Lessons I Learned in Law

Rachael Carolan on looking beyond the traditional general counsel role

July 19, 2021 Heriot Brown Season 1 Episode 5
Lessons I Learned in Law
Rachael Carolan on looking beyond the traditional general counsel role
Show Notes Transcript

In this episode of Lessons I Learned in Law, Scott Brown speaks to Rachael Carolan.

Rachael is currently General Counsel and Director of Policy at London Based technology company what3words. Rachael was the company's first lawyer and has been responsible for setting up and growing the legal function. She qualified at Herbert Smith Freehills and moved in-house on qualification to Accenture and also spent time at 2 of London’s hottest startups, GoCardless and Deliveroo.

Rachael shares the three lessons she has learned in law including:

  • Create your own path, rather than trying to follow a traditional one.
  • It’s possible to add value as an in-house legal counsel, beyond the traditional legal role.
  • In a B2C company, try to make legal part of the brand identity.

Presented by Scott Brown of Heriot Brown Legal Recruitment.

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This episode of Lessons I Learned in Law is brought to you by Beamery.

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Scott Brown  (0:03)  

Hi and welcome to Lessons I Learned in Law with me, Scott Brown, founder of Heriot Brown In-House Legal Recruitment. I'm an ex-lawyer turned legal recruitment specialist. I took a few wrong turns in my own legal career. But I'm now in a privileged position to have daily conversations with some of the top legal minds in the in-house legal community. And I wanted to share some of those conversations. And this was the reason for launching the podcast, I wanted to provide some inspiration and insights to lawyers or aspiring lawyers to learn from people that are at the top of their game. On each episode, I sit down and have an honest and open conversation with people from across the legal community to understand what influences shaped their careers. And of course, to learn some of the lessons that they learned along the way. I've had a bit of a mid-series hiatus from recording, but back in the thick of it today, I have had COVID actually over the last couple of weeks or recovered now out of out of isolation. And just to give you an idea of when we're recording England have just breezed through the semi into the semi-finals of the Euros at the weekend. So, it feels a little bit like footballs coming home. But the less I say about that, I think the better don't want to alienate any, any English fans out there. But I'm delighted today to be joined by Rachael Carolyn. Hi, Rachael.


Rachael Carolan  (1:30)  

Hi, Scott. Great to be here.


Scott Brown  (1:32)  

Thank you. Thanks for joining us. And Rachael's currently general counsel and Director of Policy at London based technology company. What three words? What three words you'll have seen advertised a lot. Recently on TV and around cities. The company has developed a universal addressing system that can assign a precise location to anywhere in the world with just three words. Rachael was what three words first lawyer and was responsible for setting up and growing the legal function. She qualified at Herbert Smith and moved in house and qualification to censure and then spent time at two of London's hottest start-ups, GoCardless and Deliveroo. She recently announced on LinkedIn that she's moving on to pastures new and a new challenge away from what three words so I'm sure we'll be keen to learn more about this later on. But welcome to the podcast, Rachael's Great to have you. Thanks, Scott. So, if you've listened to previous episodes, you know that I like to start with a few episodes about each guest. Some that you might not be aware of. So, Rachael tells me she lived in Hong Kong, Argentina, and in the US for a brief period of time. And if it wasn't for health conditions, she may well have qualified as a lawyer in Hong Kong rather than in the UK. Secondly, she was she's got an adventure site. And last week, she was in a hot air balloon over the Mendips. And she thinks that if she was a teenager during the COVID pandemic, her predicted grades would have been fairly, fairly bad reading. So keen to hear a bit more about that later. But we're going to start the episode just to learn more about your life and career via the lessons that you've learned in law, Rachael, so if you could jump in and tell me your first lesson?


Rachael Carolan  (3:26) 

Absolutely. So, lesson number one would be to create your own path, rather than try to shoehorn yourself into a traditional one


Scott Brown  (3:36)  

talk me through your career then and where you feel that that's been the case in your own your own career path.


