General Counsel Shana Simmons Describes Her Impressive Career in Law and Legal Ops

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Hello, everyone, and welcome to another episode of Pearls on Gloves Off. I am your host, Mary o', Carroll, and with me today is the amazing Shayna Simmons. Shayna is the general counsel at Everlaw, a SaaS platform that helps law firms and in house legal team companies more efficiently solve the challenges of discovery and investigations. It was at Everlaw that Shana hired and built out their legal operations, function and runs a very efficient and effective department, which we will get into during our talk. But prior to Everlaw, Shana was at Google for close to nine years, which is where we first met and worked together. And her last role there was being head of Google Cloud's Go to market legal team. Now, before that, Shayna started her legal practice as an associate at Cleary Gottlieb in New York and in London, and she currently lives in Oakland with her husband and her two kids. Welcome, Shayna. It's wonderful to have you here.

Oh my gosh, Mary, you're such a legend. I'm so happy you took the time to be with me today.

Oh, no, right back at you. Well, congrats on all your success. We've known each other a long time and I think you probably have what is like the dream career path for anyone who's thinking about being an attorney.

Right.

You started as a high profile, big law associate, you moved in house to an amazing place like Google, and then moved directly into a general counsel role. Tell me, was this kind of always your goal? Was this your dream to be a GC and a big time attorney?

It was not my goal. Like, I think I wish I was more intentional in where I ended up. Look, my dream job when I was a third grader was to be a Supreme Court justice. So I don't know if I at least made it to law school, graduated, but I think those dreams of being a Supreme Court justice and being Sandra Day o' Connor are dead. But in terms of going into Google, nothing was planned. It was all serendipitous. I went to law school having known no lawyers. I was the first in my family to even graduate from high school. So growing up in the Bronx, super poor, but I had this dream, like I told you, to be Sandra Day o'. Connor. So I went to college, taught for a few years, and my mom reminded me, my immigrant mom, like, that's cute, that's really good that you're giving back. But we talked about law school and making money. So, like, go to law school, got lucky, got into Berkeley and realized then that in order to make money, I Had to do corporate law and went back home to New York and got a great job at Clery. And I chose Clery because the people were phenomenal. I met with a diverse set of folks when I did OCI on campus interviews, went to their New York office, did some private equity fund formation, which meant I did nothing, to be honest, Mary, because I was a first year, right? What can I really do? So I did some stuff. But I got really lucky that this one partner gave me some commercial deals to do for Ports of America. So I was doing some NDAs and doing some commercial deals. And then I went to London and did all securities work. And at London, as it is for any associate, I was working like crazy. I was like Bill and I, you know, my time was my value, nothing else. I built close to 3,000 hours that year. I think I was the worst associate probably to ever be in London. And I and Veena Ha, who's a mutual friend of ours from Google, had gotten this, what he called a dream job to be a contracts manager at Google. Leaving Milbank at the time. And he kept reaching out, like, leave Clery. Like, come back. I got engaged to my now husband to an Oakland firefighter and had to figure out a way to come back west from across the pond. And after spending the night, another night at the printers with some pantyhose on and some pearls, Mary, pearls on too. I applied for a contracts manager role at Google. And it to me was like this kind of ego. Like it was an ego. It hit my ego a little bit because here I was this associate at this, what I thought was this really important law firm doing what I thought was the most sexy work on the planet.

Yeah.

And to come and do commercial work, a lot of the Clery partners kind of like, are you sure you're going to go in as a JD and Esquire, going to go be a contracts manager. And I realized at the time, you know, people talk about climbing Mount Empress. It was my time to go to base camp, right? And still learn a skill. And I had this kind of sense of myself that if I learned it and I did well, I'll get promoted eventually to the council track. And as you saw, I certainly did right. I spiked in my career. I learned my craft, I learned enterprise. I'm one of the few lawyers, I love enterprise. Give me a sales deal any day. I love sales people. I love supporting the organization. I love the engineers who build products for customers on a daily basis. So I love everything about enterprise. And I worked my way up at Google, I just worked really hard. That's not my craft. Got to know the clients and built out some teams. Pretty junior on at Google, had some fun along the way and serendipitously got this job at Everlaw again.

