Legal Software: Calendly's Justin Bouchard Talks about the Benefits of Xakia for his Legal Department

Calendly's AGC, Justin Bouchard, spends some time answering questions about what he likes best about Xakia's Legal Matter Management system for his built from the ground up legal department.

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Xakia | Calendly

Justin Bouchard was the first legal hire at Calendly and had his work cut out for him. Having built the legal department from scratch, Justin talks about his search for a legal matter management software that fit his legal needs at the time and at scale. In this 15-minute Zoom interview, Bouchard discusses what his key priorities were when bootstrapping the legal department, what technologies he considered as part of the tech stack of the legal department, how he uses Xakia and how he hopes to use it as Calendly continues to grow.

Some of Bouchard's priorities when joining Calendly's legal team as the first attorney included: 

  • Metric-tracking and Data Analytics; Ease and depth of reporting both within the legal department and to C-suite/Founders
  • CLM and ELM capabilities
  • Administrative organization for individuals and as a department
  • Ability to mark items as confidential
  • Contract management with sales and vendor relationships



Xakia: Hello everybody. Welcome to a discussion with Justin who is from Calendly.  He's the Associate General Counsel, and he has very kindly agreed to talk to us today about how his legal team works and how they use up Xakia. Welcome, Justin. 

Justin Bouchard: Hello. Nice to meet you.

Xakia: Okay, Justin, I’ve got a few set questions here, so I’m just going to put you under the microscope. Starting with; tell me about your legal team and how it services the Calendly business.

Bouchard: We are a very small, but - hopefully - growing legal department. We actually are bringing on another person currently. And we- I run the whole thing. I built the legal department from the ground up. There was no legal function when I came in, so as you can imagine as anyone else in a legal department you know that you probably walked into like a total mess which is exactly how it was. 

So, the first thing you do is go through and you build out your tech stack and you look at what your immediate pressing needs are. How you can develop and build metrics to demonstrate that you are being successful in adding value to the business and what you need to additionally grow and continue to move the business needs. 

For me, coming in, there was zero tech stacked. There was no CLM, there wasn't a legal matter management system, there was nothing in place. So, it was a full ground floor build-out from the bottom. Starting, you know, at first implemented CLM and moved from there, because immediate pressing contract needs on the- with the sales and the vendor side of the business and processing. And then, from there we started getting more out of the contractual side, and actually more into the legal side of helping and aiding, serving our internal clients throughout the business. So, as more and more legal requests came in, and, there was no real way of managing and dealing with them, because at some point everybody found out that I was in fact here and they can talk to me. And so, 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. 

We make a lot of very science and data-driven decisions here at Calendly, and that is one of the aspects that I actually liked the most about it; is when we look at the facts, when we drive decision-making. And so, in order to show that we were being successful, and adding value, and we needed more resources or support.  - Being able to give that data and the analysis behind it was very, very important. 

At that point, I began looking for legal matter management systems. And, if anyone else has ever researched them before, they're very expensive. And, as a startup company that is growing with a new, young legal department that just existed for the first time ever, getting large procurement requests through is difficult. It's untried, it's a new function. You have no way of proving previously - because you are making science and data-driven business decisions - but if you have no metrics in place already to validate the need for spend, it starts to become a very difficult and very hard thing to do. 

And, in that process, I stumbled across Xakia, and it seemed to meet all of my immediate needs as well as- I guess it was at the price point that I could actually get it through. Like, I knew I could make it happen. And, since then, and as we have grown, the features and functionality that we've been utilizing has expanded rapidly. Initially, it would be more of a system that I would use to just to organize myself and my very small team, but as more people have come on, and we have begun delegating more and more parts and assigning things to people, I started using the more robust functionality and features throughout the service. It’s been working incredible for me, to be completely honest, and I absolutely love ya’ll’s product. But yeah, and leadership, and the decision-makers who I need to see the data, really like the robust reporting that it generates and demonstrates. So, it makes my job easier with not having to run analyses through spreadsheets and everything like that, and generated charts and analytics and everything like that by doing all of that for me. Besides that, the granularity - which I can get into it - allows me to justify additional outside counsel spend on matters that deserve more attention. Or in departments that maybe they're ramping up in a different way and due to that they now have increased legal needs that weren’t present three months ago. So adding and demonstrating that value has really aided both the growth of my organization, and my ability as a whole to serve our internal clients throughout our company. 

Xakia: Justin we had like five questions to ask. I think you've answered all of them in like one shot. I've got just a couple of other maybe follow-up questions. So, I'm interested in when you talk about the robust features of Xakia that you have started to use a little bit more - which ones are you referring to? What are the primary features that you use? (Other than just organizing your own day and forward-thinking.

Bouchard: Both the Cardboard - the Cardboard is very useful for prioritizing and moving things. I'm used to using that kind of board previously and so like that kind of naturally became one of my go-tos. But as we developed and brought on more people and everything - really the Assignment and the Delegation. The Status and the Action Status. Even the Notes - while we don't put everything in Xakia for the notes, because a lot of things we do are very collaborative in a completely remote environment, and so we need a lot of input and people to view what's happening and stuff. But it's as simple as like, ‘Here's the link to the Google spreadsheet’, like, that everyone is going to be looking at, so that it can be easily, quickly accessed and used. 

