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marketing automation

AI efficiency

+2

Top CMOs Are Becoming ICs now! Why Headcount Was Never the Flex.

Jun 18, 2026

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5 min read

Top CMOs Are Becoming ICs now! Why Headcount Was Never the Flex.

The best marketing leaders I talk to are quietly walking back down the ladder and becoming ICs. They understand something the rest of the market is about to learn the hard way.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

AI efficiency

+2

GTM Amnesia: Why Your Buyers' AI Knows You Better Than Your Stack Does

Jun 12, 2026

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5 min read

GTM Amnesia: Why Your Buyers' AI Knows You Better Than Your Stack Does

Your buyers now send a machine to research you before a human ever shows up. That single change breaks most of what marketing has measured for a decade, and it explains why I've bet my company on the context layer.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

AI efficiency

+8

Brand Is Where Marketing Hides the Spending It Can't Justify

Apr 30, 2026

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5 min read

Brand Is Where Marketing Hides the Spending It Can't Justify

That's the boardroom skepticism. The irony is that most of the marketing dashboard built for itself was designed to make this exact accusation impossible to defeat.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

Enterprise Sale

+5

A Deal Took 5 Years to Close, But The Attribution Model Credited a Blog Post.

Apr 23, 2026

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4 min read

A Deal Took 5 Years to Close, But The Attribution Model Credited a Blog Post.

In B2B pipeline generation is up by 23% but the win rates are down at 18%. While everyone blames their attribution model, the thing is that they were never built their models for the most important deals.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

GTM

+5

A CFO Told Me Marketing Is the Only Department That Grades Its Own Homework

Apr 9, 2026

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13 min read

A CFO Told Me Marketing Is the Only Department That Grades Its Own Homework

I spend most of my time helping marketing teams make sense of their data. So when a CFO said this to me over coffee, half-joking, I couldn't laugh. It was a clever line, but I know how many marketers hear some version of that sarcasm every budget cycle and can't do anything about it. The worst part was that he wasn't completely wrong.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

AI efficiency

+6

She Had the Data. She Hid It On Purpose.

Apr 2, 2026

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9 min read

She Had the Data. She Hid It On Purpose.

One of our smartest customers deliberately hid her own data, which changed how her team allocated budget but chose to do so anyway. What she understood about data readiness is the same thing Billy Beane figured out about baseball scouts twenty years ago.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

AI efficiency

+5

A CMO had $2M in their pipeline, but nobody could see it.

Mar 26, 2026

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12 min read

A CMO had $2M in their pipeline, but nobody could see it.

The story of how a CMO and her team discovered $2 million in their pipeline, which was hidden in plain sight. This was not new pipeline, but the data already hidden in multiple un-connected sources.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

creator economy

+7

Why Your Creator Strategy Is Just Expensive Gut Feeling

Feb 27, 2026

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13 min read

Why Your Creator Strategy Is Just Expensive Gut Feeling

Brands are moving from broadcast to creators without any measurement infrastructure in place. What they need to define ROI next?

Deepinder Singh Dhingra
Deepinder Singh Dhingra

AI efficiency

+5

Your Marketing Data Is Lying to You

Feb 20, 2026

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9 min read

Your Marketing Data Is Lying to You

Why most marketing teams optimize for channels that directly relate to conversion and kill the ones actually causing it.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

AI efficiency

+6

Your AI Marketing Stack Is Making You Worse

Feb 12, 2026

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11 min read

Your AI Marketing Stack Is Making You Worse

Most CMOs are automating the exact things they shouldn't.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

The Moneyball CMO

The best CMOs today are not just running campaigns, they are driving revenue as well. Here I share modern marketing tactics and conversations from seasoned leaders - backed by real data. Read by teams at Zscaler, Glean, Abnormal Security, Agent.ai, Ncontracts & more. Subscribe for weekly insights.

© 2026 The Moneyball CMO.
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