Charting Your Own Path Outside of Biglaw with Jennifer Park (TFLP 090)

Jennifer Park decided to chart her own path outside of Biglaw after law school, working for a legal tech company instead. 

On this episode, Jennifer shares why she decided this path was right for her, how she made the tough decision despite external pressure, and how you can get into legal tech or another booming industry with the skills you have.  

From Uber to Legal Tech

Jennifer’s story is unique from many other lawyers on the show in that she went to law school and in her third year, she already knew she didn’t want to go into Biglaw, she was going to chart her own path. 

This all started before she was in law school, while working at Uber in Seoul. Jennifer had always been told, from a young age, that she would be a good lawyer, so that was in the back of her head, but for now she was working at Uber, at a time where everything about it was illegal in Seoul. 

They had a lot of legal issues while she was there, the police raided their office and took our computers and paper, the city of Seoul launched a campaign against Uber drivers and were awarding prize money for Uber paparazzis to catch all the drivers, and they tried to arrest Travis Kalanick, who was the CEO at the time. 

There were just a lot of legal actions happening and Jennifer was at the very center of this intersection of law, tech, and business .She had the opportunity to work with Uber’s legal team and outside counsel and seeing all that was so exciting, she was really fascinated about how law affects business and tech.

So she decided that maybe then was the perfect time to finally go to law school. She applied with the intention that she would want to become a GC at a large tech company one day. 

“You’d Be a Great Lawyer”

When looking back at her childhood and why she was told she would be a good lawyer, Jennifer believes it was because she was articulate and always had a knack for learning languages. She was also very organized, outspoken, and worked hard, qualities we tend to associate with lawyers. 

This seems to be something that’s true for many lawyers, there are so many kids who are told “you’d be a great lawyer”. The people who are telling them that have obviously good intentions, but maybe not tons of actual information about what it is like to be a lawyer. 

This can set people on this path where, as a kid, you don’t question it and somehow just fall into this career path. 

Law School Was a Mixed Bag

Jennifer knew that law school would be challenging, she knew it would be tough, and in that aspect, it matched her expectations. She loved the intensity of school, she loved the student lifestyle and studying, but what she didn’t expect was how outdated the legal industry is. 

Having come from a technology world, she had been at the forefront of innovation and now she saw the email and time trackers lawyers were using as their main tools she was shocked how little innovation there seemed to be. 

Seeing this discrepancy between what she knew technology could do and how it was being used in the legal world made law school even more interesting and exciting for her, it helped her really solidify the understanding that she loved tech and especially legal tech. 

The Pinnacle of Achievement

In Jennifer’s first year of law school, she was able to intern at a legal tech company in San Francisco and was exposed to the type of work the lawyers do at in-house legal teams. She found the work really interesting, but noticed how much paperwork and repetitive tasks there were that prevented lawyers from doing substantive legal work. That was her first exposure and from that experience her interest in legal tech was sparked. 

In her second year, she did an internship at a Biglaw firm, because she still wanted to try it out and although she really liked it, deep down, she knew she was more interested in legal technology and innovation. So by the time she was in her third year of law school, she was debating if she wanted to go to Biglaw – because she had an offer, and it was an amazing offer – or go with what felt internally aligned? 

This is a theme I see often, there is a pressure in law schools to go the Biglaw route, for the most part, it is held out as the gold standard. If you can get into Biglaw, then that’s where you should go. Maybe there’s an exception for someone who’s really, really dedicated to a particular kind of public interest, but otherwise, there’s this sense of “well, if you can get a Biglaw job, you should take it because that’s the pinnacle of achievement.”

Jennifer felt this pressure too, she says it was like tunnel vision at her school, Biglaw or nothing. 

Biglaw is not for me. 

Despite the pressure, Jennifer felt around her, she knew that Biglaw wasn’t for her. She attributes this to seeing the pain points of lawyers firsthand when she did her internships.

Having interned at both a tech company and also at a law firm, she saw how much repetitive paperwork and related tasks there were, and thought, “There’s got to be a better way to handle this.”

It was seeing the problem and the room for innovation that motivated her. In fact, it led her to find her current (and only) job since law school. She had begun seeking out the tools that could help lawyers and what startups were out there innovating, and in one of her internships, was asked to find a CLM vendor, and Ironclad – her current employer –  was one of the vendors that pitched them and did a product demo. 

Beyond her motivation to think forward, Jennifer is also really driven, wants to be at the forefront of innovation, and loves a dynamic work culture that’s fast-paced, more reasons the technology world seemed a better fit for her. 

