Built to Scale: Alice Davidson & Jenna Hunt on Evolving Legal at a Global Fintech Tipalti

Cecilia sits down with Alice Davidson, General Counsel at Tipalti, and Jenna Hunt, Head of Legal Operations. Together, they’ve built and evolved a legal function that supports one of the fastest-scaling global fintech companies—operating across 200 countries, 120 currencies, and 50 payment methods.

Alice brings a sharp securities and M&A background, previously serving as CLO at Mogo. Jenna blends legal ops with deep customer success and change management experience. Together, they’ve architected a legal org that’s agile, intentional, and built for growth.

In this episode, they talk about:

– Scaling legal with intention through global complexity

– Aligning legal operations with business speed and product evolution

– How AI tools are changing the way their team works

– Legal leadership that balances risk, relationships, and results

Whether you're building legal from scratch or optimizing for scale, this episode is packed with takeaways from two leaders doing the work side-by-side.

Follow Alice & Jenna:

⁠@Alice Davidson⁠ on LinkedIn

⁠@Jenna Hunt⁠ on LinkedIn

⁠Tipalti⁠ website

Show notes:

– Building legal systems to support global scale
– The legal ops–GC partnership model
– Fintech compliance across jurisdictions
– What legal looks like when it’s embedded in the business

Books/Frameworks Mentioned:

– “Thinking in Systems” by Donella Meadows

– “Radical Candor” by Kim Scott

Follow us on all social platforms to get each new episode when it drops.

⁠@Cecilia Ziniti⁠ on LinkedIn

⁠@CeciliaZin⁠ on Twitter/X

⁠@GC AI⁠ on LinkedIn

⁠gc.ai⁠ website

Transcript

Alice Davidson: 0:02

I think it was our first, you know, all hands with the legal team was, you know, uh someone had asked me, what does success look like for you in this role? And I right away said, you know, I want to give them something to talk about. I want to give people something to talk about at you know, Tipalti legal does things differently.

Cecilia Ziniti: 0:18

Welcome back to CZ & Friends, where we talk with legal leaders, technologists, and operators drawing innovation and excellence for their companies and beyond. I'm your host, Cecilia Ziniti. Today we're in conversation with Alice Davidson, the general counsel at Tipalti, and Jenna Hunt, the head of legal operations at Tipalti. Together, they've built and evolved Tipalti's legal function to scale with a global fintech company. And they've done it with intention. Tipalti is a finance automation and global payments company supporting payment operations across 200 countries, 120 currencies via 50 payment methods. If you hear that and think, wow, that's a lot of legal department complexity to help manage, you would be correct. Alice is a seasoned securities and MIA lawyer and former chief legal officer at MOGO. She's also a Legree fitness trainer, a mom, and someone who leads with strength and precision, as well as a friend. Jenna is a legal ops powerhouse who's built Maltese legal operations from the ground up, blending customer success, AI efficiency, strategic planning, and change management into a powerhouse function at the company. In this conversation, we'll talk about what it takes to build an agile legal team, how legal ops becomes a strategic partner, and why executive presence looks different for everyone. Let's get into it. Welcome, Alice. Welcome, Jenna. Thanks to Chinese. So excited you're here. All right. Um, Alice, what does your day-to-day look like leading legal at Tapalti is the general counsel? Give us a window.

Alice Davidson: 1:41

That is a big question. Well, I I often say, I'll answer that by saying, you know, I'm I'm a full-time business person with a legal background. I think that that is one of the myths. If anything, I like to debunk of, you know, people think legal right away they assume you're a lawyer doing lawyerly things all day. But when you're leading the the legal and regulatory compliance function for a global company, it's it's a lot more than that. So, I mean, my days are varied. There there are, of course, a lot of meetings, uh, whether it's at the executive level, with my team, cross-functional partners. But um, you know, a day could be anything from looking into international expansion, figuring out our our our licenses, dealing with privacy matters, figuring out again how a lot of my time is spent with Jenna trying to figure out again how do we scale in an efficient and sustainable way. Um supporting the growth and the velocity of the business. We take pride in topolity and getting shit done and doing a lot on a daily basis. And that's why it's it's very hard to say, you know, what is a typical day like because it honestly changes from day to day as our priorities um continue to evolve and change on the daily. But yeah, I would say, you know, all day is the same.

Cecilia Ziniti: 2:42

I love it. I love it. Um, Jenna, come into this role. How did you go about starting and scaling legal operations? Right. So I'm just thinking about the scale of 200 countries, presumably regulatory regimes across all of them. And based on what Alice just said, you know, you add a country, you don't add a lawyer. So how do you how did you think about that? And and where did you start?

Jenna Hunt: 3:02

Yeah, so I actually came um into Tipalti more in an admin role, just supporting our commercial function. So it was pretty uh commercial heavy uh supporting our commercial team and and some projects there. And then when Alice came in, I think she recognized that I was doing a lot more of that and doing legal ops, which I didn't even realize was a was a thing. So the Alice was sort of like you are you're not doing just this of this, you're you're doing legal ops. So let's create a legal ops function. So definitely um kudos goes to Alice there for recognizing that's what I was actually doing and allowing me to sort of start up that function and and and and roll with it. So we were already had a lot of things in motion, and as much as I'm sort of a one-person team, it really is the whole team supports the the operational stuff as well. Try to look at, you know, what we were doing that was taking up most of our time um and repetitively and started there with the low-hanging fruit and then and just have have grown grown quickly from from there, I guess, with various different projects and uh cross-functionally and and yeah, just really efficiency um is is a big one for us. I always say I want our lawyers practicing at the top of their license.

