Women of Legal Tech: Caroline Hill

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 141 talented and influential women leaders.

Every Monday and Wednesday, we have featured a woman from our class of 2022. Today we have Caroline Hill!

Caroline Hill is Editor-in-chief at Legal IT Insider.





Three points to summarize you and your work in legal tech.

I write about all the latest legal technology news and trends. I have been working in the legal sector for almost thirty years, whether as a paralegal, lawyer, or legal journalist. I began my career in legal journalism in 2004 at Legal Week (now ALM), then became news editor at Legal Business magazine in 2012. I took over as editor of Legal IT Insider in 2014.

How did you become involved in legal tech?

Charles Christian founded Legal IT Insider in 1995 and was looking to retire. I wasn’t sure that I had the requisite knowledge to write about technology but Charles convinced me that it was a piece of cake! The rest, as they say, is history!

What projects have you been focused on recently?

Together with my brilliant team, we have completely overhauled the website and are launching ‘Gartner for Legal’ reports on topics ranging from CRM to PMS. We have launched a long overdue events calendar, which will help people around the globe when they are trying to work out what date to choose – or avoid – for their events. We have some really exciting projects coming up too.

What do you see as the biggest challenge in legal technology today?

For law firms and corporates I think it’s probably a lack of change in culture. To really effect transformation, we need different people making the decisions, otherwise – regardless of what technology you buy – you will continue to maintain the status quo.

Has the pandemic changed anything about the way you, your firm, or your organization does business? Has the changes that have resulted from the pandemic improved or altered your work or how you do it?

I am lucky that I have always worked from home, so the shift wasn’t disruptive. What has been great has the shift to Zoom, meaning that I regularly have face-to-face chats with people who I would have spoken to on a conference call, which is far less personal.

What legal tech resource helped you the most in your legal tech career?

I read absolutely everything, as you can imagine, and I hope that Legal IT Insider has been a big help to people learning about the industry. In terms of raising my profile in the US, Bob Ambrogi has been a great support, and while I’m only on his Friday panel occasionally as it’s 8pm on a Friday my time, the fantastic group of people on the panel are all wonderful writers.

What do you see as the most important emerging tech, legal or not, right now?

Aside from the work that law firms are doing in consolidating and making sense of their data, one of the biggest game changers is low-code or no-code technology that enables end users to develop applications and automate time consuming processes. The move to double down on their Microsoft stack is also hugely significant.

What do you see for the future of legal tech?

With the shift to cloud hosting, legal technology teams already are and will increasingly be focussed on how to gain the most competitive advantage from their tech stack. They will need integrated core systems and the ability to automate manual processes. They will be habitually providing monetised services based on the intelligence gathered from their data. Legal services will increasingly be tech-led and there will be transparency and a two-way flow of data within client matters.

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

My advice is to be brave and to assume that you CAN, not that you can’t. Don’t be afraid to put yourself outside of your comfort zone. Focus on what it is that you want to achieve, and work out how you are going to get there. And speak up. Say yes if you are asked to speak publicly. Join a panel. Write an article. Make time to build your own brand. Be visible and be a role model to other women who are thinking about their own career options.

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

There are so many but one that really stands out is Dana Denis-Smith, founder of Obelisk Support and the First 100 Years project. She is such an inspiration, and any time I have met with her I come away feeling a mixture of admiration and determination to raise my game. She is a fierce advocate for women and leads by example. I have no idea how she achieves so much with the same number of hours that I have in the day!

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