#28 - Skipping the Firm, Finding a Mentor, Using GenAI - Stefan Nunn, Counsel at TravelPerk

Hello everyone and welcome to another episode of our show. Today my guest is Stefan Nunn, who is part of the award winning legal and privacy team at TravelPerk, one of the world's leading B2B travel management platforms. He's a legal counsel where he's been instrumental in fundamentally altering his day to day role in the last 12 months. He went from being what he considers a high touch reactive, conventional legal service provider, but really pivoted roles in his legal department to becoming proactive, what they call product managers in their legal departments, building experiences for their internal clients. I was super excited to have him on the show because, you know, I'm always interested in cool career journeys, especially those that involve legal operations, and Stefan is one of these. We feature a ton of people on this show who are seasoned veterans in their careers. We're talking clos, heads of huge legal operations, teams, et cetera. I love that Stefan is a junior attorney. He's only 18 months now into his role at Travel Perk and already making a huge impact on the company and on the way that they're running the department. Having watched and experienced the change in his own day to day role at TravelPerk, he now has strong views on how the profession is changing and the type of skills that paralegals, junior lawyers and legal ops professionals need both today and tomorrow. So we get into all these things today in our show and I hope you enjoy the conversation as much as I did.

So we met fairly recently actually in London and I think just within a few minutes of chatting with you, I was like, I must, must have you on the podcast because your background is so interesting. You know, so many people come to me and say, oh, you know, I'm an attorney, but I really don't like being an attorney anymore. And they're dying to make the switch, switch into legal ops. But interestingly, you actually went the other way around. So, yeah, I'd love to hear more about your background and how that happened.

Yeah, and I think, I think it, it's, it's a long, winding road and now I say that with a pinch of salt because I've only just recently qualified as a, as an attorney in the uk. So I was admitted just nearly two years ago to the role, but I think it starts all the way back. I mean, my original career aspiration was to be a vet in the uk. Yeah, I really, I wanted to be a vet, so, so I did science high school and went all the way through my intentions. But I would, I would describe myself academically as Average. I'm not the most academically inclined person in the world and I found the struggle there to transition to a higher level of education in science harder than I'd expected. So didn't get the grades. I needed to go to veterinary school and had a bit of a winding career path as to deciding what I wanted to do with life. So I went to university in the, in the UK when I was 21 when most people actually leave university and I decided to go study law. I thought I need a practical skills based education which obviously will come onto later on to it maybe to basically go out into the job market. This is just post 2008 so it was a bit tough out there for brands. Yeah and obviously not. Not as we know it now. That was the precursor to the end of the world. And yeah when went through went to a what we call a new university in the United Kingdom so it's not even Trent University but they've got a fantastic law school and I realized that actually I enjoy law enjoy like it was. I never exhort myself as someone who enjoys kind of the academia side of things but I really dug deep into a couple of things and yeah through that it was great and but there was still a barrier to access the law in the UK so rightfully so people want their attorneys to be highly academically qualified. They want this perception of intelligence that this is a bright educated person that will be able to advise them and that was becoming a barrier for me getting a training contract. So that's how I started off in legal ops. So it was, it was an easier route into the role. Well easier as perceived back then. And I started off as a contracts administrator for a pharmaceutical company called GW Pharmaceuticals and I think that's where I started cutting my teeth. So that was very formative and at the same time I self funded our legal practice course in the UK and did that part time whilst working full time for GW and did that for about two and a half years.

Wow, that's not easy.

No, no, definitely not. And then yeah still along it alongside that, you know, kind of hustling away trying to get those training contracts and still finding the doors closed to me because of you know, the framework in which we're built and starting to lean more into the contracts management side of things, legal operations. Finding that my mindset for efficiencies and standardization of processes which made sense to me and probably should give credit to my parents here, boom. Are very process minded things. My mama, we grew up with her being the you Know the, the pioneering breadwinner of the family going out and, and you know, leading manufacturing organizations in the family as a tradesman. So very deliberate in the way he does stuff. So subconsciously I think I inherited those skill sets.

Yeah.

