Our hosts and Erin Abrams, Chief Legal Officer at Via, discuss the role of in-house counsel in business decision-making. Erin emphasizes collaboration, early involvement, and building a culture of trust and safety within legal teams.
Our hosts and Erin Abrams, Chief Legal Officer at Via, discuss the role of in-house counsel in business decision-making. Erin emphasizes collaboration, early involvement, and building a culture of trust and safety within legal teams.
Via builds innovative software to enable our customers — cities, transit agencies, transport operators, school districts, universities, and corporations — to transform their legacy transportation systems into advanced digital networks.
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“ In addition to having a framework for how decisions are made, I think it's really important to have a framework around the life cycle of what you're trying to accomplish. And I think of it very much in sort of a product lens, but what I've seen be really successful at organizations, especially as they're starting to scale, is really going to the teams and saying things like, "legal can't come at the end.””
“With our joint ownership model, I think part of that means not running away from the consequences of your decision and saying, okay, we mitigated this risk to a place that the business and the legal team felt comfortable.”
“There's not necessarily tons of in-house positions for litigators, but what you can do is become a professional risk mitigator. You can kind of shift and say, okay, I'm really good at pattern recognition. I know what has led to litigation in nine out of 10 cases. So now that I'm looking at this much earlier in the pipeline, I'm looking at it and a contract that seems vague. You know, there's an area of sort of like a gray area. You know, it feels a little bit squishy to me. I've seen litigation result in similar circumstances. Okay, well, this is like a risk I can mitigate.”
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00:48 - Meet our co-host Ken
04:01 - Meet our guest Erin
09:25 - What effective partnership looks like
14:18 - Evaluating business risks
21:41 - Making challenging decisions
28:35 - Using compliance as a competitive advantage
31:35 - How to hire well
42:53 - Keep or redline?
45:30 - Where to find Erin
45:52 - Final takeaways
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Find Jessica on LinkedIn
More about Docusign
[00:00:00] I think people like to send things to legal and say, please review, please approve. We don't want to be in that mode of like review, approve, like check the box, put the rubber stamp on it. We really want to be in the trusted advisor model. In a world where agreements are the lifeline of businesses, DocuSign is more than just signatures.
[00:00:24] We're transforming how professionals create, commit to, and manage agreements. Visit DocuSign. com today to learn how DocuSign Intelligent Agreement Management can give your business a competitive edge. Welcome to in house, the podcast for in house legal by in house legal. I'm Jessica Wynn, deputy general counsel here at DocuSign.
[00:00:45] And the question of the day is about decision making. And who owns making the decision? I know you're all going to say it's the business, everything's a business decision, but the reality is the business really relies upon us as their legal advisors to really guide them in making that decision. And honestly, make the decision for that because so much of our job is how do we make the lives of a CEO or executive colleagues easier.
[00:01:18] So today you are in for a treat. We have two special guests. First, I'd like to introduce my colleague, Ken. Hi, Ken. Hi, Jessica. Good to chat with you all today. I'm fortunate to lead the product and partner legal function here at DocuSign. So we're responsible for all of the product legal guidance for the various products and services that we have.
[00:01:40] And then the partner motion, which includes integration with partners, technology, and then of course our resale motion. And prior to the, prior to DocuSign, I had roles at Atlassian and Box. Ken, you are a. Perfect DocuSign co host for us today because a lot of the questions, well, one, you have the most amazing voice.
[00:02:00] I think a jazz voice or a voice for commercials. Gosh, we're blessed, Ken. You're blessed. Let's be honest here. When I think about these decisions, it's your background as a product lawyer really stuck out to me because a lot of folks in the legal community reach out. And are asked, wait, what's a product lawyer?
[00:02:20] That sounds really cool job. I want that job. But what do you do? Ken, how would you describe what a product lawyer does? Yeah, it's a really, it's a really good question, right? It because in some ways it's one of the newer practice areas, if you can think of it as a product. practice area. And I look at it kind of in three slices.
[00:02:40] Um, and these slices change all the time. So you may ask this question to me in the future and I'll have different descriptions. The first role is more traditionally within the legal sphere, which is risk mitigation. What risks are out there helping the teams identify risks that they have, but also then many risks that they can't see just because it's perhaps outside their domain or their focus.
[00:03:00] Second piece I think about is really being a connector. And particularly at organizations of scale, but even if they're not at scale, you know, the role of product, a product lawyer can serve is really helping teams take a look at what they're trying to deliver and then making sure they're having the right conversations.
[00:03:18] With other teams, those teams can be within legal or quasi legal functions like compliance and security, or they can be in other areas. It could be if you're working directly with a product team, it could be on the go to market and sales teams. And then the third piece I think about is, and this is kind of a one that's come up lately is where weather people.
[00:03:37] And what I mean by that is we're really helping predict regulatory environments. And those predictions sometimes can be Yeah. Close to what's happening today and then further out and just like the weather, the further out you get, sometimes those predictions have a lot of vagueness to them. But often I find that a lot of folks who are building things internally, they're just trying to get a sense of, well, how do I build this for a year, 18 months, two years out?
[00:04:01] with regulations, particularly in spaces like AI, uh, with regulations changing as quickly and evolving as much as they are. Um, sometimes it really is, uh, best guesses and it is a little bit of saying, um, you know, this is where we think things are going to go, but it could change. Yeah, spot on there. Ken, we have a special guest here.
[00:04:21] Folks here today is Aaron Abrams. Hi, Aaron. How are you doing? Hi, great. How are you doing, Jessica? Thank you for joining us. I know this is your second speaking engagement for the day. So, so honored that you'd make time for us. But and before we dive in, see your background and thoughts, please tell us about VIA and what you do.
