Most outbound emails are terrible.
In theory, that should make it easy to stand out. I mean, if everyone else is sending lazy AI personalization, generic compliments, and emails that somehow manage to say “I researched you” without demonstrating that they actually did, then a thoughtful email should get their attention.
But that hasn’t been my experience.
I think most buyers have become so accustomed to deleting sales emails that anything that even smells like a pitch can disappear in a split second. They’ve seen it all before, and most of it still feels like personalization wrapped around the same sales pitch.
What I have had some success with is a different process, particularly when the prospect has already engaged in some way.
Maybe they connected with me on LinkedIn, clicked an article, attended an event, or did something else that gives me a legitimate reason to take a closer look. Sometimes the starting point is not engagement at all, but a trigger or signal that suggests something meaningful has changed inside the company.
When that happens, I am not researching the account to find a clever connection so that I can send them a templated sequence.
I am trying to answer a much more useful question: What might this person be struggling to make progress on right now, and does that problem connect to something we actually know how to solve?
That difference matters, and if you can get them to pay attention, your response rates will go up.
Jenn Allen-Knuth has a useful way of thinking about this: prompt a problem, not a product. (If you’re not following her on LinkedIn, you should be…)
In one of her examples, she uses news about a shipyard opening in Portsmouth.
Subject: Portsmouth
And then in the body, she immediately states the observation and probes for a potential problem:
“Saw the news re: the new shipyard opening in Portsmouth.
Not sure if the US welder shortage is making it harder to find (and retain) skilled labor.”
Next, she introduces an example of how another company approached that problem.
“ACME was weighing the pros & cons of building an in-house welder university vs. using robotic welders.
Open to hearing how they cut production downtime by 23% in their new plant?
Either way, looking forward to seeing you at Robocon.”
Signature block
Now that’s an interesting email. And if that company is struggling with a welder shortage, they probably will respond.
And notice how this is NOT:
“Hey, saw the news about the new shipyard.
Here’s what we do.”
Since many public triggers like funding, new executives, product launches, an acquisition, or a hiring spike are easily researched with AI today, it’s not enough to start going after those contacts with your templated sequences only to add the personalization line at the top.
You must research them and anticipate where they might be struggling to make progress in a way that would actually make them want to reply to your email.
And since you don’t know what is actually going on inside their company, you should only be striving for problem agreement.
Notice in Jenn’s example she says, “Not sure if the US welder shortage is making it harder to find (and retain) skilled labor.”
If the buyer agrees, we now have something useful to talk about.
In our case, we're looking for companies that might need some outside help from a marketing agency. So, once we find a trigger, we usually look across several different sources to figure out what may be happening underneath it.
Depending on the company, that can include LinkedIn headcount growth by function, job openings, funding announcements, executive interviews, product launches, acquisitions, partnerships, market expansion, website messaging, paid ads, customer stories, and leadership changes.
But beneath all that, we're looking for things like:
They've made a positioning change recently and that may be making it harder to generate leads for sales.
They've got new leadership and a small marketing department and may be looking to change direction.
They've hired many salespeople in the last year and marketing hires have stayed flat (might mean they're frustrated with demand generation from marketing.
They stopped advertising and maybe that's because they've been throwing money away and want to reset
Their CEO is talking about their growth opportunity, yet none of that is reflected in the messaging on the website.
And so on…
All of these are problems that I can probe for based on a trigger.
From there, we try to find one or two pieces of evidence that support a plausible business problem. Then we ask whether that problem connects to something we solve.
Only after that do we write the message.
The quality of the outreach improves dramatically once you stop asking, "What can I personalize?" and start asking, "What problem might this signal be pointing to?"
Here is the prompt I use as a starting point. You can adapt it depending on the trigger.
Research [PERSON], [TITLE] at [COMPANY].
I am not looking for generic personalization or a company summary.
Start with this trigger or signal:
[INSERT TRIGGER]
Research the company and determine what business or GTM problem that trigger may have created.
Look for supporting evidence from recent executive interviews, company announcements, LinkedIn headcount changes, hiring patterns, product launches, acquisitions, partnerships, funding announcements, positioning changes, website messaging, paid ads, and customer stories.
I want to know where this person may be struggling to make progress right now.
Do not manufacture pain.
Separate what we know from evidence, what we can reasonably infer, and what still needs to be validated.
Then identify the single strongest problem that connects to something we solve, such as generating more qualified pipeline, improving positioning or messaging, helping Sales know who to talk to next, identifying buying signals earlier, helping a small marketing team execute more effectively, or turning a broader product story into demand.
Finally, write a short outreach message that references the trigger, explains the likely business implication in plain English, does not pretend we know private information, probes for problem agreement, and ends with one simple question.
Do not lead with praise. Do not summarize the company. Do not pitch the product first. Do not use generic language like "exciting growth" or "impressive momentum." Make the message sound like one experienced operator talking to another.