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
🎬 Join us this Thursday at 9am PT!
I’m talking with Finn McKenty on Using AI Video to Stand Out — a session for founders, marketers, and GTM leaders who are done with "good enough" content.
Finn grew (and sold) a YouTube channel with over 130mm views. He’s worked Nike and Redbull. He’ll break down exactly how to go from mediocre AI output to work that actually gets results. We’ll build pro-level assets live using tools anyone can use for ~$49/mo.
If you're responsible for growth and want a real edge, this is the session to catch. I’m personally excited about this–veo3 ads have been on my “to do” list for a while but I didn’t know where to start. Finn’s going to show us start → finish how to get it done.
Now back to today’s post….
“We can help with outbound, inbound, partnerships, revops, enablement, and probably your taxes.”
Sounds impressive.
Also sounds like nothing.
The hidden cost of “we do everything” isn’t just unclear messaging.
It’s that buyers can’t answer the only question that matters:
“Is this for me… right now?”
- Every Prospect
If they can’t place you in their world in 5 seconds, they don’t reply.
Being horizontal is not the crime.
Leading horizontal is.
A wedge is the smallest, sharpest entry point into a big market.
Not: “We help go-to-market teams.”
Yes: “We fix this one painful moment for this one person.”
Great wedges have three traits:
Urgent (it’s a real problem this month)
Frequent (it happens all the time)
Measurable (you can prove improvement)
Examples of wedge shapes (generic):
“Reduce time-to-first-value for new users”
“Fix speed-to-lead for inbound”
“Standardize outbound messaging for a 10-rep team”
“Shorten month-end close by removing one bottleneck”
Rule: Your wedge isn’t your whole product. It’s your front door.
Once you pick the wedge, don’t immediately widen it by targeting everyone.
Instead: one persona, three pains.
Why it works:
You stay memorable (one buyer)
You increase relevance (multiple “reasons now”)
You get more shots on goal without sounding generic
Be specific enough that you can picture their calendar.
Examples:
Head of RevOps
VP Sales
Product-led Growth lead
CS leader
Founder selling enterprise
This is super hard for me at Skyp–we have customers in 6+ verticals, many with different titles/roles. As we work on expanding on one or two–it’s very tempting to spray and pray.
Not philosophical pains. The ones they complain about.
Example (RevOps):
“Pipeline data is a mess.”
“Reps don’t follow the process.”
“Forecast calls are a debate, not a decision.”
Example (VP Sales):
“Meetings don’t convert.”
“SDR Ramp time is too slow.”
“Rep performance is wildly inconsistent.”
Same persona. Same wedge. Different pain angles.
This is how you test without turning into a generalist.
Rule: Don’t go horizontal across personas. Go deep across pains for one persona.
The big mistake is expanding before you have proof.
You win the wedge first. Then you expand outwards.
A clean expansion path looks like:
Nail one wedge (clear ICP + repeatable win)
Add adjacent pain (same persona, next problem)
Add adjacent persona (same company, different owner)
Go broader (only after the story is already known)
How you know you have signal:
You can predict who converts and why
You hear the same language in calls
Referrals start showing up
Your “case studies” start writing themselves (because the pattern repeats)
Rule: Expand when your wedge starts pulling… not when you get bored.
We built Skyp because broad messaging is one of the fastest ways to waste a good product.
Skyp helps you pick a wedge, focus on one persona, and test multiple pain angles—so you get signal fast and expand with confidence instead of guessing your way into “we do everything” purgatory.
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