Episode 4: Interview with Jessica Zwaan, COO of Whereby

Welcome to this week's episode of Inspiring Legal, where Stine is joined by Whereby COO Jessica Zwaan on a call from New York. Jessica & Stine talks about how to scale and maintain a successful team, as well as Jessica's journey from legal to operations.


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Stine: Welcome to this episode of Inspiring Legal. I am sitting with a person that has a super inspiring background, career, and also a journey that I am stoked about telling you. I am sitting with Jessica. She has a legal background, working for a Norwegian company in New York, and is a COO. Welcome, Jessica.

Jessica: Thank you so much, Stine. I am really excited to be here. 

Stine: We are, as you know, a community of people with legal backgrounds working at tech companies and inspiring each other to really get a sense of what it is like to be a legal professional. A sense of what opportunities lie ahead. Where can we take ourselves and the journey and our careers?

Can you maybe tell people a little bit about you and your background and where you are today?

Jessica: Absolutely. As you mentioned, I am the Chief Operating Officer of a company called Whereby. Whereby is a Norwegian company. We are based in Norway, but we have multiple entities and we are fully remote. We have a presence in the US, which is where I currently am in New York. I look after the people, talent, legal, customer support, finance, and general business operations functions at Whereby. 

Prior to that, I had a background primarily in people operations. I worked in people operations for a very long time. I actually finished my law degree doing my dissertation on the legal implications of remote working cross-border in the EU. I have always been more on the employment side of things. 

Stine: What made you transition into people, then legal, and then such a broad role that you have today?

Jessica: I think, first of all, asking 17-year-olds to pick what they want to do for their career and their degree is insane to me. But, of course, when I was 17, I, like everybody else, was picking which path I wanted to walk at university. At the time, I actually was all set to go into a law degree at the University of Queensland in Australia. Then I ad worked so hard to get into that program. All of my family kept saying, well, I have a very large family, which I think makes a difference to the story. A lot of my family kept saying, it's going to be so difficult. You're going to be studying for years and years. It's going to be impossible. There's so much reading to do. You know how hard law exams are. Everyone is always crying. Me, being 17, was like, oh, my gosh, I've only just finished finishing high school. I don't want to do this. It was really scary. So, I actually pulled out of my law degree. I didn't even start it. I pulled out two weeks before I was due to start and moved into a communications degree.

I did my communications degree. I've got to say, I think the whole time I kind of didn't really enjoy it. I kind of picked it at the last minute because I wanted something else and I thought that maybe this was a line to do things I was good at. And I ended up starting to work in people operations. I think a lot of people kind of fall into something when you're kind of 19, or 20. 

And I was offered an internship and then a graduate role at BHP Billiton. I actually really loved it. And I really particularly loved industrial relations. Again, a lot of the team there had legal backgrounds. And I really loved HRBP work, which again, HR, so much HR work is very, very close to the kind of law that I probably would have looked at doing anyway, which is on the contract and employment side.

But I also really like the commercial side of things. And I think that's actually something that I'm really grateful that I had the chance to do. I think that if I would have just gone down the law path when I was 17, I would have probably ended up working in an employment firm, maybe never even gone in-house. I don't know. You never know these things, right, in retrospect. But it gave me the chance to really get to know how much I liked the kind of commercial side of the business as well workforce planning and understanding organizational design. 

That's what really drove the next couple of years of my career as I moved into more and more strategic people operations positions. And then I reached this point where, you know, “life is short”. And I said, well, I finished my CIPD diploma and I really enjoyed the employment law portion. It was something that I was kind of sick of paying for employment lawyers to be advising me on everything. And I thought I've always wanted to do this. I might as well just do my law degree finally after all these years. So I enrolled and worked full time and finished my law degree with full-time work, which was an extreme couple of years of my life. And I really haven't looked back. Yes, it's intense. It's intense. But it was great. I loved it. 

Stine: Did you feel like it was a nice compliment? I feel like work can be so chaotic, but law degrees are so, you know, practical, whatever it needs to be - check the boxes. 

