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LegalTech – Lawyers’ need for perfection clashes with tech’s need for iteration

Sondra Rebenchuk reveals the hardest part of technology implementation

A title like “Legal Technology and Process Improvement” might bring to mind images of someone who has been coding and hacking since Grade 6. 

Luckily, the team at Blake, Cassels & Graydon LLP is not one for stereotypes. 

“I had really never before contemplated working in legal tech. I didn’t really understand what the industry was. I didn’t know any of the players. But [someone] asked me for help, and if I wanted to join her team and get involved,” says counsel Sondra Rebenchuk, who worked as an AI practice consultant before joining Blakes.

“I was just at a place in my life where I was saying yes to opportunities, so I said yes.” 

Rebenchuk came to Osgoode Hall Law School from the west coast, landing a role at Goodmans LLP. But while her start may have been traditional, she got creative from there, working at a communications firm that specialized in proxy battles and mergers, followed by a stint in South Africa with her husband’s family. From there she joined Kira Systems, a Toronto tech company which helps businesses parse unstructured contract data and perform due diligence. There, she worked on training artificial intelligence with legal data, eventually working with clients across North America before falling into her current role at Blakes.

“Working in this space meant that I was able to address a lot of the challenges that I personally faced when I practiced, and that was very rewarding to me,” she says. 

“And I think that there were a lot of moments in those years when I was practicing where I realized that there was really an opportunity to do things differently. But I didn’t know how. I hadn’t turned my mind to the fact that it could be technology.” 

Rebenchuk will be speaking at Canadian Lawyer’s LegalTech Summit on May 26 in Toronto, in a session focused on practical tips for choosing the right technology. The big challenges, she’s found, aren’t always around the obvious questions, like which tools to use to go paperless.

“Especially with something like going paperless, make sure that you have a really, really good internal communications plan at the very beginning: ensuring that you’re talking to everyone at the firm who could be impacted, collecting their feedback, understanding their needs,” she says. 

“When you’re out there, and you’re looking at different document management systems, making sure that you’re choosing a solution that isn’t just something that you’ve read about and think is interesting, but actually fits the firm.”  

Legal tech always seems to fall short of the fast and powerful consumer technology available today, she’s found. Lawyers can have an “all-or-nothing” tendency, she says: to prefer either nothing or a perfect, complete system, with no compromises.

“A lot of the new technology in the legal space is helping to address pain points in very specific tasks. So, whether it’s contract review, generating signature page packages, automating agreements that are drafted over and over and over again — these are all very tiny pieces of work,” she says. 

“So, start to get comfortable with the fact that the technology will not be perfect. It won’t be able to do exactly what you can do. Setting the right expectations will make people more successful.”

Luckily, says Rebenchuk, there are more resources than ever for lawyers to learn about technology, as more mainstream legal publications explore the issue, in addition to stalwart blogs such as Legal IT Insider and Artificial Lawyer. In-house counsel have an additional resource in outside counsel, she says, adding that her firm has offered legal technology information sessions for in-house teams. Soon, she hopes, law schools will be another hub keeping lawyers up to speed on technology.

“If you start to think about technology as something that you’re in control of, and is something that can actually help improve your practice — not just something that runs in the background, that sometimes crashes or is sometimes too slow — that can be really powerful,” she says.

Hear more from Sondra, who is a speaker at the upcoming Legal Tech Summit on May 26. Visit for more information.

GCs favouring legal tech over external counsel

Clyde & Co expands liability practice with NY team hire… Gowling WLG appoints UK chair…

GCs favouring legal tech over external counsel
In-house legal teams are handling larger volumes and complexity of work and are looking to technology to help.

Rather than outsourcing more work to external law firms, general counsel are focusing on how tech can drive efficiency within their own legal teams according to a new survey.

The research from Konexo, the alternative legal services business of global law firm Eversheds Sutherland, found that 63% of in-house practitioners say they are dealing with increased pressures compared to 12 months ago.

These pressures include demands to reduce costs, while coping with a lack of resources, and a resulting impact on team culture.

“General Counsel today are operating in a rapidly evolving business landscape,” said Graham Richardson, Partner and Head of Konexo. “Despite developments in the sector, legal services have not yet been at the forefront of this evolution. However, as legal teams are increasingly asked to do more with less, technology, new operational processes and big data are rewiring how in-house legal professionals conduct their work.”

The survey shows that just 19% of respondents are planning to ease pressure through greater use of external counsel while increasing their tech usage in areas such as document automation and intelligent data analytics.

“There is significant scope for innovation in the industry and there is a real opportunity for in-house teams to assume a more strategic purpose in their organisations and outsource more, but not back to the traditional law firm model. Technology driven ALSP, with fixed-price models, will be a big part of the solution and we will continue to see the rise of legal managed service providers,” added Richardson.

Clyde & Co expands liability practice with NY team hire
A team of three experienced lawyers will enhance the global Law Firm Liability, Regulatory and Investigations Group at Clyde & Co in New York.

