In my law practice and in my work for the New York State Bar Association, I am fortunate to work with some of the most well-respected thought leaders and visionaries in our nation on technology issues and how these issues relate to and impact the law and our justice system.

I recently spoke with four of the top women attorneys in North America who practice in the digital space, and our conversations are presented here. All four offer fascinating insights on how women can succeed in technology-related law.

Each of these women makes clear that one does not need to have taken computer courses or need a technology background to become successful in the digital space. They provide a roadmap on how to successfully enter the tech field regardless of your gender.

All four talk about their paths to success and leadership, and how they have marketed themselves is a lesson in creativity, hard work and perseverance. Each speaks to the importance of having a mentor or sponsor who can provide guidance and give advice on career development.

All of these women have been prescient in seeing how technology will change our world and in adapting to this ever-changing field. All stress the importance of seeking out new opportunities and note how becoming involved in bar association committees and trade organizations has been critical to their professional development and advancement in the technology world.

Shoshanah Bewlay

I oversee the Division of Legal Affairs (DLA) within the New York State Office of Information Technology Services (ITS). ITS as a New York State agency provides statewide IT strategic direction, directs IT policy and delivers high-quality IT services to 53 New York State agencies that serve more than 19 million New Yorkers. The ITS DLA includes attorneys, legal staff and technical staff assigned to the departments of house counsel, litigation and eDiscovery, and investigations. As Chief Counsel, in addition to my general duties to my client ITS, I provide advice and guidance to state agency executives concerning: legal and regulatory compliance with state and federal requirements for technology procurement and contracting; statewide technology policy; statewide IT strategy alignment; and IT audit and internal controls.

Gail Gottehrer

I'm the Co-Chair of the Privacy, Cybersecurity and Emerging Technologies Practice at Akerman LLP. My practice focuses on the legal issues created by our increasingly data-driven and connected world, and potential legal and regulatory obstacles to emerging technologies. I provide advice on data ownership and data privacy laws, such as the GDPR and the CCPA, cyber-risk and security, and emerging technologies including autonomous vehicles, biometrics, and smart cities.

Sandra Rampersaud

I am Co-Head of the global eDiscovery and Data Analytics function at UBS AG, and the Global head of the Litigation and Investigation Services within that function. I am responsible for the integrity and quality of the bank's data needs in the context of internal and regulatory investigations, and litigations, across the globe. I have regional teams set up in the Americas, Europe, and APAC who are specialists in their region and manage the requirements regionally, and collaborate with their counterparts across the globe to meet demands that have global data requirements.

Maura Grossman

I wear a number of different hats in the technology space. As a professor at the University of Waterloo and at Osgoode Hall Law School, both in Ontario, I bring together graduate computer science and upper-class law students to study Artificial Intelligence: Law, Ethics, and Policy. It is the only course in the legal tech space that I am aware of that is both cross-institution and cross-discipline. In my New York law and consulting practice, I serve as a special master overseeing electronic discovery issues in several high-profile federal court cases. I also serve as an eDiscovery expert and provide technology-assisted review (TAR) services for matters both in the U.S. and Canada

How did you first get involved in the digital space and how has it changed over time?

Maura Grossman: I first became involved in technology in late 2006, when the Federal Rules of Civil Procedure were first amended to incorporate the concept of electronically stored information or ESI. I was then counsel at the New York law firm, Wachtell, Lipton, Rosen & Katz, and my mentor there, Meyer G. Koplow, astutely foresaw that eDiscovery was going to become a significant and increasingly important part of litigation and encouraged me to pursue this as an area of specialization. Since then, my practice has focused almost exclusively on electronic discovery and legal technology.

Gail Gottehrer: Through handling class action cases involving large volumes of documents, I've had the opportunity to use the cutting-edge technology of the time for discovery. As the information generated by litigants and sought in discovery has shifted from being in hard copy to being primarily digital, that technology has evolved from document scanning to technology-assisted review and tools that recover data from phones and other devices. My focus in the digital space has expanded to emerging technologies such as autonomous vehicles, drones, robots, biometrics and wearables, and data privacy and security. 

Sandra Rampersaud: Serendipity. I graduated law school in 2003 and, after a year as a federal law clerk, my first assignment at big law was to lead the discovery in a matter with complex electronic data needs. It was the first of its magnitude at the firm, and I had to become an "expert" very quickly. At that time, technology was relatively unsophisticated offering basic linear review capabilities, and it was unfamiliar to many since hardcopy review was still occurring and terms like "metadata" were frightening to lawyers. I viewed the opportunity as a chance to learn something new that might differentiate me from the rest. Little did I know at the time how true that would be, and that instead just complementing my skills as a big law commercial litigator, eDiscovery would become a specialty in itself.

In the past 15 years, significant changes have taken place in the development of legal technology, and even with the impact that eDiscovery has on the day-to-day operations of how a business manages its data. The law has developed from a place where there was no guidance to where today businesses and lawyers can consider discovery requirements in the context of what is reasonable and proportionate. That has been a critical development from a business perspective because costs of eDiscovery in larger matters had been increasing at alarming rates. Technology, also, has come leaps and bounds, with algorithm-based and artificial intelligence functionality being made available to improve our ability to find the data we need, within a reasonable time at a reasonable cost, and defensibly. And today, eDiscovery subject matter experts are now required to have a seat at the information governance/records management/data disposal table because eDiscovery is recognized as an important stage in the lifecycle of business data. 

