DEEP READS

Chili Piper's Positioning, Exposed

One day, I got mad at all those negative teardowns I kept seeing. The result was this deep dive into Chili Piper’s positioning, as explained to me by the CEO, Alina Vandenberghe. Not quite an ebook, and almost a comic book. Let’s call it an Exposition.

Jon Itkin
Founder, In the Kitchen
February 2, 2026
9 min read

The Bottom Line

The first-ever (and maybe last) Positioning Exposition

Once upon a time, LinkedIn was overrun with Monday morning messaging quarterbacks, offering their insights about everything billion-dollar tech companies were getting wrong.

You’re on my website…so I’ll be 100% honest.

When you go on LinkedIn and dunk on big companies, it says a lot more about you than whoever you’re talking about.

Specifically, you’re saying that:

  1. Because somebody’s copy doesn’t align with your personal taste, it’s wrong
  2. It’s OK to make grand proclamations about a company “failing” without any data 
  3. You have no idea how hard it is to do messaging for big companies, probably because you’ve never had to

It’s not a great look, especially for people who’ve actually been there.

Getting messaging through a big company approval gauntlet is brutal, and many talented people have died on that hill.

My annoyance, for all the above reasons, led to a wild idea.

I would do “teardowns,” but only if the people responsible for the messaging participated.

I wanted the inside story about how companies were positioning products, the strategy behind it, and how it was going.

Luckily, the first volunteer I got was a great one: Alina Vandenberghe, Co-CEO of Chili Piper. 

She was incredibly candid, and also very brilliant. 

She told me the whole story, warts and all, in vivid detail.

I wanted to make an asset that did her story justice, broke down all the juicy details, but didn’t take itself too seriously.

The result was what one commenter called “a brilliant abuse of Figma.”

The Exposition, in full

You be the judge.

The asset lives as a Figma prototype. You can access it here

When you view it, please be aware that some pages scroll a lot, and others don’t. Make sure you view the prototype set to “fit to width.”

Go a little deeper.
If you dare.

Long-form writing may be a dying art. But if you love a good stemwinder, these are genuine, human-being-made articles that explore topics that don’t fit in a 600-word box.

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Written By Jon Itkin

Chili Piper's Positioning, Exposed

The first-ever (and maybe last) Positioning Exposition

Once upon a time, LinkedIn was overrun with Monday morning messaging quarterbacks, offering their insights about everything billion-dollar tech companies were getting wrong.

You’re on my website…so I’ll be 100% honest.

When you go on LinkedIn and dunk on big companies, it says a lot more about you than whoever you’re talking about.

Specifically, you’re saying that:

  1. Because somebody’s copy doesn’t align with your personal taste, it’s wrong
  2. It’s OK to make grand proclamations about a company “failing” without any data 
  3. You have no idea how hard it is to do messaging for big companies, probably because you’ve never had to

It’s not a great look, especially for people who’ve actually been there.

Getting messaging through a big company approval gauntlet is brutal, and many talented people have died on that hill.

My annoyance, for all the above reasons, led to a wild idea.

I would do “teardowns,” but only if the people responsible for the messaging participated.

I wanted the inside story about how companies were positioning products, the strategy behind it, and how it was going.

Luckily, the first volunteer I got was a great one: Alina Vandenberghe, Co-CEO of Chili Piper. 

She was incredibly candid, and also very brilliant. 

She told me the whole story, warts and all, in vivid detail.

I wanted to make an asset that did her story justice, broke down all the juicy details, but didn’t take itself too seriously.

The result was what one commenter called “a brilliant abuse of Figma.”

The Exposition, in full

You be the judge.

The asset lives as a Figma prototype. You can access it here

When you view it, please be aware that some pages scroll a lot, and others don’t. Make sure you view the prototype set to “fit to width.”