Transcript
Speaker: I think legal operations is harder than people make it out to be because it's real easy to implement some software. But if you're just implementing it without thinking about like, why are we doing this and what's the outcome we're looking for and does this actually do that? And if it doesn't, is it something we can fix?
Speaker: Then it's a big mess. Where your service providers, that's especially easy to do, right? Because you could just be a ticket taker, an order taker. mean, we work at Zendesk. We are the lead-in AI ticket platform, right? It's very easy to become order takers. So for us, and this is something that Catherine and I worked on together, even at Google Cloud, It starts with a shared understanding of the mission of the department.
Speaker: Catherine and I don't start any strategy session, so to speak, any off-site, any on-site without that mission of the department, which is to facilitate growth while mitigating risk in that order.
Speaker: Hi everyone, Akshay Verma, the Chief Operating Officer at Spot Draft, and also the host of our podcast, Spot Draft Beacon Voices, and excited to have a little bit of a unique conversation today with Shaina Simmons, who is the Chief Legal Officer at Zendesk, and her Chief of Staff, Catherine Che, who have been working together for about six years in various different companies.
Speaker: and really excited to talk to them about this relationship, which i as I have told them several times now, find to be one of the most important, if not the most important, relationship within the legal department and probably will evolve to be one of the most important across companies that as we move forward.
Speaker: But really excited to hear about their experiences, learn from them, and talk a little bit but about what they see coming down for legal departments in the new age of AI and operating efficiently. Shaina and Catherine, welcome to the podcast.
Speaker: Thank you. It's great to be here with you. Thanks, Catherine. Yeah, and like, I know we've had a couple of ah ah times trying to get together on this. I'm glad you guys are making the time, but I wanna start with an overarching question about the two of you. And Shana, we'd love for you to start on this one. When you first started working together with Catherine, like the very first time, tell us a little bit about that and tell us how you think that's influenced your relationship today.
Speaker: Wow, so I guess I'll start. So we first started working together at Google, in Google Cloud, where I led the first ever Google Cloud go-to-market product council team. So it was a new team, new to the business, new to legal, et cetera. And that meant that the product council team was working across prod dev, commercial, the CISO, marketing, partner teams, and professional services to build the products, systems, and processes that we thought the customers really needed, not just what Google thought the regulators needed, but what did the customers need and what did their regulators need.
Speaker: And in a fast move in business like that, and I think cloud has been incredibly fast moving and we're seeing it move again that fast, the data mattered. And what I realized about Catherine then is that she had a unique and incredible gift for taking the data, finding the story, and turning it into something that served both the customer and the business. Yeah.
Speaker: And what's made that partnership work and what kept us choosing to me, and and Catherine is probably going to give me a funny face at this point. What kept us choosing each other over the years, I think, was trust. I think we both value honesty, integrity, and the willingness to keep growing as people.
Speaker: And not just as like a lawyer or as an executive, but as a person. yeah um You know, Catherine is a continuous learner. You should ask her about her bookbinding skills recently.
Speaker: And she definitely pushes me to be better, right? In fact, some of her pet peeves have become mine, which I'm sure makes her secretly very happy. But she hasn't expressed that happiness yet to me. I think it's just she's holding it and is she's so proud and happy. But also what's made our partnership so strong is that she's never been and will never be a version of me.
Speaker: Yeah. Some executives choose chief of staffs that somewhat mirror them or begin to mirror them after that time. But if you've met Catherine and you've spent any time with her, she's her own person with her own strongly held point of view. and I think that's exactly what makes working together so powerful. We've given each other, we've made room for each other to grow.
Speaker: And because of that, I think we've both gotten better. But I'd i'd love to hear from Catherine. This would have been so much better if you would have done it with like with us not together so we could like see how it pairs up. So I'm now curious to hear from Catherine.
Speaker: you get to hear in real time. And honestly, what a great introduction, Catherine. I'd love to hear your take on it too. and And one thing I'd love for you to add, if you could, in those early days at Google, was there a seminal moment where you kind of felt like, hey, this is somebody I want to continue working with?
Speaker: CATHERINE RAMPELLO- um So I actually haven't heard this story before. um and I'm gonna be processing it for a while. um i joined Google Cloud um working for one of Shaina's direct reports.
Speaker: And i think with Shaina, there's no, it doesn't take long before you have that seminal moment, right? Because she, in a way, unlike anybody else, she has this extraordinary vision for what she wants her teams and actually the company to accomplish. Um, but she's also like the most empathetic person I've ever met. And that is a very weird combination. i think not just in tech, but in life to have somebody who is so smart and has such a clear vision and for that vision to be so big, but also like be the extreme opposite of a jerk.
Speaker: Um, So it really, it didn't take very long. And i hadn't been at Google Cloud for very long before Shana was like, hey, i just accepted this job Everlaw.
