Archive

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

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

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

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

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

Your AI Agents Target Customers Picked in One Forgotten Meeting

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

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

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

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

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

How to audit event attribution before somebody cuts the budget

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

AI Agents

How to report marketing contribution so finance can trust the number

Sep 11, 2026

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8 min read

How to report marketing contribution so finance can trust the number

Two reports that tell you whether your number is real, the sheet that fixes it, and an honest account of where this method stops.

Deepinder Singh Dhingra

AI Agents

Doing Marketing Correctly Will Cost You Your Job

Sep 3, 2026

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9 min read

Doing Marketing Correctly Will Cost You Your Job

The marketing that wins deals makes your numbers look worse first. Allison Snow on why that is a comp plan problem, not a measurement problem, and what to negotiate before you spend.

Deepinder Singh Dhingra

AI Agents

I Told a Customer She Could Replace Us With Claude Code. Here's Why She Didn't.

Aug 27, 2026

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6 min read

I Told a Customer She Could Replace Us With Claude Code. Here's Why She Didn't.

An Ops leader looked at a dashboard we built in 15 minutes and asked why she couldn't just build it herself with Claude Code, and I told her she could. This newsletter argues that AI made the interface free, so software value (and a marketing team's value) now collapses to the two things claude can't replicate overnight: the governed context underneath and the harness around it. It closes on her five words, "the insight's great, but what do I do with it now?" - as the real bottleneck of this era.

Deepinder Singh Dhingra

Archive

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

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

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

Your AI Agents Target Customers Picked in One Forgotten Meeting

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

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

How to audit event attribution before somebody cuts the budget

How to report marketing contribution so finance can trust the number

Doing Marketing Correctly Will Cost You Your Job

I Told a Customer She Could Replace Us With Claude Code. Here's Why She Didn't.

The Moneyball CMO