No Support for Paths Outside of Biglaw

One thing that seems true for many law schools is that there is not support for alternative career paths. There’s support to get clerkships, there’s the OCI go to a large law firm option, and there’s the niche if you want to do public interest, but if you don’t fall into one of those buckets, there really isn’t, at most law schools, support for any alternative career path. 

Jennifer found this to be true at her school as well. There weren’t really any resources for students who were trying to do something other than Biglaw, or clerkship, or even public interest. That’s part of the reason why she felt really nervous, and almost discouraged, looking for another career path other than Biglaw in her 3L, because she just couldn’t find any help and was left on her own.

Finding Her Own Support

Undeterred from the lack of traditional support, Jenn went to work connecting with and learning more from others in the tech and legal tech worlds. 

She reached out to everyone she could find on LinkedIn who were alums from her law school who were not doing law. She basically found former lawyers working in technology. 

She Googled people, cold messaged many people, did a lot of networking, and hired a career coach. She only met with her coach three times, but she was so helpful at motivating Jennifer to believe in herself that she was allowed to pursue another career path other than Biglaw. 

This idea of cold outreach is something we talk about inside The Collaborative all the time. I know that as lawyers, especially as law students, it’s easy to think, “why would this person want to talk to me?”, but the reality is, especially if they’re a former lawyer, there’s generally a pretty significant level of eagerness to help people, especially those who are in a position like the position that they used to be in. 

There is this recognition that, if you’re wanting to do something different, there are a lot of things that are pushing against you doing that, and discouraging you from doing that, they can really help in making those transitions or thinking through your options. 

This outreach can feel nightmarish to many, even Jennifer says she just had to be very disciplined about it, it wasn’t something she loved doing or felt naturally inclined to do.  And I think it’s natural for us to feel, “Oh, I’m going to impose upon someone,” but that’s not the case, you can’t make someone talk to you who doesn’t want to talk to you. If they’re willing to talk to you then they’re making that choice and accept the gift that that is. 

Jennifer also shares that the more you practice, the easier it gets. After a few informational interviews, it will be easier. Now Jennifer feels like it’s almost part of her personality and if she sees a startup or person she is interested in, she will message them and get coffee, people are more open than we think. 

Telling Her Parents About Her Alternative Path

In the end, Jennifer didn’t tell her parents about her choice to work in legal tech, and not Biglaw, until 2 weeks before her new job started. She wasn’t particularly scared of telling them, but she didn’t want to be distracted while studying for the bar, which she was taking that summer before she started her new job. 

When she did tell them, they were supportive. Her dad was more nonchalant than she expected, saying, “Oh, it’s your life. Do whatever you want,” which was a very shocking response, he was surprisingly blasé about it. And her mom was a bit more reserved, asking if she was sure, questioning how much money she would make, but she came around. 

Jennifer’s advice for those of you who may feel torn between taking an alternative path and/or telling your parents is to just make your own decision. Do your own thing, try to release the need for external validation, and after you figure it out, communicate it to your people, wait until you have something tangible to share. 

Landing a Job with Ironclad

During her third year of law school, Jennifer was grappling with which direction to take and was doing a lot of these informational interviews with people in legal tech or who had left the law. 

One of them happened to be with someone from Ironclad, the vendor she had researched and seen a demo of during her 1L internship. 

During their chat, he mentioned that Ironclad was hiring, was she interested? She said yes, sent her resume, and the rest is history. 

Now she works as a legal engineer, which is what they call their deployment team. When a customer purchases their software, she meets with them to do process discovery and offers her expertise on legal operations and business processes, and helps them streamline and optimize their process using Ironclad’s software. It’s a lot of consulting and she gets to work with a lot of different teams, because contracts touch a lot of different divisions.

On the other end, another huge part of her job is the technical aspect where she customizes Ironclad’s software for clients’ needs. She has had to learn “light” coding, something she never would have believed while she was in law school. 

Many Jobs Need Your Skills

One of the main lessons Jennifer has learned as she has charted this new path is that many jobs need the skills we have as lawyers. It’s not that she got into legal tech because she loved coding or had experience with it, it’s the current skills we have that are marketable. 

This is where she sees the breakdown, that often lawyers are bad at marketing themselves. It’s really about crafting a narrative about yourself when you’re applying to jobs, and when you’re interviewing, finding the skill sets that overlap and framing it in a way that is applicable to the job that you’re applying to. 

You definitely don’t need coding or any type of technical skills to work in legal technology. And in general, there are so many transferable skills that you can carry from your current legal job to a tech job. For example, Jennifer knows an ex-lawyer who is on Ironclad’s marketing team, she knows a litigator who was a civil rights attorney for 10 years running his own firm now who now does the same job as her. 