Speaker: I was like, hey, i was going to have this conversation with you in like nine months. But if you have room for a chief of staff, when you're over there, I would love for you to consider me. um And I was trying to figure out where to work this into our conversation. And this seems perfect. I think Shana is the Natalie Nekase of CLOs.
Speaker: Who is that? who he yeah i know Natalie Nkose is the head coach of the Golden State Valkyries. Oh God, I should really know this. We have season tickets. My wife's going to kill me. They are the first they are the first team in the WNBA to be help to have a billion dollar evaluation. lot of that is what the owners and the president have put into it. But Natalie Nkose is the head coach. And she, is like the competence at the Golden State Valkyries gives me like such joy because if you watch her in her post game press conferences, the wins are always what the team did and the losses are things that she takes on herself. And she always puts the team first, the way they built that team.
Speaker: that basketball team is that it's not, did the star get to shoot? It's, did we pull together as a team and did we win? And the bench is really deep. And that's what Shana always strives to build as well. And the other way that they're the same that I don't necessarily think is common in legal departments is that Shana wants us to have fun together. She wants there to be joy at the workplace.
Speaker: Right. So this is, listen, I'm obsessed with the Valkyries. I've only gone to one game and I'm obsessed with them. So this is like in this moment in time, one of the highest compliments I can pay somebody is for them to be the Natalina Kase of anything.
Speaker: and And as much as I didn't recognize the name, I know actually know a lot about her because my wife has had season and tickets for two seasons now. I'm actually attending a chalk talk with Natalie after game on Sunday with my son. She played high school basketball here in Palo Alto, just in our backyard. She's up just kind of a local legend.
Speaker: I totally understand what you're saying now, but I didn't recognize the name up front. So I totally get that. um One more thing for you, Catherine, because I think for you, as you think about executing the vision with Shana at Zendesk and what you've done in the past, are there some consistencies that you see that you guys have brought to Zendesk that you get to kind of just absorb and and take forward without much of a conversation anymore?
Speaker: Yeah. um So with Shane, it's always company first, company, what the interest of the company, the interest of the department, and then the interest of any individuals involved, including herself. um And so it's really easy to know what the what the goal is.
Speaker: We might differ in the right way to get there. And we have conversations about that and figure out what's best for the team and, um, what with the priorities that have been put in place, what's the best way to get there. But it's really easy um because we're going to do what's best for the company and what is going to help the company achieve its strategic goals every time. Yeah.
Speaker: Dana, I'm going to go over to you to help us from your perspective, as you think about how legal departments should be structured, what they should be prioritizing beyond just, yes, we have to serve the company goals. Are there consistencies that you've seen, and you've worked at some of the largest companies on the planet, but are there consistencies that you've seen over time that really help you hone in on the strategy and the vision for Zendesk?
Speaker: Yeah, I think a lot of people use the word strategy to mean a lot of activity without always having a shared understanding of the mission. um And in an in-house legal department, I think you said it best, like where your service providers, that's especially easy to do, right? Because you could just be a ticket taker, an order taker. I mean, we work at Zendesk. We are the lead in AI ticket platform, right? It's very easy to become order takers. So for us, and this is something that Catherine and i worked on together, even at Google Cloud, it starts with a shared understanding of the mission of the department.
Speaker: Catherine and I don't start any strategy session, so to speak, any off-site, any on-site without that mission of the department, which is to facilitate growth while mitigating risk in that order.
Speaker: Yeah. Right. And once you're aligned on that, and once we're aligned on that, everything flows from there. I mean, when I say everything, I mean, Catherine and I spend hours on anything from the job descriptions, career ladders, right? Like thinking about that talent book bucket, right? The who, the how they're working, right? The work, the budget, the structure, all of it goes back based to that mission.
Speaker: Then from there, we divide the work pretty naturally, right? We set priorities based on the business's priorities. Again, I don't know how you can be in any GNA function at any company that's trying to transform, especially you right now in the time of AI. And we think about what the department needs to look like and what it needs to do to support those priorities.
Speaker: yeah So yes, um thank you, Catherine. I'm kind of big picture and focused on the vision, um the legal, the business direction and making the big calls. But Catherine is exceptional at turning that vision into execution.
Speaker: And that doesn't come easy. I say that because not everyone is like, yes, I'm sold. Yes, this is the way we go. Because some people naturally like to just respond to tickets. That's just what we do, to check the box. And she makes sure that the department is organized, aligned, and actually moving.
Speaker: And I think one of the ever lawyers said it best before we left. He said, Chuck, he said, you know, Catherine has made, has the ability to turn the red tape and turn it into glitter, right? That's how they've described the work. i I come in with the glitter already because I don't have the skill set of turning anything into glitter. So I got to go to the 99 cent store and get my glitter. But Catherine can turn the red tape into glitter and with the glue spark glitter around. Right. And so, but again, it's by putting the company's mission, the legal department's mission, and the priorities aligned to what the company needs to achieve.