The trio from Hinshaw & Culbertson comprises new partner Rick Supple together with Of Counsel Anthony Davis and Janis Meyer.

Supple’s focus is representing law firms and lawyers in malpractice, disciplinary and other ethics related litigation and investigations. He also has a litigation finance advisory practice.

Davis and Meyer have built a practice advising law firms on legal ethics, risk management and all aspects of the law governing lawyers.

“We have strong trial capabilities across the US, which this team will enhance while providing us with the ability to work with, advise and defend law firms across the country,” said Carolena Gordon, Chair of Clyde & Co’s North American Board.

Clyde & Co launched in the US in 2006 and has seen strong expansion in recent years. It now has more than 60 partners among more than 350 people across 9 US offices.

Gowling WLG appoints UK chair
The UK LLP of Gowling WLG has announced its next chair following the decision of incumbent Andrew Witts to return full-time to his practice.

He will be succeeded by long-standing corporate M&A / private equity partner – and leader of the London team – Andy Stylianou, from May 2020.

As well as currently chairing the UK partnership’s Representative Council, Stylianou is a founding member of the firm’s Diversity Forum and a mental health champion.

Witts meanwhile, will build on his recent work with the firm’s Latin America launch in Brazil, and with the firm’s international fraud and disputes team, which will benefit from his full-time return to his own fraud and asset recovery practice.

Becoming a techno-lawyer can set you apart

Today, technological competency is an ideal addition to a lawyer’s skillset, says Daniel Lo

The legal industry is a conservative and unchanging profession. After the financial crisis, the legal industry started to feel the need to transform as clients began demanding cost-effective solutions to their legal problems. Client frustrations around the high cost of legal services include the billable-hour model, charging out of trainee hours, the high cost of preparing simple agreements and regular box-checking exercises such as due diligence.

We have seen an acceleration in technology adoption in traditional areas of law such as legal research, e-discovery, document storage and automation, billing and accounting and case and practice management. Recently we are seeing the focus expand to areas such as tools or marketplaces that connect clients to freelance lawyers, tools that allow clients to complete legal matters and documents by themselves, use of legally binding digital signatures, data and contract analytics, law practice optimization and much more. With the advent of blockchain, smart contracts and artificial intelligence, this pace of technological adoption does not appear to be slowing down, with many eyeing the US$600 billion global legal market. Although most legal technology out there right now is nowhere near perfect and still requires human supervision, it is only a matter of time that it is sufficiently perfected and becomes commonplace.

Deloitte predicts that around 114,000 legal jobs are likely to be automated in the next 20 years. Most of them will be junior roles.

Automation of routine processes and specifically defined legal tasks have made for more efficient delivery of services. Automation has reduced the need for lower skilled roles such as legal secretaries (as we are seeing the prominence of virtual and AI-based assistants), while new high skilled technologists roles have risen to manage the implementation of new technologies. There is further scope for even highly skilled roles that involve repetitive processes to be automated by AI and self-learning algorithms. The further proliferation and acceptance of legal tech in the wider legal industry will mean that future skill requirements for lawyers will involve some form of data analysis and technological acumen. Law firms will likely scale back on hiring on the junior end, and instead will focus on lawyers that have a solid grasp of using legal tech tools and the ability to understand and adapt to new legal tech, enter the “techno-lawyer.”

The impact that technology will continue to have on the legal industry is wide reaching. Law firms and in-house departments will see the growth of more non-lawyer roles and hybrid legal roles that involve the management and analysis of data. The number of traditional lawyers needed will decline, which creates an opportunity for those willing to learn and adapt to new technological requirements to progress faster than the traditional lawyer.

Career-path-wise, partners at a law firm can now choose to focus on an alternative path of managing teams that develop technology applications and initiatives in addition to choosing the typical streams of a technical ‘grinder’ or the ‘rain-maker’ business development path. This also opens doors for junior or mid-level lawyers that are looking for alternatives to legal practice but also want to keep one foot in to leverage their legal training.

Since legal tech is in such a nascent stage, how do you become a techno-lawyer?

1. Develop into a cross-functional lawyer

Being a lawyer just isn’t enough, purely legal roles will begin to dwindle (at existing legal tech companies this has already happened). As a first step of expanding your value proposition as an adaptable lawyer, consider pursing skills and experience that you enjoy and legal-tech companies or tech-optimized law firms can leverage, such as event planning, marketing, data analysis or market research. Develop these skills alongside your legal know-how to show you adaptable and able to learn new non-law skills.

2. Stay up to date and engage

Trying to break into a new industry means there are few experts in the space, the knowledge base will continue to grow exponentially. Subscribe to industry experts and stay on top of the latest legal tech tools and developments. Share your knowledge and develop a familiarity with the subject by writing articles, blogs, producing vlogs and posting on social media. Attend legal tech and blockchain conferences and seminars where you can network with other legal tech enthusiasts. Get the dialogue going with those interested on how you can get involved and throw around ideas on how legal tech can improve your practice. Become a matter expert and start to develop a reputation as the go-to techno-lawyer.

