The Skyp Newsletter
Insights, tips, and strategies for modern AI-powered outreach and sales automation
Insights, tips, and strategies for modern AI-powered outreach and sales automation
Quick heads up before next week’s issue.
I’m doing a live webinar with Finn McKenty — 130M YouTube views, video work for Red Bull, Nike, and Element — where he builds a video ad for Skyp live, on camera.
No script. No safety net.
The point isn’t to show a perfect output. It’s to show what the workflow actually looks like when someone who knows what they’re doing runs it.
Back to today’s post…
If you sell into a busy category, it’s tempting to conclude:
“This market is crowded.”
Usually, the market isn’t crowded.
Your message is crowded.
Because everyone in the category says the same three things:
“All-in-one”
“AI-powered”
“Save time”
“Increase revenue”
“Best-in-class”
That’s not differentiation. That’s background noise with a logo.
The good news: you don’t need a new product.
You need a new angle.
Features are easy to copy. Angles are harder—because they come from taste, focus, and a point of view.
Don’t sell the tool. Name the villain.
“The real problem isn’t leads. It’s lead decay.”
“The real problem isn’t outreach volume. It’s message sameness.”
“The real problem isn’t churn. It’s failed activation.”
A clear enemy makes your category feel new.
Most categories compete on the wrong metric because it’s convenient.
Pick a metric your buyers actually care about, and own it.
Examples of “better metrics”:
time-to-first-value*
speed-to-lead
forecast confidence
sales cycle variance
cost of inaction (not cost of tool)
Owning a metric is how you stop being “another option.”
*Time-to-first-value is what we focus on at Skyp, but we call it “time to bacon” because we think people are busy and they want to push a button and get what they want as soon as possible. And who doesn’t want bacon?
It makes sense to us, anyway.
Same category, smaller entry point.
Instead of “we do everything,” you lead with the one job that is urgent, frequent, and painful.
Wedges sound like:
“Start with one workflow.”
“Start with one team.”
“Start with one segment.”
This makes adoption feel doable—and makes you easier to remember.
Tell a story that makes the buyer feel smart for choosing you.
Not “we have features.” More like:
“Most teams make mistake X. Here’s the smarter path.”
“The best operators do Y. Here’s why.”
“Everyone is optimizing A, but the real lever is B.”
This is positioning as a point of view, not a checklist.
Most buyers are secretly buying risk reduction.
If you can reduce perceived risk, you win even if competitors have more features.
Risk reducers:
timeboxed pilots
guarantees / risk reversal
“start without IT”
minimal change management
clear “what happens if this fails” plan
Rule: A safer decision beats a better product.
Sometimes the best way to stand out is to say:
“We are not the thing you think we are.”
That’s anti-category positioning.
You define what the category is doing wrong—and take the opposite stance.
Examples of anti-category frames:
“Most tools add dashboards. We remove decisions.”
“Most platforms require a rollout. We start with a 7-day test.”
“Most solutions sell automation. We sell consistency.”
“Most vendors want you to migrate. We plug into what you have.”
You’re not insulting competitors. You’re rejecting the category’s default assumptions.
Rule: Anti-category works when you can credibly explain why the category’s default is broken.
Skyp is not an AI SDR. We do outbound with AI. We might even replace (or enhance) your SDRs. But an AI SDR we are not. Eww.
You don’t need a rebrand. You need a quick experiment.
Here’s a simple 48-hour angle test:
Pick 3 from the five above. Keep them punchy.
Example formats:
Enemy: “Stop losing deals to [villain].”
Metric: “Improve [metric] without [common pain].”
Wedge: “Start with [small scope]—prove value fast.”
Line 1: observation / villain / trigger
Line 2: consequence + question
20 outbound messages (or DMs)
1 LinkedIn post
5 conversations with friendlies / customers
What you’re looking for:
“Interesting—tell me more.”
“We’re dealing with that.”
“How do you do that?”
“Timing is good.”
If you get polite likes but no “tell me more,” the angle is still crowded.
Rule: The best angles create questions, not compliments.
We built Skyp for this exact problem: categories where everyone sounds the same.
Skyp helps you generate and test different angles fast—across segments, triggers, and pain—so you can find the message that actually creates conversations (instead of shipping another “AI-powered all-in-one” paragraph into the void).
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