Cecilia Ziniti: 4:12

Um can you unpack that a little bit? What do you when you say top of the license, what is that uh practice?

Jenna Hunt: 4:18

Yeah, so I mean just as an example, right? Like lawyers negotiating NDAs is not practicing at the top of their license. So that was sort of a you know a low-hanging fruit for a lot of people. Um, I guess a low-hanging fruit of what we want to tackle, but for us, and it was just establishing those playbooks, um, empowering the business to make decisions, empowering the business to negotiate those things, creating automated workflows for pre-signed NDAs so that we don't need to even have legal involved. So things like that were again, it's these repetitive small things that sometimes feel like a quick, a quick little ass from legal. We added all those up and realized that's where we were spending the bulk of our time and not on these strategic initiatives. We we kept pushing the strategic initiatives down the priority list because of the on fire, you know, daily ass from the sales team or the stuff that's, you know, those little things that the quick, the quick fixes. And but we were we were not having the bandwidth, not having the time to tackle those strategic things. So Alice also is great at really reprioritizing us on that point. We're spending too much time on the the daily small things that we don't really need to be spending time on, right? Like we we want to be a partner to the business, not you know, coming in just doing these little daily tasks.

Cecilia Ziniti: 5:28

So pulling on that partnership thread from Jenna, Alice, so it sounds like you you took like an architect mindset to the to this legal ops function. Put us in in your head when you did that and you know, maybe a little bit about tapping Jenna. Obviously, she's very talented, but how did you think about creating this function? And was it something like you were specifically hired to do, or or say more about that?

Alice Davidson: 5:50

Yeah. So, you know, when I came in, I knew I was inheriting a team of brilliant legal minds, attorneys and non-attorneys, but what was missing was sort of a strategic element, right? It was we were just executing, we were kind of responding to the business needs, uh, really focusing on, you know, revenue at all costs, generating revenue. And I think that was part of the um um, you know, legal trying to re represent its value of we're not a cost center, we're enabling sales, we're enabling revenue. And that's really where the focus lied. Um, I think there were many ideas, just uh a lack of, you know, a executive sponsorship to allow this to happen. But also, you know, I clearly saw that there was an opportunity for legal to be elevated as a function internally and and for the breadth and the scope of the function to become a lot bigger. At the same time, I knew I was not getting any additional headcount, right? I knew our bookings were gonna increase the next year. And and sort of up to that date, you know, the team kind of grew commensurate with that of, you know, bookings are increasing by X percent or revenues expensive to increase by X percent, we've got to add another lawyer. Your earlier point of, you know, we're going into a new jurisdiction, we have to add another lawyer. And I knew that at our size, you know, a pretty sizable team. Um, I think when I joined Jenna, we were 11 or 12 to non-attorneys and nine attorneys and about a thousand employees. That's a pretty, pretty good ratio. So there was this need to kind of take a step back. And to your point, re-engineer or re-architect, the way that we work internally as a team, but also the way that we support the business to continue to sub, you know, do the great things we are doing. One of the things I said, I've never seen a better relationship between a legal team and sales, is what I had witnessed coming into Tipal Team. And we can get into that a little bit later because it got to a point of over-enablement and over-reliance. And so it was, you know, how do we sustain the great that we built, but you know, lean into automation, lean into technology, lean into enablement and education so that we could create more self-service, that thereby, you know, as Jenna said, enabling our attorneys and non-attorneys to practice at the top of the license and actually do um the more strategic things that move the needle. One of the first things I said, I think it was our first, you know, all hands with the legal team was, you know, uh someone had asked me, what does success look like for you in this role? And I right away said, you know, I want to give them something to talk about, at fault illegal, whether it's a you know, particular transaction or something that we did, the way that we employ technology, but it's just really the way that we deliver value and deliver legal and services. And and it's really premised upon that partnership. I think I've heard you both say the word, and and you know, going away from being counsel and being an advisor to being uh to borrow from our friends in the world of HR, a legal business partner, right? And and and trying to uh change that perception and the way that that relationship worked.

Cecilia Ziniti: 8:28

So that that's amazing. We've got kind of the architect, you tap Jenna, you're you're doing this, you've got these strategic goals. Jenna, what are the key ways that you and Alice collaborate? And how have you defined kind of what the GC does, what legal ops does, and then empowered everyone on the legal team to step up to become those legal business partners?

Jenna Hunt: 8:47

I mean, I like to think I'm I'm Alice's right hound gal. Um, we work very closely together. But at the same time, she's really empowered me and and the rest of the team to she has that trust in us um and has empowered us to, you know, we're on the ground doing, you know, we we we're seeing where these issues are or where these lack of efficiency is and to go fix it, right? So she has been fabulous in that sense of, you know, I can I can count on her to be the seat at the table for us at the executive level um and be an influencer in that in that point of view. And she's been fabulous there. And we've gotten so much support with the projects that we've wanted to do to support the efficiency on our own team and how we work with um the other teams cross-functionally. Um, it's just, you know, open communication and keep each other updated on what's going on. Again, like I she's there when I I need help for our escalating something, but she's really left myself and and the team to to build what we need to build to make our lives better, and again, to have the lawyers, you know, practicing at the top of your license to not have this over reliance on on legal for things. Um yeah, really empowerment, I think, is like a key differentiator that I've experienced here at Topalti and with Alice is that there's trust there, which is I think is is big. I love that.