3. Learn how to code

Learning code isn’t for just computer science majors anymore, many post-secondary institution are making it mandatory for first year students to learn it (think Harvard University and their introduction to computer science class).

I believe that learning code should be mandatory for law student and lawyers to learn and should be part of any law school and articling curriculums. Learning the new literacy of code will give you a significant advantage when it comes to advising legal tech businesses or working within one. It also gives you the distinct edge of being able to translate between the two equally daunting languages of code and legalese. After delving a bit myself, to my surprise I even found similarities in the two languages (Assigning a variable in coding is basically setting up your defined terms in legal speak). The two main programming languages lawyers should consider learning are either Python or Javascript. However, I was advised that Python is the default language these days. There are many services out there that you can use to learn on your own for free or for a fee, such as through Udacity, Coursera and Codeacademy.

If you are willing to learn and embrace this new career path, you will be well prepared for the disruptions that lay ahead and will lead an exciting career as a techno-lawyer.


The state of legal tech

Very late last year, Tel Aviv-based business-to-business company LawGeex announced that total 2018 investment in legal technology — a.k.a. “law tech” or (more frequently) “legal tech” — had surpassed US$1 billion.

That was up from the US$233 million invested in 2017, said LawGeex — a four-year-old, 80-employee legal tech firm that has itself attracted US$21.5 million — more than half of that last year.

An arguably more modest view was provided by San Francisco market monitoring website Crunchbase News, which told Canadian Lawyer in late December that total global legal tech investment for 2018 stood at almost US$700 million — up from the US$250 million it reported for 2016.

Also in late December, Stanford CodeX — a database run by Stanford University’s CodeX Center for Legal Informatics in Stanford, Calif. — tallied actual legal tech firms worldwide at 1,107 — just less than half the number reported by Netherlands-based legal tech website Recent Thomson Reuters research, meanwhile, reveals a five-year 484-per-cent increase in global patent filings for new legal tech, with the U.S. and China among the most prolific applicants (Thomson Reuters is the publisher of Canadian Lawyer).

LawGeex vice president of marketing Shmuli Goldberg says that despite the industry’s apparently “explosive” growth, it remains “very early days” for the legal tech industry due to lawyers’ low adoption levels.


Toronto-based lawyer Mitch Kowalski — a professor of legal service innovation at the University of Calgary Law School and author of the book Avoiding Extinction: Reimagining Legal Services for the 21st Century — is bearish by comparison. He says legal tech remains stuck in “hype mode” in a “bubble that will burst and taint the entire sector.”

Says Kowalski, “Just like the fog of war, there seems to be a lot going on out there with legal tech, but it’s becoming more and more difficult to keep up with all the players. Like the boom, it has become nearly impossible to sort out what’s real and what’s just good marketing.”

Kowalski adds that while the market is seeing increased acquisitions, and while there have been a handful of big funding rounds, this is “very normal for nascent sectors.”

Furthermore, most rounds have been small.

“This suggests that while there’s healthy interest in legal tech, venture capitalists are not willing to go ‘all in’ unless there is a proven, compelling business case.”

Addison Cameron-Huff, a Toronto lawyer and computer programmer who follows legal tech closely, agrees.

“Canadian venture capitalists really want to see revenue or, ideally, profits. They are conservative compared to U.S. counterparts,” Cameron-Huff told Canadian Lawyer via email.

About hype, he says, this applies mostly to artificial intelligence legal tech startups.

Machine learning and analytics …

Nick Robertson is chief operating officer at Relativity, an 860-employee, Chicago-headquartered B2B legal tech company with offices in London, Krakow, Hong Kong, Sydney and Melbourne. Set up as a software company in 2007, Relativity attracted US$125 million from Iconiq Capital in 2015 and claims 180,000 users in 40 countries, including 198 of the 200 biggest U.S. law firms.

Robertson says the big change in legal tech right now is an upsurge in machine learning and analytics. Adoption is up a lot during the past five years, he says, with “85 per cent of Relativity’s customers currently licensing machine learning across all their matters.”

Robertson says he’s seeing one person get through multi-million-document sets in days. That’s “staggering” given that five years ago that probably would have taken months and hundreds of lawyers.

… Improved documentation and drafting, too

Toronto-based Carla Swansburg is general manager of the Canadian operations of Epiq, a 30-year-old U.S. company that employs 4,200 people and outsources document review to lawyers. She says big current legal tech developments include better document automation and more sophisticated drafting tools. Meanwhile, Swansburg also sees increased “visualization” of legal research — with tools such as NexLP and Brainspace creating “powerful ways to present information and quickly absorb data.”

“In the U.K., some of the larger firms have automated initial drafts of suites of deal documents like financings, [while] in Canada the focus has been on automating NDAs, employment agreements and other, less complex documents,” says Swansburg.

