5 Questions with Allison Westmacott

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If Grayscale is a bridge between crypto and traditional finance, Allison Westmacott is like a bridge inspector, ensuring the span is sound and up to code. As Vice President, Legal & Compliance, Allison Westmacott works to ensure that Grayscale’s communications, actions, and offerings meet or exceed legal and regulatory requirements. (Fun fact: she and her team have read and approved every word on this website.) Recently, she took time to share insights from her career and her time with us

If her insights inspire you, explore open positions at this link.

1. What brought you to Grayscale? Walk us through your career.

After I graduated college, I briefly became a legal assistant; I’m not sure if it was the slower pace or that I wasn’t interested in the type of law being practiced, but it just wasn’t a fit for me. Around the same time, there was a lot of talk about additional regulation in the financial services industry and the hiring of compliance professionals. I quickly realized that this could be what I was looking for, and I started working at a comprehensive wealth management firm. Without going too far into the weeds, this was a great opportunity to really grow as a compliance professional in such a highly regulated industry.

From there, I went to Horizon Kinetics, where I became a true compliance generalist, working with a variety of investment products and supporting compliance functions across the entire organization. This is also where I first learned about Grayscale and all the interesting things that were happening in the crypto space. I had great mentors at Horizon who supported my learning and growth and wanted to see me continue to progress in my career. When the opportunity arose for me to join Grayscale, everyone at Horizon was really supportive, which made the transition that much easier and natural!

2. Your role has given you experience providing difficult feedback to colleagues. How do you approach this constructively?

I once heard compliance described as “the world’s longest four-letter word.” Compliance can evoke negative reactions in some, but it has always been important to me to make sure that my colleagues have the exact opposite reaction and understand compliance officers and the positive contributions we make to the business in general and to their role in particular. I believe the best compliance programs are the ones that are respected by employees and where the employees feel respected in return, and I have always strived to build those sorts of genuine and reciprocal relationships.

While a huge part of my job is explaining the implications of non-compliance and let’s be honest, sometimes saying “no”, I make sure that I am firm but clear in my reasoning and that I am always available to discuss any questions or concerns anyone may have. I know it sounds simple but generally it’s not what you say, it’s how you say it.

3. How do you think investors can most effectively mitigate risks when they’re exploring investment opportunities?

Read everything! The disclosures and fine print in investment materials can seem tedious, but they really are there to provide the extra information needed to help make financial decisions. It’s also important to make sure you know what your financial goals are and how much risk you can and are willing to take on. And if you’re not sure, never feel uncomfortable asking questions! If you have a particular question, chances are that someone else has had it before and there’s a professional out there who can help you find the answer. Staying informed is critical when choosing whether to proceed with an investment or not.

4. What’s a unique consideration when working at the intersection of crypto and traditional finance?

The pace of change! In traditional finance, a rule or regulation may not be updated for many years but in the crypto sector, the landscape is constantly changing. As a consequence, we have to keep up with what is happening not only on Wall St. but also in policy discussions in state capitols, Washington D.C. and jurisdictions around the world.

I know some may disagree with me here, but I think that digital asset managers and traditional asset managers are becoming more similar over time. Ultimately, we both care about investors and that doesn’t change if the industry you’re in is more traditional or digital asset-based – though I appreciate that now I get to wear a sweatshirt and jeans along with my compliance hat.

5. What advice do you have for someone looking to start a similar career?

Generally, compliance extends across an entire organization and because of this, you will most likely collaborate with individuals at all levels. Learn as much as you can about the industry and the specific rules and regulations for any specialized compliance functions you are involved with. At the end of day, you were hired to help protect the organization, its employees, and its investors so never be afraid to ask questions or seek more information.

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