The newest member of Ironclad’s executive team is Damon Mino, VP of Sales. Damon comes to us from DocuSign, where he built DocuSign’s Legal Vertical sales team. Before that, he was an early employee at LinkedIn, where he started his career in Sales after a decade practicing law.
Damon’s story is filled with unexpected turns, always faced head-on and, if his transition to Ironclad is any indication, embraced with a palpable and infectious excitement. He started his career in law, thinking a law degree would help him fulfill a childhood dream to become the General Manager of the Oakland Raiders. When he landed a job as a paralegal at Oracle and saw how promising tech was, he changed course, embarking on a successful legal career in tech. Before ultimately transitioning to Sales — a move very few lawyers make — he had already worked in legal operations, as a lawyer at Gunderson Dettmer, and then finally as in-house counsel at 3PAR.
I sat down with Damon to chat about his career, and I got way more than I bargained for. We talked about a lot of things: finding love, overcoming risk aversion, leaving the law, to name a few. Buried in all Damon’s stories are fascinating life and career nuggets for anyone who’s interested in growing themselves and their careers, but Damon’s stories are particularly illuminating for those of you who are lawyers interested in transitioning from law to business. I’ll summarize a few key takeaways that I found particularly interesting here, but read the rest of the blog — you won’t regret it:
- If you’re a lawyer looking to transition from law to business, you must first have confidence that you have what it takes, because you do. You have all the “raw skills” — communication, analysis, rules of society — you need to succeed in business.
- Confidence is necessary but not sufficient. You also need to cultivate your network, especially your friends who aren’t lawyers. At the risk of stating the obvious: if all your friends are lawyers, your next job is probably going to be in law.
- Don’t be afraid to fail because you’re going to have to (repeatedly!) in order to learn business. Most business jobs are not things you can learn by reading a book; they’re things you learn by trying, failing, and learning from failures. You have to do the thing, you have to carry a bag. (If you, like me, don’t know what “carrying a bag” means, read on.)
- Last but not least: you can find love in (truly) the most unlikely places.
So, I did some LinkedIn research on you and you have a very unique background. You don’t often see lawyers go into sales, but that’s what you did: you started off your career as a paralegal, went into legal operations, was a corporate lawyer, and then transitioned into Sales. So I’ll just start by asking, how did you make that happen?
You know, it’s a great story. I was actually a happy lawyer! When I made the switch, I was in-house counsel at a company called 3PAR. We had just gone public and were scaling like crazy. I was in charge of all of Commercial, we had a general counsel, and we had another guy who did all Corporate. So it was the three of us, and we were building this legal team from scratch. It was really, really fun.
Out of the blue, I get a call from a gentleman named Brian Frank who had been my old Assistant General Counsel (my old boss) at Ariba. At that time, he was head of Sales Operations at this little startup called LinkedIn. Back then, they were very, very young, with maybe only 50 million users. And Brian said, “Damon, I want you to quit being a lawyer and come lead a Sales team for me.” And I told him, no way, things are going great, why would I do that? Keep in mind, this was 2007, 2008; we were still deep in the financial crisis and Tech 2.0 hadn’t happened yet. LinkedIn just did not seem like a good opportunity.
What made you take the job at LinkedIn?
I had been a VC lawyer, so I put out feelers with people who knew what was hot and what was not. My VC friends told me, hey, keep your eye on LinkedIn. They’re the real deal. They’re not just making a resume poster, they’re building a really incredible data analytics solution which nobody’s thought of. Long story short, I went in and decided to give it a shot.
So I go into interview, and during the first round, I met this person who was to be my co-manager. I am now married to her. I literally fell in love with her during that first interview. That lightning strikes, love at first sight thing is real!
Wow! What did you guys talk about during the interview?!
We talked about operations, we talked about building a sales team, we whiteboarded — all the stuff that I love! I just fell in love with the way her mind works, how she thinks. It was crazy. At that point, I was in my mid-30s, happy being single and wasn’t thinking about marriage at all, but I literally fell in love with her then and there.
