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Chili Piper Uses Podcasts and The Juice to Close in on Calendly

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It’s always fascinating to see how two top competitors in the same SaaS niche approach the market. 

Do they try to slug it out in the same spaces, fighting to gain an inch in the Google SERPs or a specific social media channel like LinkedIn? Or does one cut its loses in one space to gain an advantage in another?

In the battle for meeting-scheduling dominance, we see the latter play out.

Launched in 2016, Chili Piper is a SaaS appointment scheduling tool that’s geared towards B2B marketing, sales, and customer success teams. It helps them convert leads into attended meetings, book demos, improve inbound conversion rates, and basically streamline all things meetings. Chili Piper boasts an impressive roster of high-profile clients, including Gong, monday, Shopify, and Airbnb.

Chili Piper's homepage explains how they double conversion rates for B2B revenue teams.

Chili Piper’s primary compeitor is Calendly, a massive product that you’ve likely already heard of, if not already used. It’s another meeting scheduling tool, one that basically changed the game with its freemium model and viral growth. From solopreneurs and small business owners to enterprise companies, Calendly helps anyone and everyone save time from the dreaded back and forth of meeting planning. 

So, the question is: how does Chili Piper compete with such a ubiquitous product? 

The answer: by targeting users on the upper rung of the ladder – the corporate ladder, that is. A distinguishing feature of Chili Piper’s marketing approach is its direct targeting of “B2B revenue teams.” Instead of winning users with a free product and building up a relationship for down-the-road expansion — the way Calendly, Loom, and other product-led companies do. Chili Piper focuses purely on a target audience that needs more than just meeting scheduling. 

The channels Chili Piper leverages to reel in its audience of experienced marketers, SDRs, and customer success teams is a perfect example of targeted marketing in action:

Industry-specific podcasts and content distribution and discovery platforms. 

Let’s get into it.  

The Fight for Meeting Scheduling Dominance: Chili Piper vs Calendly

When looking at some key metrics, the fight between Chili Piper and Calendly appears to be something of a David vs Goliath situation.

Calendly is definitely Goliath — it was founded 3 years before Chili Piper, has raised significantly more capital, brings in over 60x the web traffic, and has gained tens of millions of users with a viral freemium product. 

Comparing Calendly vs Chili Piper in terms of founding date, funding, traffic, and users.

Taking a closer look at the Calendly vs Chili Piper battle, through the lens of organic performance, the picture looks even worse for the newcomer: 

Comparing Calendly vs Chili Piper in terms of organic search performance.

It certainly looks like Chili Piper is getting its clock cleaned by Calendly, doesn’t it? Now let’s look at how this came to be. 

A few months ago, I took an indepth look at how Calendly rode its product-led growth model to a $3 billion valuation. Check it out here in full for a complete understanding of the strategy behind its success ( you won’t regret it). 

For now, here’s a quick summary of the areas where Calendly accels: 

  • Capitalizing on the virality of an in-demand freemium product
  • Capturing users with well-designed landing pages and blog posts
  • Leveraging the built-in backlink success of a product built around link sharing
  • Using LinkedIn to reach SDRs and make headway with enterprise accounts

But before we get too down on Chili Piper, there’s an interesting point to consider: Despite Calendly’s apparent advantage in market presence, number of users, and growth model, Chili Piper isn’t as far behind when it comes to the target audience of B2B revenue teams. 

Calendly is currently used by over 50,000 businesses, while Chili Piper has over 45,000 paying customers.

Of course, these are both private companies so the exact number of enterprise users is impossible to know. But, at least in this specific leg of the race, it seems like Chili Piper is making things more competitive. 

So, how do they do it?

The Key Difference: A Top Down vs Bottom Up Approach to User Acquisition

Before we get into how Chili Piper stays competitive despite being outmatched across quite a few different marketing channels, let’s looks at how it compares to Calendly in terms of target audience and acquisition method. 

As a company leveraging product-led growth, Calendly aims to turn people into users as quickly as possible. They cast a very wide net, knowing there are plenty of people across industries and company sizes that need a tool for easy meeting scheduling. 

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