Yeah. So I'd love to go back a little bit because your story is so interesting and I love what you said about sometimes we kind of have to take a step back to move forward and, you know, you realize you're what, maybe what you graduated with and what you wanted to do coming out of school, you start doing that for a few years. And I was the same. I wanted to be an investment banker. I wanted to be on Wall street from the day I was a little girl and carry a briefcase and wear the, I'm not surprised, the skirt suit, you know, and power suits. And I discovered very soon that that really wasn't for me and had to kind of find myself.

So.

Yeah, I love that you did that. And you know, I think similar to you, I had that confidence that it's going to be okay. I know that if I find something else, I'll knock it out of the park and I'll work hard and I'll get promoted and so was that scary for you or did you kind of always have that confidence?

I mean, it was even scary for me when I came to Overlord, quite frankly. Right, yeah, of course there's that fear. I would love to say that, oh, I don't live. Fear probably motivates me, and that probably comes from having an immigrant mom who made sure that I had to do well in school growing up to get out of the Bronx. Right. Like, it was very important. So, yes, of course it was scary. Like, I could have, in my. I could have gotten not stuck. I think contracts manager is a great position and a great career for other people, but I had other goals and someone that had just spent $200,000 in student debt at UC Berkeley. And so of course, it was part of me that was scared. But once I got into it, like, I, I knew that it wasn't that hard. Right. Like, I, I love to find a common need in place for people. Right. I think it is my. I've learned this, my enneagram personality type to, to be the helper. And so the beauty about deals and enterprise is that both businesses are partners. And once I realized that, I had that empathy for the customer and, and I had the empathy for the salespeople. Their jobs are hard.

Yeah.

SDRs, I think, have the hardest job on the planet. And so once I used and I leaned into my superpower of empathy to get these deals across the line, I knew that the promotion would, would come forth. But I also knew, Mary, I learned from the firm that just like not having my head down in the sand just to do the deals was not going to get me promoted. It was important for me to learn like all the other parts of the business. So I knew what the clients were thinking. I knew by my second year what our competitors were doing in their deals. Right. And the way to way to help my deals was to figure out what are other people offering? How can I help our clients figure out what we need to do to get enterprise ready? Because Google is a lot of things, but what it wasn't when I was at Google in 2011 was an enterprise company. Right. And so I am really proud of being on that journey to help us become an enterprise. Help Google. Sorry, not us. Us at the time.

Yeah. And, and let's back up for a moment because I think the other thing that's really interesting is the transition from the law firm associate to the in house person. And there are definitely. I know I felt coming from a law firm, even on the operations side, it was a whole different ballgame. And I know that for watching, you know, young associates move, it's a different set of expectations, it's a different way of working with clients. What were some of the challenges or lessons learned or aha. Moments that you had moving from the way you were trained at a law firm to performing in house?

Oh gosh, I stopped wearing pantyhose and I joined. But I think some of one, I had been trained, right. Time is value at the law firm. You're billed like the money makes money off of your time. Correct. But I also was all work, Mary. Like I was just, it was all work. I still work a lot. I'm one of those people that I, I like to work, actually, I like working. But it was all work for me, like very unhealthy. And my BlackBerry, I said I slept with it. Right? It was, I woke up to it, I slept with it. And going in house, I was able to see the Mary's of the world, the Christians of the world, the Dan Cooks, the Julie Haniger's, the Halimas. Right. Of the world to realize that there was much more to what I can bring to the table by bringing more of me. Right. And so while it was just Shayna, what I can do for the client, at the time I was involved, I evolved as a person in house. I looked around to see that all of you were excellent at what you were doing, whether it was operations, managing, or your legal craft. But you also had other interests in other lives. And we talk about it over lunch and we talk about it there and, and bringing that into with my clients and being more of who I was and being that to the customers instead of just a robotic lawyer really helped propel my career as well.

Well, and I bet that's just it, right? Bringing your whole self and being interested in probably more of the product, understanding the company, understanding that, you know, the engineers, the salespeople.

