Calendly

During my time at Calendly over the last 7+ years, I have gotten the opportunity to work alongside many talented people across various teams, disciplines, and functional groups. When I joined Calendly back in January 2019, the company was around 50 employees and growing in size. I was living in Atlanta, GA where the company was located at the time. Since then, the Calendly brand has become a widely recognizable name. The company has grown in headcount, in addition to becoming fully distributed. The product matured beyond simple 1-to-1 scheduling. The company grew in valuation as well, surpassing unicorn status and currently valued over $3 billion (based on the Series B in 2021).

Early Days

I first started at Calendly as a Product Specialist on the Customer Experience team. My primary responsibility was to offer support to customers and get them back to scheduling as fast as possible. I loved how our small and mighty team, around 10 of us, diligently worked together to support our customers. I quickly progressed and moved to the Tier 2 team, which handled escalations, billing related tickets, and generally more challenging topics. I became a go-to person on the team for helping answer highly technical tickets in addition to helping jump in to answer questions from developers writing in about the public Calendly API.

Customer Experience to Operations

With the desire to move into an even more technical role plus the need for the company to streamline operations for customer facing teams, I moved over to the newly formed Customer Experience Operations team where my day-to-day job responsibilities changed fundamentally.

I'm proud to have worked on many projects during my time on this team. I'm most proud of the project where I helped redesign and rebuild the Help Center. I also connected a lot of internal systems, including Zendesk, Stella Connect, Qualtrics, Zapier, Jira, Airtable, and countless more. I had a lot of fun building some custom internal tools as well. I once made an app for Zendesk to help agents quickly add relevant tags onto tickets. I also helped maintain an internal legacy customer support dashboard ticket tracking app used by managers, lovingly called the Happiness/Sheepy Dashboard.

Operations to Engineering

It was becoming increasingly clear to me that I wanted to pursue software engineering. I was really enjoying the technical work, and loved whenever I got the chance to talk about technical topics with the full stack engineers. I raised this desire to my manager, and am grateful for their help in advocating for me to pursue this path. I was part of Calendly's first official cohort of their Apprenticeship Program, where I got paired up with a senior full stack engineering mentor. I learned so much from them and am beyond grateful for their teaching, wisdom, and many lessons learned. Upon graduation from this program, I officially transitioned over to the Engineering team as a Full Stack Engineer on the Reporting and Analytics team.

Product Engineering

On the reporting and analytics team, I had the chance to build product features on Calendly's newly released analytics dashboard feature. I also had the opportunity to help build some other new features as well, including the User Profiles feature for Admins.

Growth Engineering

Most recently, I've been working on Growth Engineering projects aimed at improving activation, retention, and user growth/expansion opportunities for Calendly’s core customer cohorts. Some of the product experiments have included:

More to come, check back later! 🙂

Takeaways and Learnings

Distilling 7+ years of time at a high growth startup like Calendly is hard to consolidate into just a few learnings. With that being said, here are some of my top takeaways:

Customers pay your bills. Listen to them.
Make it work, make it beautiful, make it fast.
Retention is growth.