Legal Architect, Enterprise

Wintermeyer Ventures; Toronto; Hybrid; CAD 93,000 - 173,000; Full time

Job summary

Wintermeyer Ventures is seeking a qualified legal technology professional to join the enterprise team in Toronto. You will partner with sales to understand law firm and corporate client workflows, and lead tailored demonstrations of AI-enabled legal research and drafting tools.

Responsibilities include building business cases, designing pilots with measurable outcomes, and guiding customers from pilot to broader rollout.

Qualifications

• 3–6 years of legal experience; 2–10 years considered.
• JD required; experience at a large law firm or technology company.
• Experience in litigation, employment, mergers & acquisitions, finance or insurance law.
• Familiarity with the Toronto legal market.
• Strong communication skills and ability to present to senior stakeholders.

Responsibilities

• Partner with sales colleagues in meetings with law firms and corporate legal stakeholders to understand workflows and needs.
• Lead consultative discussions and tailored demonstrations of AI-driven legal research and drafting tools.
• Build business cases for AI adoption and design pilots with clear outcomes and success measures.
• Advise senior stakeholders and guide customers from pilot through rollout.
• Share customer insights with product, sales, and marketing teams to inform solutions and messaging.

Skills

Legal experience

Client-facing

Stakeholder management

Communication skills

Education

JD (Canadian/US)

Tools

Legal research tools

Job description

About the Role

Join the enterprise team at a legal technology SaaS company, bringing legal expertise to customer conversations about AI. You will help law firms and corporate legal teams evaluate AI-enabled tools, run meaningful pilots, and adopt solutions that support real legal workflows.

What You'll Do

• Partner with sales colleagues in meetings with law firm and corporate legal stakeholders to understand their workflows and needs.
• Lead consultative discussions and tailored demonstrations of AI-driven legal research and drafting tools.
• Build business cases for AI adoption and design pilots with clear customer outcomes and success measures.
• Advise senior stakeholders and guide customers from pilot through broader rollout.
• Share customer insights with product, sales, and marketing teams to inform solutions and messaging.

What We're Looking For

• Typically 3 to 6 years of experience, with 2 to 10 years considered, as an attorney, in-house counsel, or legal engineer.
• A JD and experience at a large law firm or technology company, or with a legal AI provider.
• Background in litigation, employment, mergers and acquisitions, finance, or insurance law. Bankruptcy and insolvency backgrounds are not a fit for this role.
• Strong understanding of legal workflows, law firm operations, and legal terminology, including familiarity with the Toronto legal market.
• Experience presenting to senior legal stakeholders, with strong communication skills and the ability to build trusted relationships.
• Client-facing experience in technology, consulting, sales, or legal innovation is beneficial; interest in legal AI is valued.
• Stable recent work history, without one-year company tenures in the past three to four years.
• Authorization to work in Canada without visa sponsorship.

Compensation & Benefits

Base salary: CAD $93,100 to $172,900 annually. Visa sponsorship is not available.

Location

Hybrid role based in Toronto, Ontario, Canada. The position requires working in the office at least two days per week, with flexibility for additional in‑city client meetings.