[00:04:39] There. Great. So I'm the Chief Legal Officer at VIA. I've been with the company a little over 10 years. I recently celebrated my, uh, 10 year VIAversary, which was very exciting. Happy anniversary. 10 I got some excellent company swag, uh, as befits, um, a decade with the company. Um, and VIA is the global leader in transit tech.
[00:04:57] So we, uh, sell our transit technology software to cities, transit agencies, universities, hospitals, corporate campuses, anyone who needs to move people from point A to point B. And we generally specialize in taking like legacy transit systems and transforming them using our software and our advanced digital networks.
[00:05:16] So we really pioneered the transit tech category and we've leveraged our proprietary technology based on a system of virtual bus stops to create a network of efficient, affordable and sustainable transportation options. So we provide micro transit, that's like our legacy flagship product, but also paratransit fixed route buses and we can make them more efficient.
[00:05:36] And we also operate school, school. transport, alternative school transport, as well as school buses. And we can really provide any type of, uh, transportation, both on the software side and then pair it with the services and operations that are necessary to operate a full scale transit network. And we're providing these services in over 700 communities around the world in 45 different companies.
[00:05:57] So it's really been a pleasure for me to see the company grow in scale. When I first joined, we were a consumer ride sharing service. We only operated. In, in major cities, and I personally, I miss the consumer ride sharing service. We had $5 rides in New York City and I really miss those, you know, $5 rides in Manhattan.
[00:06:13] But we have grown and scaled all over the world, and we've turned the business from a B2C business into a B2B and a B two G business where we sell primarily software and software enabled services in the transportation space. And for the folks listening, what does B two G stand for? business to government.
[00:06:31] So most of our customers are governments. So we sell directly to cities, to transit operators, you know, mostly to public transit networks and operators that want to run their systems with more technology and more flexibility, greater efficiency, and generally greater savings. What a great product. I can imagine that a lot of those systems are very antiquated, Erin.
[00:06:51] That's one of the reasons why we feel very mission driven at VIA is if you talk to someone who's a, you know, dependent on paratransit, for example, and they're used to, you know, waiting two hours for a dial a ride vehicle, and then it comes late or not at all, and then they have to take that to dialysis, say, and they spend three years, you know, three hours of their treatment.
[00:07:08] And then they have to wait for the vehicle to pick them up and bring them home, and then the vehicle is late again. You know, that takes up their entire day. That's all they do with their lives. And if they have access to on demand services for paratransit, and they can even make a detour or make a stop, and the ride comes when it's supposed to come, they don't have to wait hours for it.
[00:07:22] I mean, it's really transformative. And we hear stories like that from our end users all the time. It is going to be game changing and I imagine the business will bloom over the next few years as a lot of companies now, including one in my backyard, a little company called Amazon, is requiring their employees to come back to the office five days a week.
[00:07:41] So we'll see how that involves traffic. It used to be a platform. We do a lot of corporate shuttles too and that is a big trend right now is that the big corporations that people have moved further and further away during the pandemic and they want their employees to come back to their nice shiny corporate headquarters, but they've moved far and there's a lot of traffic and to get people to come back into the office, you know, you need reliable transportation.
[00:08:00] You don't want to have tons and tons of parking space. You want to have more green space. So we've been helping a lot of the major technology companies in Silicon Valley with those kind of corporate shuttles to get people back to the office. Absolutely. Well, Erin, I thought you'd be a great speaker for today's question of the day about decision making and ownership of the decisions because you grew up with VIA.
[00:08:20] You grew up like when they were, when you were the first legal hire, is that correct? Yeah, I was the first legal hire and there were seven total people in the U. S. and seven in Israel too. So sort of just past the man in a dream phase, right after we raised our first round of financing. And when you grow up with the company as their first legal hire, even if product lawyer isn't in your title, it is within your job description or remit, because who else are they going to go to for advice?
[00:08:47] So I'm so glad. Thank you for joining us today as our special guest, because I'd love to hear your perspective of growing for the company as a first legal hire to now, how many employees do you have at VIA? Now I have about 1600 around the world. What amazing growth. All right, so Aaron and Ken, you're both, and as well as myself and my background, we're all have been in positions, legal positions, where we're not colleagues in the business, whether they be in sales, marketing, or the CEO, they're not just looking to us for legal advice.
[00:09:20] Or if we've done our jobs well and have gained that trusted strategic partner relationship, they really look to us for more than just legal advice. Where have you seen a great partnership being built or frameworks being used to really have an effective partnership with the business and also have clarity as to who owns the decision of whatever it is.
[00:09:46] We should go to market in this space. We should sell to this persona, the government, or even we should build this feature and all the here, all the compliance requirements. I have had a lot of opportunities to think about, and, you know, because I was the first lawyer and I got to hire and build a legal team, I got to do that in the way that I thought was my dream, my ideal way to build a legal team and to learn from all of the things that I'd seen, you know, in my career at a law firm, my career at a bank and kind of build on that here at VIA.
[00:10:14] And so, you know, I really do think it's very important for us, at least on the VIA legal team, we've spent the last year or two with an initiative where we've gotten away from what I call The review and approve model. I think people like to send things to legal and say, please review, please approve. We don't want to be in that mode of like review, approve, like check the box, you know, put the rubber stamp on it.
[00:10:34] We really want to be in the trusted advisor model where we're giving advice to the business, but the business is using our advice to make a decision. And that doesn't mean that we like abdicate our role and that we say. You know, I think the classic lawyer comes out of a law firm and they do this on the one hand.