You don’t need special skills. You just have to show interest, be interested in whatever industry you’re applying to, and figure out how you can frame your current skill set in a way that fits this position you’re going after.

Listen To Your Own Voice and Chart Your Own Path

Although it’s easy to think about industries as being very static, because in many ways the legal industry is, Jennifer’s story is a reminder that there are so many possibilities for people who are wanting to make a change, and those opportunities are just increasing daily.

Jennifer’s parting advice to anyone thinking of paving their own path is to just listen to your own voice. Don’t let fear stop you from creating your path, she didn’t and is so happy with the decision. Find the courage to step out of your comfort zone and invest in your career, it’s just so worth it.

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Sarah Cottrell: Hi, and welcome to The Former Lawyer podcast. I’m your host, Sarah Cottrell and on this show, I interview former lawyers to hear their inspiring stories about how they left law behind to find careers and lives that they love. Let’s get right to the show.

Hello, everyone. This week on the podcast, I’m sharing my conversation with Jennifer Park and the reason I asked Jenn to be on the podcast is that she has a unique story, compared to many of the people in podcast, which is that she decided to take an alternative career path. Straight out of law school, she had an offer at a Biglaw firm, but basically realized during her third year of law school that she didn’t actually want to go that path. 

So she has lots of great insight into how to chart your own path for yourself, as well as a lot of insight into how to think about getting a job in legal tech, which is where she ended up moving, if that’s the area that you’re interested in. I’m really excited for you to hear this conversation with Jenn. 

She actually just sat on a panel a couple of days ago in the collab with several other former lawyers who also work in legal tech, and as we’ll hear from this conversation, there is so much going on in legal tech. It’s a really interesting area and it is definitely one to consider if you’re thinking about taking a different path. So all that said, let’s get to my conversation with Jenn. Hey, Jenn, welcome to The Former Lawyer podcast. 

Jenn Park: Hi, thanks for having me. 

Sarah Cottrell: I am really excited to share your story. So let’s start with you introducing yourself to the listeners.

Jenn Park: Sure. So my name is Jenn Park, and I’m currently a legal engineer at a legal tech company called Ironclad. Prior to joining Ironclad, I went to law school. So Ironclad is the first job out of law school for me and before law school, I worked at Uber, launching UberX and Uber Eats in South Korea.

Sarah Cottrell: Okay, so here’s what I love about your story and I know you’ve talked about this before, but you mentioned that this is the first job that you took out of law school. So I want to get into the whole story of how that happened and you made that decision and on this podcast, that typically starts with the question of what made you decide to go to law school in the first place? 

Jenn Park: I think that’s the perfect place to start. So like the most of us, from a young age, I was told that I’ll make a good lawyer. So that was always in the back of my head, but I think what really sparked my interest was when I was working at Uber. So as you know, Uber had a lot of legal issues and Seoul, which is the market that I was working in, was impacted the most. 

So everything about Uber was illegal there and we had a lot of legal issues. So the police raided our office and took our computers and paper. The city of Seoul launched a campaign against Uber drivers and were awarding prize money for Uber paparazzis to catch all the drivers and they tried to arrest Travis Kalanick, who was the CEO at the time. 

So there were just a lot of legal actions happening and I was at the very center of all this intersection of law tech and business, and I had the opportunity to work with Uber’s legal team and also our outside counsels. So seeing all that was so exciting for me and I was really fascinated about how law affects business and tech.

So I decided that maybe now is the perfect time to finally go to law school. So I applied to law school with the intention that I would want to become a GC at a large tech company one day. So that’s why I went to law school. 

Sarah Cottrell: Of course, like you said, people had been telling you that you would be a good lawyer. Why do you think from a young age people were telling you that? 

Jenn Park: So I think it’s because I was very articulate and I had a knack for learning languages. I was very organized and just a typical what you see in a lawyer personality in TV shows. Just articulate, very outspoken, hardworking. 

Sarah Cottrell: I think I’m sure a lot of people listening will relate because I know … I mean, it’s come up on the podcast so many times now that there are just so many kids who get told from a really young age like, “Oh, hey, you’d be a great lawyer.” The people who are telling them that have obviously good intentions. Maybe not even necessarily tons of actual information about what it is like to be a lawyer, but it can set people on this path, where, as a kid, you don’t question it. Like, would I?

Would I really like this? Will this really be a thing? So, tell me about when you got to law school. So you had this experience working at Uber, where you saw in real time the really important implications of the intersection of law and tech and business and you had this idea that you would want to be a GC in a tech company. You go to law school. When you got to law school, was it what you expected? Was it not what you expected? What was your reaction? 

