Winston received a Bachelor of Commerce degree from the University of British Columbia in 1990 and an LL.B. and M.B.A. in Finance from the University of Windsor in 1993. He completed the Canadian Securities Course in 1994 and the CICA Indepth Tax Course in 1996. Winston was called to the British Columbia Bar in 1994. He is also a Certified Management Accountant (CMA). He joined Sangra Moller in 1996 and became a partner of the firm in 1999.

Winston has been involved in acquisitions, financings and reorganizations of various types and sizes, including Canadian and cross-border private and public debt and equity offerings, tax reorganizations, and mergers & acquisitions transactions involving significant local, national and international clients. He has led and provided strategic advice on various proxy contests, and negotiated and unsolicited takeovers. In addition, he has been retained as special counsel by issuers to interface with securities regulators and to provide strategic advice relating to financial and accounting matters. Winston also provides ongoing corporate and commercial advice to clients.

Winston is a member of the Professional Conduct Enquiry Committee of the Certified Management Accountants of British Columbia and was a former member of the board of directors of its Vancouver Chapter. Winston has been profiled by the Certified Management Accountants of British Columbia as an accomplished member - CMA Spotlight.

He has authored various articles, including "Re-emergence of Proxy Contests".