5 min read

How Calendly will scale to $1B ARR 🚀

A deep dive on the 'feature' that brings home $100M in ARR and the strategies that will get them to $1B!
How Calendly will scale to $1B ARR 🚀
Photo by Soundtrap / Unsplash

A tool that collates availability from your favorite calendars & multiple accounts (family, personal, professional.. you know the drill), lets the user share it via links, and allows the recipient to block time for meetings without conflicts. Sounds like a super cool plugin/feature for your meeting apps right? Tope Awotona didn't think so. He saw the potential for a massive company. And that marked the birth of Calendly. Fast forward eight years and millions of meetings scheduled, Calendly is now a $4B company with a customers base of over 50K businesses including giants like Dropbox, eBay, Zoom, and Twilio!

Calendly grew to a colossal $70M in ARR with just 5 people in marketing and 7 in sales! 🤯

Today, we examine the product-led brilliance that will bring the next $900M of ARR for Calendly!

Calendly's ARR Growth: Source

The aha moment 🌟 Scheduling should work for the recipient, not the sender! 🤔

Calendly was born out of a sales professional's conviction to solve an age-old problem - that of the rampant & messy scheduling.

Through an extensive market research exercise, Tope realized that the problem to be solved was not at the host's end and shifted his focus to optimizing the recipient's experience.

The first version of Calendly was developed in Ukraine and the company's first customer was the customer success division of Bright Bytes - an analytics company in the education space. The first signs of a viral product surfaced when customer success reps at Bright Bytes used Calendly to schedule calls with parents, who in turn started using the tool for their own use case of parent-teacher conferences! It was clear that the aha-moment associated with a recipient-first scheduling tool (the moment a meeting is booked) was delivered!

What followed was continuous product development that broke down scheduling to its modular segments, with industry-specific solutions (image below) and integrations with large team workflows (zoom, slack, CRMs, etc) taking center stage.

Calendly developed their product to encompass the entire scheduling flow!

I ran out of budget 🤕 - PLG virality to the rescue!  

‘I went for broke and put every single dollar I had ever made into it. I didn’t quantify how big it could be, but I knew it was such a great opportunity that I literally put everything on the line.  If it hadn’t taken off, it would have set me back many, many years.” - Tope Awotona on going all in for Calendly's development

Much of Calendly's inspiring growth can be attributed to the intrinsic virality associated with the product, the free access to core functionality (funnily, a consequence of Tope not being able to afford a billing software), a seamless user experience at both ends of a meeting and the never-ending obsession to attend to customer requests.

The PLG motion quickly took shape of a Growth flywheel, and alongside a frictionless self-serve product flow, the early sales team of 3 (led by Rachel Williams, Director Sales & Partnerships) was able to successfully upsell the premium (focused on customizability) and pro (focused on teams) offerings.

"Calendly is a truly viral product. There is no single user version of engagement with Calendly; it’s only relevant when there are at least two people involved—the meeting planner and the meeting invitee" - Oji Udezue, Ex- VP product @ Calendly
Calendly;s pricing plan involves a free to use version and premium offerings

From $100M to $1B - what's next for Calendly 🤑

2020 and early 2021 showed clear signs that Calendly, despite being profitable for consecutive years had no intention to slow down. This was marked by:

  1. 2 CXO hirings - Patrick Moran (CRO, ex-Quip CMO) & Jeff Diana (CPO, ex-Atlassian CPO)
  2. Launch of Calendly enterprise: Organisation scale offering packed with admin features and additional support privileges
  3. Series B fundraise of $350M at a $3B valuation (led by Openview partners)

With Tope announcing a revenue target of $1B, Patrick was tasked with building the enterprise offering (extending customized B2B solutions), new marketing channels (product marketing), and leveraging upsell opportunities for the 10M+ strong pool of Calendly's self-serve users!  

Building the Sales machinery 🧑🏻‍🔧 - Managing lead flow, using PQLs, and people

Process: In order to be additive to the exponential growth rates of the yesteryears, Calendly had to layer its self-serve process with product-led sales. The new GTM of Calendly focuses on optimization of lead flow, usage of PQL's, and segmentation.

Lead flow:

  1. Lead discovery is led by the sales development team
  2. PQL's are passed on to a segmented account executive (AE) team
  3. The principle of land & expand, and an emphasis on continuity further tasks the AE with expansion
  4. Customer success sits at the bottom of the funnel with the core objective of churn reduction and customer delight.
  5. Calendly also invests heavily in product marketing, building customer stories around the tool's multi-industry, multi-scale use-cases!
Lead flow and workflow segmentation @ Calendly

PQL's: The sales development team, powered by data and tools now qualify leads based on:

  1. Account information: Team size, industry, geography, etc.
  2. Usage signals: #meetings created, #integrations used, time spent in the system, features used, referrals for teammates, etc.

to segment customers from the self-serve pool, enhance visibility for the outreach team, and custom-sell premium offerings - increasing the efficiency of the team and improving customer experience!

"Demand gen looks different than just MQL's and SQL's, it's conversion rates on the website, it's understanding the signups. You know I have a robust database with literally over 10 million users right and, its about how I navigate that database and segment" - Patrick Moran on modifying demand gen at Calendly

Team: This streamlining of processes and a need to accommodate the volume and scale of high-velocity + strategic sales warranted more resources and boy, has Calendly used their fresh round of funding well! The sales team of 7 that Patrick Moran inherited is now 40+ strong with a strong emphasis on strategy, enablement and Product-led sales aligned distribution of labor

Sales org at Calendly

Way forward ⏩


Calendly's (arguable) 50% market share in the US scheduling market can be attributed to its dominance in the B2C and C2C segments. B2B is a market where Calendly will probably foray into, for which they are expected to integrate backward with added functionality, similar to Docusign. We are very excited to see how Calendly's product-led sales playbook bears fruit and are excited to see them achieve the $1B ARR target!