Jenn Park: So it was kind of a mixed bag. So I knew going to law school would be a great intellectual challenge and it would definitely … We all hear 1L horror stories. I knew it was going to be tough. So in that aspect, it fit my expectations and I love the intensity of the school and going back and being in a student lifestyle and studying, going to the library. So I enjoyed that part.

What I didn’t expect about law school and the legal profession is coming from tech, I just saw … My first second month into law school, talking to all these lawyers at networking events and from recruiting events, I saw how outdated the legal industry is and I think that’s definitely because my job before law school was in technology.

So I was at the forefront of innovation and I saw the type of technology that lawyers were using were email and timekeeping tracker tools. So I was just very shocked that how much or the lack thereof, innovation in the past couple decades in the legal industry has been.

Sarah Cottrell: I feel like there probably few industries that you could say are, at least stereotypically, less innovative than the legal industry and I know that, for sure we’re seeing that change a little bit. We can talk about that more, just with the explosion of legal tech and legal innovation and those sorts of things, but I can absolutely see how coming from tech into law school, into closer contact with the legal profession would be a little bit jarring. 

Jenn Park: I think that it’s just legal industry is so ripe for innovation and there is so much potential, and I think seeing that was really interesting and exciting for me and overall going to law school is really what made me realize that I’m passionate about tech and legal tech. So I think overall, it was, going to law school … I got a lot out of going to law school. 

Sarah Cottrell: So you said you originally went to law school thinking that you wanted to be a GC at a legal tech company. For most people, the path to that might be the stereotypical like, go to a firm for a while then go in-house blah, blah. So you had this idea of what you want to do in your mind, then you get to law school, you see both how not innovative much of the legal industry is but then also the potential. So were you still thinking that was the direction, the direction of being a DC, that that was the direction you wanted to go or did you start to think, maybe there’s something else I want to do? 

Jenn Park: So I did go to law school with the intention of becoming a GC at some large international tech company one day. So I did my first year internship, 1L internship at a tech company in San Francisco at an in-house legal team. So that’s where I was exposed to the type of work the lawyers do at in-house legal teams.

The work was really interesting but I think the big thing I noticed was how much paperwork and repetitive tasks there were that prevented lawyers from doing substantive legal work. So that was my first exposure and from that experience is what sparked my interest in legal tech and legal innovation. I did do my 2L summer at a big law firm, because I still wanted to try it out and I really liked it, but I think still deep down, I knew I was more interested in legal technology and innovation. 

By the time I was 3L, I was debating, do I want to go to Biglaw because I had an offer, and it was an amazing offer. I would have been really happy to go back to the firm, but I also had this other interest that I couldn’t shake off. So 3L was when I had that internal alignment and just being honest to myself. What’s right for me at that time? So, I think until probably near even graduation, I was still thinking about it back and forth. 

Sarah Cottrell: So let’s talk a bit about that. Because that part of your story, I think, brings together so many different threads of conversations and themes that have come up on the podcast. There is a pressure in law schools to go the Biglaw route in the sense that, I think for the most part, it is held out as the gold standard. This is where you … If you can get into this, then that’s where you should go. 

Maybe there’s a little exception for someone who’s really, really dedicated to a particular kind of public interest, but otherwise, there’s this sense of well, if you can get a Biglaw job, you should take it because that’s the pinnacle of achievement. We’ve had many guests on the podcast who have shared about even getting into law school and not wanting to go the Biglaw route originally, and then just feeling like they ended up on a conveyor belt of OCI, summer, they got an offer and they went and then ended up looking around at some point and being like, “How did I end up here?”

So obviously, that wasn’t your experience, in the sense of you ultimately made a different choice and we’ll talk more about that, but I’d love for you to talk a little bit about your experience of did you feel that pressure of this is the thing you should be doing? The Biglaw path is the path you should take, if you care about achievement or whatever. Was that something that you felt and how did you deal with that?

Jenn Park: 100%. I think the moment you step into law school, everyone gets this tunnel vision. It’s Biglaw or nothing. I definitely felt that pressure and also, I think it’s interesting, because the legal profession really cares about pedigree and the name value. So once everyone around you … When you see everyone around you going for certain jobs, you just get sucked into that mindset and it’s almost like a race, especially during OCI.

People were very cagey and competitive, which I thought was interesting, because my classmates, my 1L class was not competitive at all. Was actually like a really positive, warm community. So that was a very interesting switch, the observation I had, but definitely when I made … Making the decision not to go to a big law firm, was definitely difficult and part of it was definitely other people questioning me.