Speaker: Yeah. Actually, I'm going follow up on that a little bit because I think Shana's underselling something that she does that um I think is kind of the key in how all of it works. She sort of mentioned it, which is um we don't want to be order takers. But beyond that, Shana doesn't care how busy you are, right?
Speaker: You can win the busy contest and still have lost because you're not having impact and you're not having an impact on out on the outcomes that the company is looking for. So she's this is not realistic, but she says, like, I don't care if you work two hours a day, as long as you're having the impact and the outcomes that you need to have. um But it's like if somebody had a job where they could get those impact and outcomes done in two hours, she would be fine with that. I don't think that we live in a world where it's low. Yeah, I had imagined a world like Catherine and I were going to come to Zendesk. We were going to transform the department and we're going to wearing leather jackets and like hanging out, like yeah like drinking at three. And but that's um that's not going happen, right? We're not in that world. But at least we want to have fun while we're working pretty hard.
Speaker: There's also like a... as I think as humans, we tend to think of things in binary. So... um like we're either giving white glove service to our stakeholders or we are not giving them service at all. um I probably lean toward, I want to hear a few complaints from our stakeholders because that tells me that we're probably really close to where we need to be in terms of getting them to self-serve, um figuring out what we've like, that we've automated the right things. um
Speaker: Shana likes to hear how great people think legal are. I'm always a little bit nervous about that. Are they really, are they big fans of us because we're doing too much? imagine it's more, it's more if they weren't saying anything that you'd be worried, but if they're going out of their way to tell you how great you are, I think that's a pretty good sign.
Speaker: I haven't seen that. It's a sign up white that is kind of glove service. And we are not, we are not resourced for white glove service. That is for sure true. your Your point around this busyness, both of you, the busyness, the effort, right? You go to law school and you are praised on effort and hard work. You go to a law firm, you are praised on how many hours you bill. That's about effort. can be distributed around a bunch of clients. It's not necessarily about the impact. It's such a shift.
Speaker: When you go and you work in-house, because now you are part of running a business and impact in whatever way the business needs impact to be measured is one of the most important things that you need to think about. So making that shift, how like to talk a little bit about tactically, if you can.
Speaker: how you get the department to think that think that way. And and and I will say 90% is probably lawyers and there are probably some legal professional roles in there as well. But how do you get the department to start really believing that that's what's important and then shifting the way that they operate in order to get to that to that impact is most important mindset?
Speaker: Yeah, we're not going to share all the secret sauce here today because one day we might have to go on our own and have our own consultancy business. Right. So that we can then sell that. there, but I think it is in the way I think it's, um, you know, and and I know it's interesting that I did talk about the job descriptions, right? That, that, that is something that you can take AI right now. Yeah. And there's plenty of job descriptions on there and you can say, make me a job description for a product council.
Speaker: Yeah. And it's a generic job description. You can check the box. It has the right adjectives, the right verbs, the right outcomes. No, Right? It is how do I look at this job description to understand that this is the impact that I want this person to have?
Speaker: And when I say impact, it is, i want you to go above and beyond of just, again, answering the questions the prod dev team. I'm just giving product example, but thinking beyond of what we need to build for the future, for the regulators, for the products, for the customers,
Speaker: But not only that, especially in this AI world, it might not be anything legal, but it might just be an ease of use. It might be a design thing. But think about that. i love this story because we have um ah product council on the team and he's our healthcare product council. and and And, you know, was he's just incredible at thinking about the customers.
Speaker: and And his manager said to him, as as as we were talking about this impact, like go make $7 million of healthcare care costs with healthcare. No one ever tells a lawyer to go do that.
Speaker: Nope. But that's the kind of department we're running where it's like, go tell me how, what you've done has tied to ARR because the rest of the company are looking at these metrics and they're looking at ARR and they're looking at this. Tell me how that, or what have you done to so to help turn this week?
Speaker: What have you done to help contraction this week? To start for them to think about the business drivers that are driving our business folks and everywhere. And so, again, it goes back to performance management. It goes to the talent. It goes back to this vision of facilitating growth.
Speaker: Right. and and And I think a lot of it ties to that. Yeah. Catherine, do you have a hard time at all at times with maybe with with Shana's direct reports, are other lawyers really kind of getting on board with that mentality? Has that been a challenge at all? Before she answers that question, can I tell you who she has a hard time with the most?
Speaker: Yes. Is me. Yeah, well, but it's hard time with me. Why is because i say yes way too often. Right. I'll let her answer this question afterwards.