It’s the cloud, stupid

Yet it’s cloud computing — and the legal operations-related opportunities it’s enabling — that dominated the more than 20 interviews Canadian Lawyer did for this story with legal tech lawyers, leaders, academics, techies and commentators.

Jon Kerry-Tyerman is a vice president at Everlaw, an eight-year-old, 100-employee U.S. legal tech firm that attracted US$35 million in funding in 2018. He told Canadian Lawyer via email that, while “two or four years ago, some purchasers still avoided the cloud and treated it as a fad,” nowadays, the legal services industry regards it as “inevitable.”

Relativity’s Robertson agrees, saying cloud computing — along with the growth of legal software-as-a-service (SaaS) tools — is impacting e-discovery in a “big way” as organizations increasingly move their data to the cloud. For example, says Robertson, 96 per cent of Fortune 500 companies use “at least one Microsoft cloud offering,” with a rise in cybersecurity-related risk among the forces pushing lawyers into the cloud.

“A few years ago, the prevailing wisdom was that the most secure solutions were on private clouds. That’s no longer the case, given the massive investments being made by companies like Microsoft,” says Robertson.

He adds, “If a company’s data starts in the cloud, they don’t want to move it for purposes of an investigation or e-discovery . . . SaaS delivered via the public cloud offers customers unparalleled flexibility and an increased confidence about hitting deadlines and responding to the courts and regulators.”

AP whats …?

Cloud computing has, in turn, enabled legal tech’s other big news — application programming interfaces, or APIs — which is computer code that allows apps to work well together. The technology has fuelled much of the growth at legal tech heavyweight Clio, a 320-employee company based in Burnaby, B.C.

Clio’s lawyer in residence, Joshua Lenon, says that Clio published its first API in 2012 — a “pioneering” move that allowed Clio to offer customers integration with other best-in-class software solutions such as Fastcase and QuickBooks Online.

Essentially, says Lenon, APIs have allowed Clio to take a “collaborative market approach.” Alongside acquisitions such as Lexicata and collaborations with Alt Legal — a New York legal tech firm focused on IP docketing — Clio has used APIs to solve problems “we would have had to tackle.”

Says Lenon, “Together, APIs and acquisitions have allowed us to focus on our core strengths and [to subsequently] leapfrog our development forward by years.”

After all, says Lenon, “some user needs are so niche, Clio cannot build them any time soon.”

One constant remains

One not-so-new defining characteristic of the state of legal tech is, of course, mounting client pressure on law firms for less cost and more transparency.

Keith Lipman is co-founder and CEO of legal tech company Prosperoware, an 85-employee, nine-year-old U.S. legal tech company with more than 300,000 users, including half of the biggest U.S. law firms and a quarter of the U.K. ones. He says bigger and bigger in-house teams are applying “tremendous pricing pressure” to law firms unprepared for the “fundamental shifts” being unleashed by legal tech.

Relativity’s Robertson agrees, saying in-house lawyers are seeing an imperative to treat legal and litigation as an operation “like any other in their business.”

And to put that another way, Cameron-Huff says many clients dislike what he calls law firms’ operational “black boxes.”

Nowadays, he says, “clients want to know how things are progressing — really the intrusion of the KPI-managerial mindset into law firms.”

It’s perhaps easy to see why when a 2018 study involving legal academics reportedly saw LawGeex’s AI tool achieve an average 94-per-cent accuracy rate, higher than that of 20 top lawyers (85 per cent). Reported Crunchbase News at the time, “It took the lawyers an average of 92 minutes to complete the NDA issue-spotting, compared to 26 seconds for the LawGeex AI.”

Go, Toronto!

Amid all this change, Matthew Peters — national innovation leader at law firm McCarthy Tétrault LLP — says Toronto has a chance to turn itself into the world’s first legal tech supercluster.

Peters points to Toronto-headquartered legal tech major players Kira Systems and Blue J Legal as evidence. Kira, with 130 employees and five of the biggest Bay Street law firms as clients, attracted US$50 million in its first external funding round in 2018 — by far one of the largest legal tech rounds to date. The same year, 33-employee Blue J attracted US$7 million in Series A funding. The latter company — a University of Toronto startup — has 120 clients, including law firms Osler Hoskin & Harcourt LLP, Fasken, Gowling WLG, Miller Thomson LLP and accountants Collins Barrow.

Says Peters, “Downtown Toronto has a very strong concentration of clients and law firms. Then you’ve got MaRS, Ryerson University’s Legal Innovation Zone, the Creative Destruction Lab, Thomson Reuters and OpenText Magellan … Big buyers, big users.

“It’s an incredible legal tech ecosystem, stronger than that of Silicon Valley, New York City or London, England,” says Peters.

In fact, Ontario-born Andrew Arruda, the CEO of U.S. AI-focused law tech firm ROSS Intelligence — which opened in Toronto last year — says that if he could have done anything differently, it would have been to “expand our engineering presence in Canada sooner.

