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Roberta Sydney

Independent Board Director & Advisor

Plaxall, Inc. | Tiedemann Advisors

Boston, MA, USA

Roberta Sydney
Matthew Swift
Gert Sylvest

Roberta Sydney’s Biography

Roberta Sydney is a highly respected executive and thought leader with three decades of experience in financial services and real estate development. Roberta offers her expertise as an Independent Director and Advisor for companies in a range of industries, notably real estate technology, wealth management and manufacturing.

As a senior executive and board member, Roberta has helped numerous companies achieve significant growth, including large, traditional organizations, emerging companies and venture capital-backed startups. At wealth advisory firm Tiedemann Advisors, she draws on her leadership experience in facilitating and guiding high-growth opportunities for financial services companies. As a Director at Plaxall, Inc., a commercial real estate and plastic thermoforming manufacturer, she utilizes her extensive real estate development experience to guide the company’s varied investments.

Roberta's additional advisor and board roles include serving as Chair of the Boston chapter of Tiger 21 and as Trustee & Advisor for Beth Israel Deaconess Medical Center, a renowned teaching hospital in Boston. She also serves as an Advisor for pioneering real estate technology companies Cobu, RentalBeast and Embue.

In 1999, Roberta founded Sydney Associates, Inc. as a multigenerational family business focusing on real estate development, asset management and property management. As CEO, she employed an entrepreneurial approach in the acquisition and development of residential and commercial properties and successfully managed nine million square feet of property. After stepping down as CEO in 2016, she served as Chairperson until 2019.

Roberta is a sought-after speaker on governance and real estate topics. She has spoken at leading universities, such as Harvard Business School and Dartmouth’s Tuck School of Business, and at events held by renowned organizations, including The MIT Center for Real Estate and Women Corporate Directors.

Roberta’s Newsfeed

Business Wire
LendingHome Hires New CFO and CMO to Help Drive Continued Growth

The company also named Cherie Yu as CMO and added Roberta Sydney, a real estate entrepreneur, CEO and senior corporate executive with a long record of leading successful companies, to its board of directors. "I'm looking forward to advising LendingHome,” Sydney said. "I believe in the products and people at LendingHome and I'm excited to work with the team.”

The Anywhere, Anytime Workplace

Seeing the present as a 'massive transition point', Roberta Sydney urges companies to recognize a great opportunity to rethink their workplaces and prioritize worker well-being. Notably, Sydney discusses how the female presence in the workplace has changed and how a remote or hybrid workforce will require leaders to think differently about creating cohesion, spreading culture, and inculcating values.

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Roberta’s Background

Sydney Associates, Inc.
2016 - 2019
Boston, MA, USA
Sydney Associates, Inc. is a midsize real estate developer, asset and property manager, and multigenerational family business founded by Roberta in 1999. She served as Chairperson before a successful exit and earn out in 2019.
Sydney Associates, Inc.
Founder & CEO
1999 - 2015
Boston, MA, USA
As CEO of Sydney Associates, Inc., Roberta led regulatory compliance, investor relations, as well as tenant servicing for operations, brokerage and leasing. Under her leadership, she ensured shareholder returns of more than 15%. She was crucial in maintaining strong relationships with major tenants, including Bank of America, Trader Joe’s and CVS.
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Roberta’s Gallery

Board Positions

Tiedemann Advisors
Board of Directors
Nov 2019 - Present
New York, NY, USA
Founded in 1999, Tiedemann Advisors is one of the largest independent investment and wealth advisors for high-net-worth individuals, trusts, families, foundations and endowments.
Plaxall, Inc.
Board of Directors
2017 - Present
New York, NY, USA
Plaxall is a family-run company that specializes in commercial real estate and plastic thermoforming manufacturing. Roberta also served as Chair of the Compensation Committee.
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Advisory Roles

Chair | Advisory Board
Boston, MA, USA
Cobu is a real estate technology and services company that makes it easy for residents to connect with neighbors turning apartments into homes.
RentalBeast, Inc.
Somerville, MA, USA
Rental Beast is a real estate technology company that helps streamline the real estate market with its SaaS platform to enable agents, brokers, landlords and tenants to work more effectively.
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Current Board Positions

TIGER 21 logo TIGER 21 logo
Chair | Boston Group
2018 - Present
Boston, MA, USA
TIGER 21 is an exclusive peer membership network of high-net-worth entrepreneurs, investors and executives.
Beth Israel Deaconess Medical Center
Trustee, Advisory Board & Neuroscience Advisory Committee
2014 - Present
Boston, MA, USA
Beth Israel Deaconess Medical Center (BIDMC) is based in Boston and is part of the Beth Israel Lahey Health system. It is one of the world’s top teaching hospitals as part of Harvard Medical School.


