This is Stare Down the Bull. I'm your host, Susan Hunt. Around here, we tackle the hard stuff, how to lead with clarity, leveraging AI, and turn strategy into real results. My guest today brings a powerful perspective on how to do exactly that. Let's dive in. Hello, everybody. Today on Stair Down the Bull, we're joined by Lauren Nardoni, known to many as the Velvet Hammer. Lauren currently serves as general counsel at CB Insight and previously led legal at LivePerson, where she earned a reputation for balancing toughness and grace. She's the kind of counsel every sales executive dreams of, sharp, strategic, and unafraid to step into the arena when the stakes are high. Welcome, Lauren. So happy to have you on the show. Thank you so much, Susan. Wow, what an introduction. Well, it's all true, every bit of it. We've had some really fun, exhausting times working together over the years on some very big contracts. We sure have. Whenever I ask what I think about legal, I always say it depends on who you're working with, but they should be a super strong partner in any sales executive or sales rep's life. So the smart reps always make sure that they figure out how to work well with executives. So that kind of just brings me to my first question. What first drew you to legal? And what do you love about being on the business side of legal? Because that's your expertise. Well, I wish I had one of those great stories where I always knew I wanted to become a lawyer. But for me, it was the fact that my parents really encouraged me to try to find a way to use the argumentative side of me and my knack for really wanting to debate in a more productive manner than in my discussions with my parents and my family. So smart, so smart of them. So really going to law school wasn't at the top of my mind. I actually went to college wanting to be a journalist and didn't like it and then decided I'm much more analytical and I'm much more of someone who really likes to dissect the details and understand the logic behind the decisions that are being made. And so with the encouragement from my parents to find a more suitable place for the argumentative side of me, law school and I became a perfect match and have been ever since. Oh, that's awesome. Yes. Yes. I didn't know that about you, but that is like, I wouldn't consider you argumentative. I consider you very constructive in the way you have conversations with people. I've grown over the years. Yes, we all do. We all do. Or we just spend all of our time in trouble, which is fine, too. So you're now. Go ahead. Oh, so I want to answer the second part of your question about what really drew me to the business is when I first started out as an attorney, I really had no idea what I wanted to do and what areas of the law were of most interest to me. And I think as a young attorney, it's really important to take risks and to jump in headfirst into kind of everything just to see where you feel like your energy is most utilized to the best that it can be. And for me, in one of my first roles as an attorney at Guardian Life Insurance, I got to work on really incredible, heavy negotiations with the big software players at the time, like Oracle, and negotiate hundreds of pages of software licensing agreements with the senior attorneys on my team and said, this is really fun. This is really interesting. And at that point in time, I think our chief technology officer had retired and we brought someone new in who was really into expanding. AI hadn't come up a lot at that time, but was really interested in expanding where we were investing from a technology perspective. So working with Microsoft and Google and Oracle and Amazon and really getting exposure to what was really out there from a tech perspective, I said, I need to be in that space. And that's what drew me to LivePerson after that for about a decade. Well, that's great. Yeah, that was a great experience learning all of that and then being able to kind of flip the script a little bit and negotiate as a technical software attorney with Fortune 100 companies, really, is what you and I worked on mostly. I'm sure you work on other stuff, too. But, yeah, that's really an amazing road that you went on to get there. So now you're general counsel. I'm actually chief legal officer now. Chief legal officer. I apologize. At like a really young age, honestly, I think that's really a miraculous achievement on your part. Can you tell us about how that's going and what you think about being in this role now? Yeah, absolutely. So I spent about 10 years at LivePerson sort of really grooming my career and growing as an attorney and learning from a lot of mentors and really fantastic advisors for the 10 years that I was there and got the opportunity to join CB Insights as general counsel a little over a year ago, working under Manlio Corelli, who's CEO, where we worked together at LivePerson. And he was really looking to bring in a new general counsel to really help drive the business forward, drive innovation forward, drive revenue forward, and really wanted a strategic partner in legal to help do that. And so when he asked if I was available, it was really one of those once in a lifetime opportunities where there was no way that I could say no. And so I've been here now for a little over a year. And the reason why my role shifted from a general counsel to a chief legal officer, was because as the year progressed, I was really stepping into a lot more areas to help the company grow and improve in data privacy and compliance and security, AI governance and risk management. And I really wanted to ensure that the breadth of my role and responsibilities was really more accurately reflected in my title. And so for me, that's been a great testament to the trust that I've built with Manlio and with our other executive team leaders and the trust and respect of my colleagues at the company, including our sales team. That's awesome. And I love