Jessica: It was almost meditative. Like, I can read this and then you go back to work and it's like everything is spinning around you and changing all the time. 

Stine: I know. Anyway, I really enjoyed that. That part of it. I'm thinking about how you go from being in Australia and then working with people, taking your law degree full time and ending up in Norway as the COO.

Jessica: So I never actually worked in Norway. I was working in the UK for a Norwegian company. But how did the transition happen to the UK? I'm a first generation university graduate. My parents had never been to university. And for them, really, their vision of success was to finish their degree, whatever that is, and get a job. And once you've done those two things, then you don't need to do anything else for the rest of your life. And like I, you know, the world is obviously so much bigger than that, but it's really difficult if you haven't got role models in your life that have done more than that, like that haven't got more experience than they're expecting from you, if that makes sense.

So I started working for BHP off the back of my graduation and I was there for almost four years. I really loved the job and I really loved my team. And I had a dog and a house and a car and furniture and all this stuff. And my manager slash mentor at the time, Monica, actually, e had a one-to-one together. And I just explained to her that I was looking for something bigger to work on at work. I felt like there were more things that we could be doing and I was working on interesting projects. We just wrapped up this really great project around increasing representation of Aboriginal And Torres Strait Islander members of the community and into the business. And she said, have you thought about just leaving and moving to a different country? And I was so offended at the time. I was like, oh, my God, she's trying to fire me. This is so unprofessional. And then I, you know, we obviously had a long conversation and I realized that actually what she was trying to get me to do is just to make my world bigger.

And she did say, like, you're always welcome back. You can always come back to the team. We still are connected to this day. But I really think that without having somebody that had kind of like this broader perspective on life really just say to me, like, try something different. Just go and do it. I probably would never have been able to give myself permission just because I'd never really seen it. So, yeah, I'd never actually even been to Europe when I moved here. I was here in the UK. I packed up all my stuff and moved n a couple of months a very long time ago now. But, yeah, that's my story.

Stine: Amazing. So today, being the chief operating officer at Whereby, and you have, of course, also said, I think, the legal team as well at Whereby and hired people.

Maybe could you put a few words on what are you looking for when you're hiring people for your legal team? What's the skill sets and the traits that you find to be the key ingredients for the hire that you're looking for? 

Jessica: Yeah, this is a great question. For me, I think the thing that is the most important is probably something that may be surprising to some people.It's not necessarily having the most backed-up legal knowledge in any specific area. So it's not someone saying, oh, I've seen everything before in terms of sales tax law and blah, blah, blah. I don't care about that. 

What I really care about is someone being able to solve problems themselves using legal thinking. So being able to kind of identify which laws may be relevant to us. And that obviously comes through the education that they've had, the legal education they've had. But the kind of most important thing to be able to do with that is to think commercially, think how the business thinks. If you have an engineer that wants to implement a new cookies banner that breaches some legislation somewhere, it's not enough, I think, just to go to them and say this breaches legislation. 

No matter how hw smart your analysis has been, no matter how brilliant your knowledge is, the business will reject that kind of approach. So being able to come back and really explain, well, this is the parameters in which we have to operate. These are the ways that we can solve this problem. Potentially. Here's some examples of other companies that have done this successfully. These are the kinds of ways that I look for somebody to be able to kind of approach legal work within a startup and just be adaptable with that as well.

Stine: So when you're then looking to hire a person, are there specific ways that you are maybe identifying that? Like how do you or how would a candidate that would be applying for a role at Whereby be able to persuade you and show you that those are the skills that they have? 

Jessica: Yeah. So I think there are kind of two parts to my answer to this. The first part is not a very great answer, I'm sorry to say, and that is honestly, honestly, companies receive so many resumes and whatever advice I give you about how to format or approach resumes. Somebody else or 20 million other people will be giving me conflicting advice. That's just the nature of, unfortunately, how CVs work. You know, many people go out and say, keep everything on one page, make it succinct. Other people say, to make sure that you've got output-driven metrics on things. Maybe it's a combination of all of those things for different people.