[00:10:48] On the other hand, it's a business decision. This isn't my problem anymore. Go take it. You're in the business. I just give the advice. And you don't have to live with the consequences of your advice. I think being an in house lawyer, you absolutely do have to live with the consequences of your advice. So we have a framework, I think we would kind of refer to it as a 50 50 ownership model for risk and decision making.
[00:11:07] So. We try to agree between legal and whoever is the business stakeholder, whether it's sales or marketing or growth, whatever the team is, you know, around a particular business decision, sometimes there's multiple stakeholders, we try to agree. Okay, here's our legal advice. You know, here's what we recommend.
[00:11:23] We understand there's only a few. You know, legal is one type of risk. We're also weighing that against financial risk, reputational risk, you know, technical risk, the risk of doing nothing, you know, competitive risk, the risk of someone else doing this better, faster, cheaper than us. So weighing all of those inputs and then kind of trying to align on, are we going to go forward with this?
[00:11:40] Are we not going to? Are we going to take legal's advice? Are we not going to take legal's advice? And saying that we kind of co own. that risk, the, you know, the risk tolerance. And if for some reason, you know, the, the product lawyer, say we're talking about product law, you know, the product lawyer says, you know, I think that we should implement these compliance requirements in the following manner.
[00:11:58] And the engineer who's working on it says, well, actually, I don't think it's possible to do it in this way. And, you know, we need to, you know, to make the product as elegant as possible. We have to, you know, skip a couple of those requirements and, you know, Can we prioritize them? If we can't reach alignment on that, then we escalate it, and it goes up the pyramid.
[00:12:13] So it'll go up a little bit further, and then, you know, if it gets all the way up to me, and then I'm talking to the chief product officer about it, if we can reach sort of alignment and we say, okay, this is what we're going to do. Then it's not just like legal said to do it perfectly. The business said to do it, not at all. And then the, you know, the consequences fall right where they may, the business and legal agreed. And we both own the consequences of those decisions.
[00:12:32] And if that doesn't work, and we can't reach that level of alignment, we keep going up until we bring our CEO in and then he weighs in. Okay, good. I was going to ask who serves as a tiebreaker when the co owners of a decision can't reach a mutual agreement of sorts. So it sounds like then it's the CEO or some other senior executive that serves as the tiebreaker.
[00:12:53] But it's not always that the CEO comes in. It's that like it gets escalated at levels, you know, throughout the business and then, you know, it might start out at the principal level and then go up to the SVP level and then you bring in like some directors and we're not a very hierarchical organization too.
[00:13:07] So whoever is the person. You know, who is responsible for that topic might come in and it might be like, you know, even though I'm the chief legal officer, I'm running point on this issue. Then I'll come in and I'll talk to the regional salesperson who has a different perspective. But if we can't align, then we escalate.
[00:13:22] And if there's no one left to escalate to, then we bring in our CEO. He's super hands on. He loves to solve these kinds of business problems and weigh in and constantly, constantly be calibrating our risk tolerance. So it's appropriate to where the business is today. Aaron, do you ever have someone kind of say like, I'm going to listen, I want to take that risk, like someone who's not who's maybe at the principal level or somewhere below the CEO?
[00:13:42] And does that work in the way that you think about the framework? Yeah, absolutely. That does happen sometimes. And sometimes I can say, Okay, like, here's my legal advice. My legal advice is that, like, to absolutely minimize our legal risk, you should not do that. But you're saying you want to take that risk.
[00:13:56] And what does that risk mean that risk? It means, you know, you're not like going to go to jail. There's no criminal penalties associated with this. You know, that's a red line that we would not cross. You're not subjecting the company to like major reputational harm. You're not subjecting the company to like a likely revocation of our license.
[00:14:10] We're not going to have to stop operating. Those are kind of like the red line, you know, do not cross kind of factors. But if it's like, you know, we might, you know, be told at a future point that this could be, you know, better, we could improve our best practices. You know, it is possible if there was enforcement activity, there could be a fine associated with this, although it's de minimis.
[00:14:28] You know, those are the kinds of risks that the business is empowered to think about taking. And, you know, even if I would not necessarily say, well, if I was in your shoes, I wouldn't take that risk. I think it's okay for someone to tell me, I thought this through, you've explained to me the consequences.
[00:14:41] This is a business risk I feel comfortable with. And for me to say, okay, I sign off on your exercise of business judgment in that case. Yeah, and I think, and I think that gets into that great gray area of like a regulatory fine. How is that a business risk? But I think this sort of lays it out to say, like, ultimately, when it comes down to the value of say, launching that feature or product faster, and or the the mitigation steps that we need to take, they're just going to take some time to get there.
[00:15:06] That's where it becomes a business risk. And I re I really appreciate the fact that you laid out like there are sort of no go zones, right? There are just certain risks that we don't take and that a principal or a director or someone below the CEO can't sign off on. Yeah. This topic really though, you know, can, um, when we were Discussing this topic as a potential podcast episode.
[00:15:26] A lot of the challenges I see is in action because there's no owner who's gonna make the final call. No one wants to raise their hand and be like, let's do this. Let's take on that risk. Aaron, it seems like the culture at BIA is. You don't have that challenge, but as a lot of organizations grow larger and larger, the ownership becomes a lot more ambiguous.
[00:15:49] So Ken, you know, at DocuSign, we have almost 7, 000 employees and we're publicly traded and we're pretty large now. It gets harder. It gets a little bit more ambiguous, right? Who the owners should be to make the call. Any insights, Ken, from your legal experience as to an effective way to get a decision made and who owns that decision?