The Reporting is very robust, and as far as the other features; one of the big aspects that sold me on it was the fact that I can mark matters as confidential. It seems so small on the surface, but as a privately-held company, the leadership team and the CEO is very, very conscious of high-level very specific things like M&A deals, funding/raising/financing - all of those very, very, you know, confidential just, you know, discretion everywhere. And so, being able to limit the involvement of who can see and who can be in those matters was actually a big component of being able to get it in, because previously they had actually used a totally different system for organizing and getting everything that nobody had access or visibility into. And so, at the very least I have built up the confidence that like, ‘Oh you don't have to worry about it’. And so, more comes my way I get better- I can give better advice, because it's more proactive instead of reactive because they can trust that it's not going to be seen by people that don't need to see it and that the information is in fact locked-down. So, that's- it seems like such a minor thing to be able to just push that little button, but it's really fundamentally changed a lot in the way I operate and how I interact with the high level and the C-Suite in my organization.

Xakia: Fantastic. And, in terms of the analytics that you’ve referred to, talk to me about Dashboards, Reports - which ones you like or lean on the most around that- communicating the metrics that make the decisions or informed decision-making amongst the business partners.

Bouchard: So, usually I- we do it on a monthly basis. So, basically we do a month in review kind of deal where on a monthly basis key business department and function owners throughout the company report on their OKR's, their metrics, their progress directly to the C-Suite. And it's- it's a very long meeting everybody goes through, but it allows everybody in the company to sync as to what is going on. So, being able to put it up and throw it up and have the executive summary and the short executive summary are the most used. I use them every single month, every single time, because they don't want the detailed granularity that I may want in terms of like, ‘Oh hey, we're getting more IP requests, now, I need to divert resources or, look at bringing specialists for that (maybe on a temporary basis’. Instead it's more- it's pure volume metrics for them - on the most part. Between that, and being able to flag critical issues. They like to be involved in-the-know. And obviously it's their business, and it's very nice to be able to - as part of the executive summary - have that list of things that are considered critical matters that they know are in progress. That are either large strategic goals that happen to have legal blockers in place that are being worked on and works in progress, or matters of risk that just need to be brought to their attention for a decision at a path forward and a policy to be laid-down. 

We are hyper-growth startup, so a lot of the policies and procedures and how things are done have never existed before. We're growing at such a rate, that the pains that we experience are at a different level, because we’re throwing 100 people who have known each other for two months into a room and be like, ‘Here's the problem. Fix it’. And that generates problems on its own, and getting them- and jumping around between all of that. So, being able to show areas that maybe they don't previously have visibility, but people come to me and ask; they want the advice, they want the help and being able to report that, put it in, market is critical, and flag it so that I know that I can inform leadership about it both to get guidance and to tell them that there may be a delay because there is a roadblock. Or if this has been removed so we've got to go ahead/all clear - whatever it may be - that's been very helpful. 

For me, personally, 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. People know this. I know this. Leadership knows this. So, being able to look at things and decide what we're going to automate, create self-service for, how we're going to deal with constantly-recurring matters that pop up in an automatic fashion; whether that be a full automation system or self-service knowledge base - those are a lot of the things that I look at in the development of my function and where I see the strategic vision for my Department to grow. 

Xakia: That’s fantastic. And so, I think I know the answer to this, but I feel that maybe you're not yet using the Legal Intake tool so we'll have to revisit those- 

Bouchard: I am actually. Not as much,  though. The reason is because we communicate so much on Slack. The- that's where it comes in, and so I usually just end up manually adding it. So, for most common requests, like, I've created - the Templates; very useful. I have created a plethora of templates for the common things that come in, whether it's a customer support ticket that like there's something wonky going on and they want me to come in, or like you know it's a legal issue that's popped up regarding you know refund request or whatever it may be. Those are very minor issues, but they need to be reported. They’re still taking time. They're still taking my team's time. They need to know that there is a volume of these that is coming in, that is requiring allocation of company resources. So being able to get those in is important. The Intake Tool itself, I get people to use it for big things. If you're going to try to give me you know one-page rundown about a topic in Slack. Please just, put it in. You know and I’ll tell them, like I'll just flatly tell them. So, like, the little things typically come through on Slack. C-Suite just won't use it 'cause they’re C-Suite - they email. All email. Like, most of them- some of them don't even use Slack about it, so, it's going to be email with multiple people chained on it and everything like that but I have your Gmail plug-in so, I add it directly from there. Like, super quick and easy. And beyond that, yeah, that's generally how it gets used in my function. 

Xakia: That’s awesome. And so, my last question is whether you have any quantifiable improvements or changes that you can identify through the use of Xakia.

Bouchard: Oh, absolutely! I have my hiring plan approved. I mean, basically, like, I can show like, ‘Look we have this many resources, and this many matters. We’re increasing by X amount on a monthly basis. You can see, as we continue to grow, things have continued to ramp up both on a contractional level and a legal matter level. So, at some point there is going to be- and I can warn them. I can tell them; like, ‘At some point, we're going to hit a backlog and it's going to happen, because this is an unsustainable level of growth. And because of that, I can make my arguments for procurement functions; for additional personnel, for whatever I may need very, very effectively and I can do it in advance, so it's not already a problem. And that helps me a lot, because when you're in the weeds, you don't have time plan on how to get out of the weeds, because you're stuck there doing it. And 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.

Xakia: That’s fantastic. Justin, anything else that you wanted to add to the discussion today? 

Bouchard: Make a Slack integration and I will-

Xakia: Oh. Well…

Bouchard: I hear that it is in the works! I've heard- I've heard rumors.

Xakia: We can take it offline, and I would be very excited to talk to you about that. - Thank you very much for your time Justin.

Bouchard: No problem, thank you.