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Alexander Su

Chief Revenue Officer


Creator, Off the Record

San Francisco, California

Formerly associate Sullivan & Cromwell

JD Northwestern

BA Carnegie Mellon

note: Alex was the Head of Community Development at Ironclad Inc. at the time of this interview.

If at first, you don’t succeed… Now legal tech executive and LinkedIn Star

Alex Su

On using LinkedIn as a sales tool and building a personal brand

On startups providing opportunities

On where to begin for those struggling to leave law

On his pitch to get a legal tech job with no sales experience

Listen to interview:

Full Transcript

ex judicata:  With us today is Alex Su. He is head of community development at the legal tech stalwart Ironclad. But to many, me included, he is known as a thought leader on the business of big law as well as the legal tech marketplace. He has a legion of LinkedIn followers, an incredible 87,020 and 4000 subscribers to his Off the Record newsletter. I’m also a subscriber.

Alex is also known for his humorous videos portraying what is essentially a humorless culture. You are our second video star, Alex. I don’t know if you’re familiar with the Crazy Hot Matrix.  If not, look it up sometime.  You won’t be disappointed.

You’re kind of like a hero to disenfranchised law firm associates and, to a lesser extent, in-house lawyers. I looked up, “disenfranchised”, just to be sure I was using it correctly. Essentially three components alienation, victimization and cynicism. I think that pretty well captures the mindset of most Biglaw associates.  Alex. Welcome. Thank you so much for joining us.

Alex Su: Thank you so much for having me.

ex judicata: Why don’t you tell us a little bit about what you do at Ironclad?

Alex Su:  Sure. My title is Head of Community Development, which means a lot of things. It’s not quite marketing, it’s not quite sales. But as a legal technology company, we are always concerned about engaging in a two-way dialogue with our target market. And so, we have a community team and my job is to engage in dialogue through social media, but also in-person events like conferences, meetups, things like that. It’s an amorphous job.  It’s what I’ve often called a ‘unicorn job’ because it is designed for my unique personality, strengths and weaknesses.  I love it, but it is often very hard to explain, to say, my immigrant parents, what exactly it is I do at work every day.

ex judicata:   You had a traditional background for someone with their sights set on a law firm partnership.  Good law school, work in Biglaw for an elite firm, a judicial clerkship and then returning to that elite firm.  At what point did you start to become disillusioned, either with the practice or with the institution, the large law firm?

Alex Su:  When I was in law school, I didn’t really feel that I was headed in the right direction.  It wasn’t until I started practicing at the big firm that I sensed that something was wrong.  I couldn’t quite put my finger on it, but it felt like the job was not really aligned with what I wanted out of a job or a career.  And that’s not to say that Biglaw is wrong for everyone.  It just so happened to be wrong for me.  And I remember I was assigned on a litigation matter for a very large client, and I think we had to submit a privilege log.  Now, I understand a junior associate like myself would be responsible for creating that privilege log, formatting it, making sure there’s no typos, making sure the columns are aligned etc.  

I remember very distinctly being on this conference call and a senior partner, who’s like maybe 10 or 15 years into the partnership, relaying to the client how the privilege log was designed, what was boldfaced, what the columns were.  And I thought to myself, ‘Wow here’s a guy who has impeccable credentials and experience who seems like a very sharp, brilliant person.  And at that stage of his career, he was still focused on detail-oriented work’.  Nothing like what I had expected a trial lawyer to be, which is which was the whole goal of me going to law school.  I wanted to be a trial lawyer. That’s why I joined the litigation department.  That’s why I clerked for a judge.

So, it was at that point I thought, well, if I keep working hard and doing this for years, I might not ever be able to get out of it.  I think that was the first moment I thought maybe I should try to see what else there is out there.

ex judicata:  I understand completely. I had a sort of similar experience.  I’ll just relay it quickly.  When I was working for a Biglaw firm, I went into a young partner’s office. This was way back in the late 80s where we used large, hard copy legal books.  Online was virtually unknown.  In looking at the partner’s bookshelf I saw one book that was out of place.  The only book that was a paperback.  It was Fear and Loathing in Las Vegas, the Hunter Thompson book.

I thought, wow, that’s kind of odd but kind of cool sitting there on the shelf. I had to ask him about it.  “Say, I see Fear and Loathing in Las Vegas on your shelf.  What did you think of it?  He goes, “No, I’ve been meaning to get to it.  But, you know, the last two years, I just haven’t had the time.”  Once he said he didn’t have time to read one paperback, I knew I was done.  That’s not the kind of life I wanted.  I quit later that same week.

Kind of like what you’re relaying, it sounds like that that conference call with the partner and privilege log was the triggering event for you.  And you began thinking ‘Okay, what else is out there?’ and then you wind up leaving the Biglaw firm.  Did you have another job already lined up when you quit?  What was your status?