Shoshanah Bewlay: I began my law career in private practice in law firms in New York City and San Francisco, where I worked on the defense of large corporations in securities and tender offer litigation. In that role, I quickly became familiar with electronic review of large-scale discovery - the practice that has become known as "eDiscovery." This specialty introduced me to the management of not only legal staff, but also the vendors and technicians who support the IT systems that run eDiscovery platforms. I managed multiple eDiscovery vendors over the years and was fascinated by the speed and accuracy with which technology rendered large amounts of material - which would previously have been stored in mountains of boxes in a bleak warehouse in the middle of nowhere - into a form that could be easily aggregated, sorted, searched and meaningfully and comprehensively reviewed at my desk in the office. As I grew into managing both legal and non-legal teams and entered New York government service, the opportunities to manage and advise in the technology field increased, and I broadened my experience with technology into a more general IT practice.

What would you recommend to a woman if she is interested in becoming involved in the digital space?

Gail Gottehrer: I encourage women, and especially women lawyers, to pursue careers in technology-related fields. Because it's an area that is constantly evolving, practicing in this space requires the ability to think outside the box and assess potential risks despite uncertainty, all of which enables an attorney to be a valuable asset to her clients. I recommend that women research the technologies that interest them, learn as much as they can, and then seek out opportunities to develop their expertise. This can be by approaching a partner at your law firm who is working on a technology-related case and asking to be staffed on that case, by volunteering to help a colleague who is writing an article or giving a presentation on a technology-related topic, or by getting involved with a bar association or affinity group committee that focuses on that area of the law, such as the New York State Bar Association, the American Bar Association, and the National Association of Women Lawyers.

Sandra Rampersaud: I don't think being a woman in the digital space is much different than any industry. Around the globe in all areas of work, we have to keep striving for an equal work environment, but that should not deter anyone from pursuing their passions. The digital space, in particular, is important because many jobs in the future will be impacted by technology so the more you know about legal technology and the laws governing it, the better positioned you will be to grow professionally.

Do you need a computer science degree or to have taken courses in computer science in order to become involved in the digital space?

Shoshanah Bewlay: I did not take a single technology related course in law school! I fell into technology through my work in a large law firm's commercial litigation practice - being at the right place at the right time, just as eDiscovery was exploding as a practice.

Gail Gottehrer: It's not necessary to have a computer science degree or a computer science background to get involved in the digital space. You need strong reasoning skills, the ability to apply existing legal concepts to new technologies and situations, and a willingness to ask questions and learn. 

Maura Grossman: I do not believe that someone needs a computer science degree, or to have taken computer science courses, to become involved in or successful in the technology space. One does, however, need to have at least a basic understanding of data, analytics, statistics, and machine learning. I did not take my first computer programming course until this past year, but having knowledge of what is involved in programming, how technologists think and how to communicate with them, and understanding how to properly evaluate the output of machine learning systems and other technologies is essential. Most of these can be learned through some combination of reading, attending CLE programs, and experience. That said, if one has the opportunity and the chops to study and excel both in law and computer science, one should go for it, because that combination of skills is rare and would be highly sought after in this day and age.

What advice would you give junior women lawyers who want to pursue a legal career 
in technology?

Maura Grossman: I would advise them not to be afraid to specialize. Becoming a "go-to" person in a particular area can make the difference in your career. Read everything available in your area of interest, look for opportunities to speak and write, and seek out mentors in your field. Often, thought leaders are more than happy to correspond, meet for coffee, and make suggestions or introductions. Be persistent and reliable, and don't be discouraged by naysayers or negativity. Tune out the noise and follow your passions rather than the bandwagon.

Shoshanah Bewlay: Technology is a fun and exciting field that is rapidly changing. That makes it a bit different from other practice areas that have not changed much since the Magna Carta. Technology is ubiquitous now, and as technology continues to advance, people increasingly will have to grapple with the governance and other issues this phenomenon raises. The field is wide open. Don't be intimidated by the language of technology: embrace it. Like any language, you can learn it through immersion, osmosis, context and practice.

You are all at the top of your field. What obstacles have you encountered in getting to this 
point in your career?

Maura Grossman: The obstacles I have faced are probably no different than those faced by many successful, driven women working in male-dominated professions. They can include a variety of negative reactions for being outspoken and choosing to defy roles and stereotypes typically assigned to the female gender. It has been noted by some that women often have to be at least twice as good as their male counterparts to succeed because they are held to a higher standard. It is not uncommon for a woman to express an idea at a meeting only to have it ignored and later attributed to a male colleague as "brilliant." Despite these kinds of obstacles, there are plenty of men and women who are more than willing to help and to promote women on the merits, and those are the individuals to seek out as you maneuver around the others.

