So the 2026 FIFA World Cup started yesterday, and it “distracted” me from sending this post earlier this week… enjoy this with your morning coffee over the weekend 🙂

As some of you may know, I am an amateur photographer. I love to think about frame composition, lighting and telling a story with each photograph. 

Film was the only medium when I started learning photography from my dad.  With film you could get 24 or 36 frames per roll, that is it!

I found that the “limitation” of 36 frames forced me to pay attention, slow down, anticipate and make each exposure a deliberate choice. 

Today, some of the best photographers I know still shoot like they only have 36 frames per roll. They use the 36-shot limitation to build intentionality, discipline, and a more personal vision.

The best revenue teams are starting to operate the same way.

AI has removed the constraint of effort. In the process, it may have removed the filter of judgment too.

Every client outreach used to take time, research, or thought. Now it costs almost nothing, so almost nothing gets filtered. Layering an LLM on top of a shaky workflow is not a substitute for thinking hard about what is truly the problem your client has. 

Buyers feel it. Data shows 73% of B2B buyers actively avoid vendors sending irrelevant outreach, and 67% prefer a rep-free buying experience because traditional sales interactions stop delivering value.

Proper personalization e.g., {first name}, {company name} is just table stakes; however, the relevant message lies in thoughtful contextualization.

"You just hired a contractor outside your primary domestic market. Here's how your cross-border payroll workflow is about to break."

That kind of message can't be faked with a better prompt. It requires organizational depth and understanding of the customer’s objectives. In most companies, that depth of knowledge doesn't live in outbound sales.

It lives with the post-sales team. 

The highest-value thoughtful contextualization in your company (why things work / don’t work)  is usually sitting with the team traditionally ignored for new pipeline opportunities: Customer Success.

Customer Success Managers (CSMs) know where adoption is breaking, which teams are expanding usage, which customers are using the product for one workflow but asking questions that point to three more. They know the stakeholders who were never mapped in Salesforce.

I saw this firsthand at Google, where post-sale signals revealed why media budgets were migrating to competing platforms before the issue appeared in the sales forecast. Once we unified the customer view and built targeted support motions, we reversed the trend, improving CSAT and reduced escalations.

Strategic account expansion can generate revenue several times larger than the initial land. 

CSMs,  because they are already sitting closest to the commercial opportunity, can systematically understand expansion signals, pipeline targets, and customer objectives. It’s not about simply adding more pipeline, it is about adding the right opportunities that will make the effort worth it. 

Build a clean Warm Handoff Loop: when a CSM uncovers an adjacent use case and hits a defined qualification marker, the opportunity routes to an expansion AE. The AE handles pricing and procurement. The CSM stays positioned as the customer's trusted advisor. 

Post-sale intelligence becomes pipeline without corrupting the relationship.

Most companies treat the 90-day renewal window like a crisis. If it feels that way, the operating engine failed months earlier.

Renewal dates are lagging indicators. By the time an account is "at risk," the real failure has already happened.

Build around the First 100 Days instead: Did the customer achieve the business outcome they bought the software for in the first 100 days?

This requires dashboards built on early signals: activation thresholds, time-to-value milestones, stakeholder coverage, expansion signals from adjacent teams.

If an account misses those milestones, an operational alert triggers immediately. While churn may not be imminent, the account is telling you something early enough to matter.

In a recent webinar, the CRO of Consensus shared a story about an account that looked like it was going sideways. Utilization had collapsed. A $200K churn was on the forecast.

Most companies would have discounted and escalated. Consensus went CRO-to-CRO. What they found wasn't a product issue, the buyer had a high-stakes keynote coming up and needed to look good in front of their business.

So Consensus helped build the slides and stripped out their own branding.

A forecasted $200K loss became a three-year renewal plus $200K in expansion. Over $1M in total contract value.

That didn't happen because someone sent a more personalized email. It happened because the team understood the context and approached it with discipline before they raised the camera.

Pull your top outbound sequences. Ask one question: if you swapped this prospect's name for a competitor's, would the email still make sense?

If yes, pull it. That's automated noise dressed as outreach.

AI has made it easy to take unlimited shots. The advantage now goes to operators who invest the discipline and context to make every shot matter.

If you found this valuable, please forward it to a colleague who's building a GTM operation that punches above its weight. It really helps!

Jose Celorio Founder, GTM Reloaded
Former Strategist at Google, Mastercard & Deloitte Consulting

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