That is an incredible story. And so you got the job and worked together at LinkedIn?
Yes. We built a team from scratch together. Without exaggeration, we worked about 50 to 60 hours a week in each other’s presence: commuting together, working all day together, coming back to the city, going to a café and doing email together. We’re both workaholics, and we dived in head first to build this sales team.
That’s an incredible story. I want to dig a little deeper into how you made the transition from law to sales. Lawyers ask me how I transitioned out of law all the time, and I think people will be interested in hearing some of your advice on how to do that.
I get these questions all the time too. So, before I get to some tips let me just preface with what is awesome about being a lawyer.
I think, if you’re not afraid of incurring the debt, law school is the best education you can get because it teaches you three things. One, it teaches you how to communicate excellently; two, it teaches you how to analyze; and three, it teaches you the rules of society. It doesn’t really teach you to be a lawyer; that, you have to practice. But it gives you the raw skills to be excellent at almost anything business-side.
So to start, if you’re a lawyer looking to move into business, have confidence that you have the raw skill-set for this, and moreover, that there’s no better school for developing those skills than law school. Business school doesn’t teach you these three things, no school does. So, if you’re looking to go into business — whether we’re talking about Sales or Marketing or BD — you need to learn those three things, and you can rest assured that no school teaches you the raw skills you need for business better than law school does.
There’s a catch though. And that is, since you can’t develop all the skills you need in school, you will have to develop the skills you need for these jobs somewhere, and that usually means taking an entry-level job to get to the more interesting job down the road. And it’s tough for a lot of lawyers to leave their jobs to take that entry-level job.
The other path is to go to a startup. Startups give you a wide breadth of experience. You don’t get a lot of the blocking-and-tackling training you would get if you were an entry-level person at a place like Oracle, but you’re going to be doing work that is super challenging for your brain.
The last piece of advice I would say for lawyers who want to transition into Sales, specifically, is this: if you really want to get into Sales, you need to carry a bag.
Carrying a bag means…?
You need to actually sell. You need to have a quota.
I didn’t carry a bag until DocuSign. And that’s really backwards because most people that get into sales management start as a SDR (Sales Development Representative) and then get promoted to Sales AE (Account Executive) before moving into management. But I had started as a lawyer and had all these connections, so I ended up doing a several different tiers of management before I ever actually sold anything — and selling is the most important part of Sales!
It wasn’t until my last four years at DocuSign, after I had built the Legal Vertical (a team that sold exclusively to law firms) that I started selling. At first, I sold to all sizes of law firms, but by the end I was only working the largest accounts. Along the way, I learned to sell to all different accounts: from VSB (very small business) all the way to Enterprise, from slip and fall litigation shops to Latham & Watkins.
So in sum, you need to learn how to sell as quickly as you can. And that usually means working at a place that will give you a chance to carry a bag, carry a quota. At a big company, you’re probably going to have to be an SDR first before you’ll be able to sell full-cycle, but at a startup, somebody might give you a chance and actually have you start selling without having the traditional experience.
Selling is something that’s terrifying for a lot of lawyers because it’s not something you can read a book about or study for. It’s something you’ve got to do just do. There’s a lot of trial and error, but at the end of the day, it’s just like learning how to be a lawyer: you learn it by doing it, by practicing it. The skill set you need, you already have: communicating, analyzing, understanding the rules of the game — those are skills every lawyer already has, and they’re all you need.
There’s also a big psychological component to it that you’ve alluded to a couple times — you need to have confidence that you have the raw skills, but you also have to transition from a world in which your job is to avoid risk to one in which you’re taking on a lot of risk. I’m interested to hear what the psychological transition was like for you, how you handled that.
That is a really good question. I’m thinking about each of the big career transitions I’ve made. At every single one, I can tell you in all honesty that I understood, very logically and very viscerally, that I was taking an extraordinary amount of risk. But I was comfortable with the risk because I felt like the problem I was being hired to solve was one I was confident I could solve. For me, I’ve always been more excited by possibilities than scared.