I think the other thing is at a firm, you don't learn how to be more efficient. You just don't learn because again, you're billing your hours. So efficiency is number one. When I was at Google, this is why my first hire, and we could talk about that later, was a legal ops manager. When I came to Everlow at Google, I was like, there are ways I could do this more efficiently, not just for me, but for my colleagues. Right. And so if I'm negotiating a deal, there is no reason that if the same issue comes up for my colleague Agnieszka or from my colleague Supreet, that I can't keep a fallback matrix for folks to understand why we made the difference or for us to benchmark and keep that alive as to what other folks are doing. And so I think, unlike the law firm also in house, I learned how to be more efficient, Mary. And how to use operations and tools and tricks to just make my job go smoother and make others go smoother as well. Yay.

Well, you know, I love to hear that. And you and I were at Google together, of course. You were there for almost nine years. I was there for 13 or so. And I think that it was a, I hope you agree, a very magical time and a magical place because we experienced some serious hypergrowth. And I think that's why we were so hyper focused on efficiency. And how can we get more done because there's only limited hours in the day and the business was exploding. Tell me about your Google experience. You know, how much growth did you experience? What was the culture like? Like, why was it so magical to you?

Oh my gosh, it was just, okay, let's talk about the growth and then I'll talk about the magic that has nothing to do with the growth, but to do with it, I think. So the growth. When I started Google, we were negotiating, we were selling free Gmail to businesses. Right. Like the concept in 2011 was wild. And it was five bigger deals and I would get worked up over $30,000 deal with some company who was buying Gmail. That's how it started. When I ended, right, I had already the, the legal team at the thought at that time supporting enterprise had more than has grown more than 10x. Right. And so we have to train folks. We should bring them in no longer. Oh, go ask Shayna about that. Go ask, you know, Dan about that. Like we, we kind of had to build documentation and processes that people can follow. Our clients went from 300 to 30,000.

30,000, right.

And I think it was magical because each time someone came in, the business changed so much. Legal almost became the encyclopedias of this is the why, this is the how, this is what we can do. And so the business allowed us to be more than just lawyers. It allowed us at all times to be not in this silo, but to lend our business acumen to let them know what we've seen before, to let them know what the customers are asking to help them, to help translate to them what the market's looking like, how it's shifted and how to build the products that weigh in to sell. And so for me it was just, I'm so intellectually curious. I'm so excited by change. And so the whole time was exciting for me in terms of socially. I grew up at Mary. You saw me pregnant with my two kids at Google. I had two baby showers at Google. I, you know, I just really grew into being more of who I was. We talked about being busy a little bit. You talked about this, you know, the sense of like figuring out who you was. I found myself at Google. I didn't have the time to check in when I was at the firm with who I was, what was important to me. But I was always driven by the mission, but also found the time to know that managing people was something I was good at managing and bringing out the strengths in others was something I liked. So let's move in from being a lawyer to also managing. Being involved with the business is something that I loved. And going from the lawyer, helping build the products, understanding the flow of data, you know, figuring out what the FUD is in the market so that I just found myself and I and I and I spent. Plus we had a lot of fun while doing it, right. We didn't take each other seriously. We had so much fun. But also we didn't talk about DEI as much like we didn't talk about it. We just walked it. Like the teams were incredibly diverse. Like it was just, it was from personality types to demographics to people's experiences to people's schools. And I just found that it was a place where everyone was able to bring his or herself. I laugh, I tell someone, you know, there wasn't even one way to dress. You had someone wearing Lululemons, right? One day you had Mary wearing pearls, you had Daryl wearing a suit, right? And so it was just, it allowed us to be ourselves. And to me, it is truly a special place and it is what I hope to build in my department and at the company today.

Yeah, I think it was magical and it was the culture, it was the collaboration, it was the bringing your whole self and the dei, I think that was there naturally. I think you're right. I was talking to another ex Googler legal department person just yesterday and we were kind of reminiscing and he said, he remembers when we actually brought in, we acquired a company, we brought in some lawyers from the outside and that lawyer walked out of their first meeting like scratching their head. And he said to this, this new, new team member, you know, what was, why, you know, why was that such a shocking meeting? And he said, well, you guys sat around and talked about everything that needed to get done and everyone was jumping in saying, yeah, I'll take that piece, I'll do this, I'll work with you on that. You know, by the end of the meeting, everyone had their marching orders and was like volunteering to do stuff. He said, if that was my old company, we'd all be looking down at our Blackberries or what have you and like trying to hide our heads and not raising our hands. And that was it. Just, it was a special time. We were growing so fast. Everyone was kind of in it, rowing in the same direction and really collaborating towards the same goal. I think that was really unique. And then I also love what you said about just being intellectually curious and getting involved with all parts of the business. And this is what I think really makes someone successful in an in house legal department, whether you're in operations, whether you're the general counsel, whether you're an in house lawyer, is that you have to kind of look beyond the walls of just being reactive and just being the lawyer or just, you know, doing kind of what work comes your way. It's about seeing we, we in legal have just such a broad spectrum of views and touch points across the company. Maybe unique, uniquely so. Like we know what's happening with the product, with the sales, with the finances, with the real estate. I mean the privacy, like, you name it. And because of that, if you know what the company's goals are, you're really able to add a lot of value. Right. To the leadership team, to the other teams that you're working with, and letting them know what you're hearing, what you're seeing cross functionally, because you have that role.