Alice Davidson: 10:07

And you need that when you're sorry, Jilly. I was gonna say you need that when you're doing something different, something new, right? There is no playbook for for what we're trying to create. As Jenna said, you know, you don't even know legal ops was a thing. That's it's becoming a a term in the last few years, but people are still trying to define exactly what that is. So I think with that sense of trust and that sense of kind of trial and error, knowing that, you know, we might not get things right the first time or not at all work, and that's yeah. Yeah. And there's been a lot of that. And and there's been a lot of things of, you know what, you probably should not prioritize that, but you only, you know, you learn by doing. And and unless you trial these things, um, and especially again when you're when you're trying to innovate, right? That's part of being innovative, is you're doing things differently. No one's done it before, or you're challenging the way things have been done in the past. And and with that ha you know, has to come trust and and um discretion as well, right? To to be able to that enablement, that empowerment piece, and and you know, we're we all have different ideas and and putting them to fruition, testing them out and seeing what sticks. And not all of it does, and some of it does. And yeah, we we continue to trial and error from that perspective.

Jenna Hunt: 11:05

Yeah. And challenging each other as well. I think that's a big piece that I love about our team is you know, even like I can Alice will say something and she allows me to challenge her on it. And I'm, you know, I'm usually I'm not always right, she's not always right. It's a very like, there's not this hierarchical, like, listen to everything I say, and that's what goes. We we challenge each other back and forth. The whole team, you know, we get together, we have these very productive conversations and challenge each other on things when, you know, someone's leaning one way or another, we think we need to solve a problem this way or that way. So that that piece as well is kind of fits into the empowerment. But I know that, you know, Alice isn't gonna fire me if I if I challenge her on something because I can see it sometimes from a different lens than her. So that's what makes our team great is we're all coming in with different backgrounds and different lenses. And it's nice, like as a non-lawyer, that my voice is heard as well, which is is fabulous.

Alice Davidson: 11:53

So non-lawyer perspective and voice is so refreshing, right? Among a sea of lawyers. And I think that's that's part of the the success of having a legal ops. And and not that all legal ops people are not lawyers, but to the extent that you can bring people of different backgrounds. Jenna, for example, customer service, right? And and you could tell when you speak to her, you could tell that she's done that for a year, she's got that customer-centric mindset, right? And that is, I think, what makes her so well liked and also trusted within the organizations by other departments, right? Is that she knows how to talk to customers and end users, et cetera. And, you know, lawyers can often get kind of caught up in in the legalese and uh and the negotiation, et cetera. And and and the human element can often sort of disappear a little bit. And and so I think the infusion kind of of you know the traditional legal with with legal ops and having non-attorneys on the team is is part of the secret sauce, right? To having a success.

Cecilia Ziniti: 12:43

I think it's amazing. I mean, yeah, the secret sauce aspect of like this is something that I thought about. It's like I um came up as an in-house lawyer at Amazon, and customer obsession was a value, and it was a question of like, can in-house legal display customer obsession, not only for your internal clients, but also for the end users. And my experience, you absolutely can. And in fact, it's a huge career differentiator if you can. And so, you know, unsurprising, um, you know, these two are humble. But when we were negotiating uh, you know, our agreement, they they are GCI customers, but we were speaking about that. We worked with our security team and you know, we resolved the considerations and we talked about SOC2 and what have you. But in that meeting, the security person told us, I hope you'll allow me to say this. He said, Jenna and her team want this tool. They really know what they're doing. I love them. I will do what I can in my power to ensure that we have the security practices that we need to get what they want. And that kind of buy-in, I think reflects the deliberate work that you've done and reflects this approach that you just described.

Alice Davidson: 13:45

Yeah, no, that's um, thank you for that little reminder. I was not in that, but that that is exactly what happened, right? And and when you get that buy-in and that um that partnership, right? And that trust again with your with your end users, with your customers, they reciprocate it. And when when you need something, because at the end of the day, at that point in time, we were a customer of the security team, right? And we were trying to we were seeking their approval on something. We wanted to move forward with something quickly, and that you know, that partnership went went both ways. And um, thank goodness.

Cecilia Ziniti: 14:13

Yeah.

Alice Davidson: 14:13

I mean, I think we had you up and running before they actually approved, but we're not gonna tell anyone that.

Cecilia Ziniti: 14:17

Well, we'll we'll we'll we'll keep that but between between us and our listeners.

Alice Davidson: 14:21

Between us and everyone who might listen to this.

Cecilia Ziniti: 14:22

Yeah, exactly. No, I mean it doesn't have been a benefit of selling to legal teams, is uh they can get us approved. Although I will say I have been, we have been giving eggs for the AI approval and governance process. Recently, we uh we got GCI presented to uh to an audit committee of a board, um, and that was very similar where the company had an AI process and this was what they were doing. And we were actually the first instance of a business team presenting a use case to that committee. So it worked out great.

Alice Davidson: 14:51

That is very cool.

Cecilia Ziniti: 14:52

All right. So let's talk about talk about basically kind of more a little bit on leadership. So, Jenna, you say you're a tech implementation survivor. So so that's besides the kind of uh reminding me of the show, which I have affection for. What's a project that that tested your resilience, like or something you're proud of that you worked on?

Jenna Hunt: 15:10

I mean, I I feel like it's a badge of honor in the legal ops community saying you had a failed CLM. Like every everyone uh has at least one under their belt. But um, I always say it it was in the moment it was frustrating that we had a CLM um implementation fail. And when I got hired, I kind of got thrown in into it and we tried to make it work for about a year. But that experience I learned so much. I learned so much about like the process of being a part of the implementation. And because of my customer success and sales background, I was so used to being on the other side. So it was like it was so interesting to finally be like the customer and have to go through that process. So I learned so much about just that part of it, and also that's how I knew okay, this wasn't the right product for us, but now I know what is, right? I know what didn't work, I know what we actually need, I know now what problem we're actually trying to solve because before it was just, you know, we and fair enough, we kind of just got sold on this end-to-end solution that we didn't need and didn't fit for our business. So it just wasn't the right fit and it wasn't what we needed. But that experience just helped me grow too so much as a legal ops professional of understanding that whole process and understanding why it failed and you know how we could make sure that didn't happen the next time. So and yeah, right now we're implementing two other new pieces of legal software, which are going well. So that's exciting. But yeah, it's uh it's definitely a badge of honor, I think, in the legal ops world. And beach, as everyone knows, can be difficult. As I always say, like with GCAI, it was uh didn't even feel like an implementation, it was just an on switch. I love it. Easiest legal AI to get on board with because there is no implementation. Yeah, no, I I mean I'm and the craziest feature velocity.

