Calendly Delivers a Seamless Employee Experience With Docusign eSignature for Salesforce

Meetings are the lifeblood of any business, but setting them up often takes a lot of time and back-and-forth emails. Calendly turned solving this scheduling nightmare into a $3 billion company.

The company’s automated scheduling platform helps over 20 million people, including 86% of the Fortune 500, take the hassle out of coordinating meetings—so they can focus on closing deals, hiring candidates, building relationships and growing their business.

Freeing up time for the moments that matter is a core part of the company’s ethos. Digital technologies play a big part in bringing that to life. “We’re getting great leverage out of digital tools like eSignature that provide a better experience for our customers and allow our teams to focus their brain power on things that really matter instead of redundant tasks,” said Kate Ahlering, chief revenue officer.

Creating a friction-free agreement flow 

Calendly was on a steady growth track long before work from home and Zoom became the norm. Adoption of Calendly for Enterprise grew 61% year over year in July of 2023, and the company continues to capture the lion's share of the scheduling market. The problem? Its sales agreement process couldn’t keep pace—and the company was missing out on valuable automation and insights.

Before Docusign eSignature, Calendly was using PandaDoc to execute agreements—but because it didn’t integrate with its sales stack, and a lot of manual effort was required, adoption never really took off. “We were using Trello boards to track tasks, but we didn’t have any metrics or details around things like how many deals were out for signature, how long they were taking, or where they were getting stuck,” said Sarah Jackson, head of revenue operations.

Docusign eSignature makes it easier for reps to close deals—faster—by keeping them in the tool where their most important data lives: their CRM. eSignature works seamlessly with Salesforce, enabling reps to generate order forms, renewal agreements, NDAs and MSAs with a single click directly from the opportunity. Now, everyone knows where a document has been, who’s seen it, and where it needs to go next—without leaving Salesforce.

Growing e-signature adoption 8-fold

When evaluating e-signature tools to streamline the sales process, Calendly ultimately landed on Docusign for these four reasons:

1. Trust: Customers know and trust Docusign. 

2. Security: Security is a top priority, and Docusign is well-known as one of the safest electronic signature solutions on the market.

3. Convenience: Agreements are automatically stored in Salesforce records once they’re signed.

4. Ease of use: The rev ops team wanted to eliminate menial tasks and automate as much of the agreement flow as possible.

For sales reps that tend to be “quite picky” about the tools they use, the massive increase in e-signature adoption has been a huge win for Calendly. 

According to the CRO, the biggest measure of success has been sales users’ silence. “It’s just a natural part of what they do every day,” said Ahlering. “I think that’s the most we can ask for as sales leaders…that our teams operate new tools without any friction or commentary.”

Moving upmarket with Docusign

As Calendly grows and expands upmarket, it will continue to scale how it uses digital technology to meet the scheduling needs of teams at organizations of all sizes.

Beyond sales, Calendly also uses eSignature in HR and Recruiting. That’s where the ability to have sub accounts for different teams comes in handy. Recently, the company licensed Docusign Click for the self-service side of its business, providing a fast and secure way to capture customer consent on things like changings terms and conditions and free trial signups.

“We’re off and running with Docusign across our entire organization and digitizing all the things that we sell or procure,” said Ahlering.