416-486-1295 / 8:30am - 5pm / 250-250 Eglinton Ave. W., Toronto, ON M4R 1A7 [email protected]

Who We Are

At Win-Bar Insurance you’ll get to know your broker by name…

Brenda Wintraub

[email protected] | x. 226

LL.B., Principal. For more than twenty years, Brenda has worked closely with clients who own luxury properties and vehicles. She brings a long-standing relationship with Chubb Insurance to the table as well as her legal background.

  • Osgoode Hall Law School, L.L.B., 1983
  • Principal Broker, CAIB
  • Registered Insurance Broker of Ontario (R.I.B.O.) since 1988
  • Executive Women’s Forum for female insurance executives
  • Member of Insurance Brokers Association of Ontario (I.B.A.O) since 2003.
  • Climbed Mt Kilimanjaro at 40, doesn’t mind when her son beats her at tennis, and loves pizza with anchovies. So, the pizza part is true.

Jay Wintraub

[email protected] | x. 224

B.B.A, Principal. Jay brings a business education (with a specialty in sales) and experience in the corporate sector to his role at Win-Bar. After more than two decades of working closely with commercial clients Jay is adept at navigating the changing marketplace.

  • York University, B.B.A., 1986
  • Registered Insurance Broker of Ontario (R.I.B.O.) since 1986
  • Member of Insurance Brokers Association of Ontario (I.B.A.O) since 2003
  • Member of the Royal & Sun Alliance Insurance (RSA) Broker Advisory Council, 2005/2006
  • An avid tennis player and golfer, Jay loves to travel with his family.

I think of myself as an advocate. My job is to navigate the complex world of insurance for our clients. And to come up with a solution as discerning as they are.

Brenda Wintraub


Our goal is to provide practical and practicable solutions.

Jay Wintraub


Contact Us

(416) 486-1295

Sasha Balkissoon

Vice President Personal Lines & Private Client Manager / High Value Home

Maria Alvaro

Personal Lines Broker / Home & Auto

Cheryl Ross

Personal Lines Broker / High Value Auto

Andrea Carrozza

Personal Lines Broker / Home & Auto

Donna Evans

Commercial Lines Broker

Brenda McCutcheon


Get in touch!


For general inquiries, please submit a message here and an agent will be in touch with you.