Rachael Carolan  (3:41)  

Absolutely. So, in my case, it started off along the traditional route, so qualified, Herbert Smith, free hills, and very much felt like a black sheep, when it came to handing in your applications for which department you wanted to qualify into, because mine was very flat. I'm outta here. I'm off to move into a business. Although at that point, I was I was looking around and I was, I was interviewing, I was certainly interviewing Accenture. But at the time, I hadn't yet had an offer from them, but I was just sort of set on qualifying elsewhere. And I think at the time, that really wasn't the dumb thing to do. I think it was a big surprise to everyone I'd worked with, certainly to my supervisors very much, very much made me feel like a bit of a rebel to be honest or that albeit looking back now, I think that's become more and more common these days. And it's perhaps sort of less of a black sheep thing to do, but certainly at the time, that really was not the done thing to do. And I actually didn't have many examples to look to you have to other people have done a similar thing and craft their own role from qualification onwards.


Scott Brown  (4:57)  

Yeah, I think I think traditional advice anything that I've seen from recruiters is do your three, five years black letter law in a law firm, if you want to move in house, that's, that's generally regarded as the time to do it. Or I think, like you said, traditionally has been the case. But how did you know that that was what you wanted to do?


Rachael Carolan  (5:19)  

I'm sure there were a few different things. So, I mean, number one, I did a common while I was at Herbert Smith in Bank of America, Merrill Lynch, which, again, is not like anything I've moved into now, I certainly haven't gone to an investment bank. Very different from being in tech. But nevertheless, when I was there, my supervisor at Merrill Lynch gave me a much longer, longer leash, so to speak. And then the one I was on a habit Smith, and, you know, I'm sure, relatively speaking that the value of deals that I was working on in comparison to her were, were very low, given sort of how Junior I was, but I felt like I was almost thrown in the deep end with that qualification in terms of always working hand in hand, with the business and working directly with clients on negotiating high level deals, which I felt like I was someone who learnt best by doing rather than rather than shadowing. And I'd always felt like that. And I certainly also felt with my career that for whatever reason, I felt like it was on an upward treadmill, I wasn't sort of settling for doing things were set pace. So, I wanted to sort of take the bull by the horns and, and really just carve my own way, way quickly. So, I think it's a mixture of those two things. But equally, I'd always had a strong passion and interest in in tech and felt that I would satisfy that interest area more. If I was to work, as I say, sort of hand in hand with people that were working in that area, and that weren't necessarily lawyers


Scott Brown  (6:54)  

understand what got you into law. With that interested in tech that you had,


Rachael Carolan  (7:00)  

in terms of what got me into law? Honestly, there's no, there's no sexy answer to that one. I think I honestly didn't know what I wanted to do, I think it was, it was one of those careers where, if you were good in certain areas, it was sort of the career to consider. And I'd certainly sort of progressed in in subjects that perhaps made you a better fit for law, albeit I don't subscribe, but there are certain subjects that would make you a better lawyer anymore. And I did a degree in law and sort of didn't think as much as I perhaps should have, in terms of other careers at that time. So when went for that sort of initial training period, and decided that she, I can do this, but maybe not in the traditional route of spending sort of three years post qualification at a law firm, I can definitely make a career out of this that I will readily enjoy. But I'll do it my way,


Scott Brown  (7:56)  

that's good. Good to pioneer in that way and have the confidence to do it and go out and back yourself to move into the areas that you enjoy how much thought went into that I enjoy these areas, I'm good. That's what I do as well, I'm going to pursue


Rachael Carolan  (8:11)  

I certainly always knew that the areas that I enjoyed the most were the areas where I was interacting directly with both sort of counterparts on big deals. So other companies, but also where I was helping teams and, and business people get things done. I was never someone that enjoyed sort of more of a back-office role that was thinking about something and doing research for long periods of time, but not actually ever really applying that to anything or, or sort of interfacing with people on a day-to-day basis. So I thought a long time about that, and what sort of career and certainly what sort of business would suit me the most to take forward those interest areas. And I feel like my moves since then have definitely taken all of that into account.


Scott Brown  (9:04)  

Did you ever consider at that point, not being in the law moving away from a legal role?


Rachael Carolan  (9:10)  

Absolutely. Absolutely. did. And, you know, I think perhaps later on in my career, you know, potentially there is scope for me to move into perhaps a completely non legal role. But I'm very much enjoying it at the moment. And certainly, I think the roles that I've taken in house, and we can perhaps go on to discuss a bit more it's never strictly a legal role that you're doing. It's always something a bit more that you're adding at the same time. So that's definitely given me a lot back in terms of sort of both my career progression but also just general interests.