Speaker: um Can you be in Brazil for this customer? Yes. And then this country? Yes. Can you excuse me one more thing? Sure. Why not? Right. And that can create friction sometimes. Catherine is much more measured and thoughtful about the trade-offs, but I think that's also what makes us work so well together. I create this motion, she channels it, so the left friction becomes leverage, and I think that's where the magic happens, and that's where she creates her her her her glitter. But I'll turn to her to to because I think she has a real real anecdotes about how this might cause some friction between folks and with her and the department.
Speaker: I'm not going to name names we don't know how you get name names. Anytime you get more than one human in a room, there's going to be some differences of opinion, right? And these lawyers are not dumb.
Speaker: My colleagues, um none of my colleagues anywhere have been dumb. Everybody's got their opinions based on the things that they're seeing. um But when it comes to the expectations of the department, it's actually really easy because I'm here to help you meet Shana's expectations.
Speaker: If you choose not to listen to my advice, you're a grown adult. I can't make you, ah can't make you do something you don't want to do but i don't have to say anything. I don't have to be like, Shana, can you go squash this person because they're not doing whatever? um i just wait because eventually I'm,
Speaker: Eventually there's going to be a project where somebody is like, no, I don't have to do it that way. and then Shane is like, why did you do it this way? Because this is not the outcome that we're looking for. This is not the value that we're looking for. This is not tied to ARR or the company strategy or whatever. um when I was able to let that go and working for Shana makes it easy to be able to let that go. Like my day gets easier. I don't have to chase people as much for things. Like this is the expectation of the department. You do excellent work. You facilitate growth while mitigating risk and you do it in that order. We're not eliminating all of the risk for the company. And if you're not on board with that, it's going to be really hard to be successful.
Speaker: yeah Wait, don't you have a new quote or something like, let go or find out, f around and find out or something. Isn't there a new song? We were in a one-on-one and I said something.
Speaker: Shada started laughing. She was like, I don't think people understand how much you live by F-A-F-O.
Speaker: i will often just be like, go with God.
Speaker: And suffer the consequences if you don't. Listen, I don't know everything. i don't know everything. I'm not always right. Right. And these are smart adults who have their own perspective. I might be wrong.
Speaker: Let's try it your way. Totally fine. And the thing is, is like Kevin says that, but it sounds like she still puts the team first and tries her best to help. everyone put the outcome. But I think there's a difference between, and I've seen her step up and I can see, I'm not silly where things don't meet expectations and Catherine will lean in is there's a difference between coddling and enabling other folks, right? And if Catherine's role was to coddle everyone in the department as well, yeah right, to meet my expectations or the business yeah expectations, then we fail to build the system that's going to succeed both of us.
Speaker: yeah And what... what I, my goal for in any department I'm leading and any job I have, right, you can hire me to be your child's babysitter, right? When you get home, the house will be a little bit cleaner than you left it. The kid would have done something, you know, like we're going to leave behind something better than when we left it off, right? And by Catherine constantly chasing and catching balls from the department that might not meet expectations, even though she's put the systems and frameworks in place,
Speaker: that will meet where the business needs to be, then I think at a certain point she's also hurting the system, if that makes sense. And I think that's where the go with God comes from, right? It's like, then I have to see that and I have to make tougher decisions on either do I have to fix the framework, do i have to fix the system or do I have to change the people?
Speaker: i I think the drawback, I think one drawback of having Shana and me together is we don't want stuff to fail and we don't want stuff to break. But what I've learned is that if legal is always twisting itself into pretzels or tap dancing for our lives to keep things in other places breaking, Shana and I disagree on this, I think in some ways, she really doesn't want to see things break.
Speaker: yeah um I'm a little bit more comfortable with it because it's when things break that people realize, oh gosh, this is inappropriately resourced or we have the wrong people doing it or, oh that highlights like a systemic issue that we were not paying attention to before. um so I'm a little bit just like I'm more comfortable with people complaining about legal. um I might also be a little bit more comfortable with things breaking.
Speaker: Yeah. Hopefully it's not mission critical and you things really are to that level. i actually I actually really like the way you articulated that of a big sports fan. And there's an old adage like, everybody's great. Everything's fine as long as you're winning.
Speaker: But sometimes you need a loss or two to be like, yeah, we got to fix. and Let's do the football analogy because it's fresh in my head. Our O-lines run blocking isn't as great as we thought. And if we're going to go into the playoffs and we're going to go win some games, we have to really run block better. And by the way, that was highlighted in that last loss in the regular season. Doesn't matter as much right now, but come playoffs, it's one and done. You're done. So I actually really like that analogy. And obviously there's a balance to be struck between um hearing too many complaints, in which case things are are continually going wrong, but hearing the right amount so that you can recalibrate. like I actually really like the way that you articulate that. um I have a question for the two of you. So you talked a lot about um how to set things up for the department, what matters. Would it be too crude to call that the setting of a culture? Is that appropriate? Does it make sense or is it something else?
