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

AI Agents

+3

Your AI SDR works perfectly, on 45% of the facts

Aug 20, 2026

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6 min read

Your AI SDR works perfectly, on 45% of the facts

84% of revenue teams use AI at the top of funnel. Most are not getting the meetings they were promised. The problem is not the emails- it is everything the agent cannot see before it sends them.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

AI Agents

+3

She built an "AI ops detective" to catch what her team forgets

Aug 13, 2026

•

7 min read

She built an "AI ops detective" to catch what her team forgets

Weisi Kang from Glean on the agent that fixes her pipeline in minutes, and why the next great CMO comes from ops.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

AI Agents

+3

From "AI Said So" to AI Is Spreading the Wrong Answers

Aug 6, 2026

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4 min read

From "AI Said So" to AI Is Spreading the Wrong Answers

Shadow AI is already standard practice: people and agents are querying company data outside governance. The harm isn’t in “AI” , but on confident answers without shared context. Durable fix is a governed context layer that encodes real definitions and data access so every agent (and person) answers from the same truth.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

AI Agents

+3

We Found Almost $5 Million in a Reconciliation Everyone Missed

Jul 30, 2026

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5 min read

We Found Almost $5 Million in a Reconciliation Everyone Missed

This story uncovers $4.4M in missing marketing spend and $5M CRM error, showing why poor data is one of the biggest obstacles to using AI agents effectively in revenue teams.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

AI Agents

+3

AI Is Making You Sound Like Everyone Else

Jul 23, 2026

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8 min read

AI Is Making You Sound Like Everyone Else

Everyone has the same models and tools that use the same infra underneath them. Similar prompts and almost look alike content or campaigns. Mari Strom, an advisor to RevSure and Growth & Integrated Marketing Head for HP believes that the CMOs who will win the next three years are the ones who refuse to sound like everyone else.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

AI Agents

+3

More Agents Made Your GTM Worse

Jul 16, 2026

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4 min read

More Agents Made Your GTM Worse

The teams that moved fastest on AI agents last year are now the most confused about why their pipeline is a mess.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

AI Agents

+6

Stop Feeding Your Best Channel

Jul 9, 2026

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4 min read

Stop Feeding Your Best Channel

Your best-performing channel looks great on paper because of what it earned in the past. But past returns and future returns are not the same number. This issue is about why your dashboard hides that difference, how saturation, lag, and one dead deal quietly distort your budget decisions, and the one rule that forces any recommendation to be honest.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

AI Agents

+3

AI Said the Quiet Part Loud. A Team Freaked Out. But It Was Right.

Jul 2, 2026

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5 min read

AI Said the Quiet Part Loud. A Team Freaked Out. But It Was Right.

The moment your team pushes back on an AI recommendation is the most valuable moment in the room. Don't waste it.

Deepinder Singh Dhingra
Deepinder Singh Dhingra

AI Agents

+2

Your AI Agents Are Working From a Half-Built Map

Jun 25, 2026

•

7 min read

Your AI Agents Are Working From a Half-Built Map

Most GTM pipelines doesn't run on software. It runs on one person who knows how to connect it all. And when that person leaves, chaos breaks.

Deepinder Singh Dhingra
Deepinder Singh Dhingra
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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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