One super important thing, though, that has helped me deal with the risk, are the connections who referred me. I trust them, and that helps mitigate the risk.
On a related note, people often theorize about what makes the Bay Area such a great environment for entrepreneurship and startups and it’s really simple. It’s something Reid Hoffman saw a long time ago, and why he started LinkedIn. It is the network. Why did I make the first leap? Because I trusted Brian Frank. Why did I make the leap to DocuSign? Well, DocuSign’s CEO, Keith Krach, was the founder and CEO at Ariba, where I really started my in-house legal career. Why did I make the leap to Ironclad? Because Ironclad partnered with DocuSign and then I got to know Jason over the course of a year.
It’s always about the people. Maybe I do have a risk tolerance that’s higher than others, but I’m never going to leap into any of these changes completely blind. I’ve got to know the people.
I think a very important practical piece of advice for people looking to transition careers is, lean on your network, lean on your friends. If you’re a lawyer looking to transition into business, make sure you make the effort to network outside of just the legal community because if you’re networking just inside the legal community, well then, that’s where you’ll always be working.
Speaking of making the leap to Ironclad, let’s talk about that. When you left DocuSign, you had just built the Legal Vertical, which is DocuSign’s selling arm into law firms, and you had built this from the ground up. This was your baby, you were doing great, and you were happy. What made you give that up to come here?
I’ll tell you, the last day at DocuSign, I got extremely cold feet. I was thinking, what am I doing? I just had the best quarter of my career — not just at DocuSign, but ever. And I felt really paternalistic over this Legal Vertical that I’d built and was now handing over to someone else.
And then, my first day at Ironclad, I went to two onsites (sales demos). I was thrown into the fire, my computer didn’t work for the first couple hours, it was a typical first day at a startup.
But you know what? I came home that first day and I was just elated. All of the doubt melted away in that first day.
To answer your question, I was ready to build again. I love creating, I love building things, going from first principles and making things from the ground up. I think even when I was a lawyer, my favorite part was drafting, and I think a lot of lawyers can relate to that. Most lawyers have a big piece of creativity within them that unfortunately the practice does a really good job of stamping out.
Why build here?
I saw the product, I saw the customers who were signing up for it, and I just freaked out. If I saw Ironclad when I was an attorney, I would’ve killed for it. When I was a paralegal at Oracle, I had to build a portal with crappy little workflows and URL links for our sales reps to pull down an NDA.
There’s always been this business problem of balancing legal teams’ time and resources against business clients need to get agreement versions approved quickly, and now Ironclad has solved it. It doesn’t just free up lawyers from administrative work, it also automates the back-end diligence and lets you search through terms instead of having to manually go through old agreements. And it’s not an old web-form bolted on to a database. It’s new. It’s real.
So when I saw the product, I got really excited about it, and moreover I got excited about evangelizing Ironclad to lawyers. I don’t know if “evangelize” is the right word, but it feels like we’ve got an important calling to spread the gospel here. It’s like when you discover this secret that’s really life-changing and you want to tell all your friends and family about it. That’s what Ironclad is right now, and I want to lead everyone to it.
I think, if you ask any good salesperson what they want to do, it is to sell a product that they themselves love. They don’t want to trick anybody. They want to share the secret that’s really life-changing and tell everybody about it.
Ironclad is the #1 contract lifecycle management platform for innovative companies. L’Oréal, Staples, Mastercard, and other leading innovators use Ironclad to collaborate and negotiate on contracts, accelerate contracting while maintaining compliance, and turn contracts into critical carriers of operational business intelligence. It’s the only platform flexible enough to handle every type of contract workflow, whether a sales agreement, an HR agreement or a complex NDA. The company was named one of the 20 Rising Stars on the Forbes 2019 Cloud 100 list, and is backed by leading investors like Accel, Y Combinator, Sequoia, and BOND. For more information, visit www.ironcladapp.com or follow us on LinkedIn and Twitter.
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