Yeah, I think it's. It's really special. I. I think it is a privilege and an honor, and I think it is a super. I think it is for all of us as lawyers or operators in the legal department to lean into that horizontal view. And, Mary, there's one thing you didn't mention is the people. Yeah, we get to touch and feel a lot of people every day. And so how do we make people feel better about their jobs? Also, how do we help the business know that they're not clear in their priorities? So you've got people running around over here doing something that I don't think is that important to you. Right. And so how do we not burn out people as well? And I think it is. We also have just such a. I don't know. Also, we don't talk about Laura set in culture, but I think in a way, we also really can infuse and help a culture as well.

Yeah. Okay, so I have to ask. Everyone always wants to know what it was really like to work there. So what. What kind of favorite memory or favorite story do you have of your early days at Google?

Oh, my gosh. I have. This is. I'm gonna. Gosh. So this is kind of sad, but exciting, but after the Trayvon Martin death, I don't know if you remember, but our chief legal officer at the time and Alphabet, David Drummond, like, walked over with a bunch of us. The Black Googlers network had planned to march. Right. And to see him take the time. And we all walked over in hoodies. And the investment he put into societal causes at that moment, I was like, I am at the right place. Like, I am growing as a lawyer. I am having so much fun. And there's plenty of fun memories I've had dancing on dance floors, even with you, Mary. But I think also that impact on social justice and knowing that we could play a role in the largest societal issues really was one of my favorite memories.

Yeah. And seeing leadership and leading by example and really making it important to the whole department was meaningful. So how has the transition now been to general counsel? How long have you been now doing this role at Ever Law?

I joined Everlod over two years. A little over two years ago. And it's so I have to say I miss my friends. I grew up, like I said, I have, you know, I feel like I have my little brothers, my big brothers, my uncles, my aunts, my cousins, my sisters, my brothers, you know, all at Google. So I miss the camaraderie because obviously it's not as big and it's not as scale, but it's fantastic because what I loved about being a lawyer at Google, I'm able to do on a day to day basis as a general counsel and as a matter of fact, just day dig deeper into the quantitative measures behind the qualitative. Right. So understanding, digging into understanding what drives ndr, right? How do we think about ndr, nps? How do we get to the revenue growth? Why year over year growth is important, but also looking at the people processes from not just the lens of the lawyer to say, well, you know, this can get us into some trouble with some plaintiffs lawyers. But yes, that's important. But also how do we set the tone so that this is the right place for everyone to bring them best selves? Because there is as a woman of color, as a black woman, there's this incremental kind of burden on us with how we show up every day. And it kind of as we move up, it kind of, we learn to let go of that weight. But I remember what it was like to be at Cleary, right, and have that burden and what it was like earlier in my career. And so how do I help set a company? How do I help create a company where folks can don't have, we can make it a little less burdened to be themselves at work. And so it's been fantastic, it's been great. My colleagues have been great. And I love that we're building a product for lawyers like you all are. We're building a product to make it more efficient for lawyers to do their job right. This is like all things that are in my wheelhouse ironclad more than I probably saw Everlaw, because I am a commercial lawyer at heart, but also that we do it with this underlying mission of promoting justice by illuminating the truth. It just speaks so core to what we do today and the work that we do with giving it, give it away to free with Everlaw for good.

That's fantastic. How was that sort of initial transition? You kind of touched on it earlier, the imposter syndrome. It's intimidating. I would imagine it's very intimidating because the scope and the breadth of the role of a general counsel is Going to be very different from, you know, this practicing commercial law or practicing corporate law. How was that for you?