Scott Brown  (9:49)  

Yeah, we'll come on to that a bit later on. You mentioned supervisors, maybe raising an eyebrow on that. What was their reaction when you when you told them you weren't sticking And in private practice,


Rachael Carolan  (10:01)  

I think the first question is why? And also, what are you going to do? I certainly remember those being the top two questions. And I think eyebrows again, were raised when I said, I'm not entirely sure at this point in time, but I definitely have a general idea of where I'll move to. It just hasn't been confirmed yet. So I honestly think people thought I was sort of just jumping off a cliff in terms of my, my career trajectory. But it all worked out for the best thankfully.


Scott Brown  (10:35)  

Yeah, to put yourself put yourself out of that comfort zone. Rather than following the beaten track. Yeah, I remember as a, as a lawyer, myself, thinking of myself as a senior associate, and not really, not really loving what I was seeing. So yeah, I think it's a brave decision to make. But you've got to follow your passion. And I think too many people stick around for the sake of it, because it's because it's the thing or for the paycheck efforts. And then that's something that you can get too used to as well, in private practice. But that's another that's another story, I guess.


Scott Brown  (11:22)  

Maybe gone to your second lesson. Can you share that with us, please?


Rachael Carolan  (11:26) 

The second lesson is it's possible to add value as an in-house legal counsel beyond strictly your traditional legal role.


Scott Brown  (11:35)

Tell me a bit more about that. Where did you first learn this?


Rachael Carolan  (11:38)  

So, I think for me, what I what I noticed, after a while of being an in-house counsel is that quite often, it's those that are in the sales team, that are bringing in the money that are getting the obvious recognition. And that's of course, extremely important that I wouldn't have a job if it if it wasn't for the sales team. But I think it's important for everyone to have recognition, it's certainly a depressing thought to be sort of constantly churning out work and doing it at a very high standard for no one to recognise that. But the problem I saw with being an in-house lawyer is that sometimes it's really difficult for people unless they are in the legal team to really recognise sort of the value that you are bringing in the work that you're doing. So certainly, it's not the done thing for someone to walk up to your desk and say, you know, thank God, Rachael, we didn't break any laws in China last week. Thanks for spending, you know, a month thinking about how we launched into China and not breaking any laws, or, you know, the ICAO isn't investigating us this month, well done for being on top of all of the global privacy laws, like that just doesn't happen. So, I think that for me, what I noticed that was when I when I was inviting the business when I was sort of stepping beyond just the strict legal role that brought both more recognition, but also, it broadened my role. And it was useful for me in terms of career trajectory and career progression. So for example, I see myself more is sort of head of problem solving almost. So when someone comes to me, it's, it's generally one of two things either something's gone wrong, or they need to do something. And they're asking me like, how do we do it? So I'm not going to come to them and just say, Okay, well, the law says XYZ go away and you know, work it out. Now, I'm going to do that part. Make sure that we're on top of that, but also think more broadly about the best way we go about delivering on that thing that the business wants to deliver on and, and quite often, that will go beyond just the strictly legals and when you do that. I think you elevate your position within a business, and you bring more to the business as well. And you're more closely aligned with also what's going on in the business at the same time.


Scott Brown  (14:06)

Yeah, it's good and necessary and type organisation as well that has that has that approach, but also the individual, what advice would you give to someone, an in-house lawyer who's maybe feels trapped and doing business as usual work? How could you elevate yourself to giving non legal advice or being that problem solver?


Rachael Carolan  (14:26)

That's a really good question. I think first of all, you have to really understand the business inside and out. You really have to understand what are the key drivers for the business right now? Like where are we currently are? Where are we heading? And what are our main challenges and then also tailor that to your stakeholder that you're talking to you on any given project? So you know, if you're talking to the head of product, they'll have very specific KPIs and challenges that they need to deliver on this year. And I think it's all about When you're talking to them about that specific project that you're advising on, can you think of any areas that you can actually pick out and say, Well, how about we think about this aspect to it as well? Or have you thought about this as well and really tailor that both to? What does the business need to achieve this year? But also, what are the specific challenges and things that are on this stakeholder's mind? And also, just be creative? Just think outside the box a little bit? I definitely think there's, there's scope for that.


Scott Brown  (15:27)

Yeah, good advice. But just add a little pause from the from the lessons go back to the facts that we mentioned earlier on that people might not know, but it sounds that you've, you've travelled a lot and had maybe itchy feet in the past and lived in some pretty cool places. But Hong Kong clearly had a bit of an impact on you, if you felt you might have qualified there. What was what was it about Hong Kong that appealed so much?


