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.

Articles

Oct 23, 2026

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5 min read

Anthropic's AI Agents Spend 80% of Their Time Waiting for a Human

In interactive sessions, Anthropic's agents spend about 80% of their time waiting for a person to reply. Output went up and junior hiring went down. This issue gives you a 30-minute Friday sweep that puts your decisions where your agents can read them.

Deepinder Singh Dhingra

Oct 15, 2026

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6 min read

I Called AI SDRs a Scam. This Week We Launched a Digital SDR.

Human judgment is often an unwritten rule. Most of what your reps call judgment is simply rules nobody has written down. Any org deploying AI SDR need to sort the two before AI touches your pipeline. Vercel also had a similar problem with inbound and they landed on 14 rules, eventually. This issue shows how any marketing or sales team can write their own rules.

Deepinder Singh Dhingra

Oct 8, 2026

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5 min read

Your AI Agents Target Customers Picked in One Forgotten Meeting

Most companies decide who their target customer is in one meeting, they put it on one slide and never look at it again. Now their AI agents are using that slide to pick who to contact and what to say. Randy Brasche who has been both a CMO and CRO, explains why that is a problem, and how to fix it this week.

Deepinder Singh Dhingra

Oct 1, 2026

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4 min read

We are giving AI agents permissions faster than we can understand them

Meta's Muse synced 187,462 messages after a user believed he had declined access. As agents connect to more of our work and lives, the bigger problem is knowing what they can actually see and do.

Deepinder Singh Dhingra

AI efficiency

+4

Sep 24, 2026

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10 min read

$750M Speech AI Company’s Marketing Head on How to Kill AI Slop

Content is now the cheapest thing a marketing team makes. Knowing how a customer actually feels is still the most expensive, and plenty of teams have quietly stopped paying for it.

Deepinder Singh Dhingra

AI Agents

+3

Sep 17, 2026

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8 min read

How to audit event attribution before somebody cuts the budget

Event attribution is wrong at most companies, and when we mapped it across different organizations we work with in the last 4 years - there were three common problems. And each problem can be detected and requires a specific fix. In this newsletter I am sharing an AI prompt to audit all these three problems using two Salesforce exports.

Deepinder Singh Dhingra

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Featured

AI efficiency

+6

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

GTM

+3

Jan 15, 2026

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9 min read

Marketing Departments Should Be Suicide Squads

Have you built the organisational culture to kill successful channels before they become liabilities?

Deepinder Singh Dhingra

AI efficiency

+5

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

AI efficiency

+6

Mar 13, 2026

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12 min read

Data Is Not Your Problem, But 5 Conflicting Versions Of It Is

Marketing has their numbers, Sales has theirs and Finance has a third. Everyone walks into the same room with different data and nobody leaves with a decision. How to build one revenue truth?

Deepinder Singh Dhingra

marketing funnel

+5

Jan 29, 2026

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10 min read

Why Your Marketing Funnel Is Working Against You

Most marketing organisations are optimising the wrong thing. They're punishing buyers for being human. And the system they built to operate at scale has become their biggest blocker.

Deepinder Singh Dhingra