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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Moving Upmarket Is Harder Than Your Board Thinks

Every board wants to move upmarket. Few appreciate that it requires a fundamentally different sales motion, a longer cycle, and a product that wasn't built for enterprise buyers.

Alexander Shartsis

GTM

Your Buyer Has Already Decided Before They Talk to Sales

Sep 4, 2026

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3 min read

Your Buyer Has Already Decided Before They Talk to Sales

70% of the B2B purchase decision happens before a prospect ever speaks to a rep. Most growth teams are still investing like the decision happens in the demo.

Alexander Shartsis

GTM

The "No Decision" Loss Is the One Worth Obsessing Over

Aug 31, 2026

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3 min read

The "No Decision" Loss Is the One Worth Obsessing Over

Losing to a competitor stings. Losing to inaction is a different kind of failure — one that usually points to a positioning or urgency problem rather than a product gap.

GTM

Your Sales Cycle Is Longer Than It Needs to Be

Aug 28, 2026

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3 min read

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

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Archive

Moving Upmarket Is Harder Than Your Board Thinks

Your Buyer Has Already Decided Before They Talk to Sales

The "No Decision" Loss Is the One Worth Obsessing Over

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

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