When Execution is Cheap, Judgment becomes Scarce

When Stripe was still small, the Collison brothers decided to focus on a handful of their Startup cohort at Y Combinator. They had interest from hundreds of potential customers but chose depth over breadth.

A little-known practice at Stripe. Engineers were asked to sit in on failed sales calls and watch screen recordings of developers abandoning integrations. Docs were rewritten based on drop-off moments, not feature completeness. This is why Stripe’s docs read like a tutorial written by someone watching over your shoulder.

The brothers spent time understanding how those specific companies built products, what their developers cared about, and whether Stripe’s approach to payments would actually matter to them. They maintained judgment at the scale at which it worked.

By the time Stripe opened up more widely, they understood their customers deeply enough that execution could compound on real insight. The judgment came first, while the systems followed.

The Execution Surplus

We’re living through an odd moment. The tools to execute have become remarkably accessible. Research that took days now takes minutes. Decks generate themselves. Forecasts, content briefs, and competitive analyses flow faster than we can use them.

The bottleneck has moved.

A decade ago, a decent GTM operator won by outworking competitors. More calls, more content, more meetings. Effort was the limiting factor. Today, every team has access to the same execution leverage. AI writes the emails, automation books the meetings, and analytics surfaces the signals.

The hard work now lies in deciding which emails matter. Which meetings to take? Which signals to ignore?

Judgment Scales Differently

Execution scales with tools. Judgment scales with context, experience, and accountability.

A junior rep can send personalized outreach to 900 accounts in an afternoon. The tooling exists. Knowing which 42 accounts are actually reachable, which 13 have budget timing that aligns, and which 7 deserve the founder’s time. That knowledge comes from closing deals, losing deals, and learning which patterns repeat.

In enterprise GTM, this gap widens daily. Execution becomes abundant. Judgment becomes scarce. The teams that understand this pull away from those still optimizing for output.

What Judgment Actually Looks Like

When Salesforce was expanding beyond its initial SMB success into enterprise accounts, Marc Benioff started flying to meet with individual CIOs at large enterprises, spending days on single accounts that hadn’t committed to anything. The team had built momentum with hundreds of mid-market companies. The execution machine was working.

Salesforce’s flagship conference, Dreamforce, is often framed as a celebration of customer love. Internally, Dreamforce was optimized first for partner dominance.

Benioff read something different. Enterprise required a different motion entirely. He studied political landscapes, understood procurement cycles, and built relationships that would take years to convert.

That judgment of recognizing when the playbook needs to change, even while the current one works, separated Salesforce’s enterprise motion from competitors who kept optimizing their SMB playbook at larger companies.

You see judgment in smaller decisions too:

• A VP of Sales stops the team from chasing a logo everyone wants because the buying committee lacks real authority.
• A founder delays a product launch because the market narrative needs more time, even though the feature works.
• A marketing leader kills a campaign with strong engagement metrics because the personas don’t match the ideal customer profile.

These decisions create discomfort because they involve saying NO to things that look productive. They require believing that constraint creates more value than volume. That activity and progress differ.

The Questions That Matter

When execution becomes cheap, the valuable questions change.

“Should we do this now?” replaces “Can we do this?”

“Which accounts are worth the friction of reaching?” replaces “How do we reach more accounts?”

“What does the data not say, and what do we believe anyway?” replaces “What does the data say?”

These questions require someone to own the outcome, to have skin in the game, to accept that choosing one path means abandoning others. You can’t automate these decisions.

Where Judgment Fails

Two failure modes appear repeatedly.

The first: analysis paralysis. Teams that treat every decision like it needs a framework, a model, a consensus process. They value judgment but make the act of judging so heavy that nothing moves. Judgment works through making calls with incomplete information and adjusting as you learn, not through perfect analysis.

The second: abdication. Teams that delegate judgment to systems. “The model says we should focus here.” “The playbook says we do this next.” Models and playbooks serve as tools for execution. They don’t substitute for thinking.

Consider how Figma approached enterprise expansion. They had data showing demand across dozens of verticals. Dylan Field and the team focused on design and product teams first, saying NO to marketing teams, engineering teams, and other buyers who wanted in.

The data would have supported broader execution. The judgment was to stay narrow until they truly understood one motion. When something stops working, someone has to override the system. That’s the job.

Building Judgment Capacity

You can’t scale judgment the way you scale execution, but you can build it.

Atlassian built one of the most successful enterprise GTM motions by letting individual contributors and small teams buy and deploy their tools without sales involvement. Every other enterprise SaaS company was building outbound teams and going top-down.

Atlassian’s “No Sales Team” story is famous. What’s less known is how close it came to breaking. In early enterprise pilots, Atlassian noticed deals stalling not because buyers disliked the product, but because procurement departments didn’t trust a company that wouldn’t negotiate.

The Atlassian founders believed that empowering their team to learn what actually drove adoption, watching thousands of organic buying decisions, would build better judgment than optimizing a traditional sales playbook. They were right. By the time they built an enterprise sales team, they had years of experience recognizing patterns in how software spread within companies.

The best GTM leaders I know do a few things consistently:

They create space for their teams to make real decisions, rather than just follow processes. A rep who’s only ever run a script will never develop judgment about when to break it.

They reward good calls, alongside good outcomes. Sometimes the right decision still loses. Celebrating only wins optimizes for safety over judgment.

They make their own thinking visible. After a tough call, they explain why they chose what they did, showing how they weighed the options and teaching judgment through observation.

They accept that building judgment compounds differently than deploying tools. Slower, but durable.

The Advantage

Here’s what changes when judgment becomes your edge:

Snowflake’s early GTM shows this clearly. They entered a market with entrenched players such as Oracle, AWS, and traditional data warehouses. Every competitor had more resources, more salespeople, and more marketing budget. Snowflake couldn’t outspend them on execution.

Snowflake rejected standard ICP thinking. Instead of “data leaders” or “CIOs,” they built an internal persona called “The Skeptic.”

Frank Slootman and the team made precise judgments about where to compete. They focused on data teams at companies with cloud-native infrastructure who were frustrated with existing solutions. A specific profile where their advantages mattered most.

This precision created:

• Teams that stopped chasing every opportunity because they knew which ones fit their motion.
• Faster movement on deals that mattered because distractions fell away.
• Trust with customers because the team sold what was real, avoiding overpromising.
• Teams that got better over time because they learned to think beyond executing.

Competitors could copy Snowflake’s architecture. They couldn’t copy the accumulated context of hundreds of decisions made well about which customers to serve and how to serve them.

What This Means for Enterprise GTM

Enterprise buyers are drowning in outreach. Everyone has the tools to reach them. Everyone has the data to personalize. Everyone has the automation to follow up.

They respond to precision. Knowing what they actually need. Showing up at the right time with the right message for the right stakeholder. Because someone made a call.

This stems from judgment, orchestrated execution.

As execution continues to get cheaper, and it will, judgment will continue to get more expensive. The gap between teams that understand this and teams still optimizing for output will widen.

The question lives here: whether you can decide what’s worth executing in the first place. That’s where the work is now.