And then applied, applied it to my professional career. I'm the first person in my family to be degree educated and yeah just took it forward and found a career path where I could essentially do some paralegaling stuff. But mainly I was doing the operational side of things and getting companies in shape, essentially getting those, finding those skeletons in the closet and trying to sort them out. And, and that's how, that's how I started my legal ops career and which culminated in a role within a global financial services institution where I eventually trained.

Awesome. And, and was that something you were seeking out or did you kind of just. You were interested in legal, so you started, you know, as you said, contracts, administration and other things and just because of your personal interest and initiative blossomed into kind of more of a legal operations role. Right.

That was an, it was an interesting blend because I think the, the interest of legal ops and you just alluded to then at the start here are people that are a qualified attorney that want to move into legal ops, is that I think legal ops and legal sit very well alongside each other, especially when you're really junior because you, you can come in and add value. Whereas when you're specifically a legal, a junior legal counsel, you get a lot of the administrative and you don't see how you're moving the needle even when you're in an in house team. So I've always worked in house, I've never worked in private practice and so to opinion on there is out of my remit and even then I found, you know, I wasn't moving the needle in my legal profession and it became quite disenfranchising to be honest. But then the legal upside of things is that even from day one when you're a contract administrator, you can see how you're adding benefit. And it also frees you up to. Once you become efficient, you create bandwidth within yourself to upskill yourself in those areas. And I think that is what kind of allowed me the capacity eventually to take on a training contract in the uk which is two year obligation, which was all done during COVID Yeah. So it's all done remotely. I'm that like generation of junior lawyer that didn't see their supervisor for a year and a half and yeah, I think it just became a bit of a passion of mine and has stuck with me and really blossomed again in my current organization where I feel like Travel Perk, which is the organization I work for now, which is a friend of Clock and a friend of Ironclad, is really behind this and particularly with our management in the team and people in LT sponsorship.

Well, and let's talk about that for a bit because I think what you've done at Travel Perk and the role that you have as well as your leadership team's belief in, you know, like you said, efficiency and operations in technology embracement is, is fascinating. And you know, you haven't been there that long. Like you said, it's been a couple years and you've had a huge impact. You've already worked on so many things. I also find your background super interesting because you have not worked at a law firm, you didn't do any private practice and so you're coming from this without sort of previously being jaded by the available hour or this is the way that we, we do things in the legal space. You've kind of created your own journey but been in the legal space for in different roles and different backgrounds. So yeah, tell me, tell me what it was like to join Travel Perk and kind of the culture, what it's like there.

So the, the company is an incredibly young company founded in the mid 2010s in Barcelona and it's just hit around 1200 employees. When I joined there were 600 employees. So that kind of tells you the hyper growth strategy we're on and it's all about, you know, delivering our stakeholders and our customers a seven star travel experience which is frictionless. It gives you the needs that you want and that boss that we take into the legal team in that we build. And this is something that I haven't heard that much from other in house legal teams and especially the external councils I engage, we build products for the business so that being, you know, low to zero touch for our stakeholders that is natively within their environment. And then the beauty of that then is you're not seen as the typical legal team as in I've got to get past legal. Legal is seen as an enabler and that's very much driven from the vision of the, of our general counsel and our legal director. But everyone in the team is empowered on the same mission and we try and look to, you know, grab those milliseconds or those seconds and build a product that anyone in the business can use. And we're definitely kind of pushing that in every area of our bau. Because then your lawyers become, especially your junior counsel, which is your cheapest resource, become more strategic in that they're working on higher value tickets. You're the right things. I have friends in private practice and they tell me that they're working at 11 o' clock at night. Dating documents. This, this is, this isn't what you want to be doing when you're a junior council, but that's just the way in which things work and travel Perks ethos is very much like work smart, work hard, but don't work longer, don't absolutely have to, but it is very much reinforcing the business that that's the way it goes and, and that's what we've done as a team.

And it's such a unique and innovative perspective. I don't think I've ever heard anyone say, you know, we're not just here to deliver legal services. We consider ourselves product managers to the business. That is, that's pretty cool. And you guys, I know, really embrace technology and you're always looking to, you know, new ways to leverage technology to do things better. But you guys have only been around for 18 months. I met you months ago. So even then it was less time, very quick to do that. What kind of gave, you know, you and the rest of the legal team and maybe even your GC the confidence to just like rip and replace and like redesign, you know, from scratch the way that it's kind of always been done.

