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Heather Stevenson

Heather Stevenson is an accomplished, results-focused lawyer with an entrepreneurial drive to innovate and a demonstrated history of success. Heather believes that the best in-house lawyers don't just provide excellent legal advice. They serve as key business partners, providing guidance based on a deep understanding of both the law and the company's goals, which moves the company forward by maximizing potential gain while mitigating legal risk.

Tell me a little about your background and how you ended up where you are now.

I took the scenic route to my role as Deputy General Counsel at Boston Globe Media Partners (the publisher of The Boston Globe,, and STAT News). It’s been a whole lot of fun.

I started my legal career as a litigation associate at Sullivan and Cromwell in New York, doing securities and shareholder derivative litigation almost exclusively. I am so grateful for my time there. I learned a lot, and my colleagues were great people and terrific lawyers. But I also realized pretty quickly that I did not want to spend my career in big law. Plus, there was something else I wanted to try.

In 2014, we moved from New York to Boston and opened Thirst Juice Co., a plant-based juice and smoothie café and community located in Downtown Boston and one in Wellesley. Building and running Thirst was one of the most challenging and fun things I have ever done. I learned more from that experience than I ever imagined I would.

But a few years in, I missed thinking like a lawyer. I love the reading and analyzing, the debating and the strategizing. So I started searching for Boston area legal jobs, and I was thrilled to secure a position as Legal Counsel at the Globe. The original job description was for someone to review and negotiate contracts. I still do some of that, but my job now is much broader, and every day looks different. I work on everything from public records matters to privacy to IP and litigation. I love it!

What has most surprised you along your journey through the legal profession?

I have been pleasantly surprised by the differences between practicing at a law firm and practicing in-house. Both have their benefits and drawbacks, but sometimes, now that I’m in-house, I almost feel like I’m in a different profession than when I was at a firm.

Some things I’ve enjoyed about being in-house and that differ from in a firm are that being in-house allows becoming closely involved with the business I’m advising, that efficiency is valued, and that the scope of my practice is broad.

What are your thoughts on technology in law practice, and do you use any tech tools to help you do your work?

I am excited about how technology is and will continue to improve the legal industry, though I also think now is also an essential time for lawyers – including me – to learn how to assess the actual value of tech, rather than just getting excited about shiny new tools, which is easy to do.

As a small legal department, we don’t need or have a lot of fancy tech tools. We have a contract management system, which is basic but helps ensure we can find our contracts and that we don’t miss important dates. Perhaps more important, though, we effectively leverage tools the whole company uses (G Suite, Slack, and Zoom) to collaborate within the legal department and across departments and to simplify our own work and that of our colleagues. We use the technology we have to solve for challenges we face, and at least we haven’t needed anything more complicated.

What remains the most significant misconception people have of lawyers and why?

Too many people still think that the best lawyers are “bulldogs,” and only that kind of lawyer can’t succeed. This isn’t true.

Though there are very successful aggressive lawyers, not every aggressive lawyer is effective. And those who are bullies or unreasonable do a disservice to their clients. Being mean, or even worse, unethical, is highly ineffective eventually. Plus, mean lawyers effectively treat every interaction as zero-sum, missing out on the opportunity to increase the overall value of a given interaction for everyone.

There are also many highly successful kind lawyers. It is possible to advocate for one’s client’s position while still being kind to the opposing party. And the lawyers who opposing counsel enjoys being around, view as reasonable and easy to work with, are often more effective at getting what they need for their clients.

What would be your one piece of advice to a recent law graduate/new lawyer?

Take ownership over, and be intentional about, your professional development and career starting today.

The legal profession is uniquely structured, allowing us to work hard and achieve some version of “success” without ever being intentional or strategic about what we are doing. This is a trap.

Don’t assume that the obvious options presented (a law firm job through on-campus interviewing, working for the government, clerking, etc.), or even doing those jobs in the most typical order or for specific lengths of time, are your only choices. Explore other options that already exist or that you wish existed. Then make sure you get the training and experience to prepare yourself for that path. Prioritize growth experiences and try never to miss an opportunity you know will be meaningful because you’re too busy billing hours. If you aren’t getting the training you need in your current job, speak up, find a new job, or find a way outside of your job to get the experience you need.


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