Alice Davidson: 16:46

I was gonna say the craziest feature velocity. I think you might take the award for that. We request something in the morning and it's there by the afternoon.

Jenna Hunt: 16:54

I love it.

Alice Davidson: 16:55

I love it. If I can add to Jenna, Jenna, to your point. You know, when I came in, that was kind of the tail end of, you know, the writing was on the wall of like this is not gonna work. And I I I think you and and others on the team knew that, but there was still this fear of failure, right? Of well, we've spent all this time and effort, we've invested this money in this, you know, camera if it was a three-year contract because you managed to get us out of it and get our money back. But oh no, she's still nice work. Yeah, she's a great red right hand. It was again to my point about empowerment and you know, not being afraid to fail. And I said we walk away from this, it didn't work. Let's cut our losses today instead of you know going forward with like that's okay to me. That's not a failure. That's we've tried something and it didn't work. And there was all these circumstances, and you know, of course, the company wanted us to do a post-mortem. And now it's uh sort of been like one of the poster children for poor implementations, but we're proud of that because again, we walked away and we recognized and we took the lessons away. And and now, you know, two years later, we're in a very different position. And you know, we're not getting second guessed by the business. We that we've sort of we have the trust that we're making the right decisions, making the right choices and the right investments because again, we've learned from from what didn't work. And often people are so hard to cut their losses, right? Um, and and I think that's that's the biggest again part of of innovating and doing things differently and and and trialing and airing and and legal ops, really, for that matter, more broadly.

Cecilia Ziniti: 18:13

Yeah. So what do you know based on that project? What do you, you know, what you you mentioned you've got two going well now, Jenna, and then um obviously kindly mentioned GCI is going well, but what what are the kind of either tenants or takeaways or you know, when you did that retrospective, which by the way, uh I don't like calling them porosmodem because it's like somebody died. And so we call it a retro. Um that's that might be an Amazon term too. But um, so what are the things now that that you know, like your sort of legal ops tenants or things that you're looking at when you're implementing these big systems, Jenna?

Jenna Hunt: 18:44

Um I mean, even before I get to the implementation point of just selecting something is like taking your time, actually understanding what problem you're trying to solve. I think it's funny, even like when we're helping internal customers with vendor contracts and you ask them that question, it's like, I don't know, you get caught up in the sales cycles and the, you know, the the the fancy things, and you're trying to the salesperson convinces you that they're solving all your problems that you didn't even realize you had, and then suddenly you've got this, you know, piece of technology in your company that doesn't connect to anything and why implementation failed because we didn't think of those things beforehand. So just the the pre-signature part for for me was like the where we went wrong and where we really turned around on and in in terms of how we, you know, chose and are still, you know, purchase the two that we're implementing right now and and for ones going forward of really taking the time to, you know, it's it's more work and seems frustrating and it's gonna slow you down, but it's worth it because then you are actually purchasing something that does solve the problems that you're going to solve. And then just understanding too that the data piece, right, is always the garbage in, garbage out. I I hear a lot as well in the legal ops community. If you're needing to import legacy data into something, like actually truly understanding what does that mean? What data cleanup do you need to do, or what can the vendor do, and that type of thing. So the the pre like signature part for me is like the biggest learn, like where we learned our lesson of figuring that point out. And then and then same with time, like even this this time with implementation, it always is gonna take way longer than you think it is going to. Even that's been a lesson for me with a lot of these recent ones is our you know, go live date has kept being pushed, being pushed, being pushed because like life happens. There is stuff that comes up every day, like Alice said, every day is different. You always think I'm gonna have the afternoon to, you know, focus on this, and then suddenly that afternoon is gone. So everything takes a bit longer than I think. And that's even been, yeah, recently a learning for me is trying to not yeah, underpromise, over deliver in terms of timelines, I think is a good one.

Cecilia Ziniti: 20:42

There's a far side cartoon or something where a software vendor is like showing somebody, you know, heaven and it's beautiful, and then the scene cuts over and it's hell, and they're like, Well, what's going on here? And they're like, Oh, that was the demo version. It's like so, yeah, you know, basically this idea of like really thinking through it in advance. There is a concept too, I think, in League Lobs of like go slow to go fast, where it's like it's not our instinct as a fast growing company, but then to like hit pause and kind of like take that time on the front end to then not have that on the back end. That's that's great advice. I love that.

Jenna Hunt: 21:14

And think about the downstream effects too, right? Like there's again, we work with a lot of teams. And so it was like, okay, if we're gonna have this piece of technology that affects this workflow, who is involved in this workflow, right? Like really thinking about those stakeholders, involving them, making sure they're aware. What new technology do they have on their roadmap that might be changing, right? That's another thing that people often don't think of. Okay, this is gonna fit in with X piece of technology. You purchase it, and then suddenly you find out that you know, sales got rid of X technology and is now using Y, and suddenly you're stuck with something. So it's a lot of just trying to think ahead to those downstream effects of where things are gonna break or go wrong, or you're gonna get pushback from the other teams that you know you're working with or that are integrated in in these pieces of technology is is big. I think you just think this is for our team. So, you know, it's our decision and our decision alone. But again, we work with everyone and everything, everything's connected.

