qualified candidates for their open roles — a proven cold offer. A VC partner reaching out to healthcare founders offering free advice from a three-time CRO in their space. A D2C e-commerce play targeting founders of brands with 7+ years in business, under $30M raised, positive growth signals.

Every single one. Brilliant targeting, thoughtful messaging, legitimate value. Crickets.
The recruiter got one guy who said “I’d be keen to look at your candidates” — and then the thread went dead the second it pivoted toward a sales conversation. The D2C campaign? 7% LinkedIn acceptance rate, essentially zero replies.

This isn’t one company with a bad product. It’s a pattern.

post-effort

I was catching up with a founder friend who said something on a call that describes the change we’ve seen in GTM: “We’re in a post-effort world.”

He means that hard work, smart execution, and relentless iteration used to be enough to scale a GTM engine. You could write better emails, test more subject lines, refine your ICP, improve your sequences, and results would compound. That flywheel doesn’t spin the same way anymore.

Three years ago, the personalized landing page Steve built — one that basically says “I went through your entire business and here’s a mini-proposal” — would have blown people away. Today? Nothing. Not because it’s bad. Because the threshold for what earns someone’s attention has shifted so far that even exceptional execution doesn’t clear it.

it’s not just outbound

I recently read PricingSaaS’s 2025-2026 analysis of PLG vs. SLG across 498 SaaS companies. The data tells a remarkably similar story from the product side.
The line between product-led and sales-led growth has collapsed. Companies aren’t picking one model — they’re mashing them together. Of the 40 companies that changed their freemium model in 2025, roughly half tightened or eliminated free access and the other half expanded it. The market isn’t moving in one direction. It’s splitting.

Credit-based pricing adoption grew 126% year-over-year. Figma went through the entire AI monetization lifecycle in four quarters — standalone add-on to embedded credits to free-tier credits — searching for the right model in real time. Notion killed its $10/month AI add-on entirely and just baked AI into every plan, metered by usage.
These are companies experimenting at speed because the old assumptions were showing signs of slowing their business down.

The report’s core finding — PLG and SLG have collapsed into one thing — mirrors exactly what I’m seeing on the GTM side. The distinction between inbound and outbound is dissolving. And what’s replacing it feels less clear, at least for us.

the gap

The GTM operator I hired made this point better than I could: everything he builds now, he tells his clients, is not a meeting generation system.

It’s an awareness system. The goal isn’t to get someone to say yes to a call. The goal is to figure out if they’re even willing to assess whether they have the problem you’re trying to articulate.

The sales process used to be: top of funnel → discovery → demo → evaluation → close.

Now there’s this vast, unmapped territory before the funnel even starts. A space where you’re trying to create enough trust and deliver enough value that someone will eventually, on their terms, when they acknowledge they have the problem you solve, consider you.

That’s a fundamentally different business than most of us planned for.

the uncomfortable part

I started this experiment thinking there were two outcomes: either we’d find a glimmer of traction I could pour fuel on, or we’d get a definitive signal that these initial set of hypotheses were not going to work.

I got the second one. From the best operator I could find. Using the most sophisticated tools available. With messaging that was objectively excellent.

And that means something. Not just for Journey, but for how I think about what’s possible in B2B right now.

Either you have the perfect product for the perfect problem at the perfect time — lightning in a bottle, the kind of PMF where go-to-market almost doesn’t matter because the pull is that strong — or you commit to the slow, trust-based, audience-first approach that takes months or years to compound.

The world where you could have “somewhat” PMF and scale it through GTM effort? I think that world is gone.

The opportunity though is that there are a new set of hypotheses to go test (for example, are these people more available to reply via email?).

More on this to come…

Let’s keep it going.

Cheers, Danny