the advocacy for yourself. And if you're doing the work, you're stepping into the job. In fact, I was just on with another incredible woman leader and she said, do the job that you want so that when the time comes to put you into the next spot, you've already been doing that job and I know that you're capable of doing it. And she did that for years and years and years at Verizon and end up being the CIO. So I thought that was, yeah, that was really good mentoring advice. And that's exactly what you just did. So good for you. It's awesome. Thank you. Let's switch a little bit to the partnership between sales and legal, because I think that this is like a really underestimated part of the sales strategy and the sales process. And I think that it's really important that salespeople, especially new ones that are coming up understand the very, very important relationship that happens between these two areas. It's not a situation where you are fighting each other. A legal gets this rap that they're deal killers or whatever. What do you think about that kind of commentary in general? I always take that sort of commentary in stride And my answer is well you haven worked with me or my teams before because we are never the place of no We are never a bottleneck We are always coming from a perspective of what the solution and how can we come up with a way to get to the place where we need to be, whether that's getting a deal over the finish line, whether that's helping to convince the security or privacy team on the client side. We can do what they're asking for, but just in a different way that fits with our tech stack or the AI that we're leveraging. So I think what really helps to make the partnership strong is you have to build trust over time, right, I think is quintessential to that. But the way that you build the trust over time is, and this is what I did when I first joined CB Insights, was you have to take some time to first understand, well, what are their pain points, right? What's going on that's making their day-to-day job difficult, not easy, or is really just a pain, right? And what can I do as the new leader of legal to help remove that and unblock it? And I think some of the steps that I took when I joined CB Insights helped to reframe the expectation that sales should have when they come to legal, right? Legal should always, in my mind, be viewed as a partner, a coach, a mentor, a business advisor, a strategic thought partner, and not just the team that gets my contracts done. We should be the team that you're coming to and saying, I don't really know how to solve this. I'd love to get your advice in perspective. What do you think we should do? What options can you help us come up with? And I think once they understand that you have the knowledge and the expertise and that you want to partner with them to get to that solution, it completely changes the way that they view the legal team. And it also completely changes the way that legal is viewed within the company and the organization as a whole. Yeah, I think it's kind of an old school view, to be honest with you. An older type of corporate attorney would spend all their time saying no, which I guess is the safest thing. But that has clearly made a big change in the last 20 years in that the whole purpose of legal is to get to a place with your customer that you can both say yes. Right. And that if you start from there as what the goal is, I think that that makes things much clearer for both sides. I mean, the customer wants to get to yes, too. They're getting pressure from their business partners or whoever is actually wanting to do the buying to get to yes. So I think from that perspective, the people that I've worked with over the years, for the most part, are really, really good with legal. There's very few that are not great at working with legal. And when they're not, that's a discussion I think the sales executive needs to have with the salesperson because it's critical. It's critical to everything that they do. And I've battled some pretty tough attorneys at AT&T and over the years, like really tough attorneys that just wanted to win every little point. So you need to have the help of your counsel internally to get a deal done always. Yes. Yes. What do you think a strong sales partnership looks like? Like if you were to arrange it, how would it be arranged? Susan, they would just be you, right? Thank you. Just speaking from the deals that we worked on together at LivePerson. But no, I think some of the key skills and traits that come to mind for me are wanting to learn, right? I think when a sales leader and a sales rep wants to learn and understand why we can't say no to some of the clients ask and comes from that perspective so that they are empowered and feel empowered to drive a conversation with their own respective economics. buyer or business champion, whatever term might be used for who wants to buy our technology. I think that's really a mission critical component. The second, I think, is really just remembering that we're all humans, right? There's an emotional side to what's happening in this deal, right? The sales rep and the sales manager and leader's livelihood. And I think it's really important for the legal contact to have that perspective in mind that even if the deal is small, even if the deal isn't slated to get done for three months from now, the sales rep getting this deal done is mission critical for them hitting their quota, getting their commission and supporting their family, supporting their livelihood. And I think having that perspective and reminder, it is often not miss, but it's sort of pushed to the side, I think, sometimes, especially when we're slammed, you know, during the end of quarter and have a lot to push through. I think we can sort of forget that. I think that those two perspectives really are what helped to build a great foundation and framework between sales and legal. I think