Alex Su:  So, when I thought about leaving, I figured I would try something different. And there was a temptation to go to another Biglaw firm.  Certainly, you could continue to get paid well and it would be a pretty seamless transition.  But I thought, okay, it’s fine to make a mistake once.  Like maybe I chose the wrong job.  For me, it was not okay to make the same mistake twice because then I’d be doing it to myself.

I resolved to go to a different type of law firm.  I went to work for a plaintiff side, smaller firm.  In California where I had just moved to from New York.  I was still practicing law

so it wasn’t that scary a move.  I was still doing litigation, so it wasn’t too much of a jump.  It was only a slightly different change in the environment.

But I had a feeling that that the smaller firm might be better for me because the things that a large firm valued, the things that you needed to thrive in that environment were not for me.

Alex Su:  I looked at my own life and I’ve never been good at those things.  Like a basic example is being detail oriented.  It is not my biggest strength, although I will say that having gone through the process of working at a large firm, I had gotten better. But it was never something that came to me naturally.  And I remember growing up, the teachers always saying, ‘Hey, Alex, you’ve got to stop making these careless mistakes.’

I went to the smaller firm and long story short, that job didn’t quite work out. There were good things about that job. There were bad things about that job.  And I was kind of frustrated because I thought I had done well in school so why was I having such a hard time working as a lawyer. And so, it was around that point where I decided big firm didn’t work.  Little firm didn’t work.  Let me do something more entrepreneurial.  I’m going to start my own solo law practice, which is completely different, right?  Being a business owner, which I’m sure you can relate to, is totally different.

ex judicata:  Yes, that is a whole other world.

Alex Su:  As a solo then I’m loving the freedom of the job.  I can choose the kind of work that I naturally gravitate towards.  I found I loved business development, marketing and sales.  But the challenge was that I just didn’t have the time and bandwidth to focus on the work itself.  And so, I didn’t make very much money. I started looking at my numbers and thought maybe this isn’t going to work out for me.

And so, by then, I was 6 years out of law school and had 3 jobs in a row that weren’t quite a fit for me.  At that point I thought, well, let me start back from the from the beginning.  ‘What am I trying to do with my life here?  What am I good at?  What am I bad at?  What do I really want to do?’  And that kind of set the stage for me, making the pivot to joining a legal technology startup.

ex judicata:  At that point, were you looking at other kinds of opportunities or was it always something that was going to be adjacent to the practice of law in some shape or form?   In this case, like legal tech.

Alex Su:  I wanted to stay in something that was adjacent to law because I’d invested so much time and energy into a legal career.  I didn’t want to throw it all away. And yes, law school teaches you to quote unquote, ‘think like a lawyer’.  But I also had learned all of these other skills and I wanted to now use them.  So, I knew that I wanted to do something law adjacent.  And I wasn’t sure what that was but it would have to involve dealing with people.  Maybe some element of sales or business development, in a less bureaucratic environment.  I had this checklist of things that I wanted to make sure I would have in my first job out of law.  Because, again, I didn’t want to make the same mistake twice.  I was like, I have a lot of knowledge now. I’m a little bit older and more experienced, and I should use all this information I have learned when I pivot.

ex judicata:   And in doing that–because a lot of young attorneys are now finding themselves in this position of trying to get a job in business with no direct experience –what was your pitch to the legal tech company when you hadn’t really done any traditional sales work?

Alex Su:   There were two things that I had going for me. The first was that they were hiring.  You know, typically in startups when they hire entry, they hire entry level salespeople. It’s typically like new college grads with no work experience and no experience, obviously, in the particular field.

So, my pitch was I may have no sales experience, but I know so much about what you’re selling.  In this case the startup was focused on e-discovery technology, software that you use as a litigator.  And I had used a lot of different e-discovery technologies as a litigator so I could tell them credibly that I had this experience that I could bring to the table.  

And then second, I was willing to take a pretty big pay cut. I think that the pay cut is what gets in the way of a lot of lawyers moving who are unhappy with their jobs.  Here, I took a pretty dramatic one (compared to what I could make in say a law firm) because of the situation I was coming from.  A failed business that didn’t make very much money.  I thought, ‘Hey, any W-2 job is better than what I had before’.  

It was a long haul from being a Sullivan and Cromwell associate, but I thought, okay, I’m making a calculated bet, taking a pay cut in the belief there was a lot of upside.  I could also bring a lot of value to the company.  And if it turned out that I’m not great at sales, I could also share that legal knowledge and experience with my teammates.  So, I felt like there were so many pieces in place for me with this startup that it was going to work. The company felt the same way. They hired me quickly. So yeah, that was my first job post law.

ex judicata:  And If I’m remembering in one of your columns, Alex, I think you had pointed out that if a startup is growing, really building, that’s a great time to join. Because even if you don’t know what you’re doing, there’s enough stuff going on that you’ll be able to find your own way.

