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Following a Career Path of Enthusiasm and Change

Ariana Vojvodic interviews Molly MacGregor

Dear readers, it is with great pleasure that we introduce you to the story of Molly MacGregor, the Customer Success Specialist at Juralio.

Molly had, initially, the best of intentions to follow the traditional career path, however, after graduating from her law degree in Dundee, she decided to embark on an alternative career journey, which she says is: “even better”.

We are delighted to share Molly’s story. The reflections on the influences that propelled her to pursue the path of legal technology serve as an indispensable reminder for all of us, both young and seasoned professionals, to take more control of our career growth.

Ariana: Hi Molly, it is a pleasure discussing your journey into legal tech today. As you know, we have a unique interview format here at The Legal Technologist – we like to keep things fun and human centric.

That’s why we would like to follow this structure: 1) starting with your Persona; 2) discussing your Mission; and 3) hearing about your Vision for the future.

Molly: Thank you, Ariana. I am looking forward to this!

Ariana: Let’s start with your Persona. Could you please start by describing what motivated you to pursue a non-traditional role after graduating from your LLB?

Molly: It was actually the circumstances of the pandemic, back in 2021 when I was completing my final year at university, that had given me plenty of time to think about what I actually wanted to do after graduation.

I loved doing law. I thought it was interesting, but it simply felt like there might be something else out there that was not as strict of a career path as the traditional training contract. I started thinking about all the possibilities that my degree offers, and given that I didn’t know much about legal tech, I decided to explore it. In a nutshell, I knew that there was an industry, but I was not entirely sure what it encompassed or even if it was available to me as something that I could do as a graduate.

I was fortunate to have had the insight into Juralio during my degree, which is when I realised legal tech really interests me. I thought to myself: “These are people who are taking an industry that is usually quite slow moving. They’re trying to do something different with it and figuring out what can be done, sounds way better than what we’re doing right now.”

I found it exciting that this kind of energy and enthusiasm for development was growing at the time, even though everything else felt like it was frozen in time because of the lockdown circumstances. It felt to me like this industry of legal tech was literally buzzing.

Ariana: Do you have a legal tech role model, or do you remember when was the first time you heard about it?

Molly: When I started looking into legal tech, I realised that a lot of people had left their traditional careers and moved into these spaces. Leaving a career that you had already built for something new and unexplored seemed like an incredibly brave thing to do. This made me realise that there was definitely something worth exploring there.

Catherine Bamford was one of the names that came across immediately. And again, it was her enthusiasm and openness about her journey through legal and then legal tech that was really exciting to listen to. Catherine was a big influence to me, as she opened my eyes to how legal tech was something tangible that people are actually interested in moving forward with.

At first, I found the idea of joining legal tech quite scary because it made me question how I wanted to use my law degree. Ultimately, what helped me decide to choose the first steps of my career was the support the existing legal tech community provided me, such as my amazing colleagues and people that I met, like Marco Mendola.

It was also people like Eve Cornwell and Annabel Pemberton who created podcasts about their journey that helped me figure out things, as their transparency demystified what it really means to work in the industry. I have definitely not regretted my decision, and I am grateful for all the legal tech resources that were available to me.

Ariana: Could you share more about your insights into legal tech during your degree and how these helped make your career choice?

Molly: I was fortunate that my university was trying out an additional module, Law and Technology in the World, which I had the chance to join in my second year of university. My lecturer, Stuart Cross, was simply amazing.

Again, it was his enthusiasm that really drew me in. As part of the module the guest speaker was our CEO, Graeme Johnston, who explained the industry perspective. This was my first encounter with Juralio and I was able to go along to their offices in Dundee to meet the team and see what their roles entailed.

I feel lucky to have had that opportunity during my studies as it gave me a chance to get enthusiastic about their product and see the kind of vision that they had as well.

Later when I realised they had a position open for a Customer Success Specialist it seemed too good to be true. I decided to try out for the role.

I believe I received the offer because I understood exactly what the company specialised in, thanks to my insight into the industry during my degree.

Ariana: Do you think it would be helpful to organise insights into alternative career paths for students and graduates, similar to the traditional open days and vacation schemes?

Molly: I think that’s a really good question. I think this would be a good idea. Whilst online sources are great tools to demystify the industry, it was actually the networking experience which gave me the confidence to reach out to the team to find out more. There is a difference between simply looking at a job description online and being able to  speak to the team, understand what they were doing and why they were doing it.

It took me two years to actually apply for the role anyways, so it’s not necessarily an immediate confidence boost. But it is definitely worth it because it completes your understanding of who you could become and what you could create.

Having more insight into the actual companies and how they meet their clients’ needs would be valuable for students who are typically heads down in books and don’t get that kind of real life experience. I have always thought that practising interacting with firms would be more applicable to your career than explaining laws in three thousand word reports.

Ariana: Legal Tech is still a vague term for many. How familiar were you with the scope of your role before starting?
Molly: Customer Success can sound like a scary title, and a lot of the titles in legal tech are quite big and ambiguous I would say.

When it comes to how you apply them in legal, it can also be completely different. If we observe the role of customer success in larger corporations, we can see they’re really established and branched out into support teams and success teams. Roles in a startup need to be more general, which appealed to me from the outset when I applied for the role.