the other component that I see in a lot of success relationships that I've had over the years is where the sales rep or leader really can take responsibility for some part of the negotiation. You and I did this a lot together at the MikePerson where we would sort of tag team a little bit. You might play bad cop and I might play good cop for one term negotiation and then our roles would switch and I'd play good cop and you play bad cop. But I think being able to negotiate well together and sort of being able to have the sales rep drive some of those negotiation points home really helps build greater trust with your legal counterparts who know that they can rely on you to stay aligned and to support them rather than what happens sometimes is where you get kind of thrown under the bus a little bit in front of the client. Yeah. Sometimes intentionally because you don't want to take the heat yourself. So that's a predetermined thing that might happen. I do think that it's really important for the salesperson to stay in contact with the business leaders and talk honestly with them about the things that we're really struggling with on a contract that impacts our company. Because a lot of times these giant companies think that we can support the same type of everything in a legal contract that they can when we're a much smaller company, you know, like extensive, crazy long terms and payment terms and that kind of stuff. So I think that it's important if salespeople talk to their business leaders and say, listen, this is really a problematic thing for us. We have to go all the way up to the CEO. He never approves this. Can you talk to your legal so we can kind of come to some sort of medium conclusion on this instead of having to go a route that we know is going to end with the same commentary from our CEO that we always get. And it's up to the business partner on the customer side to go and talk to their legal and say, hey, can we do this, this, and this? Give them options and figure out how to do things. So salespeople, really good salespeople are perfection at doing this kind of work. It's important work. It's important to get things done. The business leaders on the other side do it every day with every negotiation. They might be doing 10 different negotiations at one time. The sales rep might be doing one at one time. You and I are doing 10 at one time, but a sales rep might be doing one. So it's very important that they can strategically talk to their customers and try to move the ball forward whenever it seems like the two legal councils are stuck on policy, internal policy that's not changeable kind of thing. And to that point it not only speaking to whoever that buyer is but it might be connecting the sales reps manager with someone that more senior on the buyer side What happens a lot at LivePerson is we might get blocked because we negotiating with someone who's at the director level, but really what we need to unblock the customer treating us as a vendor as if we're just like every other SaaS vendor is to rise up to the VP or the SVP level and push on procurement, push on legal to unblock as well. That's always a really helpful mechanism as well. I really do think that there's always a way to unblock pretty much almost every issue except for the really, really big ones, which there are two or three. And, you know, it's like if we're getting tripped up on some little issue, we're not going to get through the big stuff. We're just not going to get through the big stuff. So that means we're not talking to the right person. Yeah, it means we're not talking to the right person. You're absolutely right. So I think that's a great place for salespeople. I actually went to work for a company after Nuance where I had negotiated like $1.8 billion worth of contracts over my term in telco with customers to a company that I had salespeople that worked for me that said, oh, we don't get involved with legal. We just let them do their thing. And when the deal's done, the deal's done. And I'm like, what are you talking about? I don't want to get involved in that. I'm like, all of you need to get involved in that. You need to be pushing things. You need to be making sure that things are on track, that you're getting the amount of time, that you're driving the meetings, you know, so that they're scheduled one on top of each other. And it was a big company, a really big company. And that was their attitude. And I changed my whole sales team's attitude about that and got them involved. They were scared because they hadn't. I was just going to ask you, was it coming from a place of fear were coming from a policy. And to me, what I was hearing is it came from a place of fear. Yeah, it came from a place of fear. And they hadn't done it before. And these people had worked there forever. And it's just the way it was. And I was like, that's crazy. This is your money, your deal, your responsibility. You're the one that's going to get screamed at if you don't make your quota or you don't get this deal done on time. And I would just start bringing them into different deals so they could hear how I negotiated and how I worked with legal and kind of changed the way that they did business. And it drove more business faster. That's all it did. It didn't hurt anybody's feelings. It didn't upset the attorneys. They probably were frustrated that nobody was ever showing up for their calls. And it got deals done quicker. Well, it's interesting. It reminds me, it makes me think, and it reminds me a little bit of how times the legal team is not viewed in the way that it should, right? Coming from a place of no or coming from a place of fear, but really the legal team is the one group within an organization that really gets a full circle, holistic view of what's happening across the entire organization. Revenue deals, security, data privacy, compliance, corp governance, finance, HR, right? Like you name it, we're somehow