What I probably look for at that CV screening stage is someone with enough experience that I can see that they are capable of handling the level of seniority that I'm giving them. So if someone's coming out with maybe one-year PQE and I'm looking for a senior, that probably isn't going to work. And then someone that maybe has worked in the same kind of industry, meaning startups. I don't need someone to be working in SaaS or it doesn't matter if they've been in e-com or anything. And obviously, there are going to be some jurisdictional considerations there as well. So if someone has a law degree out of Kenya, they may not be super applicable if I'm looking for Norwegian privacy. 

Now, the better answer I can give you, hopefully, is how we think about it on practical projects. So once we've identified a kind of selection of candidates that we believe have the raw materials to really do this role, we always give a practical project and it is always paid. We make sure that we always compensate people for their time that they spend doing these projects. And really, it's only a couple of hours. One of the things that I try to bake in there is this kind of level of ambiguity and problem solving and commerciality that someone would need to show us. 

So, for example, something that we've done in the past is there's a new piece of legislation. Let's just pull something out of the air. Let's just say GDPR. Let's go back to 2016. GDPR has just come out and we need to do training for all of our managers on what their obligations are. Can you please create an email to send to the managers giving the highlights of what they're going to be learning after they finish the training and maybe five or six slides to talk them through for half an hour?

And what that's really trying to get out of them is what are the key pieces of legislation that matter to the people you're talking to? So try and figure out who's going to be in this meeting, what are they looking for? And also be able to kind of tailor that effectively to that audience. What we're not looking for is a huge ream of information that is almost impenetrable to somebody that doesn't have a legal background or a bunch of slides that someone will sit through and their eyes will glaze over and they won't be interested in hearing about it anymore. So, you know, using examples of how it might apply to our business or pulling out ways that somebody might need to think about this in the future. These are the kinds of things I think are really beneficial. 

Stine: So given the fact and the reason why I may be asking you this a little more is that you have such a unique background coming from people and culture and then also hiring and having that degree yourself.

What do you think is one of the key, let's say, things that are people going in-house, either applying to where by or considering going in-house at another tech company should really consider before applying? What is different from, let's say, working at a law firm or working at another type of company? 

Jessica: Yeah, well, I've never been on the firm’s side. I've always worked with the legal teams in any company that I've been in-house. But I can tell you one of the things that I've had repeated to me by multiple people that I've worked with, you know, friends at school as well, is just how much more chaotic the work you're looking at will be. There's no better way to describe it. I think you may get a certain degree of chaos from clients coming through to you. Like I did a placement in an employment law firm and you do get a bit of chaos from clients not knowing exactly what they should or shouldn't be thinking about or maybe saying like, I know you said not to email them, but I've already emailed them and this is what I said. Like, these are the kinds of things you deal with. 

But in a startup, it's much more likely that you're going to have a VP of sales approaching you and saying, hey, I've just found this, I just sent this email to one of our customers that had a bunch of documents in it I shouldn't have sent. What should I do? And then you're all of a sudden going to have to kind of respond to this quite quickly. Meanwhile, someone else might tag you in a long discussion on Slack about sales tax in India, something you have no knowledge about and you have to work with finance very quickly to understand it. You're not going to be working safely within the kind of framework of whatever business unit you've been assigned to. 

You really will be touching almost anything. And sometimes you'll probably feel a bit silly. That's just a part of it, that you'll feel like you don't know everything. And you definitely will feel like you don't know everything about what you've been hired to do. But you have to remember that your job is very different. It's no longer just to advise on the law and like a functional area or a firm practice speciality. It's now to be a voice for the company in terms of what legislation is going to affect them. And that's a much more commercial kind of work. 