Speaker: I never thought about it this way. um And I'd love to hear- It wasn't on the list you sent us, actually. We're both actually very- one of the things Catherine has taught me, I used to think it was like, I was like, that person looks so natural up there, right? When people would go to public speak, and Catherine's like, yeah, because they've prepared.
Speaker: And I'm like, oh, so I've got to put in time to prep. No, but I don't, I think part of it is a culture. But i I, the reason I struggled with that is culture to me is, should be ever changing.
Speaker: And even in a, department, there's going to be pockets and there should be pockets of different cultures. And I think even at a company, I think what's most important is that you have that common mission and the common values. So the how. The reason I say that is that the culture that I would find in the compliance part of the organization might look and should look a bit different than what I would expect to see in the commercial side of my organization. Makes sense.
Speaker: Right. And so that's why having a hard time with it. I would say more. There's these values that we abide by. There's a general culture. But again, we're a very global distributed, again, it's the same thing, the culture when I go to the Brazil office and hang out with the employees there is very different than the culture of Manila and Japan, right? But again, the values and the how we work and the mission are all aligned. And so that's a hard time with that culture. yeah
Speaker: there's There's a tie that binds, even though there might be geographical or team-based differences. um I think yeah i think i i get what you're saying. Catherine, sorry, were you going to say something? well Well, so I have some background in compliance and ethics, and they we talk about culture a lot there. And I think for me, culture is not...
Speaker: Culture is tricky because people think about, oh, we have to build this culture of whatever. and I really think culture is an outcome of the values and the mission and the objectives that you and Shana were talking about, that you get this you get this culture that to Shana's point, is different wherever you go. but if you try to get the same culture everywhere or culture as your focus, you're sort of missing the point.
Speaker: Yeah, i think I think that makes sense. Well, like one one thing that really struck me, Shannon, about what you said is how much the people side of the equation, and I don't just mean the people who are there, but the intention that you put behind their performance, their growth,
Speaker: because that has a direct tie to the business outcomes for the company. I've interviewed and worked with a ton of GCs, not enough, actually very few.
Speaker: Think about that connection. I am neck deep in it now because I'm at a series B startup and we're getting to the place now where we're starting to realize, I'll use the word diverse, ah our operating models are in various areas of the company, which is leading to some real business friction now. And like, you know, I i oversee the people team. So it's it's, It's my responsibility now to take a lot of that, unpack it and see what we need to do differently. So that actually really struck a chord with me personally in what I'm doing and what I need to do at Spot Draft as we grow. Because I now truly I'm seeing the numbers play out in front of us. Without it, we actually can't get to the next level. It's not going to happen. But you don't typically, I have not typically heard CLOs, GCs, the top lawyers at companies really talk about that connection and and put a lot of intention behind it. Where did that come up for you? Like where where did you see the importance of that in your career?
Speaker: The importance of what? Like the people? Yeah, connecting not just who we hire in terms of good talent, but then I'll say setting them up for success, which is around like what are their job expectations? How are they communicated? How do we measure their impact? What is the performance management like and how we tie that back to the company outcomes?
Speaker: Yeah, I mean, I think it is something that it's not just me. It's me and Catherine. I think it's something we've done together. Right. And I think we've grown. more intentional about it. This is no lie. And Catherine, we had our CLL directs. I meet with my team every week. And I'll just give you an example is when we both got here, we have an incredibly talented team in Manila that was doing really manual work that can be done with um not even a AI, with software, right, with a tool. um
Speaker: And my first business trip, I'd say, I think it was my first, was to go to Manila with Catherine, right? To say, look, we've got a big chunk of the team here. What are they doing?
Speaker: How are they doing it? Are they fulfilled? Do they find value in our work? Right. And Catherine today, and I tie it back to this morning's call, Catherine today, i don't think she was threatening to leave. and I'm not sure. We haven't had our one-on-one yet. So we'll have that this week. um But she said in front of everyone, you know, if when I leave Zendesk, right, I'm super proud because the Manila team sits under Catherine and she just came back from Manila where she was for business, doing some compliance training a meeting with the teams, et cetera, um was I'm super proud that the Manila team is making such impact and they understand how the work that they do ties to the company's mission.
Speaker: That's awesome. Right. And at that moment, when Catherine said that, I said, like Like this is like Catherine not only cares, but I always knew that about Catherine, which is why we work so well together. It's like we both care about people. We show up very differently to people, by the way. Right. And so we show very differently. But it comes from care.
Speaker: Both of us care. And at that moment, I said, wow, the Manila team is really performing at its best. And I wish I can tell you there's a seminal moment, right, where I learned that this was important.