involved in it. And so that gives us such a better perspective of what's happening in order to bring that full construct and that full understanding to what the sales team needs, right? Yes. What their deals, it brings that knowledge, that expertise that helps. We might be seeing the exact same ask that one customer is asking. Now, we've seen that three times before. And unless sales is communicating with us, we lose the ability to say, oh, we've seen this before. This worked this way. Why don't we try this? And here's your talk track to try to move it forward on your side. So it's so, so important to keep legal involved and to really try to be the glue that keeps the ball moving, so to speak. Yeah, totally. And what do you think about bringing legal in early? Is there a best time to bring them in on a negotiation? Better than, definitely better than later. But what would be that time? They're still early as well. I hate to say it depends, but it does kind of depend on the deal, right? If it's a really important strategic deal for the company, the earlier that you bring us in, the better. Bring us in the minute that you think something is happening, whether it's an M&A deal, whether it's a strategic partnership deal. Bringing us in early to start to ask questions, get an understanding of what the business objectives are, the business goals, what's in it for each party is always mission critical. In my mind, when we get brought in too late, There's a rush to try to get agreements done, to try to resolve risks that get identified during our due diligence and review process that could have been avoided had we gotten brought in three to six months earlier. But in a regular sales deal cycle, we typically like to get involved a little bit before the order form is created, especially if it's an important customer or strategic customer. Otherwise, it's right as we're putting paperwork together, for sure. But I love when my sales team loops me in early and says, hey, I'm doing thinking about doing this kind of deal. I wanted to just run the pricing by you wanted to run the proposal that we're presenting by you. I love when they do that. It really helps solidify the strength of our relationship, but also that they they value our advice and our feedback as well and feel better and more confident in presenting it, knowing that they have our full support. So I love that. Yeah, I think that makes a lot of sense. So tell us about a time or a deal that you were working on, since this is stare down the ball, where you had to stare down the ball and deal with something that was enormous or a monstrosity and how you did it and how you succeeded in doing that. And there's been a few, for sure. I'm sure with anyone who's been practicing for more than 10 years and in SaaS and in AI, there are a number of those deals that come to mind. But for me, the one that really resonates was a large outsourcing deal that I worked on at LivePerson, where it was a very large company. We finalized the deal, I think, at like 3.30 in the morning, right before Christmas, if I'm not mistaken. How fun. It just was one of those deals that had, it almost felt like an M&A deal because we had spreadsheet after spreadsheet after spreadsheet of issues and resolutions for those issues and investigating checklists of all of these documents, working with outside counsel on both sides, working with our executive team and various other stakeholders across the organization. And I think what really helped to drive the deal forward and to maintain clarity and sanity throughout the negotiation process was to always remember we're one team, right? Whether stakeholders on the product and engineering side were driving forward on one aspect of the contract that was mission critical for us, let's just say it was KPIs that we were going to commit to. And the finance team was working on our payment terms and ramifications for the KPIs that we were committing to. We all were working as one team together. There was also a very clear sharing of knowledge and sharing of information. And really what I think it comes down to is project management, right? Legal is often, I find, often is in the role of project managing these big deals and these big transactions. We're setting up the spreadsheets. We're keeping track of who owns which open item, whether it's resolved or not resolved, making sure knowledge is being shared. And I think where legal is in that role we seeing like I said earlier the full picture right So I think that what really helped to keep the deal moving forward on the timeline that it did even though it did close quite late one night. But without that project management, without that alignment across the teams holistically, we never would have gotten to the other side of it. And there definitely were times in that deal where rubber hit the road for sure. And we had to engage our executive team to go and talk to the executive team from the outsource company and say, this is a deal breaker for us. Or if this is a deal breaker for you, here's the way that we can solve for it where we're legal hit a roadblock for whatever reason. So yeah, that deal would be the one that certainly made a dent, I think, for me. Yeah, that was a big one. I remember that. I thought that we did a very good job across the board at LivePerson of communicating when it came to doing these deals. And that kind of brings me to a question of, is it really legal's job to project manage all of that? Like, is there a better way to do that? Because you're also negotiating all the terms and trying to get the contract closed while you're project managing across 20 different organizations in a company. And I'm just wondering, is there a better way to do that? And what would it be? And this is not on our list of questions, so sorry. I think different companies approach it differently. For me, with my experience, it's always been legal. And I think that has its pros and cons. And