[00:16:11] Yeah, I think it's a great call out that especially in organizations at a certain scale that you can get sort of a decision paralysis for lack of a better term. Analysis paralysis. Yeah. And, you know, I've seen both at DocuSign, but also sort of broadening at other organizations I've worked with really early on, sort of trying to understand, well, who is going to be the decision maker here, who is going to be the responsible party for whatever the launch is.
[00:16:36] Right. And. Ultimately, then it becomes if it's a product driven initiative, right? Getting an agreement early on those conversations. I want to come back to that thought for a second, in a second, bringing them up and saying like, you're going to be the directly responsible decision maker here, the directly responsible individual.
[00:16:53] And. Getting agreement, even before you get to the issue of, right, I'm going to own this decision. Now, I think there's interesting Aaron, like in the framework that you use in some ways, you sort of short circuited that because you've said, well, we're going to have this shared decision. But I do think sometimes that organizations of scale, it is useful to say, like, we need to have early on a sense of who is the main owner here.
[00:17:15] And what's interesting is sometimes. Folks are a bit reluctant to sort of take on that role, and sometimes you spend some of your time negotiating early on, like who is going to make, be that decision maker, but ultimately when you get down into the details of the risk or the, or the sort of challenges that, that we're facing, and when you have a particular launch, whether it's trust or regulatory, it is very useful to have someone say, like, ultimately we know that it is One thing I did want to bring up, which I think resonates with what Aaron was saying is, you know, in addition to having a framework for how decisions are made, I think it's really important to have a framework around sort of the lifecycle of what you're trying to accomplish.
[00:17:53] And I think very much in sort of a product lens, but what I've seen be really successful at organizations, especially as they're starting to scale, is really going to the teams and saying, like, legal can't come at the end. We have to have a process in place. where we can come earlier on in decisions, especially some of these big decisions around new product launches or stepping into new areas or using new technology.
[00:18:16] And what I've seen be really successful with teams is they're thinking about that, that timeline framework is also then having an idea, having concepts in here of what kind of touch needs legal needs to have in that review. Are we just going to be an FYI so we know what's going on? Do we need to have some decision making early on?
[00:18:33] Because Let's say it's in the space of data governance and there's a new data use and we want to make sure the teams are making thoughtful decisions early on so they don't go off and build and then suddenly build something that doesn't fit with our current data governance structure. So I think in addition to having an understanding of who's going to make the decision, I think it's also an understanding of kind of when legal is coming in.
[00:18:54] And Aaron, it really resonated with me when you said, like, folks, all they just want us to check the box. I, in past roles, I've literally had folks like send me a form saying, please click here to approve, like thinking that's what legal roles needs to be. And there are some types of reviews where like we can just review it and be done.
[00:19:10] But I think that the scale of the decisions that we're, you know, we're talking about here, like often it's, it has to be a conversational process. Yeah, I grew up in Chicago, so we used to have this phrase, I guess we're not supposed to talk about election fraud anymore in a joking fashion, but in Chicago, they used to say, vote early and often, but I think about consulting legal in the same way, which is you should consult with us early and often.
[00:19:30] That's how it works the best, but with our joint ownership model, I think part of that means like not running away from the consequences of your decision and saying, okay, we mitigated this risk to a place that the business and the legal team felt comfortable, maybe recognizing the legal team would have liked to mitigate the risk more.
[00:19:46] But also that it's in the interest of the entire company, not just the sales team to close deals so that we together, legal and sales team decided that we mitigated this risk to a comfortable place. And then if, you know, two, three months, two, three years later, it comes back that like now this has to be dealt with.
[00:20:01] Now there's something, you know, further that, you know, we could improve our best practices or we have to respond to an inquiry again. It's not our place, legal team to say. We told you so. If only you had just not done this deal and mitigated the risk to zero, we would not be in this position. But to say, okay, we got comfortable with this risk.
[00:20:16] You know, it's not that this risk is anathema to our, our moral compass. It was a legitimate business risk to take at the time. And now we're still in it together. We're still partners. We're 50 50. We're not going to blame each other. Like we're going to help you. address the consequences of having taken this risk.
[00:20:31] Yeah, and I think, and I think, uh, at least my experience has been often when, let's just say you're in that space of a regulatory environment or regulatory review, you know, some of the most powerful conversations you can have is, here's the discussion we have that at the time, and here's the reason that we made the decision.
[00:20:45] And except for bright lines, I've had the experience that generally regulators will say, okay. We didn't agree with it, but we understand how you got here. Here's what we would recommend, right? And I think that sometimes what you're really bringing up here in addition to this shared decision making and the shared sense of we're going to own the risk, it's also you're having the conversation and you've documented the conversation and you're doing it in a thoughtful way because that can be some of the most protective elements.
[00:21:10] If you find yourself in a conversation with outside parties about. Absolutely. Why you did what you did. And sometimes we'll document that. Sometimes we'll do a memo to file and say like, you know, if this decision is ever challenged, like here's our rationale and we would take the position that X, Y, Z, and here are some cases that we looked at that we understand that maybe this is, you know, like a, you know, uh, an interpretation.
[00:21:30] There could be more than one interpretation, but we think this is a defensible interpretation. We thought about it at the time. We didn't just ignore this or take a flyer on it. You know, the team got legal advice on this topic and this is how we plan to defend the position that we took. And then, you know, if we have to go.
[00:21:44] back and look that up, then at least we started doing that work. We're not kind of back on our heels. Yeah, I love that, Erin, because sometimes we make decisions with the best information that we have at the time and at the moment. And that information can change over time and there need to be pivots. We say, you know, here's our advice, assuming XYZ, you know, assuming that, you know, we're using independent contractor drivers, assuming we're using standard size vehicles, assuming we're operating as a transportation network carrier.
