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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Your Sales Cycle Is Longer Than It Needs to Be

Long sales cycles aren't an inevitability of complex B2B deals — they're usually a symptom of process gaps and unclear next steps. Here's where the time actually goes.

Alexander Shartsis

GTM

Aug 24, 2026

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4 min read

The Best Growth Leaders Are Students of the Business, Not Just the Channel

Channel expertise gets you hired. Business acumen gets you promoted. The growth leaders with real longevity are the ones who understand the P&L, the product roadmap, and the competitive dynamics — not just the funnel.

Alexander Shartsis

AI Outbound

The SDR handoff is the most expensive step in your funnel, and it's optional now

Aug 21, 2026

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2 min read

The SDR handoff is the most expensive step in your funnel, and it's optional now

Human qualification used to be the only way to route signal to the right person. Signal-based targeting can now do most of that itself.

Alexander Shartsis

AI Outbound

Your product usage data is more predictive than your CRM, and almost nobody's wired it to trigger anything

Aug 17, 2026

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2 min read

Your product usage data is more predictive than your CRM, and almost nobody's wired it to trigger anything

In-app behavior predicts expansion and churn earlier than anything in your CRM. Almost no GTM motion is actually wired to act on it.

Alexander Shartsis

GTM

Pipeline coverage ratios are lying to your board

Aug 14, 2026

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2 min read

Pipeline coverage ratios are lying to your board

3x or 4x coverage assumes a close rate that hasn't held true in years. The math still gets reported like it does.

Alexander Shartsis

GTM

Marketing and sales are fighting over pipeline credit, and nobody agreed on the rules

Aug 10, 2026

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2 min read

Marketing and sales are fighting over pipeline credit, and nobody agreed on the rules

First-touch and last-touch attribution both tell a true story and a misleading one. Most teams never pick a model, they just refight it every quarter.

Alexander Shartsis

GTM

Your headcount ask is a story, not a spreadsheet

Aug 7, 2026

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1 min read

Your headcount ask is a story, not a spreadsheet

The spreadsheet proves the math works. It's rarely what actually gets a CEO to say yes.

Alexander Shartsis

AI Outbound

Aug 3, 2026

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4 min read

The three-part outbound motion

How to run successful outbound at any scale.

Alexander Shartsis

GTM

The board doesn't want your funnel. It wants to know if this compounds.

Jul 31, 2026

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1 min read

The board doesn't want your funnel. It wants to know if this compounds.

A slide full of funnel stages proves activity happened. It rarely answers the one question a board is actually sitting there trying to figure out.

Alexander Shartsis

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Archive

Your Sales Cycle Is Longer Than It Needs to Be

The Best Growth Leaders Are Students of the Business, Not Just the Channel

The SDR handoff is the most expensive step in your funnel, and it's optional now

Your product usage data is more predictive than your CRM, and almost nobody's wired it to trigger anything

Pipeline coverage ratios are lying to your board

Marketing and sales are fighting over pipeline credit, and nobody agreed on the rules

Your headcount ask is a story, not a spreadsheet

The three-part outbound motion

The board doesn't want your funnel. It wants to know if this compounds.

Skyp

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