you listed a number of them. I think the pros are that we have oversight of what's happening and know exactly what's going on. and where we need to pull levers. And the negative is you're also in the middle of all of the negotiations and trying to keep everyone on pace. So it's a job in and of itself. And so we're tacking on another job to the already busy job that we have. I think where some organizations have project managers, I think it's great for them to step in, but there's only so far that a real project manager can take a deal like that forward. You really need to have sort of a core steering group committee who just frankly takes ownership of their individual responsibilities, works collaboratively together and drives it forward. There has to be accountability, I think, is where it comes down to. But so I've seen it a little bit of both ways, but I'm much more familiar with with legal being the PM. Yeah. OK, thank you. what advice would you give to a sales leader who wanted to create a strong partnership with legal? Like, what do you think the first couple of steps would be? I think definitely bringing legal in early. And I think remembering to take a little bit of a step back that the legal partner that you're working with has no idea about what you've been through with this particular customer, right? We don't have any of that context. We don't know the number phone calls you've had with them, what communication you've had with them, how those dialogues are going, what their pain points are, why they're buying our technology. And so I think sharing that sort of context helps us really understand both why the deal needs to get done right now and why it's a priority for us to create the paperwork and move it forward. But in addition, it might help raise questions that maybe you haven't thought about or hasn't come up that might be really important for us as a vendor and for the client to think through. So I think that context sometimes gets missed a lot. But the other area that I think really helps to bring a strong partnership is the transparency. There has to be transparent conversations. And that, to me, means getting feedback around what's working well in the deals, what's working well the border, but where we can better support you and your respective team. I value that feedback, positive and negative, because we're not perfect. We make mistakes. Sometimes we forget that there's an email sitting in our inbox or sitting in our CLM that we have to do. And so I think being able to have those transparent conversations without any hesitation is really important. So I'm going to say to the salespeople watching this, do an executive briefing doc of some kind for your legal before you go and start with the new process. Let them know what you have been through and let them know the work that you've done and why you're asking for the things that you're asking for now before you even start the process. It's like a really simple way to bring legal up to speed quickly and give them the details that they need. Right. I love that you brought that up. I actually use that a lot when we're doing some strategic deal. The first thing I ask for is some sort of a executive briefing or a business case that helps me understand what we're doing, why we're doing it, and what the full context and full picture of the deal is. So absolutely. It should include those things. It also should include who's trying to block the deal at a customer, who's going to be really helpful to you and why. And all of those details are really, really important. I probably just like yelled them over the wall or something at you, but you got them. That may or may not have happened. I'm sure it did. One last question. If you could change one thing about how legal and sales works together, what would it be? What would it be? And maybe it's the executive briefing. Maybe it's something else. You know, it's not. What I actually really hope for is that when someone new from legal comes into a company, or if you are a new sales rep coming into a company, that you really don't come and think of legal from a place of fear, right? I genuinely always want my business stakeholders and my sales reps to think I am their business partner. I am their business coach. I am sort of their cheerleader on the side, but I'm also their velvet hammer when they need one. Yes. And that takes time to really understand what kind of legal team and legal leader you have at your company, but coming in with a fresh perspective and an open mind and leaving some part of the experiences that you've had before behind is so, so important to me. I agree. I hope that I prove every one of them wrong. And I hope my teams prove every one of those beliefs wrong. And so I think coming with an open mind and perspective would be my ask. Fair enough. I think that's a really good request, actually. And really, it comes down to mutual respect when you're working with one another. I think that that's the most important thing. You do what you do and you do it really, really well. They do what they do and they do it really, really well. So respect, I think, is the bottom line here. I agree. Well, thank you, Lauren, for joining Stare Down the Bull. That was a great discussion that I think is going to help a lot of salespeople do a little bit better with their legal counsel on negotiating deals going forward. And I would love to have you back at some point to give us an update on how everything is going at CB Insight and your chief legal officer position there. Thank you so much for having me. This was a great discussion. I'd appreciate it. Thank you, Lauren. Thank you for listening to Stare Down the Ball. If today's conversations spark new ideas, share it with a colleague and keep the momentum going. The future belongs to leaders who act, so subscribe and join us again next week. This podcast is part of the Sound Advice FM network. Sound Advice FM, women's voices amplified.
