Deepinder Singh Dhingra

I am building RevSure AI, which helps Marketing and Growth teams to see the Marketing Full Funnel, predict pipeline, help them generate pipeline in real time along with revenue predictability and more. I've spent 25 years at the intersection of data, product, and revenue - from scaling Mu Sigma into a Big Data unicorn, to building and exiting Samya.ai (Sequoia-backed, acquired by Fractal.ai), to raising $10M for RevSure. This newsletter is where I share what I've learned about pipeline intelligence, revenue attribution, and the decisions that separate good marketing leaders from great ones. No fluff - just sharp, experience-backed thinking for B2B CMOs who care about what actually moves the number. Forbes Technology Council Member, Builder and Third time founder.

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

AI Agents

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

AI Agents

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

Aug 13, 2026

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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

AI Agents

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

AI Agents

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

AI Agents

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

AI Agents

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

AI Agents

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

AI Agents

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

AI Agents

Jun 25, 2026

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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

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