February 5, 2020 4:00 am Published by

Episode 42:

Female Leaders | Are You Ready to be an Entrepreneur?

Roberta Sydney has set a new standard for female leaders within her sphere. And through her work in real estate development and asset and property management, Roberta established herself as a Female Leaders | From Corporate America to Entrepreneurship, with Roberta Sydney practical visionary, a solutions-oriented leader, and a dependable board member who delivers results for shareholders. She has built a diverse skillset with financial transaction experience, marketing expertise, IT systems implementation experience, and a proven track record in real estate development—but her primary objective has always been to ‘win the game.’

From Corporate America to Entrepreneurship

For many female leaders, it is a dream to transition out of the corporate world and into entrepreneurship. But as Roberta said, “the arc of our working-lives is never one arc, and it’s not a straight line.” Roberta was well-equipped because of the autonomous, solutions-based leadership roles she had the opportunity to serve in. However, the moment that prepared her for entrepreneurship is something we can all experience, regardless of our career paths or backgrounds. Roberta injected herself into a situation where she was forced to acknowledge the voice in her head. With the support of others, she shattered her limiting beliefs and confronted the deep-seated self-doubt that was hidden for so long—That is how Roberta prepared herself to become an entrepreneur.

Get Out of Your Own Way

Imposter syndrome is a reality for all female leaders, especially in a male-dominated field like real estate development or construction. But it can work both ways. Roberta stresses the importance of cultural fit and recommends using it as another indicator to decide when it is time to transition out. If you cannot bring your full-self to the office every day because it is not a good fit for your company’s culture, you are hindering your ability to grow as a leader. Either way, only you will truly know when you are ready. And when that time comes, everything will fall into place.

About Roberta Sydney

Roberta Sydney is CEO and Board Chair of Sydney Associates, Inc. founded in 1999, to perform development, asset management, and property management for commercial and residential real estate.

Prior to Sydney Associates, Inc., Roberta was Senior Vice President at State Street Global Advisors negotiating contract terms with major brokerage houses. She also worked at Leisure Technology, a California-based real estate developer of active adult communities. Roberta also was Senior Vice President at BayBank Mortgage Corporation, running retail originations and secondary marketing, achieving # 1 in purchase mortgages in Massachusetts for the first time ever. She began her career at The Boston Company, where she wrote the business plan, evaluated and implemented mainframe software solutions to centralize customer account information, and launched mass marketing of financial services, generating over 50,000 new accounts in the first year.
Currently, Roberta chairs the Compensation Committee and serves on the Board of Plaxall, Inc., and serves on the Advisory Boards of several private real estate technology companies, including Rental Beast, Embue, and Doorbell.

Roberta received a BA from Wellesley College, holds an MBA from Harvard University, and a Master of Science in Real Estate Development from MIT.

What You Will Learn:

  • When and how to make the transition from corporate America into entrepreneurship
  • How Roberta confronted her inner voice and shattered her limiting beliefs
  • Why imposter syndrome is a reality for all female leaders in a male-dominated field
  • The three arcs of Roberta’s career to date and how to determine your own
  • How Roberta transitioned from entrepreneurship into board membership and governance roles


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