Although deep down, I knew this was the right path for me and I wanted to go this route. If everyone around you is like, “Oh, Jenn, are you sure? Are you sure you don’t even want to practice for a year and then switch?” If you get that constantly, you also start doubting your decision. Another thing is, I’m an immigrant. So a lot of immigrant parents, it’s either you’re a lawyer or a doctor. So I think also having that conversation with my parents was definitely a challenging moment for me. 

Sarah Cottrell: I think that’s come up on the podcast a couple of times and I’m actually going to be speaking with a couple more people about that specific experience, including someone who wrote a book specifically about the experience of being an immigrant, being the child of immigrants, and the pressures. The title of the book, I can’t remember the subtitle, but the title is like, Doctor Lawyer Engineer, and those pressures are very real. 

I think like you said, specifically, when we’re talking about law school, the combination of maybe some family pressure, and then also like, you describe this internal to the legal profession, to the law school, ideas of this is what you do, if you want to be someone who has made it, it creates a very potent combination. 

So I would love to know a little bit more about your … You talked about having this realization of, this Biglaw thing is not for me, and this other path makes more sense for me. Can you tell me a little bit about what the things were that you identified about yourself and what you liked, what you cared about, what you were interested in, that made you realize that that was the path? Does that make sense? 

Jenn Park: Yep. So I think what really interested me in going to tech and legal tech specifically is that I saw the pain point of lawyers firsthand when I did my internships. So I interned in-house at a tech company and also at a law firm and I just saw how much repetitive paperwork, related tasks there were. I thought to myself, “There’s got to be a better way to handle this.”

So seeing that pain point firsthand, was what really motivated me to seek out the tools that could help lawyers with, what startups are out there? Does China innovate this practice? That’s actually how I found out about my current job at Ironclad, is when I was a IL intern, one of my tasks was to find a CLM vendor and Ironclad was one of the vendors that pitched us and did a demo, a product demo. 

So that’s how I found out about the company. So seeing the problem and the need for innovation firsthand was what really motivated me. I think that’s also part of my personality is that I love … I’m really driven and I want to be at the forefront of innovation and also I love the dynamic work culture that’s fast paced. So I think another reason why I thought going into tech was better for me is because of those qualities in my personality.

Sarah Cottrell: Let’s talk a little bit about the timeline of the process. So most people are familiar with the whole, you have OCI before your second year of law school, then you do your 2L summer. Then you said you got an offer. So you were deciding whether or not to go back during your third year and that was also the point at which you were realizing, actually, maybe I think I want to go this other direction. 

So can you any, you’ve already touched on this, but I think one of the things that has come out of the podcast before is this issue of, if you decide you want to go a different path, there’s not a lot of support in law school. There’s support to get clerkships. There’s the OCI go to a large law firm option. Then there’s the niche if you want to do public interest, there’s a whole separate thing for that. 

It’s less structured than OCI, but there is some support around that, but if you basically you don’t fall into one of those buckets, there really isn’t, at most law schools, really any that I’m aware of, there really isn’t support for any alternative career path. So I would love for you to talk a little bit about more about how you, and you already touched on it, but how you pursued learning about alternative careers and what your experience was in terms of … Well, and actually, I know we’ve talked about this before, but the level of support for pursuing something that was an alternative from those three main buckets. 

Jenn Park: To be frank, my law schools career office is great, but exactly, I think you’ve hit the nail on the head is, they don’t really have any resources for students who are trying to do something other than Biglaw or clerkship or even public interest. So that’s part of the reason why I felt really nervous and almost discouraged looking for another career path other than Biglaw in my 3L was because I just couldn’t find anything and I was left on my own pretty much.

So I think when I was becoming serious about pursuing another career in tech, what I did was just reached out to everyone I could find on LinkedIn, who were alums at my law school who were not doing law. So basically, former lawyers working in technology. I found that I was just stalking them on LinkedIn.

I Googled people. I cold LinkedIn messaged so many people, and this is what I tell my friends and strangers who reach out to me now asking for career transition help, which I can talk about later. I’m actually working on my own website so I can put these resources up and make it more scalable, instead of me having to talk to people one on one. 

So I did a lot of networking, like cold outreach and also, what I also did was I hired a career coach. So I met with this woman. I only met with her three times, really, but she was so helpful, just motivating me to believe in myself that I am allowed to pursue another career path other than big law. So that was a huge contributing factor in my job search.

Sarah Cottrell: I think it’s so interesting how … Well, I guess I would say it like this. There’s a certain level of snobbishness, like obsession with prestige in the legal industry. You see it come out in a lot of different ways, but one of the ways is what you’re describing where it was you wanted to do something different, and there just really wasn’t the infrastructure to even support that. 

