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Alma Asay

Updated: Aug 8


In her role as Evangelist at Litera Microsystems, Alma Asay is a legal technology expert and trusted advisor to Litera clients, helping them to bring innovative ways of thinking and practice to life.


Before joining Litera, Alma was the Chief Innovation Officer, Legal Solutions, at Integreon Discovery Solutions, a leading global provider of alternative legal services. Alma joined Integreon as part of its acquisition of her litigation management software business, Allegory, where she was Founder and CEO. Allegory is a platform offered in the cloud and on-premise that automates everyday litigation tasks and connects the people, facts, and evidence that litigation teams need to build their winning story in a central, secure place. Allegory is used by Fortune 500 companies, Am Law 100 law firms, and top litigation boutiques, including firms in both Vault’s “Top 10 Law Firms” and “Best Litigation Boutique Law Firms.”


Alma began her career as a litigation attorney at Gibson Dunn, where she worked on high-profile litigations for big entertainment companies, including NBC Universal, IAC/InterActiveCorp, and Cablevision.


What was the impetus behind starting Allegory Law? What were the biggest lessons you learned while starting it and then running it?


Allegory was inspired by my time as an associate at Gibson Dunn and the frustrations I felt at not having better technology to manage our cases.  When I was a first-year associate, the partner for whom I was working told me, “I want to see every document in the case.  Not just the ‘hot’ documents – every document.”  I knew full well that, if I wheeled a cart full of binders into his office, he’d look at me like I was crazy.  But I also knew I couldn’t say “no.”  I went back to my desk and started typing the relevant portions of every conceivably relevant document, along with details such as date/time/to/from, into an Excel spreadsheet.  When I showed him what I was working on (printed and bound, of course, for easy viewing), he told me to keep going.  Ultimately, we leveraged our support teams to help us create the document digests, which we also shared with in-house counsel, giving everyone on the team an easy grasp on the full scope of evidence.  Over the years and across cases, we refined our processes and expanded the scope of what we digested, including incorporating deposition testimony.  As I was asked to teach these methods to other litigation teams at the firm, it seemed crazy to me that there wasn’t software that could do more of the legwork for us.  When I asked our litigation support team about this, they pointed me to CaseMap, which was (unknowingly) already installed on my computer, but when I opened it, I couldn’t make heads or tails of it.  After doing some additional research, I concluded that the tool we needed didn’t exist.


At the same time, I was nearing the end of my sixth year and thinking about partnership track.  I had rushed through school, including skipping a few grades, and it occurred to me that, if I ever wanted to try something else, this would be the time.  I could always come back and do the required two years in advance of partnership, but if I carried on now and became partner, would I ever leave?  Having already achieved more financial security than I had imagined possible growing up, I decided to make a jump.  At first, I planned to do international volunteer work, but my friend had heard me talking about my ideas for a litigation software and introduced me to developers in Brooklyn.  After meeting with them and realizing that it was possible to bring my ideas to life, things spiraled from there and Allegory was born.


I learned so many lessons building Allegory – I think that’s the nature of being an entrepreneur, learning anything and everything as quickly as you can.  Right away, I learned the biggest lessons, the importance of carefully selecting people and finding the foresight and perspective to see beyond any given difficult moment.  These lessons resonate most because of early struggles falling out with my original development team and co-founder.  The development team came first.  They originally agreed to work for equity, but – having never done this before – we didn’t have paperwork or good definitions around expectations for how that equity was earned.  This team had never worked on a product for legal and didn’t appreciate our concerns around stability and security.  This all resulted in standstill, with the development team saying, “the product is done, we’ve earned our equity, go sell it.”  And me refusing to take Allegory to market because basic elements were still missing – it was full of bugs and I had no reassurances on its security.  We ultimately bought out the development team, raising our first round in the process.  At that point, believe it or not, my co-founder and I still didn’t have our own paperwork, which then became a priority.  My co-founder had been one of my best friends, but I quickly learned that starting a business with someone who is reliably down for a good time is not the same as starting a business with someone who is reliable, period.  With a common adversary in the development team, these issues were initially obscured, but quickly came to the surface and were exacerbated by discussions about rights and responsibilities as we sought to put together our paperwork.  Our conflict went on for months, even as our new development team moved forward on stabilizing and improving Allegory, culminating in my co-founder suing me and the company.