I think that's the face of the leadership team, how we hire. So one of our core principles in the business is ownership. We are owners. And when I went through my interview process, it was very much kind of, you can try and fail, which is terrifying to attorneys or lawyers especially, like, no, we have to get everything right. We have to cross over T and dot every I.

That's right.

But when you work in house, especially when you're in a SaaS business, like product development is issue and iterate and we obviously we use your tool ironclad. And as I said, it's a product based thing. You know, you develop based on feedback from your users. And sometimes you get things wrong. Like we've done tech deployments before and you know they've gone wrong. And it's knowing that realistically, sometimes it's not the tool, sometimes it's the process. And designing things in those ways and getting that into everyone's way of thinking, especially when they're incredibly junior in their career. And as we've had new joiners as well, that's something that we've really tried to impart on them, including our really junior members of the team who are really embracing that methodology and are following the same route I did into the profession. So it's really refreshing to see, you know, that kind of enthusiasm for building and owning their own workflows and so.

That culture that's throughout the company. Does that help also with just not even the, you know, fail, fail fast, try new things culture and mindset, but also give you budget and give you headcount and give you the opportunity to do these things or do you still have to fight, fight for that as well?

So everyone's competing for budget, everyone's competing for headcount. It's optimization again. And I think you can bring it back to what you're doing as a team. And I bring this, and this is probably a parallel to my previous role where I trained in the process and the way in which legal was done was legal was done and contract management was done. And the solution was massive. A huge organization in comparison to Travel Perk. But it was very, very much about, you know, let's add more bodies in instead of looking at how we do things. You know, it's not broken so let's not fix it. But it's not great. You know, the engine was running but it was misfiring a bit. And you don't need to just throw bodies at a misfiring engine. Sometimes you need to look at our process and that's what Travel Perks really good at now. Yeah, no secret, 600 people to 1200 people in six months. That is huge. And obviously we have, we have capacity there, but it's about everyone that's in our team and everyone that's come into our team are these kind of high growth mindset individuals. And I feel like that's been incredibly inspiring for me and something I would have, I wish I'd have looked for earlier in my career as a legal ops individual, but also as a trainee solicitor looking for those mentors and a mentor, I use the term more loosely than normal people. Your mentors can be your peers. They don't have to necessarily be that level above you or that management person. And there are, and there are people that I at this point, you know, five years ago or six years ago, when I was thinking about doing this, if I'd have looked for this organization, maybe I would have come into it, you know, with a slightly different perspective. And I think that's probably one of the big lessons learned that I'm trying to Push forward going forward. And what I do and how I interact with junior lawyers, that's part of my role.

And the rest of the legal team, the junior lawyers and all have, they.

All come from private practice actually in house again. So the, my counterpart, he's, he was in house in Spain. The management all tend to come from private practice, but most are tenured in house lawyers and our paralegal is, she's from the charity sector. So no real corporate experience in an organization, you know, where your P and L is most important thing, you know, you got to be generating revenue. We hired for personality completely there. And everyone is a grafter, which I don't know if that kind of translates across the thing, but everyone wants to work hard and is very willing to hustle. And yeah, that's the personality type that we look for. So yeah, if that's the private practice individual that comes along that wants to train, I don't think there's any issue. But you know, we have just tended to hire predominantly from in house at this point.

Yeah, it reminds me a lot of the early days of Google because we were exploding, you know, in scale as well and the things that you have to do. It almost feels like you're putting process in place while, you know, of course, while the plane is flying at full speed and juggling. How do you, how do you try to stop and assess and put things in place but also not stop and accelerate what you're doing and, and be able to move faster is a really unique challenge. What do you think that your department, legal department would look differently if you did have to, if you didn't leverage technology early on, you know, because you probably would have a lot more people, right?

Yeah, yeah. Or work a lot more hours.

Yeah, yeah.

And I think again the, again the parallel, I bring it back to my previous role where it was, it was an in house role but it, it was run like a private practice.

Okay.

