‹ Go Back

Subscribe For Exclusive Trends, Research & Data

Gain access to exclusive research, training, trends and support from the best marketers in the world.

Foundation Labs provides you with timely, meaningful, and relevant data that enables you to grow your company in a meaningful way. The world’s top SaaS companies subscribe to Foundation Labs to receive industry news and data driven insights to create a marketing culture that drives results.

We have two different plans:

Foundation Labs: Insider Subscription

Exclusive B2B SaaS growth, SEO & content case studies​
→ Quarterly reports on data-backed B2B SaaS trends, correlations & more​
→ Weekly Insiders-only email on trends, data & research​
→ Insiders-only webinars on B2B SaaS content marketing​
→ Two weekly newsletters with case studies & SaaS stories​

SUBSCRIBE $828 annually
Foundation Labs: Inner Circle Subscription

Exclusive B2B SaaS growth, SEO & content case studies​
→ Quarterly reports on data-backed B2B SaaS trends, correlations & more​
→ Weekly Insiders-only email on trends, data & research​
→ Insiders-only webinars on B2B SaaS content marketing​
→ Two weekly newsletters with case studies & SaaS stories​
→ Invite-only fireside chats with marketing leaders at B2B SaaS giants
→ SaaS reports breaking down what’s working across industries today

SUBSCRIBE $3348 annually

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

Free Content

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. 

Calendly's homepage is designed to convert a high percentage of site visitors

Calendly gladly takes in all these interested parties as “freemium” users, knowing that a certain percentage of them will convert into paid or even enterprise users. It’s not unlike Ahref’s strategy of gaining new users by giving away access to key features. Start small to win big.

That’s what I’d call a bottom-up approach. 

On the other hand, Chili Piper is interested in providing a suite of paid tools to enterprise B2B revenue teams — marketing, sales, revenue ops, and customer success professionals. All you need to do is look at the product drop down on its main menu to see exactly who Chili Piper’s marketing team is going after:

Chili Piper's product menu explains how it targets each section of its B2B revenue team audience.

Even how they refer to the target audience, revenue teams, you can see that Chili Piper isn’t going after the small business or startup owner that’s just trying to clean up their schedule without the help of an assistant. They are looking to bring in seasoned experts from across enterprise marketing, sales, and customer success departments — people who are willing to add, or vouch for, another paid tool in the tech stack if it means generating more revenue. 

That’s the top-down approach.

What’s another important trait of these driven enterprise professionals? They are constantly learning and growing. These aren’t people who will are compelled by an SEO-driven how-to post or LinkedIn carousel, they want in-depth, engaging content that directly speaks to and answers their pain points. Think long-form, immersive platforms. 

Well, it just so happens that Chili Piper uses two such platforms: targeting and winning B2B revenue teams through popular podcasts and The Juice HQ’s distribution platform. 

Targeting B2B Revenue Teams Where They Learn

To understand how Chili Piper is having success with its target audience of enterprise revenue teams, you first need to take a look at its top referring domains.  According the Ahrefs, the top websites directing traffic to the Chili Pepper website over the past two years were Sounder, The Juice HQ, and SaasHub.

Chili Piper's top referring domains by backlinks over the last two years

Bringing in backlinks from high-value, high-authority domains is a tactic used by leading brands like Buffer, Zoho, and Dukaan. It’s tried and tested. To see Chili Piper’s spin on this strategy, let’s focus on those first two domains. is a platform that provides tools for managing, marketing, and measuring the success of podcasts and other content from audio creators. They also happen to be one of the brands leading the charge for contextual advertising in audio content. 

The Juice, another SaaS platform, was launched in 2021 as a space for the distribution and discovery of B2B content. Its mission is to fix the broken B2B marketing landscape. 

As it turns out, these two channels are perfectly suited for getting high-intent, enterprise sales, marketing, and support pros in front of Chili Piper content.

Hyper-Relevant Podcasts 

Up until the beginning of 2023, Sounder offered another important service for audio creators — free podcast hosting. They have since shut down this hosting service to focus on data and insights, but up until the end of 2022, Sounder was a one-stop-shop for brands to launch content, analyze its success, and find the perfect ad placement. 

That’s all nice to know, you’re thinking, but how does Chili Piper play into all this? 

Well, lets take a look at some of the backlinks coming into Chili Piper from Sounder over the last two years. Of the 36K links coming from Sounder during the height of its podcast hosting days, three shows stand out: 

B2B Growth, Demand Gen Chat, and B2B Revenue Executive Experience. 

Chili Piper received backlinks from the B2B Growth podcast via

B2B Growth is a podcast about all things B2B marketing. It’s hosted by two experts from the podcasting agency Sweet Fish Media, who cover everything from LinkedIn carousels that gain 1,100 comments to the quarterly marketing and sales alignment meeting that every company needs. (Looks like marketing pros do like carousels after all.)

