Calendly chose Xakia to provide a foundation of facts for a new Legal Department in a data-driven corporate culture.

Calendly chose Xakia to provide a foundation of facts for a new Legal Department in a data-driven corporate culture.


Calendly makes a popular automated scheduling tool that allows users to easily book appointments; the company’s mission is to “take the work out of connecting with others so that our customers can accomplish more.” 

The software-as-a-service company is used by 10 million users monthly and serves the majority of the Fortune 500. From March 2020 to September 2020, Calendly booked more than 58 million total meetings worldwide. 

Associate General Counsel Justin Bouchard joined Calendly in March 2020. As the first Legal Department hire, Mr. Bouchard would be building the legal function from scratch – or as he puts it, “a full ground-floor buildout from the bottom.” 


As the new in-house lawyer, Mr. Bouchard soon found himself deluged with work. “More and more legal requests came in, and there was no real way of managing and dealing with them,” he said. “Managing those expectations and demonstrating that more support was needed in prioritizing matters, along with the company’s strategic goals, was a big priority for me.” 

While intake and triage was the immediate need, Mr. Bouchard knew he would need a modern matter management system that could supply the Legal Department with the data and metrics that were so engrained in Calendly’s corporate culture. 

“We make a lot of very science- and data-driven decisions here at Calendly,” he said. “In order to show that we were being successful in adding value, and we needed more resources in our support, being able to give that data and the analysis behind it was very, very important.” 

Mr. Bouchard explored a variety of matter management solutions and ultimately chose Xakia. Like Calendly, Xakia’s software-as-a-service model offered affordability and flexibility to the nascent legal team, and Mr. Bouchard saw that the software could easily scale as he grew the department. 


Mr. Bouchard implemented Xakia with an eye toward his C-suite audience. Because the organization places such a high value on data in decision-making, he embraced Xakia’s automated reporting functions early.  

Xakia reports now serve as the foundation for Mr. Bouchard’s monthly presentations to Calendly’s leadership team. He presents an executive summary with a roundup of the month’s legal activity; a list of critical matters that are in progress; and matters of risk that merit C-suite attention.  

“Leadership and the decision-makers need to see the data,” he said. “So Xakia makes my job easier with not having to run analyses through spreadsheets. It does it all for me. Besides that, the detail behind it allows me to justify additional outside counsel spend, show matters that deserve more attention, or highlight legal needs that weren’t present three months ago.” 


With less than one year in his position, Mr. Bouchard used Xakia reports to get approval for his Legal Department hiring plan.  

“I can show we have this many resources and this many matters; we’re increasing by X amount on a monthly basis. At some point, we are going to hit a backlog,” he said. “Because of data, I can make my arguments for additional personnel very effectively. And I can do it in advance, so it’s not a problem. 

“That helps me a lot because when you’re in the weeds, you don’t have time to get out of the weeds because you’re stuck there doing it. Being able to step back and spend more time on the actual strategic planning and getting leadership alignment has really driven our function in the organization as a whole.” 

Mr. Bouchard also is using matter data to look for efficiencies within Calendly’s legal operations. 

By charting the size, complexity, risk profile and strategic value of Calendly’s matters, he is examining batches of work that could be automated, eliminated or sent back to the business units with self-help tools.  

“One of my big objectives is making sure that we focus wisely on where we apply our time and energy. My team’s time is very expensive. I know this. Leadership knows this,” he said. “Those are a lot of the things that I look at in the development of my function and where I see the strategic vision of my department.” 




Business/Productivity Software

Features used
Matter Management
Matter Management
External Fee Management
External Fee Management
Dashboards & Reports
Dashboards & Reports
Intake & Triage
Deployed in a matter of days
Untitled design (7)
Collaboration improved among executive peers
Untitled design (12)
Clear reporting to inform resourcing
Asset 71 alt (1)
Improved client service
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Justin Bouchard, Associate General Counsel


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