Cecilia Ziniti: 22:06

I love that. So on that point of like the shifting business, either software or priorities, Alice. How do you how do you do OKRs or how do you do your planning for your team, knowing that, you know, like let's use a contemporary example, like tariffs or something, or like, you know, things that are not predictable, even COVID. How do you make goals for legal and run your team in that environment?

Alice Davidson: 22:31

Um, in terms of yeah, it's it's I think the one thing about goals is they gotta be fluid, right? They have to evolve with with the business and realities. And I think it's often we just get so set of here's the number, yes, you know, you're booking numbers, you're all the the sort of the corporate goals might remain the same, but the way in which we enable them might change, whether that's from quarter to quarter or even month to month. Being okay with that again, I think there's often this expectation when you set OKRs, like let's make sure we set them in a way where, you know, we get as much green as possible, right? Like let's let's make them a, you know, you you do want them to be achievable, but at the same time, then are you sort of selling yourself short by by only committing to the minimum and and having stretch goals, I think is important. And yeah, we went through sort of the first go around. We I took a step back, right? I think Jenna and the team were kind of ready to live into, okay, well, what are we actually gonna accomplish this year? Like let's have, you know, a list of deliverables of tasks. And and we're we, you know, we're in a very task-oriented, again, GSD mentality company that is very normal. But I said, hold on, there's a part of the strategic, right? There's a tactical, we'll get to that, but let's take a step back and set a strategy for ourselves. And it really started with coming up with with kind of, you know, we we thought two to three team objectives that should remain constant year to year. And it's like those objectives will then our goals, you know, we'll take the company goals, the company-wide goals, and establish our okay over that. But there's gonna be these overarching objectives that for our team strategically we want to accomplish through these goals. So for us, those three objectives have been a thriving and engaged legal team, strong business partners, and operational excellence. So that's the three things, like the the three pillars of our of our legal department. And if you think about it, you can layer a lot of things under that, right? And and there's gonna be a lot of overlap. And so even when we do go through our um, you know, annual planning and then we review it on a quarterly basis, we kind of have this. I don't know what colors we have, Jenna, they're multi-branded, but we have three colors that correspond with those three objectives that we always remind ourselves of we are actually beyond achieving this particular objective or this particular company goal, we're actually still fulfilling our broader mission and what we're trying to do as a department. On the one hand, taking a step back, having this kind of broader view. And then on the other hand, once you get into the nitty-gritty and the details, realizing that they will need to change and shift and and that's okay. And for us, for a long time, we were focused on how do we reprioritize this and you know, we're trying to do constantly doing more with less. The demands that's the great thing about being a business partner is you get more inbounds and and people coming to you. But then we started saying, okay, business, you tell us then what's important, right? Because you know, we're trying to figure it out. But really, what's important to you? I'm telling you, we out of these 10 things, we're gonna be able to accomplish four by the end of the quarter, right? You tell us which four you want to see, which ones, you know, we can plant to next quarter. And and to me, that's that partnership, right? It's it's not just, it's not a one-way street, right? And and even though we are, in a way, a service provider and an enabler and all of these things, it's we're still are a partner, right? And and we're we're still part of the bigger picture here. And and we need to have that feedback of are we focusing on the right things or do we need to shift here and there? And and I think um there's really good alignment from that perspective. And you know, we do it um at the executive level on a quarterly basis. We go through our you know, quarterly business reviews, and that is an opportunity. Even, you know, I say, okay, like looking back, that's what we did, but looking forward, this is what we're focusing on. Like speak now or forever hold your peace, if that's not that's not the right priority. But at the same time, also then reminding them of you know what we as a team are trying to do beyond just um enabling and and accomplishing these business goals and OKRs.

Cecilia Ziniti: 25:58

So much to unpack there. Jenna, what's your point of view?

Jenna Hunt: 26:01

Yeah, I I think I've seen a big, you know, transition from when Alice started the way we did eight OKRs and thought about goals. And I guess she sort of mentioned this that that would kind of let us do the way we were doing. And then this year we've we've really re-jigged it. We really went from being extremely granular to like, you know, who's doing this exact task like every month or quarter or year. And it was like, again, we were just kind of doing those for the sake of having something to say, yep, we you know, we did this kind of thing, or you know, is that something that we're doing that's a part of our job that's not really a goal that we need to be tracking, or that's not benefiting the team at all by saying, Okay, yes, we did this every month. I think, yeah, we we really took a step back, I agree, and and and figured out okay, what are what are the like the guiding lights? And yeah, we came up with those three. And I think that's always a good reminder for us with a lot of these projects when we're having those moments or even days of like, okay, like what should I be focusing on, or you know, how is this timeline for my implementation needs to be shipped? Um, we go back to the, we know, we go back to the our team guiding lights, those three pillars, and how they, you know, match to the company goals and and and again, we we meet continuously on this. So this is another thing we dropped the ball on last year is it's easy to you know put them in place and then you get to quarter three and nothing aligns with what you're actually doing. So we're being better this year of like we're meeting continually with the leaders, we're saying, okay, what's you know, what did we drop the ball on? Okay, are we moving that into the next quarter or are we saying that's no longer priority? Um, and a lot of the times it is, it's no longer priority because what was a priority last week, sometimes now is like that ship has sailed, we're moving on to something else. It's that the GSC thing, we're we're moving quickly all the time. So you have to have to shift. So there's no point of writing, you know, 300 things down about what you're gonna accomplish this year when two weeks later that whole list has already changed.