Oh my gosh. I think every day I have a moment of I want to hide under my desk because I don't know something. So I had to just become okay with being mediocre at some things, not knowing some things and just like not only doing what I'm good at and want to do, which is commercial deals. I think my first two weeks we had some employment issues and I was just like, I'm not an employment lawyer. I will get this wrong. I don't know, I guess, but let me just find out what I got okay with Mary, is just finding the right talent around me, whether it's outside counsel. And I got so lucky. For example, we're a federal contractor by finding the right government contractor council initially to badass women of color who support us. I got really lucky by finding the right employment person to help us who's now onboarded and she's a full time, part time but employee now forever law. So I think I had to realize what I didn't know and figure out where to supplement my skills and just get okay with that. The other thing, Mary, which would have driven you crazy is there was no process for anything.

Doesn't surprise me.

If a deal were to get done, they literally just emailed the commercial counsel. There was one commercial counsel at the time, they pinged him, they emailed him, they were using anyone's paper and everyone's paper and it made me uncomfortable. So initially I, before I took the job, quite frankly, I told aj, I found, I said, look, we're a legal tech company. You should understand the value of it. My first hire needs to be an operator. It needs to be a legal ops manager. And I got really lucky to find someone. And I knew that because at Google, I think while it was great at a lot of things, we threw a lot of lawyers at problems that could have been done more efficiently at operators or program managers at times. And I didn't learn that until I was leaving Google. Right. That I had the wrong people working on the wrong problem. There was ways for us to even scale even more.

Right.

And so I didn't want to make that mistake here. And so that was our first hire.

Even though you saw an amazingly well run legal ops function at Google?

I did, I did, of course. But you all didn't have that much time to support enterprise on time, so.

Yes, yes, there's a lot of projects to work on, so. And you've now touched on something that I think is actually really important for in house lawyers and general counsel, which is managing and managing people and growing a team. Because you don't have a lot of experience doing that coming out of a law firm. You've got to learn that. And I love what you said about you as the leader of your department does not need to be the person who is the expert at everything. And it takes a lot of recognition to know that you need to be hiring the best people around you and to surround yourself with the experts that you can lean on and let them shine. That's going to make your department shine. That's going to make you shine. So love that you did that and would love to hear more about kind of your first hire. And I know that you did hire your legal ops function as your very first person. A lot of general counsel I talk to are overwhelmed when they go into their new role thinking, oh my God, there's so much work to do. There's so much on me personally. I would love to hire someone just like me so that I can shed some of the work to that person.

No, I don't want another meme, Mary, you're doing it wrong. If there's. I need.

That's the right. That's the right answer. And so what. How did you recognize that though? Because I think it is a very common fallacy to just hire more people just like you so that again, you can spread out the work that's all coming to you.

Yeah, I think it's. We talked a little bit about fear, but a little. What drives me is also a sense of insecurity as well. Right. And so there's this. That is a balance of confidence. Being arrogant at some things, being stupidly, ignorantly arrogant at some things and insecure in others. Right. So if we had a lot of me's, I'd be scared that there's a lot of things that are missing. But when I was at Google, I managed really talented people who all had very different strengths.

Yes.

And who challenged me, who pushed me, who allowed me to think better. There were some folks who are way more detail oriented than I am. And so they didn't miss the, they didn't miss the dotted of the I's or the crossing of the T's. And there were some folks who were more, what's the word to put it, more process oriented than I was. So by time I turned around, there was a process for it in documentation and. And there were folks who are more technical than I was. Right. When you're at a tech company, it is also important to have all of that. And so I think I learned earlier on that my job was just to get out of the way of these people and to let them shine and to be their shit umbrella, as Dan Cook would say, and to allow them, give them the resources and tools. Right. You have. You want an athletic team.

Yes.

But the team can't move or go fast without the right resources. My job was to ensure what each of them needed. They all needed different. That I got out of the way and that I, I helped them with any obstacles. Right. What I also have is as the leader, as the manager is also the. Some of the historical knowledge, some of the personality that, you know, the personality knowledge, like how do we, how do we address this with this clientele, but also the horizontal view. And so it was my job to be as transparent with everyone so that they can do their jobs better. But yes, no, no more of me. People who are not like me, who have strengths that I don't, who I don't bring to the table.