Chili Piper received backlinks from the Demand Gen Chat podcast via

Demand Gen Chat is a double bonus situation for Chili Piper. Why? Because it’s a Chili Piper product. Hosted by the company’s Head of (you guessed it) Demand Generation, Tara Robertson, the podcast creates the exact type of content that experienced marketers who want to take their marketing tactics to the next level.  

Chili Piper received backlinks from the B2B Revenue Executive Experience podcast via

As the name suggests, the B2B Revenue Executive Experience is all about helping enterprise leaders improve the performance of sales and marketing efforts to improve revenue growth. It’s hosted by two experts from the enterprise sales training company ValueSelling, covering the most pressing issues for SDRs and sales leads. 

Each of these podcasts targets a specific subset of Chili Piper’s audience. Not only do they provide them with in-depth, captivating content on how to improve results and ultimately drive revenue for their companies (with regularly features from industry experts), but countless episodes contain links directly to the Chili Piper site. 

While the number of backlinks from has dropped since it ended its podcast hosting feature, for most of 2021 and 2022 Chili Piper was getting high quality leads from these podcasts. 

I’ll admit, I’m no podcast expert — that’s more Ross’s thing (find out more here) — but it sure looks like a medium that B2B SaaS marketers need to pay attention to. If you need more convincing, over 40% of executives, VPs, and B2B decision makers listen to industry-related podcasts. 

Whether its through an owned podcast or contextually-placed ads, podcasts are the perfect medium for targeting the type of marketing, sales, and customer success experts that Chili Piper wants to convert.  

But Chili Piper doesn’t put all its acquisition eggs in one basket. It leverages The Juice HQ, another platform that’s tailor-made for reaching its information-hungry, enterprise-level audience. 

The Juice HQ

The Juice HQ is building off some very valid frustrations around B2B content marketing. Specifically, the fact that many tactics are outdated, relying on the same old search algorithms and repetitive strategies. 

The Juice approach: connect content consumers with top B2B resources from trusted brands through a smooth, privacy-controlled experience, providing on-demand content without forms or follow-up sales emails. It’s a platform tailor-made to distribute content to 2 of the key components of Chili Piper’s revenue team ICP: marketing and sales pros. 

 The Juice HQ platform aims to increase the ROI of B2B content through targeted distribution.

As you can probably guess, Chili Piper is a member of The Juice app. It’s leveraging the distribution platform to deliver blog posts, ebooks, case studies, videos, and, yes, podcasts, to a target audience that purely consists of highly motivated, intent-driven professionals. 

When these marketing and sales experts hit Chili Piper’s homepage on The Juice, they are immediately hit with a list of the most engaging content in marketing, demand gen, and sales. In other words, the content that other seasoned professionals have gotten the most value from. 

Chili Piper's homepage on The Juice HQ app.

Killer B2B lead gen strategies; 

Handling the word “no” as a sales rep; 

A case study on Ahref’s strategy for achieving $40 million in ARR; 

The 30 best questions for vetting during a sales interview;

This is the type of content that’s typically heavily (and annoyingly) gated from the very people who need it. By using The Juice as its distribution partner, Chili Piper provides a better customer experience to their target audience and benefits from the built-in targeting and analytics features of the platform. 

The best part? Once you click on one of these “Juiced” links, it takes you directly to the actual page where the content lives on the brand’s website. No need to move content over to another platform and deal with reformatting. 

The only downside to this, at least from an investigative point of view, is it messes with organic traffic metrics. I’m willing to bet Chili Piper’s reliance on The Juice is the reason why they have such middling metrics on search — only 9.7K organic visits a month for a brand with strong domain rating and nearly 20K backlinks. 

But, again, Chili Piper don’t need to compete with Calendly and hundreds of other brands for tightly-contested SERP space, it’s leveraging engaging media formats and distribution that targets its exact ICP. 

What’s the Wait? Start Expanding Your Marketing Engine Today

If you take one thing away from this Chili Piper vs Calendly battle, let it be this: there’s more to generating long-term success in B2B SaaS than search, paid ads, and social. 

You need to round out your marketing engine by investing in more interactive, high-quality content like video and podcasting and, of course,  delivering them with a targeted distribution strategy.

No enough in the budget for an account on The Juice? No worries, we’ve got the perfect playbook for modern B2B content distribution.  

Did you enjoy this post?

Excepteur sint occaecat cupidatat non proident, sunt in culpa qui officia deserunt mollit anim id est eopksio laborum. Sed ut perspiciatis unde omnis istpoe natus error sit voluptatem accusantium doloremque eopsloi

Learn How The Best B2B SaaS Companies Do Marketing.

Subscribe today to get access to some of the best content on B2B growth & tech.