Speaker: But I think it is just something we have worked together over the years to unlock the potential because I believe in Chi, right? In a part of Chi. And I believe in a lot of things. I believe in horoscopes. I believe in astrology. I believe in Feng Shui. I believe in everything, right? I'm always looking for inspiration somewhere, as everyone knows. But I also believe in science, okay? So um one of the things is like, there's this stale energy.
Speaker: And sometimes you've got to ensure that the chi is flowing, right? And so without that purpose, it can become stagnant, right? And so that's where we are. And Catherine's laughing at my chi and she knows I believe in all the things.
Speaker: I was laughing at you saying, I also believe in science. Got throw that one in there in to make sure. i also believe in science. Yeah. just to be clear Yeah, I had an interesting conversation with my 12, now just turned 12 year old about science and a australia he's really, really into the Bible right now and he's just digging it. And we're not a very religious family at all, but he's just found something there and we were just talking about science and I told him, i was like, look,
Speaker: There was a time when people didn't understand a lot of things about the world, and now we do. And so magic and what we may have considered miracles now turn into science. It was just a matter of understanding things and how they fit together. So yeah I get where that comment's coming from as well. um Let's talk a little bit about the importance of operational expertise and operational discipline in legal departments. um I would say that in 2026, it is starting to become table stakes for CLOs and to have a partner ah who can execute on that vision is is one of the most important things. But as you think about where you may have worked before or seen that it wasn't an intentional thing, where have you seen, Catherine, would love for for you to start with this one, where have you seen seen things go wrong? where there hasn't been intention or around the operational side of things in a legal department or in teams? I think think legal operations is harder than people make it out to be.
Speaker: um Because it's real easy to implement some software But if you're just implementing it without thinking about like, why are we doing this and what's the outcome we're looking for? And does this actually do that? And if it doesn't, is it something we can fix? um Then you get, then it's a big mess.
Speaker: Right. And nobody is like quite sure, like we have all the tools or maybe if we just get the right tool. um It's more than that. You have to bring together, you know, everybody knows the people, of the processes and the systems. But those three words and encompass a lot. Right. yeah And the bigger the department is, the more complex it gets because you've got more people um and your stakeholders tend also to be bigger and the stakes are are larger.
Speaker: um so I just, I feel like if you don't have your operations working the way that they should and evolving them as needs arise, you're sort of risking undoing all of the things that you've accomplished beforehand, right? All of the great things, Shane has talked about the systems that we've put in place, um but it's not a, um I don't know if you're old enough or have watched enough TV to understand, set it and forget it.
Speaker: Sure do. Yeah. um Let's not set it and forget it. It's constantly evolving. You always have to ask questions and you have to keep after it. And it's a giant pain sometimes. Yeah. um And sometimes it's not sometimes it's not my first priority.
Speaker: And then we start to have issues. Yeah. So... I don't know if that answers your question, actually. It actually in is a perfect segue into the next part of this, because I think one of the first conversations Shana and I had, she had said something which some people might can't find find to be controversial. and but I'd love to kind of get her perspective on this, which is that I don't really believe in legal operations. But there was a really specific reason behind that, because at first I was kind of taken aback. was like, hey. I've been in legal ops for like 10 years now. i think it's pretty important, but there was a real reason and Catherine kind of hinted at it just now. But before I kind of call that out, sha can you share a little bit about your experience with that? I think it's an important one to call out if we if if part of what if part of the goal of this conversation is to make sure that we are thinking about legal departments from a legal and operational perspective to improve.
Speaker: why was that your perspective like what happened what i just wanted to have a hot take that day i just want to feel in spicy ah drink and ka laot and i am ah a lot more alike than we are i don't think they'll see that but no um no seriously it's um look We you you and i I think after we had the conversation, I double click further. Actually, i think agree more than we disagree on my take on legal ops. Right. I i think that there was just like privacy at the time became a commoditized like, you know, everyone has become these privacy professionals. They were getting all these certifications.
Speaker: They were privacy zealots to be privacy zealots and almost forgot about the reason why their privacy laws, right? It's to protect the customer, the consumer, the data, and still to innovate for that customer, consumer, and data, right?
Speaker: Both things, the consumer, the average person wants both things to be true. And they usually just want choice and transparency. Yep. Right.
Speaker: I think a lot of privacy professionals lost that. In the same way, I think that there was a boom for legal ops professionals, folks who wanted to put in software to hang hang out with vendors, in some cases, buy software, without that mission and that goal of how is it that what I'm doing aligns to the business strategy?
Speaker: Aligned to the mission, sometimes they were doing it without that mission. And what is this out what is this outcome? And I'll tell you what, and this is a mistake that we've had recently, right? And this is, we're going to see this with AI, especially generative AI a lot more.
Speaker: and And I love talking about mistakes in this way. We had someone on Catherine's team who did an incredible job working on something, a bot for us. Incredible work, right? Really forward thinking.
