Closed Mouths Don't Get Fed: Use Metrics To Tell The Story Of The Legal Department With Kathy Zhu, CEO And Co-Founder Of Streamline AI [E80]

Feeling like you’re never going to get resources to support your legal function?

Kathy Zhu has been there. Facing an endless demand for her time and limited resources to meet the business need at DoorDash, Kathy as head of Commercial Contracting, built relationships with her key customers and a process to help her team manage and communicate priorities within the company. She was so successful in showing her team’s value (and their resource needs), her clients actually donated their own headcount to the legal department so she could serve them better.

Seeing the value of process, tools and relationships, Kathy and her co-founder built a tool (Streamline AI) to help in-house legal departments manage their workload and generate metrics to make the case for more resources.

In this episode, Kathy shares how she managed “the bottomless pit of need” using Google forms as a bush fix before Streamline AI was born.

She shares:

Why transparency and vulnerability are a superpower for building relationships with your key clients
How using metrics can help you “speak CFO” and tell the story of your legal department
Why understanding the stage of the company and what’s needed can help lawyers deliver better services

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Listen to the Podcast here

Closed Mouths Don’t Get Fed: Use Metrics To Tell The Story Of The Legal Department With Kathy Zhu, CEO And Co-Founder Of Streamline AI

My name is Kathy Zhu. I’m the Co-founder and CEO of Streamline AI, which is an AI-powered intake and matter management system for in-house legal departments. A fun fact about me is that I lived on 4 continents before the age of 15.

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On this episode of the show, I’m excited to welcome Kathy Zhu. She is Co-founder and CEO of Streamline AI, which is a legal tech platform that does intake and matter management. We run in the same circles, but I invited her on the show because of a post that she did about her experience as the fifth lawyer at DoorDash and how she managed a bottomless pit of need. Kathy, welcome to the show.

Thank you so much. It’s wonderful to be here. Thanks so much for having me.

Navigating The “Bottomless Pit Of Needs” And Setting Expectations

This is great. I want to dig in and talk about that situation at DoorDash. You described a line out the door. You were the fifth lawyer there. That’s very similar to how I started and my current role at Cottage Health. They did not have an in-house legal before, and there was a Disneyland line out the door. For the first year, I said, “What did you do before I got here?” I want to talk about that and how you managed the bottomless pit of need.

To set the scene for everybody, this was in 2018. DoorDash already had thousands of employees and tens of thousands of restaurants or merchants on its platform. This is probably a surprise for everybody. They had never hired a commercial lawyer to manage any of their contracts. I was the 5th or 6th lawyer. They had 4 or 5 other people on the team. Everybody had a litigation or a policy background, which was critical to the company’s revival.

By the time they got to this stage with tens of thousands of merchants, they were like, “We probably need someone who knows how to handle a contract or two.” You can imagine what it was like when I walked in the door. Everybody was dividing up the commercial work between them, but for weeks, they’d already said, “We have someone coming. Hold on.”

They primed the pump for you to start working.

That’s right. In a way, it was great. After a couple of days of onboarding, and I started to get my hands in there, I realized, “This is such an insane amount of volume.” Even if I worked every single minute of every day, and even if I had all the headcount based on how quickly the company and the volume were growing, which didn’t happen until eight months in, so I was low-handling all of this, we can’t throw bodies at the problem. It would never address what was going on. First, I met with every single department leader that I was supporting. I told them, “All you have is me. That’s it. I’m the only one here.

To set the expectation.

That’s right. Most of the time, and this is true for every legal department, the business teams we support only see the work that they’re giving to you.

Tunnel vision. They’re like, “What could you possibly be doing besides me?”

If you are lucky, the leader of that team helps you organize a little bit of what’s going on in terms of the stuff the team is submitting, but they don’t know that you’ve got ten other teams that are pounding on your door. To your point, this huge line. What I did initially was write down every single department I was supporting. All I had visibility into was these departments. I wasn’t tracking anything else at that point. It was the first week. Even that gave them a sense. Their eyes widened. I knew I was getting through to them.