It worked for that industry. Financial services institutions, very traditional based, you know, private equity, hedge funds, asset management is a traditional industry. So to run that a bit like a law firm, it makes sense because that's what your end user's used to. But yeah, if we haven't had the leverage of technology and people that are product and process mind oriented, it would be a very different thing. It's like eating your broccoli or eating your mashed potato is, it's repetitive. It's the same thing again and again and again. That's not going to build satisfaction and happiness. And also you're not going to demystify what you're doing. And that's one of the beautiful things about blending being a council and legal ops, I find, is that people understand what you do. Now if you use technology, it frees them up to actually see what's going on. And that is where the success has been, but also the happiness of our team. I would genuinely, hand on heart, say that I work in a happy team and, and I don't know many junior lawyers that can say that. And that's a privilege.

That's really cool. And that's part of the fun, I think, of being at a, a small, high growth company where you're actually able to affect the change and the culture. That's really, that's really cool. What, what do you think uniquely suits you to do this job well, given your unique background? I mean, are there things that you took because you did legal off, because you did the contracts, administration role, that make you better suited to be a junior attorney now than, you know, if you went the traditional route, private practice and all?

I think it's a, it's a personality type thing. It's. I, I'm very interested in how things work and what makes the mechanism underneath. The joy for me comes like learning on the job. And I think that very much is, you know, going out, talking to people, collaborating with people, building something for them and, you know, seeing a positive impact that's very much like an operational side of things, like building a product, being a manufacturer and seeing that have a real world benefit as opposed to an advisory side of things. And that has always been something I've been interested in regardless of the job I've done. And that's, it's only been recently that I realized that's my North Star metric and that's what I move towards naturally. And I moved away from that because I tried. I fell into the traditional path which may not have been fit for purpose or fit for purpose for me. And very much had a crux point in my life where I realized like, I was taking quite a bit of time out of work to go do something. And when I was there, I had a moment of reflection where I was like, do I want to go back to doing what I was doing?

Yep.

No time for a change. And what made you happy? And the offer from Travel Perk landed in my inbox.

Yeah, that's amazing. You know, and I think you and I and so many people kind of fall into this world and we realize this is something that excites us, that we're passionate about, that we enjoy doing and that we're good at. But no one sort of told us that these roles existed, but they do now. And what I'm finding, like I mentioned earlier, is that people are like, oh, now I've heard about this role, that there's innovation and technology and modernization for legal. That's what my passion is. How do I, how do I do that? And you know, so many of us that I've gotten here fell into it by accident. I know that you have a passion for just the educational route and what, what can the academic institutions be doing? Should there be, you know, ways that there's credentials or professions that, that, that more people know about and is that what can we do to kind of raise the awareness and path to this profession?

Yeah, and that's a fantastic point. And that is, that's a passion of mine and something that I'm. Yeah, it is so key. So the academic institutions, you hit the nail on the head there. So once you've got into an offer, it's getting a little bit too late until you hit your crisis moment. And so we, we should look as an organization. I'm going to talk from a UK perspective here. Everything I learned at law school had nothing to do with what I did. Becoming a legal arts professional.

Yeah.

Apart from the fact that I knew how to read a contract.

Yeah. Now we hear that in the US too by the way, and globally everywhere else.

And that's, that's, that's just kind of the thing. So we, I think what we do with institutions is there is a place for academia, there is a place for learning the law. I think that's a really important tool to have. But then we look at how we look at these courses instead and do we say okay, is this something we need to build into the course or do we look at roles of like micro accreditations for instance, you know, things like project management courses.

Yeah.

I was never taught how to project manage in any of my formal training or any of my training on the job prior to being at TravelPerk. So teaching people how to use products such as Figma and Jira and Asana, you know, these PMO tools that are so natural to high growth organizations that lawyers have no clue how to do design thinking, you know, demystification. We're taught to speak in plain English now, but then it stops. And then you look at a contract and it's notwithstanding isn't full whiffs. And that's not how people speak in day to day. We should be Looking at these ancillary skill sets that would make a junior lawyer much more of a stakeholder and an equal business partner to those people that they're advising both in house and private practice. But then we should also probably look at the law itself and people coming through the route and thinking. Is the demographic of our profession reflective of the industries that we work in? Because you know, it is difficult sometimes for people to realize there's various areas in which they need to be able to communicate more effectively. And then we have loads of individuals in society where they can just, they've got that automatically in, you know, bring in project managers or developers in who speak the language of their client, whereas a lawyer doesn't. We're not trained to speak like a co, an engineer. We're not trained to speak like a project manager. That's where I think we're a really, really interesting point and I'm hoping academic institutions kind of lean into this.

