How 3 Decisions Helped Calendly Grow to 50 Million in ARR

Posted on May 5, 2020

In this episode of the GrowthTLDR, we talk to Tope Awotona, CEO and founder of the fast-growing Calendly, who are up to 140 employees with near 50 million in ARR.

We talk to Tope about the three decisions that helped to make Calendly the success it is today, how he managed to build the first version of the product without any full-time engineers, how Calendly doubled down on virality, and why they give customer support to their free users.



Time Stamped Notes:

[2:40] – Calendly is 140 employees, mostly based in Atlanta. They’re approaching $50 million in ARR.

[4:15] – Tope talks about the three decisions that helped to make Calendly successful.

1. Going Freemium. Calendly ended up a freemium product because Tope ran out of money to add the payment functionality. 

2. Hiring great engineers at an early stage

3. Not selling too soon. Tope talks about turning down an eight-figure sum to sell the company.

[6:55] – Tope talks about what it felt like to turn down an eight-figure sum for Calendly.

[7:45] – Tope built the first version of Calendly through a development agency

[10:35] – Calendly doubled down on the viral aspect of the product by making ‘Meetings Scheduled’ their north star metric. It signaled value for the customer and led to new user signups. Calendly also focused on building features for a broad set of users. One of the keys to virality is getting the balance between horizontal and vertical correct.

[14:20] – Tope focused on specific personas to better monetize the product. For example, both sales and recruitment had a higher need for the paid features that Calendly offers. Tope talks about how he decides what personas to focus on.

[16:55] – The challenge with going horizontal is people tend to leave your product when they need the sophistication of features. It also makes customer acquisition more difficult.

[18:25] – One of the biggest challenges for Tope is knowing what opportunities to prioritize for Calendly. There are so many problems Calendly could focus on solving, choosing the right ones is critical to their success.

[20:50] – The thing Tope is very focused on right now is increasing user signups, and increasing the LTV of his customers. Calendly is very focused on building more features for teams and enterprise customers as a way to increase their customer’s LTV.

[23:45] – Data, workflows, and integrations are all things that help to make Calendly highly defensible. Network effects are also something the team is focused on adding to the product.

[27:00] – We talk about the power of doing deep work and blocking out chunks in your calendar to do this work.

[28:20] – Tope talks us through how he works with the marketing team to help establish the Calendly brand, and how he wants people to think about Calendly as a brand. Two things that are important to him are the brand is seen as approachable and innovative. 

[32:00] – One of the things Calendly does that’s unique in the market is offering support for their free users. Tope sees this as a customer acquisition cost because it helps more people schedule meetings, which, in turn, helps the company acquire more users.

[33:25] – A significant advantage Calendly has is their product gives people instant gratification when a meeting gets booked. It helps foster the feeling of love people have towards both the product and brand.


– Tope on Twitter / LinkedIn
– Kieran on Twitter / LinkedIn / Medium
– Scott on Twitter / Linked / Medium