I said, “What I need from you is to have a very clear understanding of where you fall on this list. What’s most important for the company is for me to support the revenue deals and also the largest ones.” Unfortunately, I had to give them the brutal truth. I was like, “You’re number eight on my list.” They looked at that and said, “That’s the right prioritization. We are going to work with you to make when you work on our stuff as efficient as possible.”

Meeting with them and getting them on board to be on your side.

That’s right.

I don’t know that everybody does that, though. This is maybe too strong a word, but that’s a vulnerable approach to take. As lawyers, we think, “I can do it.” We don’t want to show, “I need help.” You were open with them to say, “This is where you are.”

That’s right. It’s interesting that you pointed that out. I never thought about it that way because sometimes, we want to present this front of, “I’ve got it all. Don’t worry at all. I’m going to be the super superwoman.”

I do that. It’s terrible.

The state of reality is, what is the consequence then? You have to maintain and keep this front even when you feel very stressed out. Also, I knew that that wasn’t going to be possible because the volume was too much. The state of vulnerability was perfect. What that enabled me to do was I followed up in the 2nd and 3rd week to mandate a specific way that they would have to submit their requests. I said, “I need you to fill out a form.” God forbid, everybody gasped.

In a tech company. You were like, “We’re going to put some bureaucracy in your way.”

That’s right. I said, “There’s no other way that I can manage it because I cannot afford to waste a second on back and forths with you to understand what’s going on. You have to come through this very specific channel. If you don’t, then I can’t get to it. I’m sorry. I won’t be able to.” It was from this place of complete and utter transparency, radical honesty, vulnerability.

I said, “This is what I need so I can help you,” and everybody came on board. It was incredible. They all submitted forms. They all added links. They were bending over backwards to try to help, which was also the culture of the company a little bit, too. They desperately needed help, and here I was, offering it to you, but only in this very specific way.

That’s when I realized, “This is what we, as legal departments, need to do. We’re the most under-resourced team. We need to channel the work through in a way that enables us to get through it as fast as possible.” I then realized, “I need reporting because if I don’t have the numbers, I can’t go get the headcount that I need.” You start to see a lot of these different pieces come to place. Ultimately, Streamline does all this. That comes much later. The first step was my identifying the need I had and the fact that I couldn’t find anything other than Google Forms and spreadsheets.

As the most under-resourced team, the legal department needs to channel work in a way that enables us to get through it as fast as possible. Share on X

Building A Structured System: From Google Forms To Streamline AI

How did you know to take this approach? The reflex is like, “I got this,” and then whoever is squawking and whoever is raising their hand, the squeaky wheel gets the grease. How did you have the knowledge or the discipline to set up this more structured system?

Some of it was, for sure, learning that carried over from the four years previous to that, where I spent as a commercial counsel at Medallia. At Medallia, it was a completely different kind of business. It was a SaaS business, so the volume is 100X less. Every single agreement we worked on still had a lot of complexity to it. My manager, who was the VP of Legal, ran all of commercial. He understood the power of metrics, and he knew that in order for us to track anything, we had to have it come in in a very systematic way. We used Asana.

Isn’t that a project management tool?

Yes, exactly. At the time, there were no systems that were built for legal. I saw how incredibly clunky it was to use a project management tool to track legal requests, but I still knew that it was better than working from our inbox to get out of it. It’s better than working out of our Slack.

I am going to give myself a shout-out, though. I am thinking back to when I first got into my role. We don’t do commercial contracts, but we have a pretty steady stream of these professional services agreements. I set up a process around that, and I got everybody together to help inform what that process would be. It was a long time ago. As you were talking, I was like, “I suck,” and then I was like, “I did that, too.” You do get lazy about it. Did you check in with people after you built the forms and the process? Did you keep those regular meetings? How did you build this as an enduring approach?

It’s consistency. You have to, in the early days, help people build that muscle as well. That’s not to say that I was completely inflexible. The other critical part is situational awareness, where you know there are certain times when you have to have a certain degree of flexibility. When I started building my team, I created a mission. I created an entire way of doing things with my team that made us feel engaged.

To make regular meetings enduring, it’s about consistency. In the early days, you really have to help people build that muscle. Share on X

What was that?

