It’s not budget.
It’s not headcount.
It’s not tech.

The biggest blockers to experimentation in enterprise organizations are cultural.

When experimentation is treated like a side project—or worse, a threat to the status quo—it’s no surprise that velocity stalls and progress dies in committee.

In this episode, Arun and David unpack exactly why legacy enterprise companies struggle to build a culture of experimentation, despite having all the resources in the world. And what separates the companies who succeed from the ones who stay stuck.

Why Enterprise Velocity Gets Crushed

There are two core ingredients that make experimentation successful:
– A willingness to tolerate managed risk
– The velocity to move fast and validate ideas

Both are usually missing in large orgs. Not because leaders don’t want experimentation—but because bureaucracy, slow release cycles, and internal politics make it nearly impossible.

Layer in misaligned stakeholders, global complexity, and siloed data, and suddenly even running a basic A/B test feels like moving mountains.

How to Start Small and Build Momentum

The smartest enterprise experimentation programs don’t start with the homepage.
They start where:

  • There’s less internal friction
  • There’s measurable business impact
  • There’s faster time-to-learn

That’s usually deeper in the funnel—lead forms, onboarding flows, paid landing pages. These are the areas where you can move quickly, validate hypotheses, and prove value without ruffling feathers.

Wins here earn trust, budget, and buy-in to scale the program.

Risk Mitigation: The Story Execs Will Listen To

Experimentation isn’t just about growth. It’s about reducing risk.
It’s a safer, faster, more controlled way to validate what works before you commit major resources.

Frame it this way, and suddenly even the most conservative stakeholders start paying attention.

TL;DR: If You Want to Build an Experimentation Culture in Enterprise…

Start where you can win fast.
Show how you save time and reduce risk.
Use those wins to scale the program into something sustainable.


Watch the full conversation on Episode 4, Part 1

Get the full breakdown on why experimentation struggles in enterprise—and how to fix it.


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