Amidst all of this, there were many days when it felt like the floor was falling out from under me and I wondered why I had ever started Allegory at all.  I recall, on one of the worst days, promising myself to remember that moment because, one day, things would be better and it would be important then to look back and be able to recognize that – while I couldn’t see it at the time – there was a way forward to better times.  Another moment I recall from that time was standing on a subway platform in Brooklyn when a breeze came through and, for the first time in days, I smiled.  It reminded me that, no matter how bad things got, the world was not ending, the sun was still shining, and the experience of finding joy in simple moments of nature could not be taken from me.  The first two years of Allegory were a crash course in entrepreneurship, software development, and corporate law, but ultimately, the most powerful lessons I learned were about people and perspective, which are what gave me the most strength in the years that followed.


As things moved forward, I don’t think there was a day running Allegory that I wasn’t learning valuable lessons on everything from UX design to accounting to fundraising.  But the lesson that resonated – and continues to resonate – the most is the power of networking.  By nature, I’m an introvert, but it quickly became apparent that I would have to learn to be more extroverted, including finding ways to connect with people that didn’t overwhelm my introverted tendencies.  Shortly after resolving issues with my co-founder, I moved to Silicon Valley.  The power of networking was immediately apparent.  I would meet with one person and, over the course of our conversation, they would think of ten other people I should meet – and follow that up with introductions.  At first, I thought this was weird – certainly not something to which I was accustomed as a lawyer at a BigLaw firm in New York.  But it didn’t take long to appreciate how universal this practice was and why.  For the first time, it felt like I was moving forward in all the directions I needed to go in order to build the company.  In addition to relying on introductions, I began using tools like LinkedIn and Twitter to expand and engage with a larger network.  This resulted in more opportunities to connect in person, especially at conferences.  Over the years, I met fellow entrepreneurs who became friends walking similar paths, industry leaders and reporters who spread the word about Allegory, successful legal industry entrepreneurs who invested in Allegory, experts who gave me much needed advice, lawyers who bought and used Allegory, and many, many others who helped me grow the business.  There are many things we did that may or may not have made a difference, but networking was at the core of every opportunity that resulted in our success.


Tell me about your current role. What does your current role entail?


One of the things I love about my role as an Evangelist at Litera is that it gives me the freedom to do a variety of things and find opportunities where I can add value across the company.  At a high level, I’m focused on three things: (1) increasing the visibility and brand of the company, (2) engaging with clients and the legal community to understand how we can best tailor our services their needs, and (3) helping Litera to build its expertise and scope in the litigation drafting space.


On the first, from day one, I launched into helping Haley Altman (the founder of Doxly, which Litera acquired last year) plan Litera’s first-ever conference.  Unlike many legal tech companies with widespread visibility and brand recognition, Litera has never hosted a conference.  This conference, The Changing Lawyer Live!, exceeded all expectations, which gave us something to celebrate in a time when it has been difficult to find things to celebrate.  On the second aspect, my role includes connecting with professionals across the industry, whether that’s in-person (including virtually) or online.  Connecting means more than simply introducing myself.  It means truly getting to know people and the organizations for which they work.  I love this part.  I find the people and the roles that come together to make up the legal industry fascinating.  Understanding how lawyers and other legal professionals practice is something that Litera takes seriously, even when there’s no immediate opportunity to sell a product.  They are taking the long view that, if they understand better than anyone else how the legal industry works, then they will be best positioned to serve clients with both existing and future products.  For this reason, Litera has an entire Evangelist team, of which I am only one member, free from the weight and often awkward barrier of having to “make the sale.”


Finally, I am one of the first employees at Litera to have a deep background in litigation.  Traditionally, Litera has been best known in the transactional market, for tools that allow you to create templates, re-use contract clauses, compare documents, repair errors across documents that cause problems as drafts are flying back and forth, and so on.  But the company wants to see more people using its products for litigation.  In order to get there, Litera is renewing its focus on litigation (such as the recent acquisition of Best Authority) and putting more effort into understanding the use cases for their tools as applied to litigation.  I appreciated that the executives at Litera heard me when I said I didn’t want to be pigeon-holed into litigation and gave me a role that would be broader than that, but of course, I can and will bring my experience and connections across the litigation market to help the company achieve its goals in this regard.  Even here, I get a change of pace from the Allegory days, where I was focused on litigation management, to instead focus on drafting and other litigation-related processes.  I’m also enjoying a new perspective as this includes sharing my thoughts on where it may be beneficial to buy vs. build, drawing on my knowledge and network of legal tech startups that have built compelling products.


What have been the biggest lessons you’ve learned while in the role?