Rachael Carolan  (15:50)

Absolutely. So I studied in Hong Kong for a year when I was at university had the best time of my life, but actually visited with family just before that as well. And applied to the University of Hong Kong alongside all of my UK universities. And I actually got an offer, but I remember the latch the main lecturer, basically one of the head lecturers in the University of Hong Kong saying to me, you should probably go to work if you've got an offer from work. And I think that was just strictly because they were thinking, Okay, you probably want to be an English qualified lawyer one day, and it's, you know, it's it was a well rated University in Hong Kong. So I definitely sort of took that advice on board, but equally looked to where I was potentially going to go in the UK and could see that, if I worked really hard in my first year, I could do a bit of both. So I could get a UK law degree, but equally do that that year in Hong Kong. So there was definitely a time where I was considering just going out there and doing my whole degree in Hong Kong, that didn't play out just due to sort of life events. But that was almost on the table for me. And there are definitely sort of times where I look back and think, should I maybe have done that? Because it's definitely a very, very special place to me.


Scott Brown  (17:09) 

Nice. I've never been I've never been but travelled through it and stop and stop and reload. But yeah,


Rachael Carolan  (17:17)

it's changed a lot. Now I go back quite a lot. Not recently, obviously, just due to various things. But it's certainly changed a lot from when I was there, but it's an amazing place.


Scott Brown  (17:28)

We had someone working with us last year, a law student that was there was helping us, Harry Brown, and she had started the year studying an exchange here in Hong Kong, but I think there was I think pre COVID There was all the riots going on. And then then COVID forced her to relocate back to their copy of shore and be back in Europe. But yeah, also said some pretty amazing things, but and Argentina for the


Rachael Carolan  (17:56)

time. So I was there to study Spanish, actually. But I, I didn't spend so much time studying Spanish at the end, I spent most of my time I think making friends and drinking red wine. And I have zero regrets about that, actually. But yeah, that was the aim. And it ended up as I say, just being sort of a brilliant time tasting wine. Sounds pretty good


Scott Brown  (18:21)

to take red wine and steak. Exactly. Well, well placed. One of the one of the previous guests, Randall Barker, he's worked in a number of overseas jurisdictions as a as an in-house lawyer thinks that law is a great career for travel. Virginia, would you agree with that?


Rachael Carolan  (18:45)

Well, I haven't experienced that myself. Personally, I think I've got a couple of ties to the UK currently. But I definitely, you know, had the good fortune of travelling with my, my job. So I've definitely been posted to various entities that that we have abroad. So I did that actually quite a lot more with delivery previously. And certainly, been involved with expanding to different jurisdictions and hiring in house teams within those different jurisdictions. I've also got an Australian in my team currently. So I can definitely see how you can travel with the law. And maybe one day I'll experience that sort of first-hand myself as well.


Scott Brown  (19:30)

And the hot air the hot air balloon last week. How was how was that? 


Rachael Carolan  (19:34)

That was incredible. I don't know if you've ever done that, Scott. Never. Yeah. It was on my bucket list for a while and my partner Emily knew that it was I think we just moved to Bristol on there's a lot of hot air balloons around in Bristol and I mentioned that had been on my bucket list for a while and she said it wasn't on hers because she's got a fear of heights. But she actually surprised me with it and did very well herself actually because it was a very small basket in the end. So we're sort of right off on the edge. But she really enjoyed it in the end as well. So it was it was great.


Scott Brown  (20:10)

Good. So proper open basket. Yeah, cartoon picture style god. 


Rachael Carolan  (20:15)

Yeah, very, very small one and sort of the pilot was mentioning that we can't go into an electricity pylon otherwise we'd be dead basic. But it was it was fun. Nevertheless,


Scott Brown  (20:27)

yeah, great. No, I'm pretty terrified of heights. Actually, I'm not no great. Maybe not a huge fan. Yeah. Frozen on Cliff edges a few times. Oh, no. Yeah. best avoided.


Scott Brown  (20:50)  

on to lesson number three, what's your third lesson?


Rachael Carolan  (20:53)

So third lesson is in a b2c company, try to make legal part of the brand identity. And also be very careful what your legal say,


Scott Brown  (21:02)

You've clearly worked in quite a few or a couple of consumer-focused businesses, how have you gone about doing that then making it part of the brand?