Alex Su:  Yeah, that’s right.  And that’s very different than in law, especially if you’re talking about Biglaw.  A lot of people get their jobs based on working insanely hard their first year of law school and then interviewing 2 or 3 years in advance of when they’d start their job.  And then once they’re in that job, they’re kind of specialized.

In a startup they hire very quickly, and then shortly after maybe, they raise a round of funding and then you have another chance to get in.  But you’re not always pegged to the job that you joined for. Like there’s so much work to go around that you can try lots of different things and it’s encouraged and then you may learn that you’re actually really better at something you weren’t originally hired for.  So, exactly as you said, startups provide an opportunity to try lots of things and then figure out where you belong.

ex judicata:  Okay. So that’s the Alex Su traditional career. When did you start your writing and your videos?

Alex Su:  Yeah. So, I mentioned I joined the startup to do sales as a junior sales rep, and I did well.  I did so well that I had all this extra time at work. I did well largely as the result of everything I went through earlier in my career.  I was 33 years old, and I had messed up so many things.  I had now picked a job that I knew there was a pretty good chance I would do well at. So, I did do well.

And so, because I had this extra time, I could think about where else I can contribute to the company.  Just doing what my managers told me to do was not enough.  The way that technology startups had always sold software was through cold calls and emails. That tends to work when pitching certain people but not lawyers. Like, have we ever bought anything from a cold call out of the blue?  Probably not. I never did.  And so, I thought why are we doing it this way?  Maybe there’s a better way to do it.  I had my free time and I had just started to learn about people sharing posts and generating business through LinkedIn.   .

Alex Su:  And I thought, well, that could be something.  I started doing it a little bit my first year in sales and was not sure where it would go.   I just kept on experimenting with it.  And then I think about a year in, I got my first inbound lead like someone who reached out to me and said, I would like to have a sales conversation with you.  And that kind of blew my mind because I wasn’t targeting him.  I just started posting content and getting the word out that I worked for E-discovery company.  It gave me the confidence to double down on this LinkedIn experiment.  And so, for the next five years, while in a traditional sales job at two different startups, that entire time I was posting regularly.  

Right around year 4 the pandemic hit.  I had already built out an online kind of following.  It was very small among lawyers.  And when the pandemic hit and everyone stopped being able to meet up, my following took off and my results took off.  Because I happened to be at the right place at the right time solving this problem through social media.

And I developed this brand.  And then the inbound leads started coming in like a flood.  And I was juggling all this with my sales job.  

Alex Su:  I was getting all these leads which I was careful to distribute to the other members of my team.  So, I was doing marketing’s job plus my sales job. And it was great fun.  That’s around the time that Ironclad came knocking and they said, ‘Hey, we see what you’re doing. It’s great stuff and we’re interested in recruiting you’.  And I thought, ‘Hey, I’m in a good spot. I like what I’m doing. Thank you, but no, thank you’.  And they said, we’re not looking to hire you for a sales job.  We want you to continue doing what you do on social media, engaging with the community.

And, you know, we’re happy to design this job around what you’re great at. And that was crazy to me because there was no job posting. There was no like, like formal process.  It was literally like ‘what you’re doing has tremendous value. And we see it’. ‘We want you to come join us’. And that was two and a half years ago, and I’ve been at Ironclad since doing this job engaging with the community through social media, through jokes, through meeting people at conferences, because people recognize me from the content. So, that’s my long winded, long journey to where I am now.

ex judicata:  TerrificSo at Ironclad do you have complete creative freedom?  Do you have to check in with anybody and say this is what I’m going to post?  Or, simply, you get to do what you want to do.

Alex Su:   That’s right.  And that’s a lot of confidence that they’ve invested in me and I don’t take it lightly.  In the beginning I knew very little about social media.  I did have instincts though.  I’d always had social media and knew I was decent at it when I was in college on other platforms.  So, on the professional level since I had a day job, I had to start with something small.  And that gave me the freedom to experiment and mess up sometimes.

And over the years I developed sound judgment on what’s good content and what’s bad. And how far you can push things. 

ex judicata: And then with all this going on at what point did you decide to also do a newsletter?  I assume it’s a profit-making enterprise. How much experience did you feel you needed under your belt before adding this to the mix?

Alex Su:  So, Neil, part of what I ascribe my success to is not like coming up with one idea and then just running with it.  I try lots of different ideas, the vast majority of which fail, and no one ever talks about them.  The newsletter was one of these things that I tried, and it did well.  Part of it is that I really enjoy writing.  Part of it is that even though I was doing a lot of humorous content, I wanted another channel to kind of share my interests in legal tech, sales, and all this business stuff.