So when a person then joins your team, how do you measure the success of that individual? And what goals do you set for your legal team? The thing that I've always said to my team has been what we're there to do is to enable good decision-making. That's it. Compliance is table stakes. If we're non-compliant in the basics of what we need to be compliant in, then that's a problem, of course. But what we're really there to add value in is have people come back to us and say, we'd never have been able to make that decision if the legal team hadn't been involved. Or we would have gone down the wrong path if the legal team hadn't been involved. And that often can bump into the revenue side of the business as well. So you really help speed up our being able to onboard that new client because we were able to remove certain terms of service and they wanted a heap of compliance at the same time. We weren't sure if we could do that. The legal team was able to speed those processes up.

But I think that means for me that the goals will change on a quarterly basis as needed by the business. Maybe sometimes it will be to improve the process, improve the time between the contract sent to the customer to the contract signed by X period, by simplifying our terms of service or adding some extra legal FAQs. Or maybe it would be to decrease the number of help tickets coming through about legal-related questions to the customer support team. So there are output metrics we can look at on a quarterly basis based on what we're trying to do in the business. But always, always, always the main thing is to enable the team to be able to make really good decisions. And if the team's ever working on a piece of work other than like kind of administrative to-do's that you can't look at and say, well, this will help us make good decision if I finish it, then to me, it probably isn't a priority. 

Stine: I think it makes a lot of sense to enable better decision-making and the value you're delivering to the business. How do you show that you've enabled those better decisions? And given that you're the COO, you're part of management and you would be one of the people that would be looking at the value that the team is delivering. You have a legal background and thereby, I think, a better understanding than maybe other members of management.

So how do you, as let's say, the general counsel or the head of legal, show that you've enabled those better decisions?

Jessica: Yeah, so I think that, again, comes down to whatever the output metric is that the team is focusing on. So let me try and think of an example that we did have at Whereby. One of them was around improving the pace between sending DPAs or terms of service to customers and then having them agree to those terms of services. So, say we had a new customer being onboarded through sales and there was usually a delay of five days while customers reviewed and talked about which terms they wanted to agree to in like a kind of custom contract. In order for us to enable better decision-making by our sales team, I would say one of the projects may be to decrease that time from the time of the contract being sent to the customer and signing by X amount of time. 

It doesn't need to be something that's perfectly quantified. I think you do your best and then, and the aim is to reduce it. It doesn't really matter if it's exactly by the percentage you've flagged within reason. And then I would work with, in this case, the privacy council that worked with me on this project and say, what things do you think we could work on to see this metric improve to help the sales team make better decisions around making the pace between contract and signature?

And the decision there was made that we would simplify the terms of service and simpler headers on terms of service so that customers could read it more easily to do a very simple training with the sales team. So they understood what they were actually sending out so they could answer some questions and then also to create a legal FAQ doc that was sent to customers in case they started asking questions like, what does this liability clause mean? Why have we included this? Where's the link to X? And in doing that, we were able to see that all of those things enabled the sales team to make better decisions and speed up the process of contract to signature by a day, whatever it was that we put in as a goal. 

Right. So that means that the fabric of what better decision-making looks like in terms of output can change on a quarterly basis. I don't think there's any one metric that every company can adopt and say, wow, look at us, you made incredible decisions, except for pure ARR growth. Right. Pure ARR growth shows we made incredible decisions and reacted to a volatile market, but that's just it's too nebulous for any one team to be able to draw as responsible. So I do think you need to be flexible and be thinking about every quarter. What does that improvement look like in different areas of the business? Otherwise, you'll be very unfocused. 

Stine: So having said that, what do you then think if you're like, I know you're sitting at Whereby and you shouldn't give away anything in terms of Whereby specifically.

But if you're looking at legal teams in general, what are some of the biggest struggles that you see that they should be addressed to improve the team's scalability and maybe also productivity and efficiency?

Jessica: Gosh, that's a massive question. 

Stine: We can also make it shorter.