Speaker: i really applaud the work. But when I take a step back, I'm like, well, do we save time doing that, right? do we What is the goal by doing this? Are we just doing something to check the box?
Speaker: And I find that legal ops had become that. Yeah. And when I interviewed folks you know for legal ops roles, it was there when I asked you, so tell me about something so succeeded, it was always about, I put this billing software in place. I know outside counsel fees. I've put this CLM tool in place without telling me what they really achieved with with that.
Speaker: So you then come in, sometimes you come in And you're like, okay, we have this system in place. Actually, this is causing more pain and harm for my attorneys who should be focused on something else than if we did it in a spreadsheet. I mean, Catherine could tell you there are certain systems.
Speaker: I won't tell you where that I was just like, rip it out. I don't mean, I don't care. Rip it out because it's not achieving the goal. And That's where I think we're both aligned is that role. Like you think like sales ops can't afford to just, I mean, maybe they can actually wait more than we can to just be put in in systems to put in systems that aren't going to close that make it faster to go from quote to cash, right? In sales ops, your job is to make it easier and faster to go from quote to cash.
Speaker: That is my expectation in legalism, but sometimes we forget about I'd say far too often we forget about it. I see it with our own customers, you know, the know your why of doing anything.
Speaker: Both of you raised it. I think that's that's been a huge component of what success has meant across legal departments, but very few people actually slow down to be like, what do we need to accomplish? What problem are we trying to solve?
Speaker: Before they even get to that last question on the spectrum, which is, do we need a tool for this? Do we need a system for this? And that is, you know, when I first got here and Catherine's laughing, Catherine's having kathervin already laughed in because, you know, well, I get not I won't say it's here.
Speaker: But one of the things I'll ask people, even as the CLO of Zendesk today, right, I try to get to see our employees where they are all over the world. I'll sometimes ask them, hey, why are you doing this?
Speaker: And if they cannot answer the question. Yeah. Catherine probably gets a phone call from me about the time of the day and where I am, right? And then i'm I'm having us look at the whole system because that person could not answer why they were doing something.
Speaker: Yeah. but Having an individual be able to connect with their purpose is a lot harder than i have ever found it to be. um At an individual level for myself, like that's something I've always needed in a job, but it's amazing how hard it is to to make sure that the company's operating in that fashion.
Speaker: Um, Catherine would love your take on legal technology in general, as you have been steeped in it now for a while. Where do you see things go wrong when it comes to legal technology, uh, either on, on the vendor side, like mine or on the buyer side, like yours?
Speaker: This tricky. Um,
Speaker: on the vendor side, um I'm interested to see what's going to happen to some of the legal tech providers, um given the work that the open AI's and clouds and Googles are doing.
Speaker: yeah um If you are, i don't know if your product is something that only that gets me a hundred percent of the way there and then open AI and anthropic and Google offer me something that gets me 80% of the way there,
Speaker: what what ah How are we thinking about that last 20%? um So that's that's something that I'm thinking about on the vendor side. um on our side, think we're sort of in a weird inflection point, right? Where we have to figure out is what got us here gonna get us where we're going?
Speaker: um So my point about like, do we have the appetite to do the 20% ourselves? Is there going to be a time when it's not 20%, it's actually 10%. So we're in a weird state of flux, which is why I don't have a strong opinion right now.
Speaker: Which is rare for me. I've recently learned. one of but One of the things is that I think, especially being at a tech company right now, we're tech, where you've seen that legal technology,
Speaker: has been ignored is how do we use our own tech for legal? And so I don't now believe in this legal tech business. I'm just like, okay, legal tech, y'all had a moment, right? It was a moment. It's now just tech.
Speaker: And like, do we have good tech? So at Zendesk, we are making sure that we are utilizing our platform within our team as well as we can, because guess what? When our commercial lawyers are on the phone with the customers or I'm meeting it with customers or Catherine is me, you know, what's the most compelling is that we're using it ourselves as well. and We can explain how it's used and we understand the product. And so i think this is really an exciting time in the industry when no longer are we going to be stuck. And I think this is something for you as a vendor, right? It's going be a challenge for you is.
Speaker: How are we going to make ourselves special and compelling to be tech that lawyers want to buy and no longer this legal tech business? it is it is front and center for all of us on the sell side, particularly over the last year, i'd say the last 12 months. I think it's been a, it's both an exciting and a crazy and chaotic tumultuous time. The amount of eyeballs um that the globe now has on the legal sector as a whole because of companies like OpenAI and Anthropic, I think is really exciting. I think the solutions that individual people, teams, departments and companies can craft as a result of it are fantastic. And it's actually kind of a perfect segue into the last couple of questions I have for you guys. As you think about AI in general, and I'm talking generative AI,
Speaker: for legal departments? And forget about specific tools or anything like that. But as you think about that concept and that solution coming into legal departments, do you think it's a game changer for legal departments? Or do you feel that it's ah just another tool, albeit a powerful one, that is now coming into this tech stack?