Yeah. And looking across your team and knowing where you have strengths and knowing where there are gaps and then filling those gaps, I think that's exactly how you, how you build a strong team. And I love the analogy to a sports team because you don't want everyone playing the same position.

That's right. I watch because I watch my kids. Right. They play soccer now. I. And they all just go to the ball. They all just follow the ball. Right. And they just follow the ball. But I don't need everyone just following the same ball. So it's. How do I make sure that everyone is doing, playing their role?

Excellent. Excellent. And what about those who've never worked in a department that had technology and tools or even legal operations? I know. So you, you came from Google. We had tech and tools, we had process. What would you tell them about starting this function or even investing in this idea? Because I think it's. It's foreign to a lot of people who haven't seen it in practice.

I mean, I feel like really, is it, is it that forward right now?

It is. A lot of them will tell you it's not broken. They're using spreadsheets and email and it's fine. Or they've got this archaic system from 15 years ago and they put it in and so everything must be fine.

But they haven't seen good yet.

That's right.

I think you should be speaking to them more. I think that they haven't realized like.

The, like what's possible.

They haven't realized what's possible. But also they are wasting time and energy on things that don't need to be done by them anymore. Right. And so we're, we're playing, I think a lot of lawyers. We play catch up. So I'll tell you this. So when you're in the leadership team, right, and the board members are thinking about leaders and they're thinking about growing the team and making sure you have the right like people, it's always like, is this person going to get us to the next phase? Right. GNA functions of finance and legal, we usually work with one hand tied behind our back and that's what we used to do. We're like, we've got to see this. You've got to do it. We've got to do it. Right? So when the board is thinking about, they're like, oh, is that the person that's as strategic to get us to the next level? Do we need a new GC or do we need a VP of finance? We should all be thinking about how do. Are we using our time to align our objectives to the business? Are we using our time to be more strategic? Are we even lending any strategic insight to the company? If we're not, then there are some tools you're not working because you're wasting your time. Email and pings and chat. I mean, we, as you know, we are an ironclad customer. I know you didn't even ask me about ironclad. But you know, by using ironclad, we're able to not one get out of sales's way. Because once you, once you put a lawyer or any legal person in the deal, you just gunk up the deal, you slow it down, right? We're going to all have to have our value. We're going to have to all redline something. Even I do that. Right. But if we can scale the processes and use tools and things, we have more time for ourselves to be more strategic. So I myself, I'm even trying to figure out how to find more time to just think proactively about the regulations and the evolving regulations that are coming down.

Yeah. And so in your experience, then, having built out a very efficient and effective and modern legal department, what are some of the initiatives that people should be thinking about that are important to focus on if you're going to scale, if you're going to, you know, move into the next century?

So I think, I think one is if you're. It depends, right? It depends on Consumer. It depends on if you're enterprise. If you're enterprise, which is where I love is you have to invest in a good contract legal management tool and figure out as many workflows you can put into the contract legal management solution. Right. So it is every day we're bombarded by inbound vendor requests, right. We want to use this comp Marketing has a request for an inbound thing and it seems like it's really quick. But if you're doing 24 quick inbound requests a day, that adds up. So you haven't had time to do anything. So figure out is there an isa, Right. So one is to get the tool, but there's also you have to fix the processes. I don't believe tools by themselves just fix anything. And you're an operator, you know more than I do on this. But you have to have the underlying processes and systems right. You have to have good foundational templates that are fair for both sides.

Right.