“There’s such an incredible talent pool in Canada that’s actively looking to stay, instead of moving to Silicon Valley,” Arruda told Canadian Lawyer via email.

Epiq’s Swansburg calls Canada “a great sandbox.”

“Success breeds success. There is a strong, connected support community. Also, the Canadian market here is smaller, more definable and, in many ways, more accessible — making for easier testing, and a lower risk environment.”

Not so fast

Toronto has plenty of competition, however.

The U.K. and Singapore governments are actively investing big bucks in legal innovation, most of the big English law firms are tangibly working with legal tech players, while the U.S., Israel, China, Russia, Berlin, Paris and Brazil’s São Paulo financial centre are all chasing the legal tech supercluster crown.

Canada probably has some ground to make up, says Arruda, especially compared with the U.S.

“Canada is maybe lagging a bit behind . . . [due to] the Canadian market, until very recently, being essentially closed off from international competition. There’s a lot of interesting work happening in Europe, especially in London, and I’m continuously impressed by the focus and momentum building around Asia’s legal tech industry.”

Toronto lawyer Kowalski says Canada’s “not a hotspot” for venture capital and agrees the legal market is small.

“The U.S. has a massive advantage due to size and the relatively homogenous legal market with its uniform language and common law system. The EU’s of comparable size but fractured by language and different laws, which handicaps its legal tech scene.”

Says Kowalski, “It’s noteworthy that Clio and Kira, the two most successful Canadian legal tech companies, have created products that are jurisdiction agnostic — they can be used in virtually any jurisdiction or language.”

How to be a B2B legal tech titan

LawGeex’s Shmuli Goldberg: “Recognize the exact pain points facing many in-house lawyers. Businesses want to see their lawyers doing tasks more strategic than contract review and approval. Focus on doing one thing very well. Despite the hype about AI, we are very honest with customers about what we can and cannot do. This engenders trust and builds sustainability. [Also, entrepreneurs should remember that] lawyers are change-averse, meaning you must make a very good case for change, and then show your customers value very early on so they can then show it as soon as possible to their CEOs and CFOs. Other success drivers? Prioritizing prospects and customers who were streamlining their operations and looking for tangible, quantifiable return on investment.”

Prosperoware’s Keith Lipman: “[We grew big] by carefully managing cash flow, focusing on understanding client workflows and processes, and because of our deep domain expertise and great software engineering experience. Many lawyers try to become engineers without software experience, while a lot of developers try to jump into the legal industry and solve its technology problems.”

Relativity’s Nick Robertson says that his company’s success drivers included bootstrapping and making a profit for more 10 years before raising US$125 million from Iconiq Capital in 2015. Meanwhile, Relativity has focused completely on e-discovery for 10 years, says Robertson. Furthermore, it has always invested heavily in free 24-7 customer support, documentation, training and online user communities. In addition, Relativity uses its marketing budget to add value to customers instead of for outbound marketing. For example, “our Relativity Fest user conferences in Chicago and in London, England connect thousands of customers and certified Relativity professionals during hundreds of unique educational sessions.”

ROSS Intelligence’s Andrew Arruda: “We were founded at the University of Toronto — one of the world’s leading AI institutions — by students, including AI researchers, and former attorneys. My advice for legal tech entrepreneurs? Build something you love alongside people you love working with whose skillsets complement yours.”

Clio’s Joshua Lenon says ensuring great service and a “clean, easy” user experience can turn customers into “evangelists.”

Other top B2B legal tech companies

Canadian Lawyer also approached Anaqua, Concord, Disco and Workshare for interviews. 

Boston-headquartered Anaqua (approximately 180 employees, founded in 2004) helps clients better manage patents, trade secrets and trademarks. With more than 20,000 users, Anaqua has attracted investment of US$125 million. Anaqua has two other U.S. offices and six more in six other countries. Anaqua owns established legal tech company Lecorpio. Robert Romeo is CEO. 

In 2018, San Francisco-headquartered document management company Concord (approximately 100 employees, founded in 2014) had raised more than US$51 million. Concord, also in Paris, works with more than 200,000 companies. Matt Lhoumeau is CEO. 

Austin-based e-discovery company Disco (200+ employees, founded in 2012) has attracted US$50 million, including US$20 million in 2018. Used by 50 of the top 200 U.S. law firms, the company’s software automates and simplifies complex and error-prone tasks. Kiwi Camara is CEO. 

London, England-based Workshare (approximately 180 employees, founded 1999) helps lawyers and other professionals compare, protect and share documents across devices. With offices in the U.S. and Australia, Workshare’s website says it has more than two million customers in 70 countries. Michael Garrett is CEO.

