Why Most Outbound Still Fails (Even in 2025)

I was on a string of calls this week with GTM leaders, agency owners, operators, and my own team.

Different businesses, different contexts, but the same patterns kept surfacing.

It always amazes me how often the conversation about outbound starts in the wrong place.

Most people want to jump straight into messaging. But nine times out of ten, messaging is not the real issue.

Here are five themes that stood out to me this week. These are lessons I am seeing play out across the market, and inside our own walls.

1. The biggest outbound problem is still delivery, not messaging.

I keep seeing this.
- Strong ICP definition.
- Good offer.
- Experienced sales team.
- reply rates.

Why? The delivery mechanics are broken.

Companies are still sending cold email from main domains. They are still using tracking links. They are still getting flagged by enterprise filters before the first word is even read.

Teams waste months tweaking copy when what they really need is to fix their email infrastructure.

Before you ask why your reply rates are low, check your SPF, DKIM, DMARC, inbox warmup, and whether your domain is being throttled. The pipes matter more than the words.

2. Enterprise outbound will not be AI-led and that is a good thing.

AI is transforming how we find signals, enrich data, and prioritize outreach. We rely on it heavily.

But what AI cannot do yet is replace the human relationships and trust required to sell into complex, high-value deals.

The best GTM teams are not automating their way to pipeline. They are using AI to support their humans, not replace them.

Signals and timing can be surfaced by AI. Conversations and context still need to be owned by people.

3. You cannot sell modern GTM services through cold outbound alone.

One thing that has become increasingly clear in our own growth and in conversations with other operators is this.

Trying to sell high-value GTM services through cold email alone is a losing game. The channel is too saturated, and the risk of being perceived as just another agency is too high.

Content-first strategies are driving better opportunities.
Inbound trust accelerates outbound conversion.

In our business today, the majority of new pipeline comes through founder-led content, not cold email. Outbound supports the conversation, but it rarely starts it.

If you are trying to sell trust-based services, build trust first.

4. Static outbound playbooks will not survive this market.

We used to run a productized cold email model. It worked for a while, until it stopped working.

Every client, every market, every ICP now requires a different mix of signals, messaging, and timing.

You cannot throw a single playbook at five different industries and expect it to convert consistently.

Outbound now has to be adaptive. It has to flex based on territory, culture, segment, and market dynamics.

What works for a fintech CEO in London will not work for an architecture firm in Chicago. The systems we build today need to be able to account for those differences.

5. Even great campaigns decay and fingerprinting is a real threat.

Here is something Louis and I noticed this week inside one of our own campaigns.

We had a sequence that had been performing well. Strong reply rates, good conversion. But over time, results started to drop off.

On review, it was clear what had happened. The copy had been fingerprinted.

When you scale a single script across thousands of sends, even with minor tweaks, spam filters start to recognise patterns. Deliverability drops. Replies slow down.

The lesson is simple. Outbound is not set and forget. You need to constantly refresh copy, vary structure, use deep spintax, and segment more granularly than ever.

Our new rule internally is this. No sequence lives beyond 20,000 sends without a complete refresh.

It is the only way to stay ahead.

Closing thought.

Outbound is not dead. But bad outbound is disappearing fast.

The GTM teams winning today are doing five things well:

• They invest in infrastructure and monitor deliverability relentlessly.

• They use AI to support, not replace, their sales motion.

• They build trust-first content that accelerates outbound.

• They run adaptive, signal-led systems, not static playbooks.

• They treat outbound as a living process, not a static campaign.

If you are still sending cold email from your main domain, blasting a static script, or ignoring deliverability, you are not competing with the teams who are doing this well.

And if you are seeing any of these patterns in your own outbound, or have a different take on how to solve them, I would love to hear how you are approaching it.