Skyp Newsletter - AI GTM and Sales Insights

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Insights, tips, and strategies for modern AI-powered outreach and sales automation

Written by

Alex Shartsis

The Hidden Cost of “We Do Everything”

Horizontal is fine. Horizontal messaging is fatal.

Alexander Shartsis

AI Outbound

Your Market Isn’t Crowded—Your Message Is

Mar 6, 2026

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5 min read

Your Market Isn’t Crowded—Your Message Is

If you sound like everyone else, you’ll compete like everyone else. Change the angle.

Alexander Shartsis

AI Outbound

Mar 2, 2026

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3 min read

The “Second-Order Pain” Framework

First-order pain is annoying. Second-order pain is expensive.

Alexander Shartsis

Feb 27, 2026

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6 min read

Stop selling. Start listening.

Wisdom from working with 1,000 B2B startups–and starting 3

Alexander Shartsis

AI Outbound

Feb 23, 2026

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4 min read

The Sequence Is Not the Strategy

A longer sequence isn’t a strategy. It’s just more delivery of the same wrong message.

Alexander Shartsis

Sales Automation

The most dangerous moment in a startup's life

Feb 20, 2026

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3 min read

The most dangerous moment in a startup's life

What someone who has gone $0-1mm ARR multiple times worries about

Alexander Shartsis

AI Outbound

Feb 13, 2026

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4 min read

Sales Mode vs Learning Mode

If you’re still guessing ICP and messaging, “sales mode” just makes you wrong faster.

Alexander Shartsis

Sales Automation

Feb 9, 2026

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4 min read

Your Offer Is Too Polite

Nice sounds optional. Specific sounds like a decision.

Alexander Shartsis

AI Outbound

Feb 6, 2026

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3 min read

Why Your Case Study Doesn’t Convert

If it reads like a press release, it won’t close deals.

Alexander Shartsis

...

Archive

The Hidden Cost of “We Do Everything”

Your Market Isn’t Crowded—Your Message Is

The “Second-Order Pain” Framework

Stop selling. Start listening.

The Sequence Is Not the Strategy

The most dangerous moment in a startup's life

Sales Mode vs Learning Mode

Your Offer Is Too Polite

Why Your Case Study Doesn’t Convert

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