The cold outreach disconnect
Most cold outreach looks personalized but feels automated. I’ve tested tools like Apollo.io, HubSpot, and LinkedIn – and the results were the same. Here’s what’s really causing the disconnect and how to fix it.
We all know the rules for great outreach – research, personalize, automate. So why does it still fall flat?
I’ve run more outreach sequences than I can count. I’ve used tools like Apollo.io, HubSpot, and LinkedIn automation. I’ve tested subject lines, intros, call-to-actions – all the usual tweaks.
And yet, even with all that structure, personalization, and data behind it, the results often tell the same story:
"Personalization doesn’t equal connection."
That’s the cold outreach disconnect.
We think we’re doing it right because the playbook says to research, personalize, and send. But personalization without relevance is just noise in disguise.
Everyone’s personalizing – few are connecting
Most outreach I get today starts strong. It references my company, maybe even something from LinkedIn. But within seconds, it turns into a pitch I’ve seen a hundred times before.
The truth is, automation has made personalization easy. Tools like HubSpot Sequences or Apollo.io’s email workflows can scale tailored messages faster than ever – but they also make it easier to lose the human layer along the way.
“Show me you know me” – and mean it
One of the best frameworks I’ve come across is Samantha McKenna’s “Show Me You Know Me” (SMYKM) Master Class on Apollo.io Academy.
It’s built around something that sounds simple but is surprisingly rare: actually showing you’ve taken the time to understand the person you’re writing to. Not just by dropping their name or referencing their latest post, but by connecting their challenges to something meaningful you can help solve.
“Show me you know me.” – Samantha McKenna
That’s real personalization. It’s also what separates good outreach from great conversion copy – whether it’s an email or a landing page.
My own experience with outreach
I used to run cold sequences built around the SMYKM framework. The subject line and opening lines were reserved for personalization – insights pulled from LinkedIn, company updates, or shared connections.
The rest followed a tested structure, leading to an offer like a free landing page audit.
When I later switched from Apollo.io and manual LinkedIn tasks to HubSpot’s Prospecting Agent with built-in outreach, I expected a change in results. But it stayed roughly the same.
Why? Because the tool wasn’t the issue. The results were driven by how well the message resonated, not how it was sent.
And an interesting side note: I started getting more LinkedIn connection requests accepted when I didn’t include a note. Sometimes less is more.
“It reminded me how optimization always comes back to clarity – whether it’s your landing page or your message.”
Outreach and CRO have the same root problem
Cold outreach and conversion rate optimization are closer than most think.
In CRO, we obsess over message match – making sure what we promise in an ad aligns with what visitors see on the landing page. Outreach is the same: the message must match the recipient’s mindset.
If you lead with what you want instead of what matters to them, you’ve already lost the click.
Empathy, clarity, and proof still win – whether the goal is an email reply or a form submission.
The takeaway
Outreach isn’t broken because of bad tools or a lack of personalization. It’s broken because of misaligned intent.
If your goal is to sound personal, you’ll miss. But if your goal is to be relevant, you’ll connect.
As Samantha McKenna says, “Show me you know me.” Just make sure you actually do.
How to fix your cold outreach
If you’ve recognized some of these patterns in your own outreach, here are three simple ways to start closing the gap:
- Start with relevance, not personalization
Before you write, ask: Why should this person care about what I’m saying right now? If you can’t answer that clearly, pause and rethink your angle. - Connect the dots
Use your research to bridge their challenge with your insight – not your product. Mention something specific, then explain why it matters in their context. - Test one variable at a time.
Just like in CRO, don’t overhaul everything at once. Try testing your opening line, tone, or CTA. Watch what earns replies – and double down on what resonates.
Cold outreach isn’t about writing better emails. It’s about creating better alignment between your message and your reader’s moment.
If you’d like a second set of eyes on how your outreach or landing pages come across to prospects, I’m happy to take a look. Just send me a note or connect on LinkedIn.