DoorDash had an entire principle around, “We delight our customers.” I wanted us to do the same. It wasn’t enough to meet them and give them what they want. We wanted to have every interaction feel delightful. About 600 lawyers use our platform. A lot of new customers we talk to say, “If you mandate forms or mandate a structured intake process,” and we can meet them far beyond forms, they’re worried that they lose this personal touch or lose the customer experience. It’s the opposite, because if you can get out of having all these transactional back and forths, then you can start to get into counseling.

The counseling we did happened over Slack. It happened through meetings. We could get down into the weeds. We knew what was going on. The advice was immediately useful, and it demonstrated an awareness of what was going on. The process is a tool to get you where you want to go. Back to your point of how I did this, there were tons of interactions with business people, and I love that. That was my favorite part of the job.

Not a ping pong email about, “Now what do you want?” and sending red lines back and forth. As you were talking about developing your process, you mentioned how to get headcount using metrics as a basis for getting resources. I want to talk about that, but I also want to talk about another LinkedIn post you had written that got my attention. In-house lawyers are the worst about asking for resources. I’ve struggled with that myself. There is this statement, and I live by it now, which is that closed mouths don’t get fed. How do you think in-house lawyers can advocate for resources? How can you get over that? It’s what we were talking about earlier. You’re like, “I’ve got this. I can handle it, I’m a superhero,” or whatever. How can we move through that?

Advocating For Resources: Speaking The Language Of Metrics To The C-Suite

The shortest answer I can give to you is that it has to be done through metrics and numbers, which contradicts a lot of the training we’ve had as lawyers. We live in a world of stories of narrative that we shape. The unfortunate reality is that we need to speak the language of the CFO and also the CEO. They’re talking all day in terms of metrics.

As lawyers, we live in the world of stories and narrative. But the unfortunate reality is, we need to speak the language of the CEO and CFO, who are talking all day in metrics. Share on X

I want to illustrate the power and the difference between showing up with a story and showing up with metrics. If you show up with a story, it usually sounds something like, “We are burning the candle at both ends. We’re working so hard. My team is burning out. They’re barely eating lunch. We’re cutting into time with our families.” That is very anecdotal. Honestly, the CFO hears that and is like, “Everybody’s working super hard.” They start tuning it out.

Let me show you an example of how strong this sounds if you say, “We’ve been measuring the volume that’s been coming in through the team. The volume is increasing 40% quarter on quarter. About 50% of that volume is spiking in these 2 different areas, so I need at least 2 heads to keep up with this demand. I’m not even saying get ahead. I’m saying keeping up with the growth. We’re supporting around 50 requests per month per person. If you give me this amount of budget to bring on this tool, then instead of 2 people, I only need 1 person.”

I can get behind this. I fully understand that you’ve measured this. You understand how it breaks down. You’re demonstrating not just ownership, but you’re also demonstrating that you are trying to get ahead of the problem by asking for less. It’s like, “You’re asking for less than you need,” versus showing up, being stressed out, and trying to pick up whatever crumbs they’re willing to give you. There’s one year where I asked for five heads. Guess how many finance approved? Zero. They gave me nothing. I was desperate. I knew that we could not possibly manage, so I went on a roadshow. Do you remember all those different business teams I talked about before?

You had some advocates.

I had the advocates. What happened with the advocates is I gave them all the numbers, and I showed them, “This is what your team has been submitting. This is how much the volume has increased over the past year. My impact means that our SLAs are going to double, if not triple. How does that sound?” They were panicking.

They were in there with me, and I said, “What can you do to help?” I was thinking that maybe they can go and be my advocate, to your point, to finance, but that didn’t happen. Do you know what happened instead? They said, “I have eight heads approved this quarter. It will make a bigger difference to me if you can meet your SLAs and if I had one of those heads. I am going to give you one of my headcounts.” That happened for four out of the different teams I met. I ended up with four additional heads, not from finance, but from the sales teams.

I think that the reason that happened is because you invested in bringing them into your team through those meetings. That is the takeaway here. Instead of having your wall up, being with your cape and your superhero, and saying, “I’ve got this,” you bring your business team in and show them behind the curtain. When we were doing prep, you shared a story about someone asking you, “What do lawyers do all day?” I want to talk about that story. To me, that’s a gold nugget right there. What is a better story than colleagues giving you headcount from their budget to help your team? Mic drop.

