women of legal tech

Women of Legal Tech: Natalie Worsfold

The Legal Technology Resource Center’s Women of Legal Tech initiative is intended to encourage diversity and celebrate women in legal technology. This initiative launched in 2015 with a list of innovators and leaders in legal technology and with this year’s additions, that list now includes 100 talented and influential women leaders. Every Monday, we featured a woman from our class of 2019. For our final week, we have Natalie Worsfold!

Natalie Worsfold is Co-Creator of CounterMeasure at Counter Tax Lawyers. Find her on Twitter @NatalieWorsfold.




How did you become involved in legal tech?

I became involved in legal tech because of my desire to be a better lawyer. To me, legal tech is just part of the practice of law. I want to produce high-quality work and use my time most effectively. I need all tools, including legal tech tools, to do that.

I have been a tax litigator since 2008 and our firm, Counter Tax Lawyers, has always used technology to help us work smarter. I got more involved in legal tech in 2013 when we were trying to find ways to improve our quality standards as our team expanded. We mapped out steps and templates for over 50 processes in our litigation files and built them into our practice management system to help teach team members the best way to resolve a client’s case. Then we set up an internal Wiki to help us share knowledge and have been iterating ever since.

My love of statistics and data bubbled to the surface when I was trying to find ways to measure the impact of our work and we proudly published our first performance metrics in 2016. Since then, I have been researching how to make our case analysis better and ways to improve our client’s litigation strategy. That naturally led to technology and in 2017, we started focusing on building litigation software, called CounterMeasure, that uses risk and decision analysis tools like decision trees to bring structure to our team’s case analysis and better predict case outcomes so our clients can make smart litigation decisions.

What projects have you been focused on recently?

My focus is our software, CounterMeasure. We combine legal judgment and expertise with analytics and automation to amplify case analysis, strategies, and predictions so we can quickly and cost-effectively help clients decide the best litigation strategy. Right now, I am focused on ways to improve the accuracy of our predictions and how to take our experience with our tax litigation module and broaden it to all types of litigation.

Is there a legal tech resource of any kind that you find yourself returning to or that was particularly formative for you?

I love The Lean Startup by Eric Ries. Peter Aprile and I started the Building NewLaw podcast in 2016, and I learned an incredible amount from the guests who were kind enough to share their thoughts and experiences with us. I go back to the episode with Seth Godin constantly because I think he has so much insight into the mindset shifts needed to help the legal profession embrace technology and innovation.

Events like ABA TECHSHOW, ClioCon, and Mitch Kowlaski’s Legal Innovators’ Roundtable in Toronto helped me to connect with like-minded people and feel less like I was crazy. I think that the legal tech community on Twitter is my most frequent go-to resource.

What technology do you think lawyers could look at in a different way that would benefit society?

I think society benefits when lawyers look at any technology in a more positive way. For something simple, I’m going to say video-conferencing tools. Things like Zoom and Skype are a way to connect with and understand our clients and other people, like colleagues or opposing counsel. It’s much harder to be evasive or rude when you can hear or see the person you are talking to. I think we can use these tools to increase our communication skills and empathy and to reach people who can’t travel to an office or who simply don’t have the time to travel. I think video conferences can help us stop getting lost in the overly “legal” side of law and remember this is all about helping people.

What advice would you give to other women who want to get involved in legal tech?

Just do it. Legal tech is a very broad and welcoming community, and people are eager to help. Try it out and see what you think. What’s the worst that can happen?

Give a shout-out to another woman in legal tech who you admire or have learned something from!

There are too many. I first met Monica Goyal in 2011 at LawTechCamp, and everything she talked about made so much sense to me. It was inspiring to see such an amazing lady building great tools. In 2016, I met Alma Asay at ABA TECHSHOW and was just floored at her mindset and determination. So much of her story resonated with me, and I have learned so much from talking to her. We got to interview her on our Building NewLaw podcast last year, and I just spent the whole episode gushing about how brilliant she is.

We are lucky in Toronto that we have some great innovative ladies, and I think Laura van Wyngaarden from Diligen and Mona Datt from Loom Analytics are doing great things. Also, although it’s not strictly legal tech, Lynn Norris from the Modernization Division of the Ontario Ministry of the Attorney General is a phenomenal lady doing great things to implement tech solutions in our legal system.

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