You just can't go with a template that, you know, only you have, you know, some sort of liability. I have no liability. My liability is capped at 100. So you have to figure out what's fair, what's industry standard for templates. But you also have the right have to have the right workflows for the sales teams or the inbound teams to get to you at the right time and have thresholds for that. So that's one that's very specific to enterprise or just anyone doing any contracts, quite frankly, even inbound. The next is product counseling. Right. And so I think it is on all of us to understand and on the lawyers, especially the product council, to understand the product. And once you understand and you have the right tools in terms of how we collect the data, right. You realize that there are other folks at the company that have this, whether it's the devs team or this team, and how do you work with them to collect the information you need and scale it? Right. And where do you inject yourself in the process so you don't have to see every single workflow. What do you figure out as a threshold for you to get involved? Right. So I just think that there's a way for you to look at anything. Mary, I'm also a big believer, and this is an email thing in folks not emailing one person on the team because I realized earlier in my career that it meant that that one person was like the single point of failure, one single point of failure or the single point of success. And we, I realized because I used to be that person. I used to like to be the hero, right. Like I, I closed my one of a deal when I was, you know, delivering my son. Right. So this is 10 years ago. And I remember I was like, oh yeah, I'm a hero. I close it. We don't need any heroes. That leads to burnout. And so I don't believe. And I'm always telling my team, I'm like, if someone can only ask you the question, there's something wrong. So I'm a big believer using Gmail for aliases. Right. So Legal dash product. If the product teams have any questions, we can, all the people who address it can answer it commercial. We can all answer the same question because we can go back and figure out what was answered. So I just find ways to continuously scale the work we're doing into ensuring that we're all heroes. We don't have one hero. We don't have one single point of failure, one single point of success. But I would encourage everyone to figure out the legal tools out there and just even our product. For litigators, which knock on wood, hope you know, our companies don't have a lot of litigation, but for lawyers, it's not just for in house, but it's for lawyers at the firm now to figure out where they can add value to their clients that's not just based on mundane tasks such as review and documents. Right. There's gotta be a way that we figure out how to add that value by using tools.

And in doing so, I mean for your tool, for Ironclad forever law, these are tools like you just said, are getting rid of the mundane or getting rid of the high volume, where you really shouldn't be using lawyers to do the work. I refer to that.

But it's incredibly important work, right?

No, absolutely. Absolutely. It's right. Sourcing is the way I put it. Right. It has to get done. But you want to match the value of who's doing the work or what's doing the work with the task at hand. And so it increases professional satisfaction in my view, because the lawyers are actually doing what they went to law school to do and they're happier. Do you find any of it threatening to lawyers that you know, oh gosh, if we bring in an everlough, if we bring in an ironclad, like what will I do? I mean, I know my answer, but.

Funny, because I don't know if there were any salespeople who felt Salesforce was going to be threatened into their job. Right. I don't Think you talk to any salesperson who. And I think in the same way we're just going through a revolution and we're going to figure out more alternative billing solutions for firms. Right. And I think we're going to have a less burnout. Hopefully this is a result in more diversity as well. More women, more moms staying at the job longer. So I think there's going to be so many benefits that come with ingesting and using these tools that I think is going to be a revolution. It might be slow, but I hope, my hope is that it's not threatening to folks.

Yeah. And do you even think you could operate at the speed and scale that you're on now as a company without some of the things system?

No, absolutely not. I mean we probably could, but would I want to know?

Yeah.

Would I have a team of twice the number of attorneys I do right now, which the finance folks would talk to me about and my CEO? Yes.

Yeah.

Right. Because we don't have to be involved in some of the low risk stuff that come in on a daily basis.

Yeah, that's exactly right.

I mean my. Our job is, and I tell everyone our job is to facilitate growth and mitigate risk. Right, it is. So we've got to think about what we're doing and how we're doing it.

Yeah, that's right. Okay. And so what skills do you think are kind of key and most important for someone as a leader of a department, as a general counsel? I know this is like the dream job of so many people. What do you think you need to be successful now that you're there?

Oh my gosh. I think, like I said, I think that there are so many different skills and people GCs look and feel a little bit different. I think some of the basics are to one, have a curiosity of the business and an interest and a knowledge of the business. Not just the business, but the industry, its competitors, it's going, the work that's being done and how it's being solved. So I think maintaining that intellectual curiosity two is this is probably just me personally, but an ability to navigate between the getting your hands dirty, to fix some of the processes so that we scale and grow with the company and an ability to step up and be strategic and horizontal, to see what's going on at the company, to lend insight at the leadership table, but also to help guide your team so that they don't burn out and figure out what the priorities are. Three, I think is we don't talk about this a lot. We Talk about the legal skills. And obviously you should know your acumen and have the legal skills, but is managing and inspiring people around you. I think that my success or the success of the department is really based on the success of the people that I've had that work in the department and being able to nurture their interests, be able to bring them to the forefront of making the right decisions, but also to make some tough decisions as well that don't, you know, everyone feels like they should report to the GC as you get bigger. I can't have everyone report to me because I won't be a great manager to everyone. And also I don't have the bandwidth and also to make some decisions about who the best next set of managers are going to be to nurture and build up department. I don't know if I told you, but our legal ops manager manages the commercial legal team.