Every time I tell that story, I can see it in the faces of all the different legal teams we talked to, where they’re like, “This is possible?” It is.

Was it the twofer? Was it having the metrics and having to speak CFO, and then also have allies who wanted to support the legal team?

That’s right. You’ve got to have both. You’ve got to have the part that’s factual that you can’t argue against. The other part is very much the human touch. Building the relationship and bringing people along doesn’t happen overnight, but it’s so important how you establish that relationship from the first day. It’s never too late to change. I love Brené Brown. There’s so much truth in the power of vulnerability. We don’t have to put up a front. Everybody is human. They’re dealing with the same stress, the same worries, and the same overwhelm.

Strategic Leadership & Visibility: Demonstrating Legal Department Value

If you can meet people at a very human level, it enables them to feel so much more comfortable opening up to you. I’ve had other leaders from other departments coming to me, multiple people, and saying, “How do you build a team? How do you go about hiring?” That demonstrates a tremendous amount of vulnerability, too. They’re like, “I’ve been struggling.” Whatever it is, it goes far beyond solving legal problems. That’s because I went there first. I’m like, “I’m not perfect. I’m trying to figure this out, too.” That has been part of my secret sauce.

If you can meet people at a very human level, it enables them to feel so much more comfortable opening up to you. Share on X

I made some notes. I’ve got new leaders at my company and had some questions about resources. With my former leadership, when I asked for money for tools and headcount, they said, “Stacy, we already know you work hard. Here you go. Here’s the headcount. I don’t need to spend X dollars on a tool so you can show me how much work you’re doing.” I thought that was lovely.

I had Kevin Rubin, who was, at the time, CFO of BetterUp. He was a CFO, and his advice was for the GC to demonstrate their value through strategic leadership, being part of giving opinions, and not hiding behind all the legal mumbo-jumbo that we use. He was not as leveraged on metrics, KPIs, and that sort of thing. I agree with you that being able to show your work is helpful. Let’s talk about the what lawyers do all day story because I got a good laugh out of that.

That was my co-founder, which makes it even funnier. At the time, he was a product leader, supporting one of Google’s AI products. He worked at Google for five years before we teamed up. When we met, he didn’t understand what his legal team was doing. In fact, he said to me, “Working with my legal team is the worst part of my job.”

Ouch.

I know, right? Talk about how deeply that hurt. When he followed up with, “What do lawyers even do?” I almost throttled him because I was working harder than I’d ever worked. What that showed me was that he’s not alone. There are all these business teams out there that have no clue. There’s a massive visibility problem. What he told me was, “Kathy, in order to get anything done and in order to get my product launches approved by this lawyer, I had to get on a bus, usually on Fridays, to go from Google’s headquarters in Mountain View to San Francisco, which is where all the lawyers sit.”

He said, “I had to go track him down at his desk and stand there, because every time I tried to schedule a meeting to ask what was going on, he would cancel it. Every time I sent an email to ask about what was going on, it never got a response.” What he doesn’t see is that the lawyer’s inbox may be 50 deep with escalations. Everybody is following up. The system is so broken.

Back to what you were saying about the CFO’s recommendation with demonstrating value and doing strategic work, guess what happens? The squeaky wheel. Hundreds of the squeaky wheels stop us from doing the strategic work. I’ve asked every single legal leader I meet with, “If you can get 20% of your team’s time back, what would you do?” Their eyes would start glowing. It’s like, “20% of my time?”

Those are all the projects that we keep putting off over and over because they’re not urgent, but they’re important, and they are the future plan. It’s always the future stuff that’s going to help us get ahead, but that always ends up getting pushed down because of all the fires. This is me back then when I was talking to Julian. We realized, “Why isn’t there an actual system that gives everybody visibility, so they can stop lining up, stop hounding us, and stop escalating. Why can’t they see where things are?”

