Top Lawyers: Cailey Greenberg Of Boston Beer On The 5 Things You Need To Become A Top Lawyer In Your Specific Field of Law
Legal precedent can be a guide, but the ability to think outside the box is what truly sets top lawyers apart. One of my most rewarding experiences was finding an unconventional legal interpretation of the regulations that would allow my company to do something it was very eager to do. By thinking creatively, we achieved a result that not only satisfied our “client” but also pushed the boundaries of what was possible in that area of law.
The legal field is known to be extremely competitive. Lawyers are often smart, ambitious, and highly educated. That being said, what does it take to stand out and become a “Top Lawyer” in your specific field of law? In this interview series called “5 Things You Need To Become A Top Lawyer In Your Specific Field of Law”, we are talking to top lawyers who share what it takes to excel and stand out in your industry.
As a part of this interview series, I had the pleasure of interviewing Cailey Greenberg.
Cailey is an ambitious and dedicated legal professional offering expertise in cannabis, regulatory and privacy law.
Thank you so much for joining us in this interview series. Before we dig in, our readers would love to get to know you a bit more. What is the “backstory” that brought you to this particular career path in Law? Did you want to be an attorney “when you grew up”?
I always wanted to be a lawyer. My mom tells this story about when I was eight years old, on “Take Your Parents to Work Day,” I went to school and my friend’s day who was a lawyer explained his job. I was completely fascinated and decided that day that I would become a lawyer, and I never changed my mind.
How I ended up here is a bit of an interesting journey. During law school, I worked at a small criminal law firm that specialized in drug defense, specifically medical marijuana cases, so I got familiar with the field early on. When I finished law school, I had to do my articling (the required 10-month term before being called to the bar in Canada). It was when the new medical cannabis program in Canada was launched. I spent my entire article term learning about the regulations and working on applications for companies to obtain licenses from the government.
When I was called to the bar, I found a job working in-house at a cannabis company, which was a startup at the time. It wasn’t one of the applications I worked on, but it was the only company located in Toronto. I went in as their only “lawyer,” but since it was a start up I had to wear many hats. I did HR, worked in the shipping room, and even helped out in the grow room. It was a bit of a funny time — there are pictures of me sitting among plants in a Tyvek suit with a laptop. It was definitely a hands-on experience, and I stayed in the industry and remained at that company until 2021, when I joined my current company, Boston Beer
Can you tell us a bit about the nature of your practice and what you focus on?
I’m Senior Corporate Counsel at Boston Beer, focusing on cannabis and alcohol from a regulatory perspective. My day-to-day involves reviewing everything related to our cannabis and alcohol products in Canada. This includes marketing materials, packaging, and social media campaigns — pretty much anything the public sees about the product. I also handle contracts related to these products. Aside from that, I also manage the legal aspects of privacy and cybersecurity for Boston Beer globally.
You are a successful attorney. Which three character traits do you think were most instrumental to your success? What unique qualities do you have that others may not? Can you please share a story or example for each?
I’d say one of my key traits is being entrepreneurial or a self-starter. When I first started, it was a new industry, and there weren’t clear examples of what a lawyer in the cannabis industry should be doing. I didn’t need someone to tell me exactly what to do — I was comfortable figuring things out on my own and making it work.
I think another trait is my willingness to take risks and venture into the unknown. When I joined the cannabis industry in 2013, it was still in its infancy, and I had no idea what the future held. But I saw it as an exciting opportunity. I wasn’t scared of failure, I had to carve out my own path, and that experience really shaped my career.
Do you think you have had luck in your success? Can you explain what you mean?
Yes, absolutely. When I entered the industry in 2013, cannabis legalization wasn’t even on the radar. It was all about medical cannabis at the time. But in 2016, one of the political parties in Canada campaigned on the promise of legalizing cannabis, and it actually happened in 2018. That was when the entire industry exploded. I definitely consider that luck — there was no way of predicting that at the time.
Based on the lessons you have learned from your experience, if you could go back in time and speak to your twenty-year-old self, what would you say? Would you do anything differently?
I would tell my 20-year-old self not to stress so much. Life has a way of working out, even when you can’t see it at the time. If you don’t the job you want, or if something seems catastrophic, it’s usually because life is pushing you in the direction you’re supposed to go.
This is not easy work. What is your primary motivation and drive behind the work that you do?
I actually find the work really interesting and challenging. Being in an industry with little precedent means you often have to operate in the gray area and figure things out on your own. I like that aspect of it — it keeps things dynamic and engaging.
What are some of the most interesting or exciting projects you are working on now?
Right now, I’m really excited about the launch of Emerald Hour. It’s an innovative cannabis beverage line, and I think it’s really going to stand out in the marketplace. There are so many cannabis beverages out there, but this one is unique in its approach, and I’m excited to see how it performs.
Where do you go from here? Where do you aim to be in the next chapter of your career?
Honestly, I’m really happy where I am right now. I don’t have any immediate plans for a major change. I’m enjoying the work I’m doing and Boston Beer is a great fit for where I’m at in life, and I’m looking forward to continuing to grow in this space.
What are your “5 Things You Need To Become A Top Lawyer In Your Specific Field of Law?”
Motivation and Self-Starter Mentality
- A top lawyer needs to be driven and self-motivated, as much of the work relies on personal initiative. As mentioned earlier, in my early career, I performed many roles outside the traditional “lawyer”. It was scary, but I dove in head first excited about the challenge ahead and what could become of the industry. . That self-driven approach helped me develop a lot of skills that led to being a successful member of the team.
Hard Work and Perseverance
- The legal profession is demanding. It requires significant brainpower, long hours, and a dedication to doing the work. I remember spending many nights and weekends working (in hot grow rooms I may add). s There were moments when I thought the work was overwhelming, but perseverance and dedication kept me going. In the end, it paid off, as I wouldn’t be where I am today without those grueling early years.
Independence
- As a lawyer, you won’t always have someone around to answer questions, so you must be resourceful. I started my career at a company where I was the only lawyer, so going to someone for the answer as a first year wasn’t immediately available. I had no choice but to take the initiative to research and figure it out on my own. I learned that working independently, while sometimes daunting, can also lead to valuable discoveries and personal growth.
Creative Problem-Solving
- Legal precedent can be a guide, but the ability to think outside the box is what truly sets top lawyers apart. One of my most rewarding experiences was finding an unconventional legal interpretation of the regulations that would allow my company to do something it was very eager to do. By thinking creatively, we achieved a result that not only satisfied our “client” but also pushed the boundaries of what was possible in that area of law.
Trust in Yourself
- Law comes with immense responsibility, but it’s important not to take yourself too seriously. Early in my career, I felt a lot of pressure to have all the answers, but it is important to admit when you don’t know, as long as you work hard to go find the answer. I also learned that trusting your instincts and remaining confident in your decisions is key. Just because someone is older than you or has been practicing longer, does not mean they are always right. The most successful outcomes come from trusting yourself and adjusting along the way.
This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!
Top Lawyers: Cailey Greenberg Of Boston Beer On The 5 Things You Need To Become A Top Lawyer In… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.