Cecilia Ziniti: 27:53

I love it. I love it. And GSD folks is get get get stuff done, which is um that's uh uh it sounds like a core principle at Defaulty. I love that. On that note, I guess Alice, you mentioned that you might have 10 proposed OKRs and go through a collaborative process with the business to understand which are gonna be the four that you're gonna do. Now, that is painful for us legal types, right? Like we're type A, we're used to checking stuff off on our list. What what do you do when you have those extra six? And and how do you, you know, is it like uh you go based on risk or you're just like, hey, look, like it's gonna be better to get these four done well. Like help us make that trade-off. And we and as background, I just talked with another uh guest who said the same thing, where it's like that's was a big part of her transition as a leader. So uh say a little bit about that.

Alice Davidson: 28:39

Yeah. And, you know, if I think about like different ways of of sort of prioritizing you, you think about you know, urgent and important. That's that's one sort of axis that I started plotting things on. And then very quickly, you know, everyone's like, well, that is important, that is important, that is important, that is important, that is urgent, that is urgent. And it's like, no, take a step back. Not everything can be urgent and important. Like that's just the that's the reality of it, right? Otherwise, you know, it should have been done by now. So sort of really taking again, challenging myself and ourselves on urgent for who, when, right? Important for who, like what is it actually going to unlock? Like, what do those two things mean? And and realizing that, yeah, sometimes, you know, you need to go for the low-hanging fruit and the little ones, but sometimes you just actually have to roll up your sleeves, invest the time, the energy, the amount to do the stuff that's probably at the bottom of the list because it keeps falling off, right? Because everything else, you know, is either more exciting or more urgent or more important, realizing that that is going to be an you know an enabler, an unlocker to all of the other things that you're trying to accomplish. You know, that's broadly speaking, yeah, of course there's risk-based, right? Uh sometimes you something becomes a little bit more important because the the risk has increased or the risk appetite has changed. But but at the same time, you know, I think having the trust of you know of my CEO and the rest of the executive team that I'm doing the right thing. Right. I'm in the room, I'm listening, I understand what the priorities for are for the company. Let me and my team enable that in whatever capacity we want to, right? So again, that fluidity, that that change, the six things that are on there that again, I know you want me to accomplish, but I'm telling you right now, that's not a good use of our time or resources, et cetera. Right. So it's just that I I wish I had a perfect formula, but I I think to Jenna's earlier, you know, what you said, Jenna earlier, I think where we failed or flawed or whatever you want to call it in the process last year is is yeah, we didn't come back to it often enough, right? And and then you realize that it's like, yeah, again, ship has sailed, nobody cares about that anymore. We could have now, you know, it's still dragging us down. We're thinking we're not accomplishing things. Just take it off. Don't be afraid to take things off the list. I listen, I like to your point about ticking things off. Sometimes just removing something from a list is actually even more rewarding. Like the psychology.

Cecilia Ziniti: 30:51

No, I'm the same way. We have a on my whiteboard, we've got, you know, the deals that we've closed won. And then I have basically closed lost on there. And then at one point I'm like, you know what? Nah. I literally symbolically took, you know, the dry erase board and erased them because I just do not need to be reminded of that every time.

Alice Davidson: 31:09

To be reminded of it.

Jenna Hunt: 31:10

Yeah.

Cecilia Ziniti: 31:10

Yeah, exactly. It's a it's kind of like, you know, next play, right? It's like there's this sort of like very um, you know, leadership thing around, like, you know, I think it was Coach K from Duke, and then um, you know, basically the CEO of LinkedIn, Jeff Wiener, says the same thing where it's like, okay, you can celebrate your wins in business and decree your losses, but ultimately like the thing that keeps you going is that velocity and like being able to look at that next thing, and which both of you described. So I love that. All right. So let's talk a little bit about Jenna. You talk about, and we mentioned this a little bit, being bilingual, business and legal. When do you draw on each language and what does that mean?

Jenna Hunt: 31:46

I feel like I do this on a daily basis. And I know Alice sort of mentioned this as well, but I I think this also helped me really build that rapport with our sales customer success, the business teams is um, you could just see, you know, in training sessions or emails that were being sent, it's like they're looking at it like, I have no idea what this means, and fair enough, coming from sometimes the lawyers, like the communication to the sales team about okay, this is what you need to say or this is a situation. And it was just sort of like a fear in the headlights, but almost like this like fear to admit that they didn't understand, even though, you know, fair enough, you don't speak this language, right? So I felt like I did a lot of that when I first started of pointing out like, hey guys, like that is not gonna land with a sales team who didn't go to law school like you guys did. Like it's nothing against salespeople. It just is you're speaking a different language, they don't have the same background, the same context, the same training that you guys do. So we need to make this ingestable if we actually want them to learn and and empower them to be able to do that, right? So I think we were trying to tell them things, but in a language they didn't understand. So then I when I came in, I really tried to to convert that to a because I've been in their shoes and also even I know what the customers would say to things. I'm like, that's you know, nice in concept, but in the reality, like customers aren't gonna take that as like a pushback or they're not gonna take understand that as an explanation. So like, why don't we try saying it this way instead? Um, so that I think like really helped us build that relationship as I I was kind of that person in between that then they then they came to. And and Alice and I joke about this. So it was we almost did too good of a job at that, though. And this is the risk to that that relationship building piece is that now we've almost become the department of default for things. So it's funny, we've kind of shifted from this like department of no, which you know legal teams get slapped with to now we sort of feel like we're the department of default because they trust us too much. We've been too helpful. So now we're almost in this weird situation on the other side where everyone's coming us, like if people don't know the answer to something or something's challenging, or or whatever, it's like just go to legal. So it's it's it's kind of almost an interesting thing that I would almost warn people about because it's like don't do too job at building that bridge because then suddenly like everyone's coming over the bridge and over to your side, and and we're just now we're like, oh crap, like we built too good of a relationship.