[00:22:10] If any of those assumptions change, you need to come back to us to, to, you know, to get further advice, to update the advice. So, Ken, when you were speaking, I was thinking about how one. Organizations get really large. They try to scale to create all this process and legal becomes an item apart the checklist and normally toward the end of the checklist of getting the blessing of legal to move forward and then ship the feature ship the code, etc.
[00:22:35] But you hit the nail on the head when you're like, we would be better partners if you loop this in early and often, just like your voting analogy earlier on. So can any advice for our listeners here to get looped in much earlier than just the approval stage. I mean, ideally, probably in this, you know, the strategy stage of here are the feet product features we're thinking about building and that way you're in the room where you're in the meeting, being able to speak up and say, Hey, as we think about that, think about these X, Y, Z risk so that the engineering or doesn't go off and build features that have to be changed at the 11th hour.
[00:23:12] They missed their ship date, which no one's happy about. Can any thoughts on building that relationship yet? Yeah, well, it's you ended the word with exactly where I was going to start and I think this is probably kind of a known Concept that a lot of people people speak about but I think it's important to reinforce Which is it does become about the relationship you have with the particular teams and the way that you form that relationship Can vary sometimes it can be well, I'm legal.
[00:23:36] We kind of need to be in the room That's one way to do it. Not one. I'd say I'd recommend often because it doesn't necessarily land Well, but it's also understanding Exactly what the team is trying to accomplish. So, so I look at it in a couple of levels, which is I'll often frame it with folks of I'd like to be in the team meetings.
[00:23:52] I'll be a fly on the wall and I'll actually make sure not to speak up in those meetings because at that point, especially if the team in the crafting stage, like we just want, we want them to craft and I just want to be there to pick up data points when I do speak up in either in that meeting or follow up meetings.
[00:24:08] I also am very clear and it's advice I give to folks on my team, which is. Be really sure which hat you have on the time. Do you have the legal hat? Do you have a compliance hat? Do you have a, as a shareholder or an owner in this company, like something is making me uncomfortable here. Can I explain to you my reasoning?
[00:24:25] Because, and Aaron, I'd be curious to see if this resonates with you is we're often dealing with gray areas where sometimes it's like you first see it. And it's almost that. You know, that sense of like, I know that there's something there that isn't right. And I can't quite put my finger on it, but I can't tell you how that's tied to some regulation or some concern.
[00:24:41] It's a body of many things. And sometimes it's like, I've been doing this for a long time and there's something that's just off here and you want to have a forum with your stakeholders where you're discussing that. And the reason why I bring that up is you're then sharing with them, like, I've got a concern here.
[00:24:57] Help me get past my concern rather than saying legal is saying no. And often what you're trying to also do is get. them to maybe think slightly differently about the way that they're approaching a problem. Yeah, a couple of things on that front. I would say I totally agree with you, Ken. The idea of like having a spidey sense and just knowing like something about this is off.
[00:25:14] And lawyers are really good at doing pattern recognition, especially I was a former litigator in private practice. And so if there are any other litigators out there who want to become general counsels, they can feel free to take this line and, you know, use it. It has served me well. But the idea of, you know, as a litigator, You know, there's not necessarily like tons of in house positions for litigators, but what you can do is become a professional risk mitigator.
[00:25:35] And you can kind of shift and say, okay, I'm really good at pattern recognition. I know what has led to litigation in, you know, nine out of 10 cases. So now that I'm looking at this much earlier on in the pipeline, I'm looking at it and a contract that seems vague. You know, there's an area of, you know, sort of like a gray area.
[00:25:50] You know, it feels a little bit squishy to me. I've seen litigation result in similar circumstances. Okay, well, this is like a risk I can mitigate. And you can use that same skill set. You kind of have those spidey senses that activate, you know, that you can deploy. But in terms of like the hats that you wear, I think for me, especially like sitting in the GC seat.
[00:26:07] I'm almost always wearing my business person hat, uh, and it's quite rare that I'm wearing my like captain legal hat, uh, and that's because we really have this philosophy of like same team. And we say it all the time, even if a meeting gets tense or we're like, you know, we encourage dissent and people to express different viewpoints, but we always want to remind each other like we're on the same team, we're all team via.
[00:26:25] And so We're all on Team Via's business. I'm not on Team Legal by myself, not trying to, you know, sell more via deals. Like we are all on the same team, which is the business team. So when I give trainings to the sales team, I say like, you know, I put up this little funny graphic from like Glen Gary, Glen Ross, and I'm like, always be closing.
[00:26:42] We all need to close. We're all in sales. And they just love that because that's true, right? Like if we don't sell any deals. Like we're not, we don't work at a law firm. If you work in a law firm, your product that you sell is legal services, but we don't sell legal services. No one's paying for our legal services.
[00:26:56] We sell transit technology software and I on the legal team also sell transit technology software. I just do that with the skills that I've gained as a lawyer. I love these. There's a couple things. I love what you just said, Erin. First of all, you're clearly a mother of boys because I heard a lot of Marvel references.
[00:27:13] Am I right, Erin? Oh yeah, I have two boys. Don't even get me started on the soccer references. We can do football next. Captain This and Spidey Sense. So I love that. I'm also a Marvel nerd. So that spoke to me. And then secondly, Your team mindset really spoke to me. So a story that I love to share is that when I was back, when I was the general counsel of PayScale, and I was trying to get buy in to get the company excited about GDPR compliance.
[00:27:41] No one was excited about GDPR. Good luck with that. I did. I was successful. So folks listening. Here's how I was successful was I was positioning it how we can use GDPR compliance to win in over our competition. So I literally created a presentations and simple talk tracks. For our enterprise sales org about how to use our compliance story as a differentiator against our key competitor, because of the enterprise level, compliance and security matters a lot.