Rachael Carolan  (21:13)  

So I think this is a lesson that that really came to the forefront for me at delivery, actually, specifically, and I think that was because we found ourselves in a position where some of our contracts ended up in the press. And they actually ended up in the press, I think, you know, within my first month of joining the company, so it was a real eye opener for me that you know, something which on the surface, you think no one's gonna bother to read this, this is this is all quite boring, can actually end up being a great news story. So ever since then, I've made a real effort to think through okay, what angle to this is press worthy? And equally, who are we as a business? What, what are our values? And how are we reflecting that? In our contracts and our T's and C's? You know, I think it's, it's really natural as a lawyer to just go for belts and braces and just, you know, make your T's and C's as strong as you possibly can throw in stuff that you'll never think of ever using. Just for the sake of it. And actually, I think that's really poorly reflects on your brand. When someone does pick that apart, and I think in in today's world, that's very much driven by social media. So you know, a few tweets can end up in a in a headline, I think it's more important than ever to be looking at, at what your legal terms, say, and making sure that's actually reflective of who you are as a company.


Scott Brown  (22:56)

Yeah, under the under the microscope on all on all levels and businesses like that. Has it been something? Is that something that's also filtered through war three words?


Rachael Carolan  (23:09)

Definitely has. So in both good and bad ways that we've had a lot of compliments about our privacy policy. So we've, we've had people complimenting us on how well written it is and how it puts them at ease. But equally, fairly recently, I would say, sort of an action that I had to take in in defending rip ended up in a TechCrunch article, which was another surprise, actually. So that was that was a new one. I didn't expect that to end up in the headlines, but it did. Thankfully, it was it was the right decision for us to make in terms of it was legally the right decision, though. There were various drivers at play, which weren't picked up in the article. But again, it was just another eye opener for me that that something you think is gonna go unnoticed? won't always.


Scott Brown  (24:02) 

Yeah, no bad publicity, I suppose. Sometimes. That's great. So just moving on. We spoke earlier about your announcement on LinkedIn. The other the other day, you're leaving. What three words?


Rachael Carolan  (24:18)  

Yes. So I've been a what three words three and a half years had the great fortune of building up an amazing legal team, one that I think is perfectly capable of carrying things on post me leaving and you know, I've been involved with so many things. It's been a real roller coaster and I'm leaving it in in a really great place. And I'm on to a new challenge in health tech, so that'll be a new area for me. And one that will I'm sure be an amazing learning experience. 


Scott Brown  (24:55)

Yeah, different sector but yeah, consumer focused business. In that sense as well. And you're hiring or what three words are hiring your replacement. So we'll share the link, when we're posting when this goes out. I think they'll still be going live. But your profile is a general counsel within the technology space. Are there any resources that have helped you along the way to get there that you would recommend people looking at?


Rachael Carolan  (25:28)

Absolutely. So for me, network, I think is key. So building up a strong network, what are the ways you can start that is to attend tech events in London. I mean, it's obviously difficult during COVID. But hopefully, in the next couple of months, we'll start to see more and more networking events. I think, also, you know, following the general tech press, or getting to know what businesses are out there, what they're doing, what moves they're making. I'd also say on top of that, tools, like CrunchBase will give you a great idea of, you know, which companies potentially that are based outside of the UK are thinking about expanding into the UK and then everything else.


Scott Brown  (26:13)

Good Till's for seeing what's going on and having an interest having an interest in the space. I think it's critical. Thank you. Thank you, Rachael. That that just about brings us to the end of the episode. But thanks for thanks for taking the time to join me today and walking us through your lessons. It's been great to sit down and chat with you.


Rachael Carolan  (26:31)

Thanks so much, Scott. Really enjoyed it.


Scott Brown  (26:33)

Great. Good luck in there. Good luck in the new role and bringing things to a close at what three words I'm sure you've left it in in great hands.


Rachael Carolan  (26:40)

Thank you. I certainly hope so.


Scott Brown  (26:46)

Thank you for listening to Lessons I Learned in Law and if there's a subject or someone that you'd like to hear more about or more from on the podcast, please get in touch. You can contact us at hello@brown.com or connect or drop me a message on LinkedIn. If you've enjoyed listening, please rate review and subscribe to the podcast. But until next time, thank you.