Navigating Privilege: Designing Legal Tech For Confidentiality

Can I ask? One thing that’s on my mind about a visibility tool, and there are many ways to do this, is how do you deal with privilege? When I get in a commercial contract, if that’s the portfolio, there’s probably not anything that’s super sensitive, but I’m thinking about my desk, I’ve got investigations, litigation, board stuff, and any number of things that the person in supply chain doesn’t need to know about, or the person that runs the insurance program doesn’t need to know about. Thoughts about how to navigate a privilege situation where you’re trying to show what your team’s doing?

It’s a fantastic question. it’s the question that I take and talk to investors about why you cannot have a project management tool or an IT tool like a Kira or a ServiceNow that handles requests for the legal department specifically. You need a dedicated tool. More than that, you need a tool that’s designed by a lawyer who spent their career thinking about exactly what you talked about, so that the right permissions get built in.

You actually need a dedicated tool, and more than that, you need a tool that's designed by a lawyer. Share on X

We designed a system where you can shield different types of requests from different eyes. Also, even within the same request, you can sidebar legal-to-legal conversation. You can have a privileged conversation with your HR partner and never have the business people see it. The permissions are so multi-layered and designed into the system that you don’t need to worry or think about this. You don’t even need the IT team to configure that because it’s already built in. I’ve heard some horror stories about legal using generic IT systems, and then there’s an employee escalation or whistleblowing situation. This is a real situation where the legal and HR partners were talking about that matter.

From In-House Counsel To Tech Founder: The Leap To Streamline AI

My stomach hurts thinking about it. I could see you might need a solution around that. You and I are aligned. That was something that was on my mind about it. Since we’re peppering around your transition from in-house lawyer to tech founder, let’s talk a little bit about how you went there, and then I want to find out about what it’s like on the other side of the desk. Share a little bit about how you and Julian developed this new tool, and then we’ll get into your role as CEO.

You’ve probably heard bits and pieces of this. This was a huge problem that I was running into on the legal side. Julian was seeing it on the business side enough so that we started to call all of our joint networks, all the lawyers that we had access to. We were asking them, “Are you dealing with challenges around a lack of visibility? Are you overwhelmed with too much chaos and all these requests coming in? Are you using your inbox to manage what’s going on? Are you marking something unread so that you know you haven’t gone to it yet?” Every single person we spoke to said, “Yes, and we haven’t solved this. There isn’t a tool we found that does this.” That’s when I decided, “I’m going to take the biggest risk of my career.”

I’ve said to so many people that if I found that tool, I would’ve become a customer, I would be their biggest advocate, and I would still be running commercial legal for DoorDash because that was honestly my dream job. I loved what I was doing. I’ve invested years in building these relationships. I had a team of twelve. I didn’t want to leave, but I ultimately decided, “No one else is doing this. We’re in the best situation to solve this from the legal perspective. I can’t have an engineer building this.”

It was terrifying to leave my comfort zone, leave so much that I knew behind, and take the leap. What it took was so much conviction. I had so much faith and belief that this is what the entire industry needs so that legal teams can be more empowered. It goes beyond the simple tracking of metrics of volume. I feel like what we lack is being able to show up to executive team meetings in the boardroom and say that the legal team took on work that supported 80% of all of the revenue, or maybe higher.

That’s a mic drop moment.

If we can do that and have dollar values attached. We could say, “Of everything we did, 60% of it was escalated. The T-shirt size was large to extra large.” These are realities of what we live with. We need to have some way of quantifying it, rather than talking about this case that didn’t happen or this settlement that happened. What we do, down to very concrete numbers, is strategic, aligned to company-level OKRs, contributes to X dollar of revenue, and has supported this many product launches. People sit up, and they look at you completely differently.

When we talked in prep, you talked about spending hours and hours building Google Forms, which overwhelmed me. As you were building it into more of a commercial product, you were thinking of the bigger picture, like, “I’m not just going to try to help the team manage the work, but I’m trying to develop something that will allow them to make the case to show what they do in a meaningful business way.”

That’s right. Building something that purely handles efficiency and helps us work a little bit more efficiently doesn’t quite excite me enough. What I feel on a very deep level is that legal departments do not get nearly enough of the recognition that we deserve. Talk about value, truly. If we didn’t exist, the company wouldn’t be around, most likely. To say that in a way that resonates.