I started writing about two years ago using Substack and picked up a bunch of subscribers.  I kept at it and overtime I felt I understood enough about what people want to read to start shifting the content a bit.  And then about 6 months ago I started experimenting with premium content.  Here I charge for subscriptions and talk about the nuts and bolts of sales, business development and marketing.  Now, I think, Neil, I do a lot of things that people are interested in.  But, if I find something is not working, I quickly pivot away from it.  I try to find the intersection between what I like and what resonates with the world.

ex judicata:  Which is, I think, good advice for many businesses.  I believe you spoke about this in one of your recent columns suggesting that people should try out many approaches to say sell a product, see what works and then double down on that.

What advice would you have for, we’ll say, young associates that are coming to the point where they are no longer comfortable doing what they are doing but have no idea what to do next or how to go about finding that next thing?

Alex Su:  You’re right, a lot of people have that challenge. I would say you have to know yourself.  And so, how did I, for example, know that I might be good at sales or that I wanted to do sales?  I mentioned I tried the solo practice, but I didn’t also mention that years before between my clerkship and the firm I worked on a political campaign.     I wanted to be a policy person, but they were like, ‘We don’t need that. We need someone to cold call, like on the phones and knock on doors.  I was like, all right, I’ll do it.  Whatever you need.  I never thought that I would be good at cold calling.  I think because of my personality, and that I’m able to quickly forget the rejections and failures,

I ended up being good at it.  I was really good at cold calling.  So, a side thing where I learned something about myself.

I think a lot of associates who are struggling with what to do don’t yet have the self-knowledge of ‘ What am I good at?  What am I bad at?’  So, you don’t have to make a giant leap by changing jobs right away.  Do some things on the side in between jobs or like nights and weekends.  Do something that’s not for the money, but just because you think it might be interesting or fun.  Because this way you’ll learn about yourself.  And then over time you can make a calculated bet.  When you do pivot lean hard on what

your strengths are.

Alex Su:   If I had gone into legal tech and said, I want to make the same salary as I did before as a law firm associate, they would have laughed me out of the room. So, if you’re going to make a pivot you’ve got to have some conviction about your strengths and your weaknesses.  I would double down on that and take that pay cut as hard as it may be.  Go somewhere you think you can grow fast. By leaning on your strengths you’ll enjoy your work more and have a real shot at the upside.

So that’s the advice I would give. Really understand yourself, understand your strengths and what your superpower is, and then bet on yourself by taking a pay cut, going somewhere where the job is more aligned to those strengths you’ve identified.

ex judicata:  This is this is probably outside the scope. Alex, any thoughts on how do you prepare financially?  Because one of the things we have on our website is a money management tab. You know, how do you prepare if you’re going to take a major pay cut, Did you do anything specific to prepare?

Alex Su:  Yeah. I stayed In Biglaw longer than I wanted to. I didn’t leave right away. I was like, I need to pay down debt, save up money to maybe buy a house someday or at least have a cushion.  And then when I went to the second law firm, I continued to save money and kind of live well below my means.  I think if I had a lot of obligations, I don’t think I could have made the pivot.  And I do think that some lawyers feel trapped because of their financial situation.  I don’t have any good answers other than to try to get yourself in good financial standing.

ex judicata:  A final question for you, Alex.  How do you think your JD skill set, what you learned in law school, helped you to succeed in these other careers?

Alex Su:  There are a lot of transferable skills.  A few of them that come to mind include thinking critically, breaking down arguments, being able to argue both sides of an issue– that’s so valuable in so many places, including sales.  Many salespeople are not good at that.  And so that helped me stand out.

I also think that working at a firm continues that valuable legal education.  I developed what I call coping mechanisms that really suited me well when I went into sales.  Because I was always punctual. I was very detail-oriented with my emails–which a lot of salespeople are not.  And had I not had the legal training I might have been a bit sloppier in some of my outreach.  Law school was worth it.  Working at a firm was worth it.

ex judicata:  That sounds like a perfect place to leave it.  Alex, thank you so much.

What can we look forward to in your content to come?

Alex Su:  One of the things I’ve been focusing on is injecting more creativity into my work, and that includes obviously videos.  But I’ve been drawing on my iPad with my four-year-old daughter. I’m making them into t-shirts.   And I’m continuing to experiment. I’m very thankful for what I have, but I want to keep pushing the envelope because that experimenting and pivoting got me to where I am.  

ex judicata:  Wonderful.  And we’ll keep reading the newsletter and watching the videos.  Thank you, Alex. Really appreciate it.

Alex Su: Thank you, Neil. You got it. Thank you so much.

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