Yeah.

And, and really drive in, you know, that, that full process that has kind of gone out of law and become an administrative process in some respects.

Yeah. I mean we talk so much about how the industry needs to change and modernize and I definitely have always been the school of thought that the innovation and the change is being driven out of in house legal teams because of the necessity to do things more efficiently and effectively, less so at the law firm. So you know, they will, they will be much slower to change but hopefully that's starting and then the last, the last part of the ecosystem to change is going to be academia, you know, is going to be the law schools. And again for the same reason that there hasn't been a catalyst for it. I, I'm feeling like with technology and all the buzz around generative AI, the schools are starting to think maybe we should be, you know, doing things a little differently now. Do you think there's hope?

Yeah, yeah, there must be. I'm a bit of an optimist, so I would always. I'm a bit of an eternal optimist in that where there's a will, there's a way. And we, we've seen it with various other ways. I mean the, this generative AI boom has been incredible. And I think if you believe in it and you've lent into it and we've lent into it very hard.

Yeah, I want to go too. Yeah.

And this is one of the things and it's interesting because again we're moving away from process minded frame thinking to thinking how can we create knowledge creation again.

Yeah.

So we're learning to think again as opposed because the cost of acquisition of knowledge is zero. It's a zero sum thing. You can go on Google and find what you need to find. You can ask ChatGPT now to tell you what you need to find. You don't even need to go into Google and be like, okay, now I need to summarize this report. You go summarize this report. Free 2015 now we are building knowledge curation individuals as well. So the era of the psl, the professional services lawyer is coming and in house teams are in uniquely positioned to build essentially their own mini law. And that's what's really exciting. And we need to, our academic institutions need to potentially think about this as an entrepreneurial skill set that we need to start teaching lawyers instead of your business development course. I remember doing business development when I went to law school and asking Kim, God, I don't know if that's for me. Entrepreneurship, you know, stakeholder management, how do you go out and actually get something done is where we're coming from. And tech is opening up that necessity. I can't remember who said it. Someone said to me once, you know, ChatGPT is not going to take your job. The lawyer that can use ChatGPT is going to take your job.

That's right, that's right. Yeah, I couldn't agree more. So and it just reminded me, I mean I know that Andy, your GC is really passionate about leveraging generative AI in your department. Would love to hear as such an innovative and forward thinking team, how are you guys already or starting to think about Gen in legal?

So we use a closed generative AI tool that is trained on a specific data set and within that we are using it to facilitate flow optimization. So wherein someone would come into legal, put a ticket request in, I need to generate a non disclosure agreement. They go into this chat bot and they go, I need to disclose some confidential information but I don't know what the next step is. And it surfaces up an explanation of what confidential information is, prompts them through to a public workflow. So a big component of public workflows within the organization and they can self standardize non disclosure agreements. That's really simple stuff but we're also using it to help build out responses to large scale RFP questionnaires. So again where you'd probably have a team of paralegals or you'd have a team of like bid specialists trawling through these things, we've enabled sales individuals to go forward and you know Ask these questions. These are legal questions, but you don't need a lawyer to answer them and you don't, you don't need administrative staff anymore. So what you do with those individuals, it doesn't take that job away. They are knowledge creation experts and right now that's where we're at. But we see potential here and we're exploring things in collaboration with partners on utilizing these language models to look at how in real time we can answer questions from customers on calls in relation to privacy, questions in relation to security. These key things not via a slack message to legal, but by the bot sitting there and actually helping you determine how things are going to go. Very early stages, we're very, very tentatively testing the water. But the generative AI side of stuff is you've just got to lean in. And just like I think with junior councils thinking, what skills do I need? Do I need to do legal ops? Lean in and lean into this generative AI thing? Because I was reluctant for three weeks, four weeks of it, and that passed me by. So I've had to lean in even harder. And unfortunately that, that is, if you're scared, it can be trepidatious to do so, but just get in there and ask some questions. I mean, as long as you're not sending it to, you know, external party straight away without validating the information, which I think few individuals in some cases have recently, should be fine. You should be fine. Yeah, check your backs. We're lawyers. That's what we're trying to do.