The legal departments don't get nearly enough recognition for the incredible value they bring. Share on X

We’re talking about an entire industry of people who are working way too hard, who get the short shrift, and who get labeled as a cost center. The number of GCs I’ve seen that accept that moniker without wanting to change. They’re like, “We get treated as a call center, so we’re never going to get the resources we need.”

That attitude frustrates me. I don’t like that.

We might as well give up, but surely, there must be something that we can do. We have all these new team members who are starting their careers. Folks who are graduating from law school are entering this whole profession. We ultimately have the choice and the control to make a difference in their lives, too. How do we do that?

That’s what gets me excited. That’s why I’m talking all day long, not just about managing what comes in. It’s how we elevate our entire industry so that we’re seen differently by our counterparts, and so that we’re right-sized and we can do the work that we need to do rather than getting lost in the details and going back to the building of it.

This part is no different from any other startup. We put together a prototype. It’s the very basic version. This was amazing to me. Of our first two customers, one was a Series D tech company that had almost 1,000 people. The GC saw this prototype and was like, “I want to work with you to get this to the point where I can roll it out to my whole company.” Once that happened, we built so much for that GC. Then, the product got into a better place.

The second customer we signed up was Logitech. We were like, “What are we going to do? It’s going to completely break our system in ten different ways.” It’s a huge blessing, so you take a huge breath and go for it. We implemented the product with the legal team first at Logitech. Within a year, we’d expanded 2 or 3 times in the entire global legal team of Logitech worldwide. I’m talking about teams in Switzerland, other locations in Europe, and a huge team in the US. They all came on board, and then we’re off to the races.

You’re doing it.

We were like, “This is no longer a side project.” I came on board full-time in 2022 to raise funding and do things as a CEO.

The CEO’s Journey: Setting Vision, Managing Cash, And Recruiting Talent

Let’s talk about how you made that leap. First of all, I want to say I appreciate how you’re looking at your product, not just as a tool in the toolbox, but I see the bigger mission behind it. Going back to your DoorDash example about delighting, it feels like the mission of the company is to help elevate the legal department. That’s cool. I want to hear about leaving that behind. You’re in mission control. You’re in charge. You’re not servicing. You’re not just legal anymore. What is that like?

It’s terrifying. Back to the radical openness, honesty, and transparency, at least the first three months, there was this huge thought rattling around my head. I was like, “The scope of this role is so massive.” Every morning, I’d be like, “Am I doing it? Am I doing an okay job?” No one has ever written a job description for the CEO before.

A few a-ha moments happened for me along the way, where I started to feel like I had my sea legs under me. First was getting the right mentors and advisors around who had done this before. One of them was a CEO who had a successful exit. He has seen the building from the very first day. He said, “Kathy, there are three big things that you must never, ever lose sight of as a CEO. As long as you’ve got these three things down, you’re doing an okay job.”

One of them is setting the vision for the company. It’s elevating the legal department. What is the company ultimately about, not just the tech? That’s how you get everybody aligned. The other is managing cash. You need to make sure at all times that you’re in a good position, you have enough runway, and you’re going to fundraise when you’re starting to get closer. He was like, “Managing cash is critical.”

The third is talent. Are you recruiting the very best people you can? As long as you’re spending enough time on these three things and you’ve got that locked down, everything else is icing. You need to figure out how to delegate, so you don’t do everything else, but in the early days, you are doing everything you can. I was doing marketing and PR. I was doing sales. I was copping on customer calls. There’s no part of the business I’ve not touched, including building furniture and ordering the snacks. You’ve got to do it all.

The only part that I’ve not done to date is writing code. That’s product and engineering. My co-founder is brilliant at that. Thank God because I probably wouldn’t have survived those early days. You figure out as a CEO where the bottlenecks are in the company, whatever is slowing things down, and whatever it takes to get things running. To date, I’m all of back office. I’m HR and legal.