Blueprint's Conversations with Champions: Roberta Sydney
Oct 2020
Roberta Sydney joins Proptech's Blueprint: Conversations with Champions series to discuss the developments and the evolution of real estate technology made during her time at the Sydney Associates and her strategies for maintaining construction projects and creating positive relationships with clients.
The Role of The Board of Directors During Crisis
Jun 2020
New York, NY, USA
Roberta Sydney, along with other business leaders and board members, was invited to share her thoughts on how she views leadership during the Covid-19 pandemic. In addition, she discussed the role of the board during the pandemic and offered suggestions on what boards need to do in this moment.
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American College of Corporate Directors
Silver Executive Master's Certificate
Needham, MA, USA
Roberta is accredited as Silver Level Executive by the American College of Corporate Directors. To reach this level of certification, Roberta contributed to the organization by sharing her valuable expertise, knowledge and experience gained throughout her career as an executive and board member.
National Association of Corporate Directors logo National Association of Corporate Directors logo
National Association of Corporate Directors
Cyber Certificate
Arlington, VA, USA
Roberta is a Member and Governance Fellow of the National Association of Corporate Directors and obtained the Cyber Certificate through the organization. This course focused on the cyber-security threat landscape, responsibilities of the board and management in cyber-risk oversight and featured cyber-crisis simulations.
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Specialists, Generalists, and Private Company Board Composition
Jan 2021
"Generalists—rather than specialists—make for great board directors in private companies to keep board size small, be better prepared to govern in times of uncertainty, and communicate effectively with one another and the management team," Roberta says in an article for NACD, in which she discusses the value of generalists on a directorial board.
What Makes a Good Board Director from the CEO Perspective
Oct 2020
In an article written for NACD, Roberta Sydney discusses what a CEO looks for in a quality member for the Board of Directors with the goal to advise those hopeful for a board appointment.
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Women Corporate Directors (WCD)
2019 - Present
Stuart, FL, USA
Women Corporate Directors (WCD) is the largest community of female corporate board directors in the world. The organization has over 8500 members that serve on both private and public boards across the globe.
National Association of Corporate Directors logo National Association of Corporate Directors logo
National Association of Corporate Directors
Member & Governance Fellow
Arlington, VA, USA
The National Association of Corporate Directors provides board members with practical insights through world-class education, leading research, and a growing network of directors. The NACD is the recognized authority on leading boardroom practices.
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Awards & Endorsements

2020 Directors to Watch logo 2020 Directors to Watch logo
2020 Directors to Watch
Dec 2020
Roberta was listed as one of Private Company Director Magazine's 2020 Directors to watch for her work with private companies.

Training & Management Courses

Harvard Business School Executive Education
Board of Director Program
Cambridge, MA, USA
This program examines best practices for corporate boards and explores options and opportunities in corporate board service. Attendees gain a greater understanding of the role and responsibilities of corporate directors and the challenges they can expect to face in that role.

Speaking Engagements

Virtual: The Future of Work is Now
May 2021
As a part of NACD-New England's Private Company Governance and Leadership Initiative, Roberta will be a moderator for a discussion regarding the preparation of companies for the work from home initiative and how the COVID-19 pandemic changed work trends.
Entitlement & Compensation Within Family Businesses
Panel Member
May 2021
In Part 3 of the FBA Family Business Panel, Roberta Sydney and others discuss how to handle the sensitive issues of compensation within a family business. The panel focuses on best practices and the importance of communication, while also highlighting the importance of outside consultation.
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Community Engagement

StartUp Partners
Aug 2017 - Present
Boston, MA, USA
Roberta is the Co-Founder of the StartUp Partners program, an initiative that aims to help start-ups grow and succeed. Advisors are generally executives in the Boston area that are kept up to date with new trends and developments in technology which they pass on to provide valuable feedback to start-ups.
Marathon Daffodils
Boston, MA, USA
Marathon Daffodils is an initiative that aims to bring the spirit of spring to The Boston Marathon with many volunteers contributing to plant over 100,000 daffodils.

Press Releases

LendingHome Hires New CFO and CMO to Help Drive Continued Growth
Jul 2021
New York, NY, USA
Roberta Sydney was recently appointed to the Board of Directors of LendingHome. Sydney was lauded for her success as a real estate entrepreneur, CEO and senior corporate executive. "I'm looking forward to advising LendingHome,” she said. "I believe in the products and people at LendingHome and I'm excited to work with the team.”

Roberta’s Education

Massachusetts Institute of Technology (MIT)
MS | Real Estate Development
1987 - 1988
Harvard Business School
MBA | Business Administration & Management
1981 - 1983
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