Naturally, I’ve learned a lot about Litera.  Before Litera acquired Doxly, I had never heard of the company, which seemed strange given its size and scope of clients.  Part of the reason for this is that many of its products, while used every day by lawyers and their colleagues, are not visible as “Litera” products.  For example, Metadact may do the critical work of scrubbing a lawyer’s e-mails and otherwise protecting a firm’s systems from intrusions (or embarrassing mishaps from sending out unclean files), but that doesn’t mean the everyday user knows that it’s a “Litera” product.  As another example, Litera’s DocXTools are often white labeled, so the user sees the functionality simply as a ribbon in Microsoft Office products, without any Litera brand association.  It’s hard to get end users excited and talking about your company if they don’t even know who it is providing the everyday functionality that they take for granted as a component of their e-mail or word processing software.  Over and over, my reaction to learning the Litera suite of products has been, “oh, we had this functionality at Gibson Dunn – and, of course, we needed it – but it never occurred to me that it was a separate product licensed by the firm.”  This is a challenge I haven’t faced before and a lesson in the impact of branding, both with respect to users, but also, ultimately, with respect to name recognition in the broader community.


More importantly, I’ve learned about Litera’s commitment to its employees and the power of that commitment in producing results.  We always hear about how companies should value their employees as much as they value their customers, how employee morale drives financial success, etc.  But it’s rare to see big companies actually walk that walk.  I was wary of two things before deciding to join Litera: (1) working at a company that was private-equity owned, which too often means it’s all about the “money, money, money” today – at the expense of a long-term outlook on the health of the business and team, and (2) taking on a role at a service provider where I would be directly responsible for making sales, even if not technically in a “sales” role.  (In order to build Allegory, I had to do a lot of things I didn’t enjoy at first.  I ultimately came around on many of them, including public speaking, but sales is something that is not my thing and I’m not afraid to make that clear.  I have the utmost admiration for people who excel at this role, but it’s not for me.)   Litera seemed to be the exception to the rule on the first point.  Everything I learned about the company before joining spoke volumes about the commitment of both the company and its investors to building a sustainable business with a focus on employees and without being afraid to make big investments for long-term rewards.  On the second point, they not only heard me, but didn’t have to jump through any hurdles to accommodate the role I envisioned, as they already had established the role of Evangelist, which fit the bill.


All this said, we never know how a new job is going to pan out in practice.  It is in large part because of the current crisis that I’ve been able to see – immediately – that Litera was for real.  Litera and its executive team have repeatedly shocked me with the extent to which they’ve thought about and ensured their employees’ well-being.  Among other initiatives, Litera has encouraged employees to take time for themselves and their families throughout this crisis (without impacting PTO), implemented regular all-hands calls with the CEO, during which he provides absolute transparency on the company’s financial state and the efforts the company is taking to ensure that employees aren’t sacrificed, and offered an employee relief fund in excess of a quarter million dollars for employees financially impacted (either as a result of the employee’s reduced commission opportunities or a significant reduction in household income, such as a spouse losing their job).  I find myself regularly turning to my husband and telling him, “you’re not going to believe this.”  It speaks volumes about what we think we can expect out of today’s employers that these decisions shock me.  And it’s easy to see the positive impact of the company’s approach, as the team has continued to be in good spirits and doing their best on behalf of the company, even in the most difficult of times.  It has been an enormous lesson to me in what’s possible when an employer treats its hundreds of employees with respect, clarity, and consideration that exceeds our expectations.


As many tend to conflate the two, how would you distinguish legal innovation from legal technology?


Legal technology is a very small part of legal innovation.  Once upon a time, I thought, “if you build it, they will come.”  That’s not true.  You can build powerful legal technology that does all the right things, but unless you can get lawyers themselves to innovate the way they do things, you’ll never achieve true adoption of that technology.  Innovation includes a willingness to accept the prospect that there might be a better way of doing things and the will to try.  That will may come from a mandate from firm management or clients, or it may be an inherent drive to be more efficient – billable hour be damned.  Once there, a lawyer might adopt new technology – or they may adopt new processes or new approaches to applying the law or new ways of engaging with their clients or any number of innovations, none of which may include technology, but all of which are significant in their own right.  Legal innovation can be applied without legal technology, but it would be quite rare to see legal technology applied in a meaningful way without legal innovation (I’m not including Microsoft updates here).  All that said, #legaltech is a far simpler shortcut than #legalinnovation, so I’ll continue defaulting to the former unless a point truly doesn’t include “tech.”


What do you see as the biggest challenge facing the legal industry over the next few years?


