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A Woman’s World: Leading the Way in Business With Roberta Sydney

Feb 23, 2022

Roberta Sydney is a successful entrepreneur and seasoned board director who uses her expansive expertise and experience to lead various real estate and financial services firms. Roberta is here to talk about women in business, share her personal experiences, and offer valuable advice. Diana and Roberta discuss common stereotypes, ways that women can set themselves apart from male leaders, and the necessity of women having professional mentors and sponsors. 


  • [02:10] Challenges that women face in the corporate world.
  • [04:08] How Roberta pivoted from financial services to where she is now.
  • [05:49] Why it’s important for women to have mentors and sponsors in the workplace and what the difference is between the two
  • [07:30] The differences between women and men leaders and how women are gifted in certain ways that can lead to their success as leaders
  • [11:56] What skills are needed for succeeding in the corporate world versus succeeding as an entrepreneur
  • [14:13] In order to be a successful entrepreneur, there has to be an internal dialogue with yourself where you are asking “What do I need?”
  • [16:29] Roberta shares how she mentors and what sets her apart
  • [18:00] Advice for women starting in business


  • Women need mentors and sponsors. A sponsor is the person who’s going to speak on your behalf when you’re not in the room. They advocate for you to get the new position, to get the promotion, to get the new opportunity. 
  • Stop using the word “just” to limit the contributions that you have made. Do not apologize when it’s not necessary to apologize. Understand how important culture and fit are to you in terms of your own personal growth and pursue opportunities that fit those wants and needs.
  • Women have different gifts than men in leadership, like having greater empathy, creating safe environments, and seeing and hearing the unsaid. Women are also able to build consensus more easily.
  • Entrepreneurs need a lot of initiative, self-awareness, and a lot of willingness to fall down several times and get up. There needs to be a fire in the belly to succeed!
  • When you do get stuck or are facing certain challenges, start an internal dialogue with yourself to figure out what you need. It’s important to recognize your needs and know none of us does it all alone.





Roberta Sydney is a seasoned board director and former CEO serving on the board of Kiavi (formerly LendingHome) the leading lender for real estate investors, where she chairs the Nominating/Governance Committee and serves on the Compensation Committee. She also serves on the board of Tiedemann Advisors, a global wealth advisory firm that recently announced its plans to go public via SPAC. In addition, she serves as Board Chair of HEI Civil. Her previous board service includes chairing the Compensation Committee for Plaxall, Inc., the Long Island City based manufacturing and real estate company that secured Amazon for their HQ2 before Amazon withdrew.  

The breadth and depth of Roberta’s experience comes from serving in executive and board leadership positions with regulated real estate and financial services firms ranging from large, traditional organizations to young, entrepreneurial companies. Sydney possesses a combination of leadership skills in real estate development, financial transactions, negotiations, digital transformation, marketing, and IT system evaluation. In addition to her many accomplishments, Sydney is actively engaged in philanthropy serving on the Neuroscience Advisory Committee and the Trustee Advisory Board of the Beth Israel Deaconess Medical Center, a Harvard teaching hospital.

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