Speaker: I think if you apply AI, you apply this 2026, 2027, 2028 technology to two thousand and six or raven two thousand sixteen processes and systems that
Speaker: you're not going to get that much improvement. And so my feeling is AI is super powerful right now. It is, it's a little bit scary, um,
Speaker: um it's not a mat it's still not a magic wand. nope It's still a tool. and there's still like so much work to be done with the systems and processes and figuring out what are the improvements that we need to make there um While we also, it's not a let's fix it and then apply AI, but it's figuring out how to marry the two. um i'm really frustrated because I still have not been able to build a prompt such that it drafts things to sound like Shana. And I don't know. i feel like my analytical skills are really, really good. And so I should be able to figure it out, but I haven't figured it out yet. It's so frustrating. um
Speaker: But building, like making those changes and evolving with ai i think is where I am. Yeah. Where am I on this? I,
Speaker: I i Catherine, I'd like you to share with like how you're thinking about all the the flowers as well right now in the department, because i also, I'm letting folks have fun with it right now. It's it's powerful. i want folks have fun with it, but also I'm not gonna, I don't think as you think about value and and and and what folks should be working on,
Speaker: I don't think my ah senior counsel on anything should spend like 80% of his or her day or their day building a tool either. Right. And so um right now we're letting, go ahead, Catherine, I'll let you finish with the flowers. That you're letting.
Speaker: Shayna doesn't, Shayna doesn't, um doesn't love idioms and I use a lot of them. so
Speaker: The one that she's referring to is that we're letting a thousand flowers bloom. yeah um i was at a conference a couple of months ago and heard it described in a really good way, which is that people are making kind of individual AI snacks for themselves. There department wide meals that are going to have to get built.
Speaker: And then there's like the company wide banquet. And what you don't want is for like legals making, Beef bourguignon and um finance is making beef jerky and somehow we're going make a meal out of that or ah a banquet out of that. um So we're thinking about that. We're letting people make all the snacks they want.
Speaker: We're letting a thousand flowers bloom. um But at some point, like, Why are we building these tools and who is going to maintain them and why are we maintaining them and what are we getting out of this tool? um Because every time I see somebody with like, well, I built this cool thing on LinkedIn.
Speaker: i don't they don't explain why. they never talk about the problem they're solving or the outcome that helped them get. It's just I built this cool thing, which is cool. Right. I love that. But.
Speaker: I, to Shana's point, like senior counsel shouldn't be spending 80% of their, of their time on that. They should be using something that was built for them somewhere, whether in legal or outside the company to make their work, the quality of it better or to make themselves more effective. I don't like to use the word efficient because I think efficient is connected to busyness. I want people to be more effective. Yeah.
Speaker: I like the way that's couch. like the that's couch. Shana, what do you think it means for lawyers specifically? All the way back into as we are coming out of law school now over the next few years, as you think about talent gaps or opportunities or a way of thinking for lawyers, do you think it is going to have a meaningful change in those things for for the legal profession? For me, I think you'll listen to anyone and someone will say they're advising their kids to do something different soon My advice means the same.
Speaker: Yeah. Right. Is to understand who you're working for. If you're working for anyone, right. If you're lucky and you're working for yourself, great. Fantastic.
Speaker: What they're doing, understand the product really, really well. It could be, Hey, i work at Chanel and i I, won't mind working at Chanel. I like, i like Chanel personally, but like, you know, um I do. Yeah. That's a problem. But,
Speaker: Know the product really well. Know the stakeholders really well. Know who you're serving. Know the industry better than anyone else. Know your competitors as well as you know yourself.
Speaker: Yeah. In this time of AI, that still does not change for me. Yep. And I think with that, you'll do the ah better job, right? And you'll figure out how to influence your stakeholders with all that knowledge, right? like If you're going to influence sales, the best way to influence sales might be to like, hey, you know, that competitor over there is doing this. And they're like, oh, really? Let me think about it. Or an influence product and engineer. And it might be like, hey, this is what the customers are asking for. And we're losing deals because of this, because of what they say, their product doesn't work. Right? Like, you've got to figure that all out. Well, if you want where you are to do well.
Speaker: Yeah. It's a great way to to wrap up the episode as well. By the way, i'm I'm exactly in that same boat and I'm somebody who sells an AI product out there in the market, but those things for me do not change. They don't change at all. Maybe it helps you do each of them a little bit better or a little bit differently, but it's still the foundational thing that we need to focus on. My guests today have been the amazing duo from Zendesk, Shana and Catherine. Thanks so much for sharing your wisdom and your insights with us.
Speaker: Appreciate it. The pleasure been lot. Thank you, Lakshay. All right. I feel a lot less stressed now.