Gail Gottehrer: An obstacle I've encountered is the reticence of lawyers to embrace technology, the important role it plays in the practice of law, and the need for law firms to implement technological innovations in order to remain relevant. That has begun to change, as clients have become increasingly focused on data security, artificial intelligence, and analytics, which has led many law firms, and lawyers, to become more tech-savvy.

Sandra Rampersaud: Many. However, I tend to be a bit philosophical about the "obstacles" I have encountered. I view events and crossroads that have taken place on my professional journey as key moments, which, even if disappointing, can enrich who I am personally and professionally depending on how I chose to respond. So long as I don't allow those events to define my perspective and drive, I remain master of my decisions. Getting to the top of any field requires maintaining confidence in yourself and your abilities, and continuing to demonstrate critical thinking that sees beyond just today and deliver high quality results no matter the challenge or setback.

Shoshanah Bewlay: Early in my career, I was not paying any attention to who else was working in the eDiscovery field; it seemed to be "all hands on deck" at all times! As I specialized and moved into New York government service as the New York State Attorney General's eDiscovery Counsel, I found that my ability to "translate between IT and legal" was my most valuable asset and skill. Now, having parlayed my general legal experience and my ability to translate IT to lawyers, executives and other stakeholders into a role heading the legal department of the state's consolidated IT agency supporting more than 120,000 New York State employees, I know that my gender has not been an issue at all.

Have you found organizations like bar associations and industry trade groups useful in your career development and what about 
mentors?

Shoshanah Bewlay: Yes, absolutely. Through such groups, I have made contacts that have allowed me to publish articles, participate on important committees, and be considered for awards. Working with and among like-minded attorneys has led me to this point in my career. As discussed above by some of my fellow interviewees, one sure way to meet role models and mentors is through such groups. Get involved; you never know where it might lead. I have had several mentors over the years, both male and female. Early in my career, my mentor was an experienced securities litigator who taught me to triple check everything, exploit every legal weakness in my adversary's case, and make decisions confidently and as quickly as possible. Later mentors focused on instilling concepts of servant leadership and employee advocacy to enable the best work from the people working on teams you lead. This training has proven invaluable in my current role where the volume of work requires delegation of important tasks to trusted team members, and where making quick, dependable and accurate decisions is crucial. Technology is not just about bits and bytes; rather, the IT employees I advise every day support IT systems essential to public safety, child welfare, and the mental and physical health of New York's citizens. I believe that it is imperative that the state's technology professionals get the best possible legal advice, so they can fulfill their important roles enabling the critical missions of the agencies ITS supports.

Maura Grossman: I have found industry and bar organizations to be invaluable throughout my career. When I first started learning about eDiscovery and technology, I joined the Sedona Conference, the preeminent think tank in the area of electronic discovery. I was able to learn from and network with the top thought leaders in the field. Through bar associations, both at the state and city level, I met people who were helpful in securing me speaking invitations, and who wanted to collaborate on writing and other projects. These contacts and opportunities undoubtedly contributed to establishing me as an expert in my field. 

How are you involved in bar associations?

Gail Gottehrer: I'm very involved in the New York State Bar Association, and am a member of the Committee on Technology and the Legal Profession, the Blockchain and Cryptocurrency Subcommittee, the Social Media and New Communication Technologies Committee, as well as the Transportation Law Committee. Working with NYSBA, I organize and speak at CLE programs that are designed to help lawyers stay up to date with technology and to give them practical guidance on topics such as the GDPR, the Internet of Things, biometrics, data governance, vetting vendors, and workplace technology. In addition to NYSBA, I'm actively involved with the American Bar Association, where I hold leadership positions in the Woman Advocate Committee, the Judicial Intern Opportunity Program, the Pretrial Practice and Discovery Committee, and the TIPS Automobile Litigation Committee. Participation in NYSBA and the ABA, and in think tanks like the Sedona Conference, is a way to provide education to attorneys on important topics and to promote diversity and inclusion in the legal profession.

Sandra Rampersaud: Bar associations provide excellent training and networking opportunities for all, but especially for the young lawyer. They provide opportunities to remain in touch with colleagues and friends that you make over the years, and keep abreast of developments in the law that you may not have had time to research yourself. Of equal importance are the opportunities to engage in discussions relating to the practice of law, such as how to build a book of business, how to network effectively, how to be recognized and promoted, how to be a successful woman of color in the legal profession, etc. Over the years, I have had many roles. I have been a member of the Antitrust and Trade Regulation Committee of the Bar Association of the City of New York, Co-chair of the eDiscovery Committee of the NYSBA Commercial and Federal Litigation Section, and Treasurer and Executive Committee Member of NYSBA's Commercial and Federal Litigation Section. Each of these experiences has been incredibly valuable in enabling me to be where I am today.

Are there any issues you have encountered teaching law students of this generation that are different from when you were a law student?

Maura Grossman: It remains a challenge to convince most law students that they need a technical education. Many remain focused on securing employment at prestigious Wall Street firms and do not understand how critical technical fluency is and will continue to be moving forward in whatever size firm a young lawyer joins. Social media - which did not exist when I went to law school - has led students to have far shorter attention spans, sometimes resulting in struggles with communicating thoughts clearly, which is critical to exceling as a lawyer regardless of whether one practices in the technology space.