Cecilia Ziniti: 34:03

Yeah, it's funny you say that. I literally this morning spoke with um the CLO of a consumer product package goods company, and she said effectively the same thing where legal was so good at pointing out typos that they basically became the default copy editor for the entire marketing department. And it was like, and you can kind of see how that would happen, right? We have this legal skill set, we've, you know, literally we're precise enough. And then you, you know, suddenly you're reviewing, you know, copy editing for things that have zero legal implications. So it's fascinating. I actually think, you know, for our listeners, a lot of it is gonna be like if you can aspire to do that, to kind of like almost swing the pendulum, maybe a little too far to client service and then swing back. I think that's a good, you know, it's a it's a good goal. So, and congrats to both of you for being in that position um to to have teams rely on you so much. I love and then you know, also recognizing that okay, building this longer term, we can't, we can't be, you know, reviewing uh, you know, press releases for typos or whatever. It's still legal issues. Yeah, you do that.

Jenna Hunt: 35:01

Alice does it as well. Like she's a business person.

Alice Davidson: 35:04

It's it's like that that is, you know, it's it's that demystifying lawyers. And we m we made ourselves so approachable that we made ourselves too approachable in a way, right? Again, to that point. It's that over-enablement. And it's good, it's a compliment, right? But then it's like that, it's again, it's not sustainable. And to your point, it's how do we tweak it? How do we swing that pendulum back and forth or find find somewhere in the center? On the on the language piece specifically, I this is something I'm very passionate about of, you know, I don't like just I can't I can't stand legalese and I can't stand when people talk in an overcomplicated way, you know, whether they want to show that they're the smartest person in the room. And you see this all the time between lawyers and negotiations, and it's just not part of my MO and part of my DNA. And, you know, when I came into this company, the acronyms on acronyms, on acronyms, and terminology that I didn't understand. So that's technical language that I don't understand. And I'm always the first person to say, like, there are no dumb questions. If you don't understand something, you gotta ask it. So I'm, you know, I'm I'm a very firm believer, proponent of that, and I do it all the time. And I think that also, you know, enabled people people to come to us more often now. Some of the questions, they're not dumb. They're just they shouldn't be asking us. They should be asking their manager, right? It's it's one of those things of, you know, it's not, this is not a legal question by any means. You're just you're literally asking me how to do your job. But but uh, you think they ask AI?

Cecilia Ziniti: 36:20

Well, I mean, that's a good question. So say so so full disclosure, obviously, Jenna, Jenna and Alice are users of of GCAI, but I think they've done some really creative things around the client comms. So tell me how you're using AI for that kind of use case.

Alice Davidson: 36:34

Well, um, I'm so glad you brought this up because I've I've said this to you know members of the team who might struggle more a little bit with with being more verbose and and and having me as I was like, okay, I'm having a hard time reading, understanding your memo or your email. Guess what I did? I'm like, I put into GCAI and had to dumb it down for me. Like, me, the GC of this company, has to do that. Think about the other person that is at the end of your communication. So now I truly encourage everybody on my team of run your memo, run your email, run your Slack through there. I mean, the prompts are there already for you. You guys have done the work for us in terms of landing your comms. I use it routinely for my executive team because I can also, you know, I can get sometimes cut up in the details and be too verbose. So for us, like that aspect of the tool is so important because it is. It's already, it's taking your normal, natural language, what comes natural to you, and adapt it in a way that, you know, the the recipient is going to receive that message, right? And in in the most effective way. So we use it all the time. To your point about, you know, go like I used to say that actually not not as much here, but at my former job, I'd get asked a question. I said, Well, I don't know that you Google it because I'm about to, right? You're asking me something like I'm gonna start with Google. So there's no reason why I have to do it. You could Google yourself, right? And to your point now, you know, AI has displaced Google by by being way more, way smarter. And you actually have, you know, this intern or or whatever the case may be, or aid in another face answering your questions. So it's like to me, again, it's uh it's such a it's it's so obvious and it's available to us. Why wouldn't we use it, right? And I I know how much time I have spent in the past, you know, looking and and rethinking my communication and and and you know, rewriting and is this gonna sound okay? Now it's literally the press of a button. You know who your audience is, you know what how you want to land your message, and and it helps from that perspective, which means you can still be you, you can still draft in a way that is comes most natural to you is easiest for you, but it's going to be that much more effective because it's gonna land with your audience in a way that they best receive the information.

Jenna Hunt: 38:28

Yeah, and even like what we're doing, I I've talked to you about this before, Shulia, about what we're doing with our vendor reviews. Like after the vendor contract is signed, like we've built a prompt um in our team that they then run through GCAI and it kind of gives it an executive summary almost of a dumbed up version of like, hey, hey, business owner of this new piece of technology, like FYI, these are the things that you should be aware of as like the business owner of this that are in the contract, you know, make sure that you're only you know using this many users. And if anyone else logs in, you know, we're going to be charged more other, you know, renewals, that type of thing. So we we are using it for that as well of like, hey, this vendor agreement signed now. Here's an email kind of cover page of here's all the points to be aware of and sending that to the business owner. So things like that as well. It's like just that translation of instead of you know, we always say, make sure you understand what's in the contract, and they're like, Yeah, yeah, yeah.