[00:28:14] And so our win rate against our competitors at pay scale went from 50 percent to 85%. So that is a real big difference of the business really leaned into that. Yeah, I love that. I love using compliance as a competitive advantage, and we've done that successfully quite a few times. Like, we transport very vulnerable people.
[00:28:33] Like, we provide paratransit services. We provide educational transport services. We have a special niche where we provide educational transport services to kids that are sort of left behind by the regular school bus, like foster kids and kids that are homeless. And there's special federal funding to provide alternative modes of transportation to those kind of hard to serve kids.
[00:28:51] But when you're serving that population, the thing that your customer cares the very most about is safety. And part of safety is privacy, but also the physical safety and security of those vulnerable people. So if we can go to those customers and say, we have safety on lock, we've thought all about this, you know, here's the way that we physically.
[00:29:08] It's a way that we, you know, double check to make sure that all the drivers are in compliance and have their background checks. Here's the way we respect, you know, all the different passenger data, HIPAA, COPPA, SEPA, FERPA, your whole alphabet soup. We have it all covered. We've thought of all of this. Like our salespeople are conversant in that and they can go out and tell the customer and that's music to the customer's ears.
[00:29:25] They want to hear that you've thought about these things and you've built them into your product. Yeah, and I think that sort of connecting that loop, let's use privacy as an example of, hey, there are advantages we have by maintaining the standards because our customers are going to love it. And then you sort of model that with your customer teams to say from a product and technology building perspective of these are challenges that we these are infrastructure pieces we need to put in place, but there's a value here because ultimately it makes the.
[00:29:53] products that we're building more compelling, uh, and easier for us to sell and benefits us all as a team. It's really great advice, Aaron and Ken, that having messaging about why this is a win for our customers is a universal way to get the business buy in on legal advice. Because I imagine, Aaron, with your co ownership decision making framework, oftentimes you need to be influential.
[00:30:17] to get your decision co owner to buy into your advice or your opinions. All right, for the next portion of our segment though, I do want to talk about hiring. Hiring is really hard. One of the hardest parts for all of us when we are hiring and we're now leading teams is how do we, any tips for listeners here to hire people on your team who really have that ownership mindset so that They will either be comfortable giving that advice as their more junior career to their business colleagues, or in one day as they rise, making those decisions.
[00:30:52] Because Erin, as you know, like our day to day discussions are not really generally about legal. It's about the business. Yeah. I'm very focused on when I interview to hire for the legal team, you know, I give these like case studies and that's part of our via style of hiring. You give these like lengthy hypothetical scenarios and we ask how people would react.
[00:31:08] In these hypos that we prepare and we kind of have some general ones, and then we have some specific ones for each different position. And then we give pretty much every candidate the same hypo so that we can quantitatively and qualitatively evaluate how they did on that. Um, and so for me, like that ownership mindset is really key.
[00:31:23] And so step one is like an issue spotter, where I give this like kind of complex, convoluted fact pattern and then the person is supposed to spot. You know, like law school style, spot all the issues. But that's only step one. I think that really freaks out a lot of lawyers is because like sometimes they're like, okay, like I spotted 10 out of 10 issues.
[00:31:39] Like, ding! Like, where's my prize? And I'm like, okay, so like, what are you gonna do about it? That is a lot of problems that you just identified. That is so many problems. What are you gonna do about these problems? And when I train people on my legal team, I try to tell them like, Don't bring me a bouquet of red flags.
[00:31:53] Don't collect up a whole bunch of red flags and be like, here are all the red flags, right? Like that doesn't help me. What am I supposed to do with a bouquet of red flags? Nothing. So you have to tell me, like, how are you going to address these issues? How are you going to, you know, say like, this is a no go, but this is something that I think we can do if you make a couple of tweaks.
[00:32:09] You know, we try to say like, we rarely, if ever say no, we almost always say yes, but or yes, how. So when I interview people, I look for people who either like use that language. Natively, or they can be pressed to think in that way and do that thought experiment and they don't just completely like black out.
[00:32:23] Like they're willing to engage in that sort of thought experiment of like, you know, and now how do we solve this problem? And then at the end of every hypo, I add in like a character. I call the character the reluctant stakeholder. So like there's somebody who's creating friction. There's somebody who's not on board.
[00:32:37] And then I ask them, how are you going to overcome this reluctant stakeholder? Can you give me examples of a time in your past when you've had to do that? How would you do that here? And I really listen to see how they answer like the reluctant stakeholder question. Yeah, that really it resonates with me and I just realized I'm actually perhaps a little bit meter than you because I do.
[00:32:54] I also like using hypos, but I don't give them any prep and I'll do them live in the room and just sort of lay out a hypo. But I often will do it in a panel setting where there's multiple folks on the call, which is how we do so many. Oh, they don't get this in advance. No, this is all this all. Okay. Okay.
[00:33:09] It makes me feel a little bit better. But so, so, so how I'd augment is the reason I do it in the panel is we all hear different things when someone's speaking to us. And I'm always surprised. And so a lot of what we're listening for is, was it a community? My community is one of those values that I hold really dear to myself.
[00:33:25] And it's, I use it as this conversation piece with when they were speaking about a problem, did they speak in terms of me first, I first, or did they talk about how they worked with other folks to solve a solution? Because I'll make an argument here in this. Podcast. And then the interview is that like, we're not heroes here.
[00:33:44] We're all going to be solving things together. There's very few decisions that come in front of us where we hold the keys to everything. And the first step to being a really effective product council is figuring out who has all the other keys that we need to solve this. And it has to be done together.