I knew this thanks to the insight I had with the firm, which is why I reiterate that open days would be really helpful for students who are curious and want to go into these interviews potentially with a bit more knowledge behind what they’re actually applying for.

Ariana: Now, we are curious about your Mission. Could you please share what your role as a Customer Success Specialist at Juralio entails? What does your day-to-day look like?

Molly: It’s quite varied. My role is split between product-focused and client and sales focused.

For instance, today was a product focused day, which means that I spent a lot of time working on projects.

From start to finish, this includes understanding the problems that we’re trying to solve, working with our amazing designer who’s actually over from California right now on a trip to Scotland, trying to focus on making something that’s both helpful to the legal teams but also usable and which is a lot trickier than I initially gave designers credit for. Usability is such a big thing.
On the client-facing side, my role consists of a lot of calls and conversations, essentially to identify the problems, and how we could potentially go around solving them.

It’s sometimes just being able to understand these really complex problems with law firms. A part of the job is understanding that the reason that they’ve not been solved is because they’re hard and it takes a lot of teams to figure it out.

This boils down to thinking of resolutions on those sides of things and then implementing the tool.

Ariana: What is your favourite thing about your role at Juralio?

Molly: The best part of the job is just how many different things I get to be a part of.

On top of that, being able to take part in conversations with people  that I would never have imagined that I would talk to.

This includes being able to sit down with specialists who have been doing this for years and then be completely candid around what they’re struggling with, how they see their roles, and what they want for their roles in the next five to 10 years.

I enjoy being involved in the human side of things and then being able to take that back and try and build something that actually makes a difference; a tool that people can use and get their hands on.

The variety of possibilities and opportunities is definitely the most exciting part of working in my role, but also of being in legal tech in general. You never know where you’re going to end up, which is great. 

Ariana: What skills have you developed in law school that you use in your role now?

Molly: The skill of critical analysis. In other words, the ability to simplify complex issues and texts helped me when I was starting out and needed to develop the ability to understand all the different perspectives that are involved in implementing legal tech.

Often times, teams know that they want to change but they don’t know how to implement such changes.

So, taking a step back and analysing all the circumstances to determine the best way forward is a core part of the role. A law degree sets you up to think critically about all these different perspectives.

It also taught me to be open-minded about the tasks that I am responsible for. Being a generalist means understanding that every day might not be the same tasks, however you can be part of every project, which is probably the best part of it.

Ariana: Have you developed any unexpected skills at Juralio and how does your customer-facing role add value to the team?

Molly: Sometimes you can feel like you’re just a “Jack of all trades”.

You’re jumping from one thing to another and you’re quick on your feet as you’re trying to understand people’s perspectives.

The most valuable thing to me is being able to take a step back and understand where somebody is coming from and the specific circumstances that they find themselves in. It is about a variety of skills relevant to being able to articulate the problem, and show a user story, putting it back into a product and developing it.

Being able to understand the full picture is invaluable.

In some firms, I could observe a disconnect between different teams as to why they are doing something. So, the skills of seeing things from other people’s  perspectives and having that human side of things completes the picture.
This includes compassion for the lawyers; they’re stressed all the time and they’ve got so much on their plate. So, it is about thinking about how to make their lives a bit easier, and understanding that this can be different for different people. From the developers’ side, it is about being able to explain to them the exact position that our users are in, and the reasoning as to why we need to do something in a particular way or to use this particular wording; because lawyers are very particular when it comes to how they phrase things.

Being able to be part of the client-facing side of things allows me to understand both the legal and the business perspectives, which is never something that I was introduced to during my degree but it’s something that I’m getting my head around now, which has been great.

Ariana: Do you think legal tech is a graduate-friendly sector or do you think there is still room for improvement in terms of making it a more approachable career path?
Molly: I think it could definitely be made more graduate friendly in terms of just the visibility which is what you’re doing here in The Legal Technologist. I’m a big podcast fan too, so I think these different kinds of media help introduce the industry. It is also about universities introducing it into the curriculum.
In my experience, there wasn’t a lot of expectation on being a specialist when applying for the role. I think that reflects in my day-to-day life, which is really nice.

And there’s also sometimes the opportunity to transition from a legal role into a legal tech one within the firm if you show an interest.

Ariana: Our last and favourite question to you, Molly, is what advice would you give to people who are interested in following in your footsteps?
Molly: What it takes is being able to show an interest in legal tech and  reaching out to somebody in a role that you think sounds interesting.

Simply finding out a little bit more from different people is more valuable than you would ever imagine because the connections in legal tech are so open; you meet somebody who knows somebody, who knows somebody else, and you can feel this sense of community through connections.

Another thing, although it might sound a bit cheesy, it is considering every opportunity that you can.

When I think back to how I ended up in this role, I’m glad that I decided to do that additional module and participated in the office visit at Juralio. If I had just skipped that because I wasn’t bothered that day or I just hadn’t felt confident enough to go along, I wouldn’t be here with you today.

It’s something that I’m very grateful that I’ve ended up in.

Since these things have happened, I’ve taken it upon myself to any opportunity that comes my way I will say yes to.

Ariana: Thank you so much for sharing your thoughts and experiences with The Legal Technologist readers, Molly. Your perspective is invaluable for all of us who aspire to contribute to the legal technology space.

Images: Kevin Malik, Olya Kobruseva, Ann H (Pexels)

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