It's so fun. I love every time I talk to the folks from Travel Perk, I'm so. I get really excited because it sounds like such an incredible culture and to be working in and what an opportunity to do that. Looking back, you know, what advice would you give to others to find opportunities like this? Not everyone, you know, this is not for everyone. I mean, certainly I know people who would really suffer in an environment like this and who need a lot of structure and to be, you know, a lot of routine. But for someone who is an attorney or is in an innovation role that likes to dabble and experiment and be able to work in a culture like yours, like how. How would, how would you identify that.

When you're interviewing, when you're looking for a role, look for an organization that is aspirational, that's values do align with you. Now, realistically, you look on a corporate website, they're all going to be like, you know, we believe in X, Y and Z and it's all a lot of times it's buzzwords but you can, you can look around and you look on things like Glassdoor. But the interview process is very much for you now. Like you said, it's not for everyone. This is not for everyone, this job. And that is great. Right, because you are giving a lot of agency and autonomy at a very junior age. And I think looking back for me, maybe defining my why, why I want to do what I do and what I would like to get out of a career, I think that is more than where I would have started out. What I wanted to get out of a career wasn't. I didn't want to be. It wasn't b a VA business partner that's you know, at working at the forefront of like process and development. Just happened that I've got an interest in law so I see it more as a. I'm an operations person who is also a lawyer, not a lawyer who is an operations person. Now define that. Why? And that aligns with most people in, in the organization as well as in my team. It is finding those like minded people and the networks I think are fantastic. Block for instance crafty as well, which is a fantastic organization, connected like minded people. I definitely encourage junior lawyers to build their networks and find mentors like similarly minded people who will open you up to opportunities particularly if you've come in for the in house route and particularly if you're not from a social situation where you have access to people with these kind of corporate roles. I didn't know any lawyers until I entered the industry and I know that's, that's very similar for lots of other people in my team as well and lean on them and people want to help, everyone wants to help.

That's true. Do you have mentors? And I get asked all the time how do I find one? Any advice on that?

I met my mentor by having a coffee at a legal networking event. I was just stood next to him and that's literally how it happened. There are schemes. Law schools do good schemes as well. You know the law society in the uk they're very good for that. I think sometimes people think my mentor needs to be the job that I want to do.

Yeah.

But some of the previous ones I've had have been people completely different walks of life. But you like the way they work. And it kind of comes back to that from my perspective like if you want to be a business partner in house lawyer, that's what you want to be.

Yeah.

You need to have a bit of a business minded approach. And having mentors outside of that is interesting. And good mentors will also find you. It's not just about the mentee finding them.

It's such great advice and I love that because people always ask me and I think it's not about setting up a program where you get matched to some random person. It is like you said, you had a conversation, you clicked. That person actually had an interest in your career or the challenges that you were facing and were giving good advice because they put themselves in your shoes. And whether you're the mentor, the mentee, you find a connection somehow and doesn't have to be like the same industry. There are great people that you just gravitate towards to ask for good perspective and advice from. Well, Stefan, it was amazing conversation. I learned a ton from you. I spend so much of my time talking to people in different industries and department sizes and stages of company and I spend a lot talking to folks like you who are in hypergrowth, who are really innovative, who are thinking. And then on the other spectrum, plenty of conversations with companies that have been around for hundreds of years and are, you know, people who have in the legal department all been there for over 20 years and so really reluctant to change, but are now starting this journey. And what I love about what's sort of injecting excitement and a willingness to try new things in those organizations is maybe a lateral hire has joined from a more tech savvy or innovative team that's had a legal ops or tech function and are now going into these larger companies and saying, hey, where, where's all the stuff? Where's all the stuff that I'm used to working with? And so the more we can foster this culture and mindset and then cross pollinate, you know, to other companies, I think it's super exciting. So thank you for sharing your story. Thanks for all that you're doing out there.

No, thanks very much. Yeah, absolute pleasure and yeah, really grateful for the opportunity, opportunity to have a chat and really got a lot out of this myself as well. Hope that anyone that's listening through enjoyed it as well. So really appreciate it. Mary, thank you.

Excellent. And to all the folks out there, thanks for listening.