[00:33:58] And so I do think in an interview process using hypos and using one and sometimes in a panel where you get to hear different things. Is a great way to sort of have that understanding of where that person is. The other is, and it's sort of a classic interview question and folks come prepared for it, but I still think it's useful, which is I ask folks to tell about a challenge that they weren't successful in getting past and what I'm, I'd like to, I'd like to hear in that conversation is.
[00:34:24] What was their ownership mindset in, in that? Because I do think psychological safety is really important in any organization and not every organization has it. I do think it's something that, that I know from my team I really try to instill, but miss this. It's not this idea that mistakes will be made, it's just sometimes judgments will be off or you'll think things are a certain way as a team and you got it wrong.
[00:34:46] And I think we talked, touched on this a little bit, which is it's not about getting it wrong, it's what you do. Once you understand that you are off. Do you make adjustments? Do you change your policies? Do you reset your risk parameters so that you don't make the same mistake over and over again? I think that's super important.
[00:35:02] That concept of, you know, what you're referring to as psychological safety, the idea that like we have each other's backs. And so even if you make a mistake. the legal team isn't here to say, gotcha, or to blame you, or to say like, if only you had come to us sooner, maybe that's even true. But like, if only you had come to us sooner, or if only you had done the thing that I told you to do the first time, you know, that doesn't help people.
[00:35:20] In fact, I think that's one of the number one factors that contributes to analysis paralysis, especially when you have junior people and they don't have confidence in their decision making. They don't have confidence in their judgment because they're afraid that if they make a wrong decision, they're going to get called out on the carpet for it.
[00:35:34] They're going to look dumb in front of their boss. So the idea of like, Supporting people and saying, okay, like we made that decision together as a team in hindsight. Was it wrong? Yup. Okay. We're going to fix it. Um, and not pointing fingers and not playing the blame game, but also understanding like, okay, how did, like, what could we have done better?
[00:35:50] What was off here? And like really diving into that. And I will often lead that and say like, okay, I didn't get this right. Even if, you know, there was a group decision here, like help me understand what I missed and bringing folks into that vulnerability of sometimes decisions are just going to be off.
[00:36:04] Yeah. Yeah. And I think when you're hiring too, it's really important to have people who have some level of humility. Like we really try to find people who are kind of humble, um, and of course we want smart people and highly educated people and people who have great accomplishments, but also people who are humble enough to say, like, you know, if you ask them, tell me about a time that you made a mistake and you'd be shocked how many people like just completely blank and just cannot describe a time they made a genuine mistake or they're like, Oh, I'm just too much of a perfectionist.
[00:36:28] Like that's just, you know, not good. Oh my gosh, I hate that interview answer. You know, I think you have to come up with something that is a humble example of a time you made a mistake and really explain what you did about it. And so when I'm hiring, I look for different things that can kind of give me a sense of that.
[00:36:41] Like, I really like people who've done. Blue collar jobs at various different times in their life, people who've worked and put themselves through school. When I see someone like that and who has a background like that, it makes me think, okay, like this is someone who has humility. This is someone who has some sort of grit and determination that these are really good qualities that you want to look for, you know, in someone that you're hiring.
[00:37:00] Really great advice from both of you and wearing my startup hat. I have many hats as well, not a captain, get a captain hat, but it's a startup hat. I like to also ask candidates to tell me a time when you've identified a gap in the business. Some sort of gap and what you did with that gap, that knowledge.
[00:37:18] Did they drive to improve the company or create a solution for that challenge? It's really telling about the individual that you're working with potentially. All right, for the next segment, I would like to bring up a real Life example of a situation where the company had a challenging outcome and probably got sound legal advice from counsel, but chose to go a different direction or someone who was a decision maker went to different direction.
[00:37:45] So we shall not name names, but a very popular social media platform was fined a few months ago by the FTC for violating. COPA, which stands for the Children's Online Privacy Protection Act. What advice would you have for listeners who feel strongly that the business, in this case, should have followed COPPA, but the business said, thanks for your advice, legal, but we're going to go in a different direction.
[00:38:14] Any tips or advice for counsel who's struggling in the same situation? There's a lot of power in that question. I think I'd want to sort of parse a part of The following direction on following a regulation, right? There's a huge continuing there, right? And if some organization, if a product leader or a technology leader said, I'm just not going to pay attention to COPA's requirements, any of them, I think then that's that we started going that red line area because I would be concerned about the judgment business judgment of any.
[00:38:45] Partner who would say like we're not going to file any of those follow any of those requirements if it's a nuance of let's just say it was an age requirement and they had to have some technology build and we weren't going to be able to build that verification system and it was going to take a little bit of time.
[00:39:01] It's a question of. Is there a timeline here of which that mitigation is going to happen? Are you going to come into regulatory positions, a regulatory position, a position that is complying with those regulatory requirements? But I would also try, I would recommend to anyone who's counseling on that, really try to understand what is the reasoning behind Why they don't want to comply with those requirements.
[00:39:22] Is it time? Is it money? Is it just because they want to hit their shift metrics and really start to impress on them the risk impact that they have. Certainly, if this is going to happen, say, after this conversation and they can point to this unnamed organization that didn't comply with COPA, make sure that they understand that there's a real regulatory, there's a real regulator.
[00:39:44] risk that a regulator is going to come in and have a fine to the organization or a reputational risk. And then I think it goes back to things that Aaron said earlier, which is there are certain areas for certain organizations that simply get escalated to this needs to be a CEO or an ex ELT decision. I would make the argument without knowing anything about someone's business of not complying with a regulation as important and as.
