Randy Webb

President, CEO

757 961 5215Email

Randy is President and CEO of Signature, responsible for the firm’s strategy and business development. Prior to joining Signature, Randy was with Bank of America for 18 years. His tenure at Bank of America culminated in the position of Managing Director of the bank’s mid-cap investment banking group, with responsibility for building and co-managing the East coast team. Randy was based in New York City and was focused on the firm’s capital raising and mergers and acquisitions effort within the mid-cap segment. He previously worked as Senior Vice President in the corporate finance group of Bank of America’s predecessor institution, NationsBank.

Randy serves on the boards of WHRO Public Radio, as the Board Chairman, the Virginia Museum of Fine Arts Foundation, on the investment committee, and the Elizabeth River Project, on the governance committee. He also serves as the Chair of Strategic Planning for the Board of Directors of ForKids and is a member of the Board of the Rutter Family Art Foundation. Previously, Randy was on the speaker committee for TedXRVA and on the board of the 757 Angels. He is a graduate of the CIVIC program in Hampton Roads.

Randy is a graduate of Hampden-Sydney College and received an MBA from the College of William & Mary.

Randy enjoys spending free time with his wife and three children. He also enjoys running and sailing and has traveled throughout the world. His favorite destination with the family is an annual trip to Martha’s Vineyard.


What do you do at Signature?

I’m responsible for growing the firm, but not in the way most people think. We measure our growth by our clients’ successes, so I focus on building resources and our people so they can grow the success of our clients.

What qualities make you best suited to do what you do?

Intellectual curiosity and an appetite to try new things.

What do you love about wealth management?

Helping entrepreneurs and business leaders apply their professional skills to managing wealth so they realize their long-term vision.

Why do you work at Signature instead of a Wall Street firm?

Because we have the independence to put our clients first. We’re employee-owned, so we don’t have to sell specific products or services to appease shareholders. Instead, we’re free to guide clients to make choices based on what works best for them.

What is your favorite client success story?

I remember one couple who told us that they wanted to pass on the experience of entrepreneurship—the hunt, the build, the opportunity to create something—to their kids. To share the satisfaction of the process, not just the financial results. We helped them create and execute a strategy that aligned with that goal. Since then, all three of their children have become successful entrepreneurs in their own rights.

What do you wish more people understood about their wealth?

That you can define success on your own terms.

Society is quick to tell you what success looks like: a new Porsche, a beach house, 15 cashmere sweaters. But maybe, for you, success doesn’t look like that. It takes courage to stand up for what you want, but so does being a leader or an entrepreneur.

Our clients tend to be cool like that. The majority are first-generation wealth originators, and they realize success comes from taking advantage of a non-conventional standpoint. They want to do things their way.

How can people manage their wealth more successfully?

Stand up for what you want. It takes courage, but you can choose what aligns with your values. Even if that means choosing a firm like Signature—which most people haven’t heard of—instead of a big name. Think about it: You were financially successful because you did something other people weren’t doing. You took a risk, you stepped outside the status quo. So why would you choose a traditional firm to develop the strategy for your wealth goals?

What personal accomplishments are you most proud of?

Raising good kids and hopefully being a good spouse. My kids are loving, warm, thoughtful, curious, smart, and successful.

What do you love to do outside of work?

I love to explore and to go where the energy is. I grew up sailing and living near salt water, and now my kids have too. We’re island people, and we go to Martha’s Vineyard every year.


Professional highlights

  • Building Bank of America’s mid-cap investment banking group from zero to a significant revenue contributor
  • Joining Signature and becoming part of one of the first firms to offer multifamily wealth management
  • Taking an entrepreneurial approach within organizations and satisfying unmet needs within markets

Education & accreditations

  • M.B.A., College of William & Mary, Williamsburg, VA
  • B.S. in History, Hampden-Sydney College, Hampden-Sydney, VA
  • CIVIC Leadership Institute, Hampton Roads, VA

Service highlights

  • Board Chairman, WHRO Public Radio
  • Chair of Strategic Planning of the Board of Directors, ForKids
  • Investment Committee Member, Virginia Museum of Fine Arts Foundation
  • Board Member, Norfolk Forum
  • Board Member, 757 Angels
  • Board Member, Rutter Family Art Foundation
  • Speaker Committee Member, TEDxRVA