I also wanted to just highlight what you mentioned about cold contacting people on LinkedIn, because this is a conversation I have with my clients in the collaborative all the time. I think lawyers in particular or law students feel like, why would this person want to talk to me, but the reality is, especially if they’re a former lawyer, if they’re someone who has moved into something else, I have found that there’s, generally speaking like a pretty significant level of eagerness to help people, wanting to help people who are in a position like the position that you used to be in because there is this recognition that, if you’re wanting to do something different, there are a lot of things that are pushing against you doing that, and discouraging you from doing that. 

To your point, whether it’s reaching out to other former lawyers, whether it’s hiring a career coach to help you build your confidence, that it’s possible. Those things can make a huge difference. 

Jenn Park: Yeah, 100%. I’m an immigrant woman. None of my parents went to school here. I have no network pretty much and I’m the first person to go to grad school in my family … Or in the states. So I really … Also I just didn’t grow up in a culture where it’s normal for people to just introduce themselves and go to networking events. That is just not part of my personality, but people when I tell you, you have to do it, you just have to do it. I am pretty introverted, and I am not that good at talking to strangers. 

I hate small talk, but it’s pretty much, I would say the only, only way to get a job or do a career transition. Believe me, no one likes networking. But you just got to do it, but I was actively job searching. I was doing one to two informational interviews a week. I was very disciplined about it. I just hate to say, but you just have to do it. 

Sarah Cottrell: I think I also am introverted and I also very much relate to hating small talk and really not loving networking. If you’re listening to the podcast, you should go back and listen to the interview with Ami Watkin because she loves networking, which is mind blowing to me but she gave a lot of good tips in that episode about how and why. 

I think the most important thing to remember, if you’re someone who’s like, oh, cold emailing someone or reaching out to someone cold on LinkedIn, that just seems nightmarish, you just need to think about it as making a connection with an individual person and recognizing that … I think people worry, “Oh, I’m going to impose upon someone,” but if someone’s willing to talk to you, you can’t make someone talk to you who doesn’t want to talk to you.

If they’re willing to talk to you then they’re making that choice and accept the gift that that is. I think that’s a really important thing to keep in mind and Jenn, to your point, it is possible to do these things, even if they are not something that you’re naturally inclined towards. Again, I’m very sympathetic to that because I do not enjoy networking. I do not enjoy small talk but building up your muscle in terms of being able to do those things, or just like you said, being dedicated and saying like, “Okay, I’m going to set up one informational interview a week,” or something like that can go a long way to getting you the information and connections that you need. 

Jenn Park: I definitely agree that it’s a muscle that once you start doing it, it almost becomes very formulaic and I can definitely share the formula, the outreach email, and the things I talk about to people who are interested, or listening to this podcast as well. So I used to hate networking. I guess I have to correct myself now, but I actually enjoy it now, which is so crazy. You’ll be surprised how many people are willing to help you. 

I felt like … When I was going through this job transition process, I was so thankful and so surprised that so many people were willing to talk to me. After having that positive experience, now, I think that really changed my personality, where I almost enjoy networking now and I do cold outreach, even though I’m not actively job searching at the moment. 

For example, if I see a cool startup, I would just cold LinkedIn message the founder, and we would get coffee and it’s just so cool. Now that everyone is remote, people are even more willing to network with you. So I definitely would encourage people to try it out. Honestly, after three, four informational interviews, it’ll become super easy.

Sarah Cottrell: I think that is such good advice because it really is, the more that you do it, the more normal it feels. The first couple times that you do it, you’ll probably feel like, “What am I doing?” But the more you do it, the more it normalizes it for you. So can we circle back around, because I think this is a really important conversation that I know a lot of people listening deal with, but you mentioned the other piece, in addition to the general lack of infrastructure in law schools to support people doing alternative things. 

The other piece for you that was a challenge was talking with your parents about wanting to go on an alternative path. So I would love for you to share a little bit more about how you thought through that and what that was like, because I think for many people, for various reasons, making a change and going on an alternative path when you’ve been a lawyer or you’ve gone to law school is something that … There’s real concern and worry about what their family’s reaction will be. 

Jenn Park: So I didn’t tell my parents that I wasn’t going back to my firm until probably two weeks before I started my job. That’s how I handled it. Really, I think it was … The biggest reason I would say is not because I was scared that they weren’t going to be supportive, or anything, but I just didn’t want any distraction when I was studying for the bar exam. So I still took my bar exam because I graduated law school. I worked really hard. I had this amazing offer from this prestigious firm that I worked really hard for, and considering all those factors, I was like, I still need to get my license. I want to be an attorney.

