5 Questions with Dorothy Brill

Ben B&W
Ben Viagas
Last Update 08/19/2022

Dorothy Brill leads the People team at Grayscale, but as she explains through the latest entry in our 5 Questions with... series, her responsibilities comprise not just finding and retaining talent, but building a lasting culture.

1. What has your career been like, and what brought you to Grayscale?

My career has been an adventure. Non-linear for sure. Armed with a history degree, I turned down a few entry level job offers and instead moved to Colorado to figure out what I should do. I had never been west of the Mississippi so it felt very brave at the time. I became a better skier but realized you can’t figure out what you want to do by thinking about it. I moved to NYC and began working at a boutique investment bank in institutional sales and ran a client conference in Sun Valley Idaho. I was becoming well-traveled, but the journey wasn’t over. I then decided to switch careers, becoming a high school history teacher and coach, making less money than I had paid in my federal income taxes the year before while feeling more fulfilled.

Next, I went to Cornell for an MBA with the idea to become a Head of School, but that changed after studying GE in a business strategy class. I was impressed by the emphasis that Jack Welch placed on Human Resources (HR), not only as a necessity but as a strategic advantage. This was my a-ha moment. It connected what might have otherwise seemed like a disconnected set of experiences. I committed to HR through the rest of my time at Cornell, culminating with actually joining GE’s HR program on graduation. I have held roles in HR leadership ever since. 

I’m lucky – my career has not been motivated by money, nor has it been motivated by some perfectly laid out plan. My career has been full of learning, partnering, and discovering what I’m best at. Taking a varied path through your career gives you a uniquely valuable professional outlook – just look at Dave LaValle! It’s about building yourself, and what I discovered was that I love helping others build themselves too.  Grayscale is the next chapter, where I feel like a pioneer again, helping build something special with an amazing cohort.

2. As an HR leader, you have a unique perspective on the fabric of a workplace. What distinguishes Grayscale?

I’ve been at other financial institutions and recently two alternative investment firms that were all very different. Grayscale moves faster, and is more open and transparent than anywhere I’ve been. Furthermore, it’s incredibly entrepreneurial for an investment firm. I love the drive to succeed coupled with an incredible level of professionalism. Everyone understands that we are remaking an industry, and at the same time, the workplace is so casual and down to earth. 

Early on,  I was speaking with a job candidate who asked me, “what’s the catch? It sounds too good to be true, are people really so nice and is it really such a great place to work?” I’ve been here for a while now and I still haven’t found the catch!

3. As an HR leader, you have a unique perspective on the fabric of a workplace. What distinguishes Grayscale?

At Grayscale we’ve built a team that understands that the principles of collaboration and diversity are paramount. We want feedback and input from anyone because we know it helps enhance the decision-making process. Beyond gender, ethnic, and cultural diversity, everyone at Grayscale has unique thoughts and ideas. We want to maintain an environment where this doesn’t just live in people’s heads, so we seek different perspectives, we use our voices, we listen to each other and ultimately we establish shared responsibility for shaping our business and culture.

4. How can HR leaders encourage employees to carry a healthy and supportive culture?

Employees make the culture and have responsibility for helping keep it healthy. HR leaders need to listen and help build bridges at times. The diversity we seek means, of course, there will always be a diversity of reactions and opinions. Not every decision or every tenet will make every employee happy. But creating a good culture starts with ensuring as a baseline that everyone is comfortable and believes they have a voice. HR can help clarify why decisions are made. Even if one person’s point of view in the end doesn’t prevail, a supportive culture embraces every member and accounts for disappointment. It’s an act of balance. It’s life. 

5. What advice do you have for someone looking to start their career in crypto today? 

First off, if you already know you want to get into crypto, you can start by looking at open positions on Grayscale’s job board! If you’re still wondering if it might be right for you, here’s what I’ve seen: You have to have imagination, a pioneering spirit, and be incredibly adaptable. At Grayscale, we need imaginative colleagues to see the future we’re building together. A pioneering spirit means you’re willing to take risks, can venture into new spaces without guarantees, and will act quickly in the face of danger. Crypto markets can be volatile and we aim to steer and protect the enterprise from the unexpected. Finally, only a very adaptable person will be comfortable in a rapidly evolving industry. If you like a safe, predictable routine, then working in crypto is probably not for you. Instead if you see changes as opportunities, enjoy wearing a lot of different hats, and can constantly pivot, invent, and reinvent… then you will love the adventure! 

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