How Calendly improved their 409A process with Carta

Cailey Ryckman
Director of Finance and Operations




Company size




Calendly is a SaaS company known for its scheduling automation tool. Based in Atlanta and founded by entrepreneur Tope Awotona, they’ve reached profitability faster than most companies in the startup world. Tope credits the company’s scrappy, resourceful culture for this success.

As a company dedicated to helping people become more efficient, it made sense for their finance team, led by Cailey Ryckman, to apply these principles to the way they manage equity and conduct 409A valuations.

By teaming up with Carta, they’ve saved both time and money
over their prior process.

Problem: inefficient and time-consuming 409As

Prior to using Carta, Calendly found 409A valuations cumbersome. Cailey would spend hours digging up the required data from various folders and going back and forth via email until her valuation firm had all the information they needed. Eventually, an analyst would return a single spreadsheet that required additional work before it was presentable enough to share with board members.

The fact that they are profitable and are structured as an LLC further compounded the problem, making their 409As more expensive and complex

Solution: Carta’s approach saved hours

Cailey decided to move Calendly’s cap table over to Carta. This made data maintenance and collection more efficient and also came with white glove service when it was time to conduct a 409A.

The first step was a 45-minute kickoff call to understand the more qualitative considerations with her dedicated analyst. This allowed the analyst to get a holistic understanding of Calendly’s business and future plans before starting the analysis.

“One worry was that the Carta team would just plug the data into a calculator and spit out a result, but that’s not how it worked at all. Kristoffer [their analyst] asked thoughtful questions and really got to know our business.”

Throughout the process, Cailey was able to rely on Carta’s analyst team for prompt responses to all her questions. “They were extremely responsive and took into account our unique business plans.”

Since most of the data needed was already accurate and up to date in Carta, Cailey estimates that she saved at least two hours compared to her previous 409A provider. Their subscription keeps them 409A-compliant year round more efficiently than before. As an added bonus, the finished product from Carta is in a much more presentable state, and Caily can immediately use Carta’s in-app functionality to add it to a board consent directly, rather than having to spend time formatting it first.

“The process was quick and painless, with very little work needed on my end. At the same time, the process was still highly consultative with Carta’s insightful and professional analyst team.”

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