Archive

Dive into a collection of past posts and rediscover timeless content.

AI efficiency

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

AI efficiency

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

AI efficiency

Jun 5, 2026

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3 min read

Your Board Doesn't Want the CMO It Hired Anymore

Every C-suite role is getting restructured around what AI now demands of the business. The CMO role is also one of them. While the role isn’t disappearing, the definition of the role is already changing.

Deepinder Singh Dhingra

May 28, 2026

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4 min read

The End of Dashboards

Marketing's been chasing better dashboards for twenty years. AI world was chasing better prompts in the beginning but when engineers figured out that no prompt could rescue a model that couldn't see what it needed to. They stopped tuning prompts and started fixing the layer underneath. Marketing hasn't realised it has the same problem, and the cost is showing up in dashboards frozen on last quarter's data that don't actually lead to decisions.

Deepinder Singh Dhingra

Why Your Best Buyers Look Like Cold Leads

May 15, 2026

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5 min read

Why Your Best Buyers Look Like Cold Leads

A strange pattern is showing up in B2B marketing - and most CMOs are missing it because they have not created dashboards to see it. The strongest brand programmes are losing deals to vendors with half their reputation. Brand is working harder than ever, and nothing downstream knows it worked.

Deepinder Singh Dhingra

practical tips

How to Find the Questions Your Buyers Actually Type

May 15, 2026

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1 min read

How to Find the Questions Your Buyers Actually Type

A practical guide to sourcing the real queries shaping your shortlist - from a quick 30-minute session to purpose-built tooling.

Deepinder Singh Dhingra

AI efficiency

The CMO Role Is Consolidating. Decide Which Side You Land On.

May 8, 2026

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4 min read

The CMO Role Is Consolidating. Decide Which Side You Land On.

This newsletter is for the CMOs watching colleagues get folded into CRO roles or opting for CGO roles elsewhere, watching board decks ask harder questions every quarter about marketing's contribution. Wondering, quietly, whether the next round of cuts lands on them.It is not a quiet trend anymore. UPS, Etsy, Walgreens, Starbucks, Johnson & Johnson - the CMO title got eliminated or restructured at all of them.

Deepinder Singh Dhingra

AI efficiency

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

Enterprise Sale

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

Archive

Dive into a collection of past posts and rediscover timeless content.

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

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

Your Board Doesn't Want the CMO It Hired Anymore

The End of Dashboards

Why Your Best Buyers Look Like Cold Leads

How to Find the Questions Your Buyers Actually Type

The CMO Role Is Consolidating. Decide Which Side You Land On.

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

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

The Moneyball CMO