Ones to watch …

Canadian company Closing Folders (approximately 15 employees, founded 2013) is one to watch, says Kira Systems CEO Noah Waisberg. Legal Innovation Zone managing director Chris Bentley adds that Closing Folders is used by “just about every Toronto law firm.” He also highlights Lex Machina (approximately 80 employees, founded 2010) as a “big deal” in legal tech. Lex Machina has attracted at least US$8 million. That company, along with Ravel Law (approximately 16 employees, founded 2012), is owned by legal intelligence giant LexisNexis. U.S. company Fastcase (approximately 50 employees, founded 1999) is singled out by Clio executive Joshua Lenon as significant, while Epiq Canada’s general manager Carla Swansburg highlights HighQ, Recommind (a search-focused subsidiary of OpenText Corporation), Luminance (a U.K.-focused Kira competitor) and AI-powered document extraction company iManage RAVN — a company founded by Prosperoware’s co-founder and current president Keith Lipman. 

Atrium (130 employees, founded 2017) is a San Francisco-based law firm combined with a Delaware-based corporation. Atrium’s relatively new technology platform helps clients draft and review commercial contracts and raise capital, among other tasks. Atrium has US$75.5M from investors that include Andreessen Horowitz (a prominent legal tech investor), as well as top tech incubator Y Combinator. Atrium is backed by Twitch founder and Y Combinator partner Justin Kan and was co-founded by Silicon Valley corporate lawyer Augie Rakow.

But … Don’t forget, says Cameron-Huff, the two established legal tech players, LexisNexis and Westlaw (owned by Thomson Reuters, publisher of Canadian Lawyer). “They are huge and have lots of great products,” he says. 

“There’s a bit of a debate as to whether legal tech means startups or should mean the broader industry. It should include the giants because they make the most widely used tools, and some of them are excellent.”

Tech support: law firms lining up to take advantage of tech boom

“Technology has no boundaries. Everything either is touched by it or will be in the future.”

Canada’s tech sector is booming, and law firms of all shapes and sizes are lining up to take advantage.

In its recent tech talent survey, commercial real estate and investment company CBRE placed four Canadian cities in its top 25 North American markets, crediting cost-efficient office space and comparatively welcoming immigration policies for the list’s high Canadian content.

Toronto, whose record-high fourth place was sealed by a 14-per-cent boost in tech jobs that made it the fastest-growing hub on the list for the second year running, was also joined by Ottawa, Montreal and Vancouver.

“Tech is a key sector for us,” says Viona Duncan, co-chairperson of the global tech practice group at international law firm Gowling WLG.

Still, she says, the all-encompassing nature of technology makes her client base a hard one to pin down.

The startup-rich environment of Duncan’s Waterloo, Ont. base is perfect for finding clients taking their first steps in cutting-edge industries empowered by advances in artificial intelligence, blockchain and crypto-currency. But the firm also caters to more traditional, old-world powerhouses venturing into new technological waters or dealing with the privacy and cybersecurity issues that come with them.

“Technology has no boundaries. Everything either is touched by it or will be in the future,” says Duncan. As a result, her practice group is among the most integrated at Gowlings.

“It’s unique in the sense that we interact with probably every other practice group and industry sector. We’re dealing with lawyers across the firm, nationally and internationally,” Duncan says. “Employment lawyers need help with issues posed by artificial intelligence in recruitment; we might be dealing with people in the automotive law group on driverless cars or helping the financial services group with fintech matters for banks.”

According to Duncan, the common thread running through the tech group’s diverse collection of clients is the break-neck pace of change they’re all dealing with.

“Our job is to keep up with what’s happening and relieve some of the pressure on our clients by seamlessly servicing them,” she says.

Calgary lawyer Erika Carrasco says the law surrounding drones offers a typical example of the challenges of working in such a fast-developing area.

“When I started, there were really no regulations relating specifically to drones,” she says.

Instead, when she litigated in 2016 and then successfully appealed Alberta’s first criminal conviction involving an unmanned aerial vehicle, Transport Canada categorized them in a similar way to kites and model aircraft.

Less than three years later, “it’s a completely different landscape,” says Carrasco, noting that a series of interim measures and regulatory amendments are due to culminate this June with the enactment of detailed rules distinguishing between basic and advanced drone operations and setting out fines and potential jail time for violators.

Inspired by her own experience, Carrasco, a partner at Alberta full-service outfit Field Law, led the development of a broader emerging technology practice group, focused on cyber-liability, autonomous vehicles and internet law, in addition to drones. She says her partners needed little convincing to support the group as one of the firm’s key strategic initiatives.

“I realized there was big demand out there,” Carrasco says. “And there didn’t seem to be many firms in Canada offering a comprehensive service to clients. This felt like a good way to bring a good, solid range of technology law-related services to them, rather than acting on a case-by-case basis.”

In addition, the firm remains open to embracing and adding new specialties to its list of emerging technologies.

“The law moves slower than the industries themselves, and because innovators are prepared to move on regardless of where the law stands, it’s almost more important to understand where everyone is heading, by having your finger on the pulse of stakeholders,” Carrasco says. “It’s challenging. But then, that’s part of the reason why I like it so much.”

