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: We’re hosting a live session on Thursday, Feb 26 at 9:00am PT on the most dangerous moment in a startup’s life—when teams flip into “sales mode” before they’ve learned what actually works. Join us!
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Early-stage teams love “sales mode.”
It feels productive: more sequences, more calls, more CRM fields, more dashboards, more “pipeline.”
But “sales mode” is an optimization mindset.
And optimization only works when you already know what works.
If you don’t, scaling just makes you wrong… faster.
Sales Mode: “How do we get more of this working thing?”
Learning Mode: “What’s actually working—and why?”
Most teams try to optimize before they’ve learned the basics:
Who buys
Why now
What they believe before they buy
What makes deals stall
What converts curiosity into commitment
These are volume levers. They help when the core is already resonating.
Speed-to-lead (how fast you follow up)
Conversion steps (demo → proposal → close)
Pipeline hygiene (stages, next steps, exit criteria)
Channel efficiency (reply rates, CPC, CPL, etc.)
Sales execution (objection handling, talk tracks)
These are truth levers. They create the signal worth scaling.
ICP clarity: who actually says yes fastest
Trigger clarity: what changed in their world that makes this urgent
Message clarity: what phrasing makes them lean in
Value clarity: what outcome they’ll pay for (and what they won’t)
Friction clarity: where momentum dies (security, budget, switching costs, internal politics)
Rule: If you’re still arguing about ICP, you’re not in sales mode. You’re in learning mode. Act like it.
Here’s a simple cadence that keeps learning real and measurable:
Not five. One.
Examples:
“This segment responds best when we lead with outcome X.”
“This trigger creates urgency.”
“This objection is actually the real bottleneck.”
These can be calls, emails, DMs, founder intros—doesn’t matter.
What matters is: you’re testing one idea, not “doing outreach.”
Keep it lightweight. You’re building pattern recognition, not paperwork.
Who was it? (role + company type)
What was the hook? (message/angle)
What did they resonate with? (exact words)
What did they push back on? (exact objection)
What happened next? (meeting / no / later / ghost)
Two outputs only:
What did we learn that changes what we do next week?
What are we stopping because it’s not true?
Rule: If your “learning review” doesn’t cause you to stop something, it wasn’t learning. It was journaling.
Founders need to stay close to the truth early.
But founders also can’t be in every thread, call, and follow-up forever.
Here’s how to keep signal without becoming a bottleneck:
Founders should be deeply involved in:
First 10–20 deals
First 20–40 discovery calls (or call reviews)
Any deal that stalls for unclear reasons
Then transition from “founder does everything” to “founder audits reality.”
Instead of joining everything:
Review 3 calls per week
Read 10 prospect replies per week
Review the top 5 lost deals per month
You stay close to the truth without being dragged into every execution detail.
One doc. One running log. No scattered Slack archaeology.
Keep:
Objections that repeat
Phrases prospects used
The top 3 reasons deals stall
The messages that reliably land
Rule: Early GTM is a research project. Treat it like one.
We built Skyp for teams that want to stay in learning mode without drowning in grunt work.
Skyp helps you run tight, repeatable experiments—so each week you can test a message, a segment, or a trigger and get real signal back, while still keeping the founder’s or Brand’s voice and insight in the loop.
Join thousands of sales teams using AI-powered email outreach to drive consistent, measurable results.
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