[00:40:08] I'd say has so much focus on for such as child protection is probably one of those areas that would be escalated up. And I'd have that conversation with the business owner of like, listen, this is ultimately a decision that needs to be made at that XLT level. Cause it's a major area of reputational risk.
[00:40:24] So I think when you have something that could expose the company to that level of reputational risk, you have to have, you know, executive level decision makers around the table to think about, you know, how do they want the company to be? to be perceived for us. You know, we sell a lot of our technology to government.
[00:40:39] So regulators are, in fact, our customers and we operate in a very heavily regulated space. So, you know, I don't really like this dichotomy of like, should you ask for permission or forgiveness? Um, you know, I generally think that, you know, I prefer to think about it in like a trust based paradigm. If our government customers trust us, then, you know, that trust is a very sacred thing.
[00:40:57] And so, complying with a lot of these requirements is a way that we honor that trust. And, you know, it's not just what we're contractually obligated to do, but it's the trust relationship that we have with our customers. And we wouldn't want to do something to break that trust, because that's a bond that's very hard to repair reputationally, not just, you know, from fines or, you know, contractual arrangements.
[00:41:17] So I'm hoping that for our final segment, Aaron, you can stick with us for a few minutes to for a very fun segment called keep or red line out. But for this last segment, I mean, Aaron, you know, as a DocuSign CLM customer and have probably have gone to a few of my webinars in the past about contracts and agreements that I am a big agreement nerd.
[00:41:41] So keep a red line. I want you to go with your gut. I'm going to surprise you with some questions, but I want your gut reaction. Would I keep this or would I redline it out? All right, just three questions. First, I've got an easy one. Pineapple on pizza. Keep a red line. I'm definitely redlining that out.
[00:41:57] That's disgusting. I love that. I'm from Hawaii. I am believer, no pineapple on pizza. Ken, are you pineapple on pizza kind of guy? Keep. Oh, okay. I feel like you will have a talk offline about that though. All right. Because you work at Via, Erin, driving to work in a car. Oh, I'm definitely going to redline that out as well.
[00:42:20] I think my friends make fun of me and they say the whole reason I work at Via is so that I can create. the car free existence of my dreams because I hate driving and I think it's just such a waste of time and I'd rather be doing anything other than driving. So I think if I work at VIA long enough then like nobody will need to drive in a single occupancy personal vehicle anymore and everyone can just enjoy the freedom that brings to their lives.
[00:42:42] Okay, any opinions, Ken? Oh, red line. There's no reason. If I have another option, I'll take that other option. It is a good time when you drive or I guess taking public transit to listen to your podcast like All right. Last question the general council reporting to the CFO or not the CEO? Keep a red line.
[00:43:02] I'm being so cranky today and redlining everything, but I'm going to redline that one as well. I just think it's really important structurally for the GC to report to the CEO. I work really closely with my CFO and we're super close, but I just think that her job is distinct. Like she's responsible for the finances of the company.
[00:43:18] And if every legal decision gets filtered through a financial lens, you're going to get suboptimal outcomes. Like it's just not structurally the right way to think about legal risks. You have to weigh those kind of things, you know, like in the alternative to each other and not have one ultimately filter through the other.
[00:43:33] I'm going to redline that as well. I know it's become trendy for the GC to report to the CFO, but I think structurally it's better for the GC to have a seat at the table and a voice directly speaking to the CEO. Totally agree. Well, Aaron, it was such a pleasure to have you on our podcast today. Thank you so much for taking the time.
[00:43:51] Awesome. This is super fun. This is amazing. Thanks, Ken. Thanks, Jessica. I had a blast. Yeah, this is great. And for folks who are listening, Aaron, what is a great way to reach out to you or stay in contact with you? You can add me on LinkedIn. I'm fairly active on LinkedIn. Or you can email me or, I don't know, send a carrier pigeon to drop little messages, you know, in New York City and I will find them.
[00:44:11] I don't know, whatever way you want to reach out to me. Sounds good. How very Harry Potter esque of you. Well, thank you, Ann, for your time. Hey, Ken, it was so great to chat with Aaron. What do you think? Yeah, it really was. I mean, I think there's a number of things that resonated, but I'd be curious, like, what, what jumped out to you the most?
[00:44:28] What? resonated with me the most was both your input as well as Aaron's input on some advice on the hiring process, making sure you bring in people to your organization who really have an ownership mindset and some of the tactics and tips you all shared there. What are your thoughts? We both really grabbed onto the idea of psychological safety around decision making.
[00:44:53] So it's also once you have that team in, it's also making sure that there's an understanding both as leaders and then across the team of, Hey, sometimes decisions won't go the way that we expect. And we're going to take a look at that. We're all going to understand what participation we had in that. And then we're going to, we're going to make a better decision in the future, but it's not about a gotcha moment.
[00:45:13] Yeah. I really love that because hiring the right people to your organization. It matters so much to not just to create a culture of ownership and making sure that your team feels comfortable raising a point of view that may or may not be just legal, purely legal, and also to feel safe to admit to their mistakes when they make a mistake.
[00:45:36] Any last final advice on how do we create a culture where folks are comfortable with that? And I think it's especially hard for folks who are pretty junior. Or maybe even, um, not feeling secure in their role for whatever reason. I think of it from the leadership that I try to display. I try to be very vulnerable.
[00:45:54] I try to bring up my own sort of decisions that haven't gone well. And I think that is the best way that you create that culture is by modeling it from your from yourself. And folks who are listening, I can attest that Ken lives that. He's not just saying that. Well, thank you all for listening and hopefully you embrace your inner humility and vulnerability.
[00:46:16] Thanks Ken for joining me.