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From “techie” to Lawyer, the Journey of Cassie Sadowitz

By: Travis Gorsch, @tgorsch3

Cassie Sadowitz, Deputy General Counsel, Jacksonville Jaguars

Front Office Sports is proud to have sat down with Cassie Sadowitz, Deputy General Counsel, Jacksonville Jaguars & CEO/Co-Founder, Spysie Tech. Cassie was gracious enough to have offered up her time and insight into how she created her very own full service creative agency known as Spysie, formerly Blink Promotions, and how it helped her set herself apart from a crowded candidate pool. Cassie is able to harness her background in law and technology to make herself a valuable asset to her organization. It all started by taking initiative to seek out opportunities and fostering the relationships in her network which led to even more opportunities in the future.

You received your BA from Rutgers University in Journalism & History/Political Science and JD from California Western School of Law. How important is education in your career and how well did it prepare you for your current position?

It’s interesting — actually, my background is in digital media and web design. I get the question, ‘How did you end up being a lawyer — let alone in the sports industry?’ They’re kind of different, technology, sports, and law, although there is much overlap. I am self-taught in the web space, was somewhat interested in politics, but I knew I wanted to end up in the technology and digital media realm. During law school, I was known as the law student ‘techie.’ I didn’t really intend on practicing law or have any desire to litigate. People looked at me funny because I was going through this burden of law school and didn’t even want to practice in the traditional sense. But I was able to take a wide variety of classes, including sports law, social media law, etc. and was able to aggregate my passions in an academic environment. Instead of taking a conventional route, I blended multiple areas of interest and was able to shape that into what I’m doing now.

You have over ten years of experience in website/app design and development where you created two websites while getting your JD, SportsLawSocial.com and AthleteRightsGuide.com, focusing on student athletes’ social media rights and student and pro athletes’ publicity rights respectively. How did this help you when you created Spysie Tech?

I took sports law and social media law where we had a semester-long project to do. I knew I had to do something in the digital space. The best project to showcase my skills was to build a website, so I built the two sites as part of the longer term project. Some students wrote papers and some did power points, but I wanted to take it to the next level. I put it together in a nice presentation and left the domains up after the classes ended to use as reference points when applying for internships. It was a nice segue to show prospective employers my technical skills while using sports law examples.

You’re the Co-Founder & CEO of Spysie Tech which is a full service creative agency (web design, social media, e-commerce, app development, SEO & analytics, logo design, branding, and content management). Can you tell us a little bit about how you got started with Spysie Tech?

When I was about 15 years old, I started taking on small projects with friends and family. I was self-taught with HTML/CSS, PHP, and graphic design and photoshop. The entrepreneur in me decided to create Blink Promotions, which ten years later rebranded as Spysie Tech. I freelanced all throughout college and law school in San Diego. When I relocated to Jacksonville, I branched out and grew the brand and clientele. It’s such an interesting industry. There are so many moving parts and a variety of evolving sub-industries in the digital space.

You’re first internships were with CNN as a Production Intern (’08) and FoxNews.com Production/Editorial Intern & The O’Reilly Factor (’07-’09). What did you learn during these internships? What advice do you have for students and young professionals when seeking to get experience from an internship?

For me, when I got to college I knew I wanted to do an internship. I was at Rutgers which was perfectly situated to do an internship in New York City. I worked in politics for a New Jersey state senator and decided I wanted to try my hand at the news media. I randomly applied for an internship at Fox as an 18 year old kid and they placed me with FoxNews.com because of my web experience. This provided me with my first insight into working for a major news network.

I always tell people to take advantage of these opportunities, to get in there and don’t be afraid to take risks. I was commuting to NYC by train three times per week as an 18 year old. I was fortunate enough to work alongside greatly respected people and learned a ton. CNN picked me up before I ended up back at Fox, which had me back to do The O’Reilly Factor. Having the exposure of being on set each day and seeing what goes on behind the scenes to create a successful cable television news show was invaluable.

