Steven Dickie

Steven’s practice involves providing business-critical advice on workplace law matters and representing employers in wrongful dismissal litigation, human rights applications, labour arbitrations and before various administrative tribunals.

A main focus of Steven’s practice is on advising emerging companies and technology companies on limiting and managing employment-related issues and distractions that could otherwise jeopardize the growth of the business. Where necessary, Steven guides and represents these companies with respect to employee disputes by means of strong advocacy throughout the civil litigation process.

Steven regularly advises on all types of corporate transactions, including share and asset purchase deals, and workforce services agreements. He also assists employers in drafting and implementing workplace policies, employment contracts, non-competes and non-solicits and executive compensation arrangements.

Steven  has represented both public and private sector clients on wrongful dismissal matters as well as labour arbitrations dealing with a diverse range of subject matters including drug testing, workplace bullying, insubordination, contracting out, performance pay and workforce reductions. Steven has also advised clients on union organizing campaigns and applications for union certification, including with respect to novel issues at the intersection between labour and franchise law. Many of Steven’s clients are based outside of Canada and they rely upon him to help navigate the Canadian labour and employment legal landscape.

Representative Work

  • MoonPay

    MoonPay in its acquisition of Nightshift

  • iNovia Capital

    iNovia Capital in CommerceBear’s US$10.5 million funding round

  • Signal 1

    Signal 1 in its collaboration with Unity Health Toronto and TD Bank Group along with its US$10 million Seed financing

  • Agilysys

    Agilysys in its US$25 million acquisition of ResortSuite

  • Security Compass Technologies

    Security Compass Technologies in the sale of its consulting business to Kroll

  • Epiq

    Epiq in its acquisition of Simplex Services Inc.

  • Roadmunk

    Roadmunk in its acquisition by Tempo Software

  • Affinio

    Affinio in its acquisition by NowVertical

  • Waabi

    Waabi in its launch and US$83.5 million Series A financing round

  • Higher Logic

    Higher Logic in its acquisition of Vanilla

  • Wealthsimple

    Wealthsimple in its $750 million financing

  • Yolk

    Yolk in its acquisition by Astreya

  • Borrowell

    Borrowell’s acquisition of Refresh Financial

  • Verafin

    Verafin in its US$2.75 billion acquisition by Nasdaq

  • Achievers

    Achievers in its acquisition of TemboSocial

  • Managed Sentinel

    Managed Sentinel in its acquisition by BlueVoyant

  • Lenders

    Lenders in Berkshire Partners’ acquisition of VetStrategy

  • CryptoNumerics

    CryptoNumerics in its acquisition by Snowflake

  • Rubikloud

    Rubikloud in its US $60 million acquisition by Kinaxis

  • Affinity

    Affinity in its acquisition of


Select Reported Work:

  • Canada Bread Company Ltd. as counsel in Ontario Labour Relations Board proceedings relating to Teamsters’ attempt to organize the Franchisees’ of Canada Bread in five key depots in the Greater Toronto Area.
  • Wealthsimple as an advisor on a broad range of Canadian workplace issues including providing business critical legal and strategic advice.
  • Mother Parkers Tea & Coffee Inc. as counsel on all employment and labour matters in Canada, spanning a diverse range of issues.
  • Advised on the labour relations issues related to the integration of two public hospitals.
  • Successfully resolved a human rights complaint against an employer and individual managers for a company in the entertainment industry.
  • Defended a large manufacturer facing quasi-criminal charges related to a workplace fatality.
  • Successfully resolved health and safety complaints made by a former employee to the Ontario Labour Relations Board.
  • Devised and implemented a strategy to address executive employment issues, while avoiding any disruption to senior management, in connection with the acquisition of a business with approximately 700 Canadian employees.
  • Advised a major U.S. manufacturer on complex issues involving interwoven employment, safety, regulatory and environmental risks in connection with the acquisition of a Canadian business.
  • Advised an oil and gas company on a corporate reorganization in light of the union bargaining rights attached to various subsidiaries.

Latest Insights

  • Blog Jul 4, 2024

    Court decision reminds employers to avoid ‘two-step’ offers of employment

    In Adams v. Thinkific Labs Inc., 2024 BCSC 1129, a British Columbia trial court applied the doctrine of consideration at the employment contract...

    Read more
    Court decision reminds employers to avoid ‘two-step’ offers of employment
  • Blog May 2, 2024

    Amendments to Ontario’s licensing regime for recruiters and temporary help agencies

    On April 29, 2024, O. Reg 182/24 came into force amending Ontario’s licensing regime for recruiters and temporary help agencies (THAs). The...

    Read more
    Amendments to Ontario’s licensing regime for recruiters and temporary help agencies
  • Blog May 1, 2024

    Ontario considering 27-week personal illness leave

    The Ontario government is conducting a consultation on amending the Employment Standards Act, 2000 (ESA) to include an unpaid 27-week personal...

    Read more
    Ontario considering 27-week personal illness leave
  • Webinar Mar 27, 2024

    Employment and Labour Law Insights: Artificial intelligence in the workplace

    The Q1 2024 webinar will discuss artificial intelligence in the workplace, the latest termination clause case law developments as well as the risks...

    Read more
    Employment and Labour Law Insights: Artificial intelligence in the workplace
View all Insights

Awards and Recognition

  • Chambers Canada: Canada’s Leading Lawyers for Business: Recognized in Employment and Labour (Ontario)

Media Mentions

  • Media Mentions Jun 3, 2024

    New recruiting rules take effect in Ontario July 1 — Canadian HRReporter

    The requirement for temporary help agencies and recruiters in Ontario to hold a license to operate effective July 1 is not necessarily good news for...

    Read more
    New recruiting rules take effect in Ontario July 1 — Canadian HRReporter
  • Osler News Mar 1, 2020

    Osler welcomes 11 new partners, 1 new counsel

    Osler is proud to announce the addition of 11 new partners and one new counsel across three of our offices, effective March 1.

    Read more
  • Media Mentions Jun 29, 2018

    What to do when workplace harassers are members of the public? — Benefits Canada

    For employers in Ontario, the process for addressing workplace harassment from customers or members of the public can be more difficult than when it...

    Read more



  • University of Victoria, J.D.
  • Queen’s University, B.A. (Hons.)


  • English

Professional Affiliations

  • Canadian Bar Association (CBA)
  • Ontario Bar Association (OBA)
  • Law Society of Ontario
  • Canadian Association of Counsel to Employers (CACE)