My answer to this would have been different a few months ago.  Now, I think the biggest challenge is and will be confronting how we recover from the current pandemic and the long-lasting consequences of it.  There are so many unknowns right now and that’s especially difficult for an industry that is used to things being “the way they’ve always been.”  In the end, it might be a good thing (in this limited context).  There might be more appreciation and adoption of technology (including cloud-based solutions as a whole) and new ways of doing things.  New innovations may be born out of restless members of our community.   Employers may be more open to flexible working arrangements and generally more open-minded about the ability to get work done without putting in facetime.  Clients may realize there is even more work that can be done by alternative legal service providers, ensuring that outside counsel spend is spent on work that actually requires outside counsel.  Lawyers may be forced to develop more understanding and empathy for their clients, making them better lawyers.  One can hope that firm leaders may also develop more understanding and empathy for the employees that keep their firms running, and their role as employers to ensure that employees’ well-being is not an afterthought given credence solely for the marketing power of saying “we care.”  New laws and legal issues may invigorate lawyers who have become complacent from years of practice in areas of well-settled laws.  But there are going to be a lot of hard decisions to be made along the way, at a personal and professional level.  Lawyers and law firms are going to have to decide whether this is a wakeup call that sets them on the path to innovating their ways of thinking and doing business, or whether they fall back into the old ways when this crisis passes, all the more entrenched in their certainty that they don’t need to change.  More than ever, insisting on the old ways of practice will be a decision, not a default.


What would be your advice to a new lawyer or law student seeking to dive into the legal technology world?


I would tell that new lawyer or law student to practice law.  While it’s true that many successful legal tech startups have been founded by people who didn’t practice law, I also see the greatest need – and opportunity – in our industry to be in deploying legal technology that meets lawyers and their clients, whether big corporations or individuals, where they are.  This is true not only for the subject matter and workflows that the tools embody, but also in their design and accessibility.  Lawyers and law often don’t fit the molds that are out there for building new technology.  For example, general UX principles say that you leave plenty of white space on a page, but lawyers want everything in front of them and hate extra clicks.  The credibility and instincts you develop by working among those you hope to serve with technology can be an enormous benefit – if only, ultimately, to understand why it is so incredibly difficult to achieve adoption.


In addition, while practicing, get to know everyone behind the scenes.  Too often, lawyers are concerned solely with the work in front of them and don’t appreciate all of the work that others do across the firm to support their practice.  The copy center, the mail room, the knowledge and practice management departments, paralegals, legal assistants, word processing, IT . . . .  Get to know all of them and understand what they do, the processes they follow, and the challenges they face.  When Litera acquired Best Authority, the team asked me how I created Tables of Authority at Gibson Dunn.  I had no idea.  I vaguely recalled understanding how to make last minute updates to citations in such a way that those changes would be reflected in the table, but the truth is, I would send briefs off somewhere and they would magically reappear with the TOA in place.  I’d be so much more valuable now, as we look to improve upon Best Authority, if I knew what went into creating a TOA and the processes and challenges involved in doing it (or even knew the people who did the work, to pick up the phone now and ask them).  Which isn’t to say that I can’t get there by finding people who do this work and asking them now, but the time and learning curve will be steeper than if I had taken the time to do it when they sat down the hall from me.  Learn not only “your” role, but learn about the complete end-to-end process, and all the people who get it done.  Included in that, learn about what it takes to bring technology into a firm – you’ll never be in a better position to do that than when you are in the seat of the user you one day hope will use your product.


Finally, get to know people, period.  When I started practicing law, my uncle (a well-connected lawyer) gave me some great advice, to immediately start keeping track of everyone I met in a spreadsheet – names, titles, where we met, notes about their family, etc.  This was before the days of LinkedIn, Facebook, and Instagram.  I knew I probably should do that, but I didn’t.  I was an introvert, I was happy being an introvert, and I didn’t feel the need to make a point of meeting lots of people, much less keeping track of them to reconnect later.  That was a mistake.  As I built Allegory, I thought back to all kinds of people I met along the way, or had the opportunity to meet while I still had the credibility and access as a BigLaw lawyer, who I wished I could call.  For those I had met, I rarely remembered enough details to track them down, as if they would have been inclined in any event to be forthcoming with their time and connections after one long-forgotten (for both of us) meeting years ago.  For those I hadn’t met, the hill was a lot steeper to climb to get that first introduction as a “former lawyer.”  As one example, I once crossed paths with Mark Cuban at a conference.  He was standing alone, right next to me.  I knew who he was, and I knew that one of the partners at my firm was close friends with him.  I could have said hello, I could have said, “I work with Sean!”  But I didn’t.  Turns out, Mark Cuban likes to invest in startups, including legal tech (he is an investor in Paladin, which came about because the founders were brave enough to send a cold e-mail – while successful, this is still a steeper hill to climb).  Making and maintaining new connections is much easier now, with tools like LinkedIn and Twitter.  But the mindset of lawyers is too often the same, that it’s not necessary.

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