In Montreal, litigation partner Neil Oberman at Spiegel Sohmer says the entrepreneurial nature of his clients in the city’s thriving tech space means he frequently treads a fine line between being the voice of reason and the party-pooper.

Young founders don’t always want to hear about the necessity of a shareholder agreement between partners, a tax-efficient corporate structure or the grinding reality of advancing or defending a legal claim in the courts, he explains.

“Their desire to be ahead of the curve sometimes makes them forget about the basics in law, and you can feel like a part-time psychiatrist and part-time lawyer,” Oberman says. “We try to not only be reactive but also proactive. If you can impart the need to be slightly conventional in terms of business structure and protecting intellectual property rights, then it’s much easier when it comes time to react, whether that’s to a dispute with a shareholder or infringement by a competitor.”

But when they strike the right balance, Oberman and his team feel like members of a startup’s family, he says. By helping clients develop and implement a long-term strategy, they can grow in tandem with the enterprise, adding to the legal team as needed.

“It’s symbiotic,” he says.

But it’s not just full-service firms embracing the tech law boom. At boutique business and technology law firm Oziel Law in Toronto, founder Allan Oziel has built a practice devoted to clients in innovative industries.

“Boutiques fare very well in this area because there are multiple sizes of businesses,” he says. “Large firms will take on the huge procurement projects for their existing institutional clients, but there are also a lot of small and mid-size businesses that either have tech law requirements or who are tech companies themselves and are looking for specific expertise at more affordable rates.”

Even as larger law firms start their own programs to attract up-and-coming tech companies at earlier lifecycle stages, Oziel says, there are still plenty of potentially thriving businesses overlooked.

“They have to start somewhere, and they’d rather start with someone who is capable of understanding their offering without having to spell out the meaning of the technical language they’re using,” he says.

And many of his tech law clients find a kindred spirit in Oziel, a self-professed — and self-taught — “tinkerer” who built his own computers, websites and networks in his younger days.

“Technology was a big passion of mine, and I knew I wanted to incorporate it into my practice,” he says.

Over the years, his firm has grown to four lawyers, and it now accommodates businesses at various stages of development.

“At one time, it was mainly software and hardware startups, but our clientele has grown. There are different points at which we pick them up, whether they’re seeking to raise money, wanting to go public or seeking exits,” Oziel says.

And while his own tech-savviness lends him a degree of credibility with clients, that only takes Oziel so far. He also prides himself on his adoption of cutting-edge legal technology to boost his practice’s efficiency.

“If tech-forward clients came to my office and saw I was doing everything manually on paper, they might question my understanding,” he says. “But when they come to our practice, it gives them some comfort that they are speaking with someone who cares about being up to date.”

At McCarthy Tétrault LLP’s Toronto office, Christine Ing, co-leader of both its information technology law and fintech groups, sees herself as a custodian of the firm’s storied history in the space.

And a crucial factor in maintaining that reputation is McCarthys’ ability to reflect clients’ creativity back at them in the delivery of legal services, she says.

“The firm has always taken outside-the-box approaches to providing solutions to clients,” Ing says, pointing to MT>3, its e-discovery and digital information division, and MT>Play, its recently formed global gaming consultancy.

“Technology is constantly evolving, but it’s rare that you find something completely new, and there is usually something in the law and prior commercial approaches that you can draw from to come up with a new solution,” she adds. “It takes some creativity, but it is also a lot of fun.”

Oziel expects more transformation of the field as lawyers specialize in current and yet-to-emerge technology.

“Young lawyers should start thinking about becoming expert in a very particular area and build a good practice by staying up to date and providing good advice in that niche.”

Innovations in estates law: How legal tech is revolutionizing death

New technologies are just in time for biggest wealth transfer in history

The legal profession is often criticized for its archaic and antiquated appearance. Images of a lawyer wheeling around a 30-kilogram, 40,000-page file-folder that, if digitized, could fit on an IPhone or draped in robes (or sporting a wig in the U.K.) help to drive the stereotype. In the courtroom, when liberty, property and reputation hang in the balance, the processes relied on can operate, technologically, decades behind even an elementary school classroom.

How the law deals with end-of-life planning is not immune to this stasis.

Jordan Atin, counsel at Hull & Hull LLP, is among those using technology to change that.

“I’m just a wills and estates guy. That’s all I do is draft wills,” he says, adding that how those wills are planned “has not changed in 500 years.

“You sit on one side of the desk, the lawyer sits on the other side of the desk and they say to you, ‘So tell me what you own. Tell me all the names of your kids. What do you want to do with this? And what do you want to do with that?’ and the lawyer takes down notes and then produces this big, thick document that no one really understands,” Atin says. “It’s still being done in 99.9 per cent of situations that way.”

But succession plans have never been more relevant. As baby boomers age, retire and die, an unprecedented sum will be bequeathed. Wealth Professional Canada reported in 2018 that between 2016 and 2026, around $1 trillion will pass through inheritance in Canada.

