Legaltech Startups Step Their Game Up in Toronto

A new breed of tech entrepreneur is here and they’re the James Bond of founders.

I ended my chilly Wednesday in Toronto by attending the Legal Innovations Pitchfest at Dentons LLP, a law firm in Toronto. That a BigLaw firm such as Dentons is taking a leadership role in the Toronto legal startup community is amazing, and there was no doubt among any of the attendees that it was a superb venue for the pitches.

First up for the day was ROSS. They’ve built a digital legal expert to help attorneys power through their legal research. Powered by IBM’s Watson supercomputer, ROSS will endeavor to be the next generation of intelligent legal research and monitoring.

ROSS shows the promise that Law x Tech can have on caffeine – here, in the form of a supercomputer. While their pitch was very simple and effective, when they mentioned that massive power of Watson there was a palpable energy in the full, almost exclusively suit-clad crowd. If the execution is there, ROSS has the potential to not only disrupt the legal research space but to be a real thunderball in the Canadian legaltech community.

The second company to pitch was TitanFile. They facilitate secure file sharing from a desktop, mobile device or tablet. TitanFile organizes channels around people and relationships rather than in a maze of folders. All information stored on TitanFile servers is encrypted and stored in secure facilities.

TitanFile endeavors to be the living daylights of file sharing. With a new CEO who brings significant operational management expertise, TitanFile conveyed that they are not only a secure turnkey solution but a simple one as well.

Closing Folders was up next. This startup helps corporate lawyers manage documents and signatures in legal transactions. Closing Folders automates the repetitive work required for getting ready for a closing in an M&A or corporate finance transaction so that lawyers can focus on actual legal work.

Closing Folders had superb pain point identification and discussed the huge disconnect between reality and illusion of the practice of law for attorneys which transforms many young practitioners from Mr. Yes to Dr. No.

An exceptionally good point made by ClosingFolders is that, often in legaltech, the greatest competition comes not from another company but from the status quo – just doing things as they’ve always been done. I’d argue that this is also true in many other startup verticals.

After a quick twitter and microsandwich break with a lovely view of Toronto’s vibrant financial district, we heard from Koneka. Their document engineering solutions leverage workflow, business rules, embedded applications and rich content definition to streamline the assembly, modification and production of large and complex documents. Koneka’s innovative solutions are aimed at the legal, technical and proposal document markets.

I loved that Koneka began their pitch in French, a reminder that this is Canadian tech and that, truly Canada is not enough. Their intelligent document solution has global applicability and would work well in practically every market.

Finally, it was GreatWork at the podium. This startup provides an adaptable and easy-to-use set of tools to engage all sorts of stakeholders from work teams to customers. Tailored for organizational growth and change, GreatWork seeks to make engaging people a scalable and easy to lead process.

GreatWork was a very different startup and pitch from the others. This was focused on harnessing technology to create change in what is a really interesting way.

Disappointing yet not surprising was that only one of the entrepreneurs pitching was a woman – a co-founder of Great Work. While diamonds are forever, so is the profound gender imbalance in legaltech specifically and tech generally, not that this observation is, in any way, anything but obvious.

There was no actual winner of the Dentons event, as the panel was there for feedback and support rather than formal judging. The best pitches were reminiscent of the most redeeming parts of James Bond himself – a fragrant brew of stealth, personality, and wonderful efficiency. The overall quality of the startups (and of this curated, niche event overall) is a superb leading indicator of where legaltech is heading in Canada. My best sense is that the audience was vigorously shaken, as well as ardently stirred.