Jessica: No, no, no. I think that's a good question. You know, I think Openli is not the only tool that's out there that can really improve the quality of life at work for a legal team. But it's definitely one of them. You've also got tools like Juro that are out there now. And there's a lot of legal tech. Law tech is really, I think, a very interesting area of SaaS. And I think hopefully I'm actually almost preaching to the choir. If you're already in an in-house role in a tech company, I imagine you've probably got a manager that's saying to you, like, how can we help leverage you as an individual more so you can be more consultative and spend less time doing admin and sending docs and updating things? 

But the first thing I would say is I really do believe that the job of the legal team is to be doing the least amount of kind of administrative turning as possible. You want systems and tools and things to be doing that for you. And really, you should be much more of a consultant to the business wherever possible to be able to be involved in early decision-making and to be able to kind of unblock projects that maybe need your help. And that means, I think a little bit more like a product squad with that same idea of what output are we trying to affect. What is the outcome we're trying to reach here? What's the benefit? Who's going to receive the reward for this? Is this just a compliance project? Because that's business as usual. And that's fine. But I don't think any legal team should just be doing business as usual.You should also be thinking about how I can really spread my knowledge across the business in ways that will really be impactful. 

Stine: What would your recommendation be then for, let's say we're sitting with a lot of general counsels and head of legal out there today. And as many out there, they're probably overstretched, overloaded, and overworked.

What is, in your opinion, maybe one of the best key takeaways from when you're looking at your own team and how you've improved their productivity?

Jessica: Yeah, I think it's that it's product-centric, like the kind of product ideology. Support teams and I, you know, I hate to say that legal and HR and finance are support teams, but they're also very commercial teams. But one of the reasons that you do see them get overloaded is because they can struggle with the amount of balancing of improving things, and systems for themselves. So being able to make systems work better by, you know, let's scrap all of the documents we have to send out to each customer and let's just have Openli instead. 

But the problem is, if you're so busy doing day-to-day work, it's really hard to prioritize moving across to a tool or implementing something new or changing something. And the only way to do that is to really carve out that time every quarter and say, we have to ship something every quarter that impacts something that's going to help us in the long run, whether that's decreasing the amount of time to do X or increasing our effectiveness around Y. That needs to be something that's as religious as the product team and the product teams are always doing this. 

They're always thinking like that's their full-time job, which is very different from a legal team because they also have business-as-usual work. But that comes with a reframing of things to your COO generally and saying, I know my role has been for the last year or two years fighting fires and rewriting contracts and being on calls with the sales team. I get that. But if you want to get the most out of me, what you need me to do is have a day or two a week where I'm just focused on delivering new tools, making sure that our team's ability to launch work that reduces our administrative burden. 

And that may see a slowdown in the number of fires you can fight. But what you'll end up seeing is a much bigger increase in the future of productivity and effectiveness of your team, which if you can even just say, give me a quarter, let me have a quarter where once a week, my team just work on projects and see the output change. I think that should be enough to win over even the coldest-hearted COO.

Stine: And probably also increase their motivation would be my guess.

Jessica: Yeah, exactly. And it gives you some more. It gives you things that you can be really, you know, there's only so much. There's only so much dopamine you get from those little tasks you tick off those fires you have to fight. There's nothing better than seeing this big chunky thing that's really been bothering you for six months and being able to kind of really just make it happen and see a metric improve. And I think it gives the team a lot of joy and it also really, I think it really matters that you can say when I was in this team for three years, I increased X in our customer base and I made these improvements and I was able to help us hire from the US because we needed SCCs that no one had ever written. And these are the kinds of things that are really beneficial.

Stine: Amazing. So two more small questions. And one of them is a lot of people out there are sitting in one maybe two have a seat at the table. So when you're working in the legal team, sometimes you are a part of the management group and other times you're not.

If you want to become that trusted advisor, what's your best kind of advice to them?

Jessica: Yeah, I think this goes back to the very first thing I said, which is that commerciality and being able to understand, you know, I say this to everybody in ops and people in legal that I speak to is the best thing you can do, especially when you're kind of up and coming into roles, ready to step into management, like leadership roles, not just managing people, is to be kind of almost aggressively opinionated by what other people are doing in the company. 