I didn't know that. That's really interesting.

And that is really. Because she was at the forefront of what sales was doing. She knew what sales was thinking about before sales knew what they were thinking about. And the commercial team were great at what they did. Right. But they were better by her supplementing the knowledge of what the team sales team needed and what the sales teams were thinking and putting the right processes in place for them to be able to thrive in just doing deals. Yeah.

Are there things that you've taken from what was great and magical about what we had at Google and tried to try to mimic that, whether it's the culture, whether it's the processes, the structure.

I think I got really lucky. And I. And I. And I don't know if I thank Dan Cook enough, but there was a manager that I had at Google and I think he kind of embodies a lot of what Google is. And Dan brings himself to work every day. He is who he is. And I try to embody that. I think the more that I do that, even if I'm having a bad day, my kids know about my daughter Callie, who is sassy as all heck. Right. Like, I think it allows them to be themselves. Right. And so I know that one of my team members is going to a doctor's appointment with her too, because they don't need to hide that from me because I know when the work is gonna, when we're gonna work, we're all gonna be like, yeah, done. When we don't, when we're not in that period. I think folks should be able to bring themselves. And even if that means going to a doctor's appointment. So I think there's some of that, but also just like it. You know, the other day, this may seem silly, but there was a pop up dinner. You know, the chef from Slanted Door, he had a pop up at UC Berkeley. And I just pinged the team like, hey, anyone wants to go to this pop up with me? And we went. So just trying to, you know, I don't know, Mary, you remember those happy hours we had, right? Just build in that social connective tissue tissue, especially in Covid when it can all feel so transactional and that transactional nature can burn out. Some people, especially the extroverts, bring in that so that I see them, they see that I see them and that we feel like we have that connection.

Yeah. One of the things that I that you mentioned that I think I also love about the early days of Google is you said that sometimes you have to kind of roll up your sleeves and get into the trenches and then also rise to the occasion and present and be a leader and be strategic. And that idea that your job often requires you to do work below your pay grade and above your pay grade. And that's just part of the job because you're part of the team. Right. And I give a lot of credit to Chris Chin, who we're both very close to. He was of course the very early Googler and the leader of the entire commercial team for a while and hired a lot of us and then eventually became the head of our legal tech in our legal operations team. And then of course now he works at Ironclad. So we're back together. But I think that's something as one of the first members of the legal department and having hired everyone, you know, sort of after him, was really important to all of us that you were, you put the team first, you put the department, you put the company first. And it wasn't about the individual. And I think that was.

Yeah, definitely. And I think all of my team does that. And I think that mundane, right. Like, you know, if someone's going on vacation, I don't want to bother them on vacation. So I do an essay. Isa right. I will do a deal, right. I will get involved. I will check your red line. Right. And so like while I'm at a leadership off site for eight hours during the day, I will come back and do that so that you're not burned out. But I also, it allows me to see and know what's going on too.

Exactly.

If something is broken. So just the other day we had a customer ask us, like, two customers ask us the same question. I'm like, why is this customer asking the question? I keep pushing the team. I'm like, just don't we have the answer to this right? And then I realized I just took some time and I read some of our documents. I was like, oh, I missed this because I haven't had to negotiate this, and so let me everything and figure this out, you know, And I sat with the team, and I'm like, you don't need to be right. No one is wrong here. We missed this, but this is something we can do better. And I. I love that about. About. I loved that about Google, and I love that about the department that I'm creating and the vibe that we have here.

That's awesome. And it helps you keep your. Your pencil sharp and like you said, know what's happening at. At all levels, which is great. Well, Shaina, I have so enjoyed our conversation, and it's been wonderful catching up with you here. So I wanted to just say thank you for your time and thanks for sharing your story with us here.

Thank you so much, Mary.

And to everyone out there, thanks so much for listening. As always, please reach out and suggest people you might want to hear from on future episodes and even raise your hand to be a part of this podcast. So I will see you all next time. Thanks for listening.