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A Conversation with Alum Jason Yoo

Former Stroock attorney Jason Yoo recently talked to us about his time at Stroock and the work he’s been doing since joining privately held financial technology company Affirm, Inc. While at Stroock, Jason handled complex consumer litigation, with a particular emphasis on representing financial institutions and financial services companies. Now he’s Director, Managing Counsel (Product and Litigation) at Affirm, Inc. Jason talked about starting out his legal career in Hawaii, his time at Stroock, his work at Affirm, and the challenges and benefits of working in house. He also shared how outside counsel can best serve in-house lawyers and leaders. 

Q: You worked at a law firm in Hawaii before heading over to Stroock. What brought you to Hawaii after studying in California? 

JY: I actually grew up in Hawaii. I went to school in California and moved back to Hawaii in 2008 to start my legal career there. I was at a Honolulu law firm for three years and then my wife, who is a SoCal girl, convinced me to move back to California. But Hawaii is and always has been home for me. We typically go back to visit once or twice a year.

Q: Tell us about your time at Stroock. What did you like best about working at the firm?

JY: I started at Stroock as a junior associate in 2011 and left for my current in-house role in 2018. During that time I worked in the Financial Services Litigation, Regulation and Enforcement Group in the LA office. There I had the privilege of training under amazing mentors like Julia Strickland and Stephen Newman, who taught me the singular importance of impeccable client service, whether we were defending a mom and pop in an individual action or a titan of the financial services industry in a class action. 

What I enjoyed most about working at Stroock were the people. When I was at the firm, I used to conduct on campus interviews of law students. I would tell the students that while the big firms may seem indistinguishable on paper, what really sets Stroock apart is its people. I truly considered the staff, including my wonderful secretary, Regina Harcourt, and the attorneys in the LA office, as family. We shared many personal triumphs and sorrows in addition to our professional ones. 

We operate in a high pressure and not always pleasant profession. You need good and decent people in the trenches with you and I was lucky to find that at Stroock.

Q: How did your law firm experience prepare you for being in house? 

JY: For me, it always comes back to client service. At Stroock, dedication to client service cannot be overstated. You can be the smartest attorney in the room, but if you aren’t responsive to your client or adequately managing expectations, your client may not be your client the next time around. Similarly, in my in-house role, I make sure to timely respond to my business partners at all hours of the day and ensure they are taken care of and protected at all times. Sometimes just saying “let me look into that and get back to you” can go a long way. Nothing makes people more nervous than not hearing back from their lawyers. So responsiveness is critical.

Q: What did you learn that proved to be particularly helpful when you went in house? 

JY: I think the lesson here is to keep it simple. I firmly believe that even the most complex legal issues can be made simple with enough effort. I have the great pleasure of working with some of the brightest and most intellectually curious people in the financial services industry, but even my business partners aren’t interested in listening to a protracted and tedious legal analysis explaining why we should or should not pursue a course of action. Mastering the art of precisely and concisely explaining complicated legal matters to nonlawyers in plain English is, in my view, the single greatest hallmark of an effective in-house counsel.  

Q: Tell us a little about Affirm, Inc. and your current role as Director, Managing Counsel. You really rose quickly there! 

JY: Affirm is a financial technology company headquartered in San Francisco that provides point of sale finance solutions at thousands of retailers from sectors including furniture and homewares, apparel, consumer electronics and travel. Affirm is reinventing credit to make it more honest and friendly, giving consumers the flexibility to buy now and pay later without any hidden fees or compounding interest. Our merchant partners include Peloton, Walmart, Expedia, Wayfair, Casper and many more. 

I joined Affirm as Product Counsel in 2018 and now I’m a Director and Managing Counsel at the company. I split my time evenly between product counseling and litigation. On the product side, I counsel our business teams on legal issues related to product development from inception to production. I’m also responsible for all litigation-related matters at the company, from responding to escalated complaints and prelitigation demands to defending lawsuits and arbitrations. I also counsel the business to address issues that may be raised in litigation.

Q: What are the greatest challenges you face in house? How about what you like most?

JY: As an in-house attorney, you often are expected to make important and difficult decisions rapidly and with limited visibility. In my current role, I spend much more time thinking on my feet in back-to-back meetings with the business and less time at my desk poring over briefs and memos. Although this can be challenging at times, and Zoom fatigue is indeed real, it’s actually what I love most about being an in-house attorney. In my time at Affirm, I have built very strong cross-functional relationships with my business partners and I consider this to be the highlight of my legal career to date.

When you’re outside counsel at a firm like Stroock, your client typically is a sophisticated in-house attorney at a large institution and there is a definite upside to that as well. But for me it is very exciting to come to an environment where you are meeting and forming relationships with new people across the organization every day and that’s what I love the most about this job.  

Q: What can outside counsel do to make the job of in-house counsel and other corporate leaders easier? 

JY: Keep it simple. Always provide an executive summary so that the client does not need to spend an hour distilling your memo into a one-paragraph TLDR for the business. Also, provide a recommendation. Although the client may not always agree with your recommendation, it demonstrates that you are willing to own your work, which is crucial. It also shows that you understand the real-world implications of the issue and are not simply regurgitating the law. The ability to simplify information and make it easily understandable, in my view, is what separates a good attorney from a great attorney. Clients, much like their outside counsel, are juggling many different things at once and whatever you can do to make their lives easier will be appreciated.

Q: How about secondments as a way to truly gain an understanding of a client’s needs? 

JY: I think secondments are a great idea. One of my outside counsel actually was seconded in house early in his career. He understands the nuances of performing in an in-house role and I don’t think it’s a coincidence that when I reach out to him I know I’ll get a real-world answer that I can use to help the business. I think secondments can give you a lot of great hands-on experience that you normally would not gain at a law firm. 

Q: Any final thoughts?

JY: I really enjoyed my time at Stroock and I’m always happy to share my experiences at the firm. I spent the majority of my legal career there, and I still consider some of the attorneys and staff close friends. Also, I currently use the firm as outside counsel. So that certainly tells you something.