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Anna Cheng, Assistant General Counsel at Plastiq

Anna Cheng, Assistant General Counsel at Plastiq

June 14, 2022

Tell us a bit about what you love about the product regulatory practice area or your role in general. I love that my role touches on so many aspects of the law - technology, regulatory, banking, payments, data privacy, data security, etc, - and that I have to keep up with all the changing laws in those areas, which can be a lot manage but makes for very interesting work.

What do you feel are the most interesting developments in the product regulatory area and for the fintech industry as a whole or for your specific business/industry? I think the explosion of cryptocurrency and how affects the payments space is fascinating. I’m still trying to wrap my head around cryptocurrency but it’s been interesting to see which players in the payments industry have started accepting crypto and done well with a crypto service. (FYI - my current company has not delved into crypto but I still find it fascinating.)

What advice would you give to someone in the legal field trying to evaluate a role at a startup? Startups can be a risky move and whether to join one should be carefully evaluated. I know it took me many weeks to carefully weigh the pros and cons of joining a startup, coming from a large multinational financial services tech company. But I think the biggest factor for me was whether the team(s) you’ll be working with are collaborative since “many hands make work light” and when the startup is small and scrappy, you hope for less office politics and easier collaboration and execution of ideas and strategies, even if you have to wear different hats to get the work done. Another great aspect about startups is being able to “wear all the different hats” to meet company goals, which I personally find intellectually fulfilling, even if difficult at times to learn about new areas/functions/roles.

What are the top 3 things that you think will define your industry in the next 5 years? I think the top 3 things are (1) who survives in this payments space since there are so many players now — from little startups to FAANG companies in the payments space; (2) crypto’s influence in the payments space, and (3) the evolution of regulatory oversight of crypto and the payments space.

Who are your mentors, how did you connect with them, and what are the top 3 things you learned from them? I don’t have one specific mentor but my previous 2 roles each included a female supervisor, who were both strong female leads but had opposite ways of managing their teams. One was very supportive — checked in on me and the team regularly, taught us new ways to think through legal solutions, provided guidance on how to manage unruly clients, basically, helped me become a better in-house lawyer. And the other was the opposite — rarely checked in on her direct reports, rarely gave any direction, and rarely provided any insight or guidance. And from those 2 back to back experiences, I’ve learned about what type of environment and leader I need to succeed, and I regularly keep in mind all the ways I felt empowered and educated with the help of my former supervisor as I advance and help those around me in my current role.

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