And I don't mean micromanaging and I don't mean meddling in the copy that the marketing team is using. No.I mean, understanding and really wanting to understand why are people doing that? Like, what are you trying to change and what does that mean for this other team and how are you two working together? And if you're really opinionated and really curious about the way the businesses are working together, it makes you so much better at your job. But also it makes you such a much better empathizer with the business. And you're able to really present the case studies on what you're working on in such a deeply relevant way for the entire company that it automatically becomes like we can't not invite that person because they really get how we are working together and they really care and they want to be involved in things.

And I think it can be a tough line to tread, especially if you're a little more junior. What does being aggressively curious or aggressively opinionated mean? And some people can step into being a little micromanaging or kind of nitpicky. But I would ask for feedback if that's where you're at in your career and you really just go to your manager and say, I want to start going to the commercial meeting and just sitting there and hearing what they're talking about and writing notes and understanding it. I think it'll be helpful for the next project I might work on. 

And say to the team, if you feel like I'm meddling in things, please say that I'm not trying to meddle. I just want to know, I'm really curious. I want to know how you all work together so that I can help you in any way that the law possibly can. I think sometimes people have this idea that the law is there to slap your hand when you're being naughty. But very often it's also there to help lift businesses up and make things work better. And that misconception can only really be broken down by legal professionals being really curious about how businesses work so they can say, hey, maybe there's a patent application we can file for this thing you're working on. Or, hey, maybe actually if we just implemented these SCCs into these engineers’ contracts, we could employ them in America. Like these are the kinds of things that businesses all of a sudden say, like, oh, we should invite legal because they have some pretty good ideas. Adding value and again, enabling better decision making. 

Stine: Exactly. Exactly. So this podcast is about inspiring legal.

So what would be your one advice to inspire the legal community that is listening in today? 

Jessica: I thought about this question for a long time. I think the thing that I kind of settled on in this was that there are different stages of where my inspiration kind of comes from, and I'd say at the very early stages is just for me anyway,  just learn as much as you possibly can. Love every area, even if you feel like you're never going to work in that. Just learn about it. It's really interesting and it might actually really help you later on in something. 

So if you're really junior listening and you're like, oh, I'm never going to do that. Still, just try it. Just try and find something to love about it. If you're more senior. I think that the one thing that I would really encourage and the one thing I'm really grateful for in my career is I've been so inspired by the way design designers and the design community are so good at sharing the work that they're doing together. They're incredible at collaborating cross-functionally and working on collaborative pieces of work. I think, you know, legal professionals can really do a lot from that and communities like the Openli one is a great example of this starting to really exist. Engineering teams are incredible at sharing management best practices. They're really good at showing like this is how progression frameworks should work. And these are the kinds of things that also are quite applicable, like the legal profession.

I think progression frameworks probably look fairly similar across different businesses. These are the kinds of things we can be sharing with each other in a very open way. But I would say be inspired by looking at what other functions are doing and what other functions are really good at as a community. So just bigger than the company you're looking at, try and see what you can take away from that and apply to the legal communities. 

Because I think there's this bad reputation that is very closed and not very collaborative and it's kind of a bit more old school. But almost every single person I've ever met that's worked in legal has been incredibly open and interested and intellectually stimulated by community and discussions. There are amazing Twitters. There's so much to do around looking at other functions. So I would just say that never, never close your eyes to people that aren't in legal and try and get inspiration for the teams you're working in. 

Stine: And on that note, thank you so much, Jessica. It was absolutely amazing. I have so many ideas of how what you just said can really, I think, transform a lot of the ways that we're doing things today and hopefully also inspire a lot of people and listeners out there. So thank you so much all the way from New York. And we will hopefully hear from and see you again. We are truly inspired. So thank you so much. 

Jessica: Thank you so much for having me. I really appreciate it.

Thank you so much for listening to Inspiring Legal. Remember to subscribe and if you want more information, you can always go to openli.com/community.