Skyp Newsletter - AI GTM and Sales Insights

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

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Displacing an incumbent is an outbound problem, not a demo problem

Most displacement deals are won or lost before the first demo, in whether you reached the buyer while they were open to switching.

Alexander Shartsis

AI Outbound

The 30 days after a funding round are the highest-intent window nobody times outreach to

Oct 19, 2026

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2 min read

The 30 days after a funding round are the highest-intent window nobody times outreach to

A fresh round means new budget, new mandates and a team under pressure to move. The announcement is a public trigger most outbound ignores.

Alexander Shartsis

AI Outbound

Your email and your LinkedIn are telling two different stories

Oct 16, 2026

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2 min read

Your email and your LinkedIn are telling two different stories

Prospects see every channel at once. When the messages don't match, the inconsistency reads as noise, not persistence.

Alexander Shartsis

AI Outbound

Outbound ROI is lost in reply handling, not in sending

Oct 12, 2026

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2 min read

Outbound ROI is lost in reply handling, not in sending

The campaign did its job when a prospect said yes. What happens in the next few hours decides whether it turns into pipeline.

Alexander Shartsis

GTM

Your comp plan is optimizing for the wrong number

Oct 9, 2026

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3 min read

Your comp plan is optimizing for the wrong number

Closed-won pays the commission. Retention pays the business. Those aren't always the same deal.

Alexander Shartsis

GTM

Multi-threading is a lagging indicator, not a strategy

Oct 6, 2026

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2 min read

Multi-threading is a lagging indicator, not a strategy

Reps treat multi-threading as a tactic. It's really just a readout on whether the deal was already moving.

Alexander Shartsis

GTM

Oct 2, 2026

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2 min read

Your renewal process starts too late because nobody owns it early

Renewal risk is decided in the first 30 days, not the last 30. Almost nobody owns that window.

Alexander Shartsis

Sales Automation

Sep 28, 2026

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2 min read

The RevOps tax nobody budgets for

Every tool you add has a coordination cost that never shows up on the invoice.

Alexander Shartsis

GTM

The forecast is a negotiation, not a prediction

Sep 25, 2026

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2 min read

The forecast is a negotiation, not a prediction

Everyone in the forecast chain has a rational reason to distort the number. That's why it's political, not predictive.

Alexander Shartsis

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Archive

Displacing an incumbent is an outbound problem, not a demo problem

The 30 days after a funding round are the highest-intent window nobody times outreach to

Your email and your LinkedIn are telling two different stories

Outbound ROI is lost in reply handling, not in sending

Your comp plan is optimizing for the wrong number

Multi-threading is a lagging indicator, not a strategy

Your renewal process starts too late because nobody owns it early

The RevOps tax nobody budgets for

The forecast is a negotiation, not a prediction

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