Cecilia Ziniti: 39:29

Sounds like. And also the business, right? Because we've had, you know, like I don't think, you know, I used to support BD at one of my roles where it was like we did these very complex agreements, 67-page, you know, outsourcing agreements and things. And three years later, of course, nobody who did the deal is still there working on that same project. And so having a very crisp communication of what you did. And of course, I go back to my former litigator days. I litigated a very early Salesforce contract. I represented somebody against Salesforce. And essentially the company came back and said, basically, it was a license question of whether all licenses were going to pay the same amount. And I was able to prove to at the time Salesforce that the license fee should have been a lot lower because we had a very clear email from an internal stakeholder saying, like, hey, you know, here's our contract we just signed, here's how the licenses work. And we forwarded that to at the time Salesforce. Um, and they came back and they went away with their with their extra license ask. So it's kind of this like things that you'll thank yourself for later. I mean, I love that you all are using AI for that. It's great. All right, so let's see. So let's go to lightning round. Um, this is a fast take. Don't think too hard about it. Um, so your favorite part of your job, Jenna? My team. Amazing. How about you, Alice? You stole my answer, my team. I love this. And then what's your um bold prediction? What is AI gonna be doing for you and your team in three years?

Jenna Hunt: 40:53

First thing that came to mind was like super intern. It's like intern right now. So I'm like, it's gonna be our super intern. Amazing. I love that.

Alice Davidson: 41:00

Yeah, I I think just uh it's never gonna displace us. It's just gonna make us more efficient, right? I think even some of the things that we're we're grappling today, whether it's setting goals or something like that, right? We're gonna be able to, I think, rely on AI on a lot more of the of the strategic pieces as well, I think. Again, as we feed our models and and the models get to know our business, I just think the it's just gonna become that much more powerful in terms of potential use cases and outputs.

Jenna Hunt: 41:23

Yeah, I love that. It's part of the team. Like it already is. So, and that's why I'm like it's gonna be so much further a part of the team in three years.

Cecilia Ziniti: 41:30

But love that. Awesome. All right, before we wrap, Alice, what advice would you give to someone starting off in legal ops or joining an in-house team in fintech today?

Alice Davidson: 41:40

I would say you are, you know, the fact that you're joining somebody in fintech, you you you have are you're at liberty to innovate and to do things differently. And don't be afraid of that. Don't be afraid to, you know, challenge the the status quo of what's being done at that company, challenge the status quo of of what you've done before. Just don't be afraid to to do things differently because I think particularly in in this space where you know innovation is is king, I I think sometimes we forget that our internal processes, those are subject to disruption as well. And you know, the legal profession is the last to be disrupted and one that probably needs the most disruption. So don't don't be afraid to be that force and and you know, start small or or go big and and anything in between. Yeah, just trial and error, do things differently and and learn from it.

Jenna Hunt: 42:22

You took all of it. It really is that like, um, you know, you don't need this huge background in legal ops. Legal ops still is kind of in the you know infancy phases, so there's there's not a lot of people I think that have, you know, years and years of it. But I, you know, came into it without a legal background, without an ops background, obviously had some transferable skills, but I just kind of jumped right in. And again, the trial and error. It was like what's working, what's not working, and how can I fix things and speaking up, right? Like I am just because I'm not a lawyer on a team with with lawyers, have a voice and and also, you know, find find the people that are are wanting to listen and and wanting to to give you that space to to try to try have that trial and error and and and space to grow. So yeah, I know not everyone is as as lucky as I am in that sense, but um, it definitely helps.

Cecilia Ziniti: 43:11

Thank you both. Your partnership, like it's just so clear that you work so in such a lovely way together and lead and really have earned the the trust of the rest of the business in so doing. It's such a clear example of kind of the modern legal department and what that looks like and supporting a growing business globally. So absolute kudos. So for listeners who want to learn more about you or Tipalti or follow your work, what's the best place to find you?

Alice Davidson: 43:34

God, this is what LinkedIn. This is I am the worst person at social media. So find Jenna and then she'll find me.

Cecilia Ziniti: 43:41

Find Jenna. All right, good.

Alice Davidson: 43:43

Jenna's giving us an opportunity to plug ourselves here and we're like, oh gosh.

Cecilia Ziniti: 43:47

No, no, it's good. I love it. Um, yeah, so we'll put in the show notes, we'll drop their LinkedIns. I don't know if the Tapalti team is hiring because they're so efficient, but um, if they are, this is a team you want to work with. Um, they work with a lot of Silicon Valley Bellwethers. Um, if you've ever been paid online, uh chances are it went through um Tapalti. So I'd love to hear that. Thank you so much for joining us today. It was really lovely to speak with you. I'm glad to have had the conversation with friends.

Alice Davidson: 44:10

Yeah, no, we really appreciate it. We appreciate your friendship and partnership as well. And um, yeah, thank you for making our day all of our days easier every day with GCAI. I mean that.

Cecilia Ziniti: 44:22

All right, thank you so much. Thank you.

Jenna Hunt: 44:24

You didn't ask us to plug it either.

Cecilia Ziniti: 44:25

No, there was exactly a conversation with Alice Davidson and Jenna Hunt of Tapalti, legal leaders and in-house who are driving their companies forward. And you could see from how excitedly they talked about what they're doing, how they empower the business, and how they think about legal goals, that they are really hyper-effective. And we're it's such a treat to hear from them. But if you're building a fintech, scaling legal ops, new to in-house, or just running your team with a little more clarity and care and goal direction, I hope today's episode gave you something real to work with and something to think about. Going forward, you can follow Legal and Friends wherever you get your podcast to hear more conversations like this, or head to gc.ai to learn more about how we support legal teams and we're the AI of choice for teams wanting to move fast and operate with excellence, the way that Jenna and Alice just explainated. Until next time, build clearly, lead practically, happy prompting, and always keep people at the center. Thanks for listening. Bye bye.