So I was studying for the California Bar Exam over the summer, and I got my job offer from my current employer after graduation. So that was in early June. So I had like a month and a half of knowing it and I told my closest friends who I was studying for the bar exam, at the time together near me. So I told them, and they were really excited for me. So I had that support network, but I just didn’t want any type of distraction from bar studying. 

So I told my parents after I took the bar exam, and I went back home. Then I told them, and honestly, my parents were really supportive. My dad was … He almost didn’t care. He was like, “Oh, it’s your life. Do whatever you want,” which was a very shocking response. Because I thought he would care more, because he was so happy that I got into law school in the beginning, but he was honestly so supportive, or even like, so I guess so unsupportive. He was so blasé about it. 

Then my mom was the one who was like, “Oh, are you sure? You’re going to make so much money if you go to Biglaw. You worked this hard. Are you sure about that?” So she was the one who kind of had some reservations, but eventually she came around. I think, for especially the types of people who go to law school, we need a lot of external validation. I think the fear to do another path other than law stems from that. 

So my, I guess, advice here would be just make your own decision, do your own thing and after you figure it out, I would just communicate it to your … People around you after you have something like a tangible to share, if that makes sense. 

Sarah Cottrell: Yeah, it makes total sense and I was nodding my head violently when you were talking because I was like, so true. I really think a big part of it is that many of the types of people who choose to go to law school do have this very strong need for external validation, or just were the kind of kids that got the gold stars and achieved. Then of course, legal profession is very prestige focus, as we’ve talked about, as has come up many times in the podcast. 

So you end up in this scenario where you’re used to getting your validation from external sources and being able to switch that and to be able to actually listen to yourself and to make a decision, regardless of what other people might think, it feels very different. It feels very different from what many people who went to law school and became lawyers, how they’ve conducted their life decisions before that point. 

So can you talk to me a little bit about the actual process of getting the job with Ironclad, and then a little bit about what you have done with them.

Jenn Park: Sure. So the job process, so I was doing informational interviews all through, I guess, law school. When I first started law school, I was talking to all these lawyers and in-house counsels, law firm partners, associates, trying to see what kind of practice I want to do. Then when I realized that, oh, I’m interested in legal tech, I started talking to people who work in legal tech. That really was during 3L. So I was doing a lot of informational interviews with people in legal technology, people who left the law.

Funny enough, so I knew about the company Ironclad from my 1L internship. So when I was applying to jobs end of my 3L, I knew of the company. So I searched people online, again, on LinkedIn, people who work at Ironclad and being legal type company, there were a lot of ex lawyers. So I reached out to a few of them and a couple people responded back, and we had a phone call, and one guy was like, “We’re actually hiring. Are you interested?” So I was like, “Sure. Perfect.” So I emailed him my resume. He forwarded it to the recruiter, and it’s basically a workplace fairy tale. I got the job and that’s how it happened. It was very natural. Almost.

Sarah Cottrell: So tell me a little bit about the role that you were hired for and what the substance of the work that you were doing was? 

Jenn Park: So I am a legal engineer at Ironclad, which is the deployment team. So legal engineering team is what we call the deployment team at Ironclad. So when a customer purchases our software, and our customers are all in-house legal teams at Fortune, anywhere from fortune 500 companies to small startups, and they would buy Ironclad’s digital contracting, contract lifecycle management, whatever you want to call it, software.

I would go in, and I would first meet the customer to do process discovery, and offer expertise on legal operations and business processes, and help them streamline and optimize their process using Ironclad’s software. So a lot of consulting, and I get to work with a lot of different teams, because contracts touch a lot of different divisions.

So mostly, I’m oftentimes working with sales, like finance teams, procurement teams, in addition to legal teams to help my customers streamline their business processes, in addition to the contracting process. Then another huge part of my job is the technical aspect where I would customize our software for our clients needs. So there is some light coding involved. If you were to ask me two years ago if I was going to learn how to code, I would have laughed, but I code up a little bit. Basically, it’s a lot of customer-facing work, but also, I do a lot of technical implementation, solution architect type of tasks.

Sarah Cottrell: So I think that’s so interesting, because I think a lot of people would have this idea of like, oh, you went into legal tech. So you must be super into coding, or have some special … A lot of lawyers have this idea that like, oh, if you want to go into legal tech, you have to have all of these special technical skills that I don’t have, because I’m a litigator and have never done whatever, whatever. But it’s been my observation and experience that that’s not actually true and to your point, you said like, if someone had told you like, “Oh, yeah, you’re going to be doing some coding,” a couple years ago, you would have been like, “That’s hilarious.”

So for those people who are listening who are like this experience of interacting with clients and helping them optimize their systems and helping to bring like the software, to get it to where it needs to be for each individual client, that sounds really interesting, but I don’t really have … I can’t program. So is this even a possibility for me? What would you say to those people? 

