Chief Legal Officer

About Us: WeShall Investments is a premier mid-market private equity firm with a portfolio of investments across Canada, the U.S.A, and the Caribbean. WeShall does not just invest; we build bridges with a diverse range of leaders, investors, lenders, and entrepreneurs who share our passion for making a difference.  WeShall pursues profits with principles. WeShall partners with businesses that share our values: protecting our planet, giving back to communities, and operating ethically. It's not a feel-good strategy; it's building a future where everyone wins – you, us, and generations to come. For more information, visit our website at:

WeShall was founded by Wes Hall, one of Canada's foremost entrepreneurs and his innovative and entrepreneurial spirit permeates everything we do. Wes is equally comfortable in a Bay Street boardroom or one-on-one with aspiring entrepreneurs, and he has assembled a multi-disciplinary team to expand his entrepreneurial vision.

Job Description: An exceptional opportunity has arisen at WeShall Investments for a full-time, on-site Chief Legal Officer (CLO) to lead our in-house legal function based in our Toronto head office. Reporting to the Founder and Chairman and working closely with the executive leadership team and broader business teams, the CLO will serve as the principal legal and strategic risk advisor to WeShall and its portfolio of operating companies. This position will be responsible for designing and overseeing the legal strategy, governance framework, managing risk across a myriad of industries as well as key external legal relationships across corporate, M&A, financing, employment, litigation, and regulatory matters. The ideal candidate is a seasoned, business-minded legal executive who is comfortable operating in a fast-paced, entrepreneurial, complex cross-border multi-entity platform, and can balance disciplined risk management with sound commercial judgment.  

Key Responsibilities:

• Set and oversee the legal strategy, governance framework, and risk management for WeShall and its portfolio across multiple entities and jurisdictions.
• Act as primary legal advisor to the Founder and Chairman, and executive team, providing clear, business-focused guidance on material legal and structural issues.
• Ensure compliance with applicable laws and regulations and lead policy development.
• Oversee legal aspects of M&A, joint ventures, restructurings, and financings, including structuring, due diligence, documentation, and negotiation.
• Drive standardization and negotiation of key commercial contracts, support portfolio companies major business initiatives and, advise on employment and labour matters (including executive agreements and terminations).
• Manage direct litigation and dispute strategy in partnership with external legal counsel and collaborate on insurance coverage and claims to mitigate risk.
• Lead and develop the internal legal team, define clear roles and escalation paths, and manage relationships with external law firms to ensure quality, responsiveness, and value.
• Stay current on relevant legal developments and industry trends.

Qualifications:

• JD/LLB degree from an accredited law school with excellent academic credentials and qualified to practice law in Ontario.
• Minimum 12 years of relevant legal experience with a meaningful portion spent in-house in a senior role.
• Deep experience in corporate and commercial law, M&A and strategic transactions, governance in multi-entity structures, and cross-border work.
• Demonstrated ability to operate as a trusted advisor to senior executives and boards.
• Excellent analytical, communication, negotiation, and problem-solving skills.
• Ability to work as part of a team in a fast-paced environment.
• Effective communication and presentation abilities.
• Ability to analyze complex legal issues and provide sound legal advice.
• Proficiency in legal research tools and software.
• Attention to detail and an enthusiastic approach to work.
• High level of professionalism and ethical standards.

Preferred Qualifications:

• Prior In-house experience in a private equity, investment, family office, or diversified holding company environment.
• Experience working with mid-market operating businesses in sectors such as industrial services, transportation, environmental services, and hospitality etc.
• Exposure to funds, LP/GP structures, or capital markets transactions is an asset. Exposure to construction law is also an asset.

What We Offer:

• Competitive executive-level compensation and benefits package.
• The opportunity to shape and lead a high impact legal function across a growing multi-sector investment platform.
• A values-driven culture that combines commercial excellence with community and societal impact.
• An opportunity to work directly with the Founder and senior leadership team in a flat, entrepreneurial organization.

Equity Statement

WeShall Investments is a staunch advocate for diversity in all its forms, and especially welcomes applications from members of the BIPOC (Black, Indigenous, and People of Color) community, women, people with disabilities, the LGBTQ+ community, and those of diverse intersectional identities. Accommodation is available on request for candidates taking part in all aspects of the selection process as well as part of employment with WeShall Investments. In accordance with the AODA Act, for applicants with disabilities accommodation will be provided throughout the search process.