What Next, Solo? Lawyer to Legal Tech, Deb Tesser, Zola Suite VP

Welcome to the inaugural edition of What’s Next, Solo?  Although some lawyers are content to remain pure solos or small firm owners for the duration of their career, others may wish to move onto something new – whether out of a desire to seek new challenges, or a need for steadier income or a less hectic lifestyle. Yet the path forward for solo and small firm lawyers – particularly those who have been at it for a decade or more – isn’t always clear since they may not have the same contacts or respect as a big law attorney or inhouse counsel (sad but sadly, still true). Hence, the focus of this series – to give solos some ideas for a second or third act, and how to go about finding what’s next – whether it’s a job in legal tech (the focus of the first part of the series), a judgeship, inhouse position or a career outside of law. Let me know if you have ideas for profiles, or if you’d like to be profiled yourself. 

Our first post in this series is an interview with Deb Tesser, an attorney and currently a vice president at Zola Suite VP who shares how she went from lawyer to legal tech, and what her job is like now.



Deb Tesser

Current Position, company and what your company does. 

VP of Strategic Planning for Zola Media, the team behind Zola Suite, next generation cloud based practice management and Zola Creative, a one-stop, digital marketing agency for the legal profession.

Prior to your current position at your company, how long did you practice law and where? What was your area of practice?

I’ve had quite a circuitous path in the legal profession.  At my first job after law school, I practiced commercial transactional law (real estate and asset based lending) with Peabody & Brown (n/k/a Nixon Peabody) in Boston for 6 years. I took some time off when my kids were young and then went to practice for a brief time (about a year) with a boutique law firm in the Princeton, NJ area where I worked on the underlying real estate portfolio loans that were being sliced and diced into the REITs that led to the financial crash.

I then did a brief stint with a tech startup in the legal space that went nowhere, and went back to practicing law with another solo doing residential real estate and corporate work only to realize that I was more interested in the business of law than the practice of law.

Why did you decide to move from practicing law to your position at your current company, and how did you find your current position?

After leaving the solo firm, I worked with a consultancy that provided marketing and strategic planning advice to international IP firms who were looking to develop business with US corporations and law firms. I left that gig to start my own consultancy, Today’s Practice, where I connected with innovators in the legal tech world and became a referral partner for companies with products and services for small and medium-sized law firms, one of which was Zola Media.  I saw a preview of Zola Suite when it was in beta and was blown away. I met with their CEO and he asked me to join the company and the rest is history.

What is your title at your company, and what are some of your responsibilities?  Can you describe a typical day (if there is such a thing)?

My title is “VP of Strategic Planning”, but we’re a small company and I play many roles. I can’t describe a typical day, because every day is different. I do everything from bar association and professional organization outreach to identifying and fostering relationships with referral and integration partners. I’m also responsible for developing marketing strategies and content, conference planning and business development and internal processes and procedures. I attend trade conferences and bar association events and love to network with my peers and speak on panels when I get the chance.

How does your training and experience as a lawyer help you in your current position? 

When I was in law school and during my early years of practice, I would roll my eyes whenever nonlawyers would tell me how versatile a law degree was. But now, after many years of trying to figure out what I wanted to be when I grew up, I finally get it. Certainly, having the “JD” after my name gives me some credibility when speaking with lawyers around the country about our services, but I’m also an issue spotter, writer, decent communicator and negotiator – all of which I attribute to my past training and experience.

What are some of the differences working for a technology company in contrast to working as a lawyer, either at a firm for others or in your own practice?

There is a broader range of skillsets and personalities than I’ve encountered at law firms.  And the median age is definitely younger.

What was the biggest challenge for you in transitioning from law practice to your current position?

My biggest challenge was finding the right situation where I could use my legal background without going back to practicing. I spent a lot of years looking for an opportunity where I felt I could make a difference, be given responsibility commensurate with my experience and feel passionate about the work. It’s been a thrill for me to land in a place where this is the case and, as an added bonus, get to know a lot of the people I’ve been following for years on a first name basis.

Do you miss practicing law?  What have you done, if anything, to keep your law license and legal skills intact?

Not really. I still do most of the things I enjoyed doing when I was practicing.  There is a “make it up as you go along” mentality in tech that is very liberating. When I was practicing law I always had the fear that I was missing something that would come back to haunt me.  In the innovation space, we break rules constantly. And it’s okay.

Do you have any formal training in technology or “hot” technical skills (e.g., programming, product development, data science) and are these skills necessary for your current position? 

From the time I started practicing, I’ve used technology as a tool to improve my efficiency. I was one of the first lawyers at my firm who insisted that I have my own computer and much to the chagrin of the partners, I refused to learn how to dictate (I know I’m dating myself here). That said, my approach to legal tech has always been from the perspective of an end user, not as a techie. If I couldn’t see the utility of the software, I’d move on. I think this attitude has helped me when I speak with lawyers who intellectually understand they need to adopt, but have been resistant.

If a solo lawyer was interested in following your career path, what advice would you have? 

I believe that we are all works in progress. The career paths we envision when we start out, particularly for women, may take many twists and turns. And that’s okay. If you had asked me 10 years ago if I thought I’d land a job where I’d be travelling all over the country introducing lawyers to new technology, I’d say you were crazy. And here I am. No matter how cliched it sounds, my advice is figure out what excites you and don’t be afraid to take risks. Sometimes it works out.

What excites you most about the future of legal technology?

I think legal tech is fundamentally changing the practice of law. Twenty years from now, there will be fewer lawyers and those who decide to go to law school will do so because they are passionate about law and justice, not because they don’t know what else to do with their lives.  The repetitive boring stuff will be automated and technology will make way for creative, problem-solvers who want to become true counselors for their clients, not paper pushers.

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