Positioning Chili Piper

Chili Piper needed a differentiator.

We chose the best one.

Chili Piper homepage Jan 2025. It reads: The all-in-one Demand Conversion Platform

The Pepsi Challenge

Not the famous taste test. But rather, the meta-challenge of being Pepsi.

Chili Piper is in a crowded space: Calendly, Acuity, Doodle, and dozens of others—all after the same real estate.

Knowing Calendly was the leader (Classic Coke), Chili Piper needed to provide customers with a specific and solid reason for choosing them over the leader.

Aligning Position with Product

Chili Piper had built it’s product to be favorable to companies like itself.

That is, tech companies, whose meetings were focused on one goal:

But they hadn’t yet aimed their messaging and positioning directly at the Sales department.

This is where we came in.

Clear Results

By using a sales-focused message on the homepage, and creating a litany of landing pages, Chili Piper acted on our hypothesis to great effect.

We used words like “qualify”, “convert”, and “pipeline” to speak the language of sales.

Simultaneously, Chili Piper’s product roadmap continued to cater to Sales teams.

Results soon followed, with both expansions of current customers, and new inbound customers.

This led to another round of funding.

$33 Million.

The Hypothesis

Having worked at Calendly, Adam knew the scheduling space deeply.

And he noticed a trend.

When Chili Piper landed the Sales department first, the others followed.

When they landed HR first, to schedule interviews, no other departments followed suit.

The hypothesis was, that in Sales, Chili Piper proved ROI quickly. In HR, the return wasn’t as immediately obvious.

By aiming at Sales first, Chili Piper could land, and expand.