Jenn Park: There are so many jobs that will need your skills. I think one thing that I notice from working with my friends from law schools, my old co workers, strangers who reach out to me, asking for help transition into tech from law, it’s just that they are really, frankly, bad at marketing themselves. There are so many transferable skills that you can carry from your current legal job to a tech job. 

In tech, there are a lot of different functions. So I know an ex lawyer in my company who is on our marketing team, there’s a litigator. So one of my co workers, he was a civil rights attorney for 10 years, running his own firm now. He’s on my team doing the same job as me. He didn’t know anything about tech before coming to Ironclad. 

So it’s really about crafting a narrative about yourself when you’re applying to jobs and when you’re interviewing, and finding the skill sets that overlap and framing it in a way that is applicable to the job that you’re applying to. So you definitely don’t need coding or any type of technical skills to work in legal technology. I learned everything on my job and I’m actually in a coding boot camp right now, because I found out that I’m interested in technical things after working at Ironclad for like a year and a half. 

So you definitely don’t need any type of special skills. I will say you definitely have to show interest and be interested in whatever industry you’re applying to, and just finding a role that you think sound interesting to you and also figuring out, how can I frame my current skill set in a way that fits this position I’m going after for.

Sarah Cottrell: I think that’s so helpful and I just really also want people to hear, you’ve touched on this several times, but the opportunities in legal tech are just exploding. I was setting up a panel … So this episode will release in May, just after this first panel, but I put out a call on LinkedIn for people who are former lawyers who work in legal tech, who might be interested in coming and talking to my clients in the collaborative about like their day to day and the experience of moving into legal tech and literally got so many responses that I’m going to end up doing two panels.

We’re going to do one in May and one in June, because there are so many people doing so many different types of things in legal tech. I just think it’s just clear, even in the last, what? Year and a half that I’ve been running Former Lawyer, that they’re just … So many more opportunities are being created, like so many startups. 

So I think if you are practicing law, it is easy to think about industries as being very static, because in many ways, the legal industry like traditional legal practice, is. So I just really want people to hear, and I think this comes across in your story, Jenn that there’s so much that is dynamic about the possibilities that are out there and even just, just talking about legal tech, there are so many possibilities for people who are wanting to make a change and those opportunities are just increasing daily.

Jenn Park: 100%. Legal tech is blowing up. They’re a bunch of legal tech companies just raised, including Ironclad, just an exorbitant amount of money from fundraising and it’s just a really exciting space. I met so many people who work in sales, marketing, operations who were all ex lawyers, and a lot of ex lawyers are working for non legal tech companies doing all these other functions as well. So it doesn’t have to be legal tech, either. It can really be any other tech company and doing marketing. It’s definitely possible. 

Sarah Cottrell: So Jenn, before we wrap up, is there anything else that you would like to share that you haven’t had a chance to share already? 

Jenn Park: Yeah. So I really want to encourage people that, just listen to your own voice and don’t be scared to pave your own path. Sounds kind of cheesy, but it’s really … I’m so happy with my decision. I love my current job and I have friends and old coworkers reaching out to me all the time asking for just tips on how I decided to, or how I transitioned industries, asking me for resume and cover letter help and job preparation help, interview preparation help. 

My friends would introduce me to their friends and I started working with strangers and I’ve seen so many people who had the courage to step out of their comfort zone and invest in their careers, and it’s just so worth it and it’s so meaningful for me to see all these people make that transitions.

So definitely encourage people to just don’t be afraid of doing your own thing. Your career is really long and you don’t have to be at one job forever. I am starting my own website. It’ll be Jennnpark.me. J-E-N-N-P-A-R-K.me where I put resources for lawyers and law students who are looking to transition industries. So I’ll be posting interview tips, resume tips, and just job hunting tips. So please be on the lookout for that.

Sarah Cottrell: That’s great. I will definitely put the link to that in the show notes and then I know you’re on LinkedIn. So I imagine if people want to connect with you, they can also find you there.

Jenn Park: Definitely. Just search Jennnifer Park and I’m happy to honestly, talk to anybody. Talk about career transitions, legal tech, just anything else. Really open. So definitely reach out.

Sarah Cottrell: Awesome. Thank you so much for sharing your story, Jenn. I think it’s so helpful for people to see that there are different paths that they can take. So I really appreciate you taking the time.

Jenn Park: Thank you so much for having me. This was super fun.

Sarah Cottrell: Thanks so much for listening. I absolutely love getting to share this podcast with you. If you haven’t yet, I invite you to download my free guide, First Steps to Leaving the Law at formerlawyer.com/first. Until next time, have a great week.

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