CEO’s Perspective: What Founders Seek From Legal Counsel

Talk about the legal part. I’ve interviewed a few CEOs on this show. I have a series I call the C-Suite Series. One of those guests is Evan Wong, who’s the CEO and Founder of Checkbox. That’s episode 60, if anyone wants to check that out. As you are a consumer of legal services as CEO, what do you want from those lawyers who are advising you? You’re almost like the secret shopper. He shared, “I don’t want to hear every risk. I don’t want to hear that I can’t cross the street. I want to hear informed risk-taking.” What do you want lawyers to know who provide services to people like you?

Being aware of the stage of the company is incredibly important, as well as what the stage of the company needs from the legal department. For us at Series A, we raised almost $9 million round.

Congratulations.

Thank you very much. That was a very exciting time for all of us. It’s growth right now. It’s always growth, but when you’re earlier, it’s even more important. Also, the risk profile is lower. We don’t even have enough legal work to need a full-time legal role, but what I did do was bring on a lawyer to the team. I’m so excited because he was a former customer. It speaks volumes, right?

That’s perfect.

We’ve had so many customers over the years asking to come on board the team. They love the product so much that they want to get closer to it and help shape and build it, which excites me. I brought him on. It’s a hybrid role. Part of the time is to help us develop and keep developing legal tools. To me, the tools have to fit the hand that wields them. They can’t be an awkward thing that you’re trying to twist yourself around trying to use. It has to feel seamless. You can only do that if you have people who are truly subject matter experts. I need more perspectives than just me at this point, and that’s part of what this person does.

The other part is go-to-market. This person is spending a lot of time with our customers, talking to our customers, and understanding what their needs are. Another piece is a legal piece. I’ll give you an example of something that came up around legal advice that I went to him for. It was fascinating. We are coming out with a couple of new AI products. We went on a long journey, came up with a name we loved for this legal product, and filed a trademark with the USPTO to protect the brand name. Not long ago, I saw a massive press release by one of the huge legal tech companies that’s been around for over a decade, and they announced a new AI product with the same name.

What are the odds?

Tiny odds. I realized that we do have legal rights. They never filed. We’ve done a search right before filing. I asked, “What are the different avenues? What should we do?” If someone is purely with the legal hat on without the business awareness, they would’ve been like, “You should send a cease and desist.

It’s like, “Giddy up. Let’s go.”

Exactly. It’s like, “Roll up your sleeves and put the boxing gloves on. You’re going to win. If you want to take this all the way, you’re going to win.” Is that truly what the business needs? To me, it’s not even the cost. The cost is secondary.

It’s the bandwidth.

It’s a distraction. You knew that right away. It would completely distract the team.

At the end of the day, how much time is it for you to come up with a better name?

That’s it. To me, that’s the difference between someone who’s only seeing the legal arguments versus understanding where the business is at. I would’ve come up with probably a different approach if we were a 2,000-person company.

It’s all stage. It’s what you’re saying. You told me that your most important use of time is growth. You’ve got to run. If you’re going to be distracted on this fool’s errand about a name that you haven’t even used, why would you spend your time on that? Let me ask this. Do you feel like you have to train for that? We said in your top 3 duties as CEO, 1 of them is talent. How do you recruit for that type of awareness and business acumen?

I’ve had the good fortune of talking to hundreds of lawyers at this time.

You’re like, “I can spot it a mile away at this point.”

You can. You talk to enough people, too, where you can also spot that a mile away. I’m very much in the growth mindset camp of we aren’t fixed in terms of how we’re born and how we are in terms of level of intelligence, skills, and knowledge. All of that, we can grow, change, and develop. It’s just a matter of openness and willingness.

We aren't just fixed in terms of how we're born, our intelligence, skills, or knowledge. We can grow, change, and develop; it's a matter of openness and willingness. Share on X

There are certain people who truly rigidly see the world in a very fixed way, and they’ve got blinders on. It becomes hard to shape their perspective. There are other people who are open. They’re like, “I’m going to fall on my face six times, but guess what? I’m going to learn all 6 times, and then on the 7th time, it’s going to happen.” They usually have a tremendous amount of humility. It’s true humility. It’s not like a, “Look at me and how humble I am,” situation.