I began my career in media before transitioning to law. The [Los Angeles] Angels was my first sports internship. I never thought I’d end up in Anaheim, but I branded myself and was proactive in seeking out these opportunities. You can’t be afraid to put yourself out there; you have nothing to lose. Set yourself apart from the candidate pool. When applying to internships, I always kept my website up with my current resume, and this helped me get my message across about who I am and what my skill set is. Being able to showcase who you are with something beyond a LinkedIn profile is beneficial. Figure out a way to distinguish yourself.

You ultimately decided to move on to an internship with the Los Angeles Angels (’12) dealing with Legal Affairs & Risk Management. What drew you to this career path instead of continuing the production and editorial path?

I am grateful for my experience in the news media world, but I was looking for something different. I was born in raised in New Jersey, went to Rutgers. I think the decision to go to law school in San Diego was a great personal challenge for me. There wasn’t something that necessarily turned me off from broadcast media, but I wanted to expand my education and learn from other cultures.

It started with one LinkedIn message that ultimately kicked off my career in the summer of 2012. I didn’t want to work for a firm or go into public practice. Although I utilized school resources, I did my own research on in-house positions independently, which helped me land my internship with the Angels. I found David Cohen and reached out to him via LinkedIn. He was interested in my background, took a look at my websites that I had created, and the next thing I knew I spent that summer learning the legal ropes of an MLB team. I learned so much in my short time with the Angels.

How did your internship with the Angels help you land your position all the way across the country with the Tampa Bay Buccaneers as an Associate Counsel (’13-’14)?

Timing and relationships. David Cohen ended up accepting the General Counsel position with the Tampa Bay Buccaneers and was able to hire a #2 in the legal department. I flew out to interview and accepting the position was a no-brainer. The next thing I knew, I made the move to Tampa and later took my bar exam in Florida. Maintaining connections both personally and professionally is so critical. David ended up being a great mentor for me. Never discount what people can bring to the table. Maintain and foster those relationships.

You are very versatile serving clients in law, technology, sports and entertainment, healthcare, government, non-profit, energy, finance, and higher education. What advantage does this offer you when looking to advance up the career ladder?

I think for me it’s interesting because I’ve had this entrepreneurial spirit for as long as I can remember. Carrying that throughout the years has helped me learn and evolve. There is always room for improvement, even when having a solid position inside the sports realm. There is always room for growth no matter what level of experience you have. With respect to running the business, staying current with technology, maintaining the competitive advantage, and understanding each of your clients’ needs are essential. It all elevates you to the next level. To prove a model that works in the design and consulting area has proven valuable at the end of the day, and you continually have to build upon what works.

Can you take us through an average day in your current position as the Deputy General Counsel for the Jacksonville Jaguars? What characteristics does a person need to be successful in this position?

There is no such thing as an average day, which I’m sure most people have heard time and time again, especially in this industry. We have so much going on both on and off the field. It’s a great feeling coming into work knowing the day is a clean slate. You never know what’s going to be thrown your way. The legal department is really the backbone of the organization. You have one client, which is the franchise. You are consulting and advising each department, whether it’s marketing, football, ticketing, etc. on how to remain compliant and be efficient in all that they do. Being able to do that and provide leadership across all levels of the organization is a great experience.

Always remember to keep current with your industry and technology, understand how to maximize efficiency, and continue to do your best. We have to deal with privacy issues, changes to employment laws — a lot of different intricacies, sometimes on a moment’s notice. Be aware of the issues that affect your job and understand how they affect your organization.

Parting Wisdom?

The best piece of advice that I ever received is ‘Always know before whom you stand.’ We hear the term ‘millennial’ thrown around all the time, and I think one of the most important attributes, especially for the recent graduates, is being aware of yourself and of others in varying situations. This will help take you to the next level as you develop your career. Be aware of your surroundings. Identify problems and propose solutions. Be able to set yourself apart in oversaturated markets. Keeping your personal brand and reputation clean and showcasing your talents will emphasize competence and show you are professional. Provide tangible examples of how you can be a valuable asset to the organization. And always remember that technology constantly changes how we do business. Make sure you’re current and follow the trends of the industry.

We would like to thank Cassie for her time and insight and we wish her all the best in her future endeavors!

You can follow her on Twitter here or connect with her on LinkedIn here! If you are interested in checking out her official website just click here!

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