But there are signs Canadians could muff the handoff. A 2018 poll from Angus Reid found that more than half of Canadians don’t have a will, only 35 per cent have one that is up to date and 18 per cent of those without a will said it was because it’s too expensive.

Filling these gaps are a torrent of legal tech products built to serve lawyers and clients in wills, trusts and estates.

Five years ago, Atin and Hull & Hull co-founder Ian Hull created an AI-powered, will-building tool that, depending on the situation, types of assets, tax status of family members and other considerations, provides advice about how to arrange the estate plan.

“It’s a simple process but extremely powerful. [It] covers every kind of conceivable option. But for the client [it] is straightforward, simple and visual,” Atin says.

Atin, an adjunct professor at Osgoode Hall Law School and a certified specialist in estates and trusts, says Hull e-State Planner is not about saving time. Although the tool has made him more efficient drafting wills, he says, clients appreciate the real-time visual representation of the plan specifics they are trying to communicate to their lawyer.

“It’s actually value added rather than saving time,” he says.

Legal tech products such as Atin’s and Hull’s are popping up in every practice area.

For Willful CEO Erin Bury, her idea was inspired by a negative experience with the status quo.

Bury and her husband Kevin Oulds co-founded Willful in 2016 after an unexpected death in Oulds’ family put the complexity and difficulty of end-of-life planning front and centre in their lives.

“And while that person did have a will, they had never discussed end-of-life planning — whether they wanted to be buried or cremated or what type of funeral they wanted. So, his family was arguing over all of this stuff, while trying to plan it,” Bury says.

“Being a millennial who used a lot of text-driven apps, [my husband] just wondered why the estate-planning process hadn’t been touched by technology and was still being done the same way as it had been 50 years ago,” she says.

The original plan for the app was to address a person’s death-related interests outside of the scope of a will — such as funeral wishes, subscriptions, online subscriptions and other aspects of a person’s digital footprint, she says. But research led them to find that people didn’t want to think about their own death and the “must-have” was the will creation itself. They launched the will-making app Willful in May 2017. It began in Ontario, has since expanded to five provinces and Bury says they plan to reach across Canada by 2020.

Neither is a lawyer by trade. Bury and Oulds partnered with estate lawyers from across Canada to create Willful’s legal content and initially found it difficult to find practitioners who wanted to assist in their automation.

“Because, obviously, we’re calling them and saying, ‘Hey, can you partner with us to create legal content, so people can use our service to avoid coming to you?’” she says.

However, Bury found there “isn’t a tonne of crossover” between Willful’s customer base and clients designing $2,000 wills in their lawyer’s office. The hardest part, she says, is getting people to think about estate planning to realize they need to get it done.

To help nudge people toward addressing that unpleasant topic, Sharon Hartung, a retired aerospace engineer for the Royal Canadian Air Force and an IBM executive, wrote Your Digital Undertaker. Through her exploration of estates law and background in tech, Hartung identified an incoming shift in life’s leftovers.

“I really began to realize that, in the digital age, it’s going to get really interesting for us in terms of how the estate industry is going to deal with our digital footprint, notwithstanding the transformation that’s about to happen with the largest wealth transfer and the impact of technology,” she says.

The internet will affect estates lawyers in three ways, she says. First, clients will now have digital assets: email, social media history, gaming tokens, cloud repositories and crypto-currency. A spokesperson from Deloitte Canada told The Globe and Mail that, by 2020, the average Canadian will have digital assets worth at least $10,000.

Second, there is new law emerging to change the role of an executor to fit a digital life. The Revised Uniform Fiduciary Access to Digital Assets Act gives executors a legal method of managing digital assets in the U.S., and similar laws appear to be on the way in Canada, she says.

Third, “technology is the new player at the estate planning table,” as tech entrepreneurs unleash new products like Willful and Hull e-State Planner.

NoticeConnect is also such a product. Founder Patrick Hartford was studying for the estates section for the bar exam and came across the practice of publishing notices to creditors. The expensive and mostly fruitless ordeal struck him as an obvious gap that could be filled with an online service. 

“Though it was really, I think, a way to avoid studying for the bar, I thought maybe this could be done online. And it turned out there was no reason that couldn’t be,” he says.

Hartford’s company created a website for publishing, accessing and managing legal notices and connecting them with their intended audience. In 2017, the company brought a test case to the Ontario Superior Court and the ruling confirmed that NoticeConnect satisfied the requirements of the Trustee Act. 

In the process, Hartford also found there was a need for a centralized will registry and so his company recently launched Canada Will Registry. At the time of writing, they have 84,000 registered wills, 730 law firms using the product and, once they reach 100,000 registered wills, they’ll implement a search function, Hartford says. 

“We want it to be the estate equivalent of a title search in the real estate context,” he says.

Editor’s Note: This article was corrected to clarify that NoticeConnect and the Canada Will Registry are two distinct products.

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