If there’s one trait at Streamline that we try to look at, it is the growth mindset. This is all the interviewers. I ask everybody. I’m like, “How open is this person to learn, grow, be coachable, and not feel like they know everything already?” That’s the number one key to success. Let’s go back to the entrepreneurial path, too. I’ve had so many lawyers ask me over the years, “Do you think that legal training lends itself well or not to becoming an entrepreneur?”

There’s a little bit of unlearning that we have to do. I still check myself. We spent our entire careers spotting risk. We’re so good at that that we instinctively will start looking at the downsides of how things can go wrong before we ask, “What are all the ways it can go right? What are the opportunities here?” instead of looking at the downside. That’s the biggest thing we need to let go of. Some people are innately better than others, but it’s a skill that can be learned.

If we can turn the tide on that, I think that we’re very well-served to be fantastic leaders and entrepreneurs, and go beyond our scope as running the legal department. That’s because we are so intimately connected, more than any other department, with everything that’s going on. We know everything. When I rolled into this role, I realized, “I’ve done enough supporting the PR team and reading marketing copy to have a sense of how things should be worded and the importance of wording things this way, but not that way.” There are certain types of comms. I know I shouldn’t say this.

You’ve got a high-level MBA after going through all that.

That’s right. I would encourage folks who do want to run a business one day to work for multiple different companies in different industries. If I’d only ever had my job supporting SaaS businesses, I don’t think I would’ve been as well-rounded. Since I saw so much more on the commercial side because I was at DoorDash, working with marketing and working with different flavors of partnerships and sales, it gave me so much more 360 exposure.

Streamline is a SaaS business. I learned all about the finance fundamentals, the different terms that you need, how you structure, and all these things. That all came from my experience with Medallia. The more that folks avail themselves and not stick to the, “This is the lane I know, so I’m going to keep swimming in the same lane,” that builds the muscle as well for learning and being open to new experiences.

Kathy’s “Pump Up Song”: Overcoming Fear And Embracing Growth

That’s awesome. We’re rounding the bend here. I ask all guests the same final question, and some folks get stressed about it. I am confident that you’re going to delight us with yours. What is your pump-up song?

Everyone’s going to laugh. It’s Eye of the Tiger.

No way. That’s the go-to. I can’t tell you how many guests say that.

Maybe my reason is going to be a little bit different.

Let’s hear it.

I do jiu-jitsu as well as karate in my spare time. I’ve been working towards a black belt for longer than I care to imagine. I have to spar, especially prepping for that. I had to work through so much resistance in the early days of getting into the proverbial rank ring with an opponent. This is what I would listen to to get myself pumped up and over the anxiety of getting hit in the face. The bigger narrative and story is working past fear. Some people are, but I’m not in that camp of being fearless and feeling, “I can take on the world and stare down my opponent.”

That’s why I ask the question. Before this call, I was listening to Independent Woman. I don’t know why, but it got me pumped up to talk to somebody who has gone and done it. Thanks so much for being here. I enjoyed getting to know you. I took a lot of notes, and you saw my reaction. You’ve been quite a mirror to how I’m running the legal department. It was great to have you. Thanks so much.

Thank you. This was so much fun. I can tell you’re doing amazing based on this interaction. Thanks for having me.

Episode Resources

About Kathy Zhu

Kathy is the co-founder and award-winning CEO of Streamline AI, a leading intake, matter management and workflow automation platform designed for in-house legal teams. Before transitioning to the tech industry, Kathy spent a decade practicing law. She began her career at Wilson Sonsini Goodrich & Rosati, representing cutting-edge technology companies, and later served as Associate General Counsel at DoorDash. During her four years at DoorDash, Kathy built the commercial legal and legal operations functions from the ground up, supporting the company’s rapid growth from 1,000 to over 15,000 employees.

A recognized thought leader and experienced public speaker in legal technology, Kathy is passionate about the intersection of law, technology, and entrepreneurship. Her insights have been featured in Law360, Law.com, LegalDive News, and The Wall Street Journal. In her free time, Kathy is a dedicated meditator, goldendoodle mom, and SCUBA enthusiast.

Closed Mouths Don’t Get Fed: Use Metrics To Tell The Story Of The Legal Department With Kathy Zhu, CEO And Co-Founder Of Streamline AI [E80]