Head of Legal

Position: Head of Legal
Comp: $125,000-$150,000 salary + equity
Location: Toronto HQ (3 days per week in office) (Full remote-friendly for top performers)

About Fiscal.ai

Fiscal.ai is a leading research and data platform for capital markets.  Combining a powerful research Terminal with modern APIs, Fiscal.ai is building the modern financial data company.  The firm has raised $13M in venture backing and is headquartered in Toronto, Canada. With thousands of customers and millions of end-users through their API offerings, Fiscal.ai is building the premiere financial data company in the AI era.

The Role

This is an in-house legal role for a commercially minded lawyer who wants to own the legal function at a fast-growing financial data company. You will be the first point of contact for everything legal at Fiscal.ai, from vendor agreements and customer contracts to compliance, risk, and corporate matters. You will work directly with the founding team and across every department.

We are looking for a practical operator who can move quickly, negotiate firmly, and partner with the business to get deals done while protecting the company.

Key Responsibilities

• Commercial Contracts
  Draft, review, and negotiate the full range of commercial agreements, with a heavy emphasis on customer contracts (MSAs, order forms, data licensing agreements, API terms) and vendor agreements.
• Customer & Vendor Negotiations
  Partner directly with the sales team on enterprise customer negotiations, including redlines, security questionnaires, and procurement processes. Manage vendor relationships from a legal and contractual standpoint.
• External Counsel Management
  Serve as the primary point of contact for external counsel across corporate, tax, employment, IP, and specialized matters. Scope work efficiently, manage spend, and bring matters in-house wherever it makes sense.
• External Accounting Coordination
  Work alongside our external accounting partners on matters at the intersection of legal and finance, including corporate structure, contract revenue recognition implications, and entity management.
• Risk & Compliance
  Identify and mitigate legal risk across the business. Design and maintain company policies, support SOC 2 and data privacy compliance efforts, and ensure the company stays on the right side of applicable laws and regulations across the jurisdictions we operate in.
• Corporate & Strategic Matters
  Support corporate matters including financings, equity administration, employment agreements, and any future M&A or strategic activity. Stay close to the founding team on company-building decisions with legal implications.
• Business Partnership
  Act as a trusted advisor to every team at Fiscal.ai. Deliver practical, timely advice that helps the business move faster, not slower. Train internal stakeholders on contract basics, IP, and compliance hygiene so legal does not become a bottleneck

• 3+ Years of Experience as a Practicing Lawyer: Qualified lawyer (called to the bar in Ontario or equivalent jurisdiction) with at least three years of post-call experience, ideally with meaningful time spent on commercial and technology transactions.
• Commercial Contracts Expertise: Demonstrated track record drafting and negotiating SaaS, data licensing, vendor, and enterprise customer agreements. Comfortable owning a deal from first draft to signature without hand-holding.
• Business Judgment: Ability to weigh legal risk against commercial reality and give clear recommendations. You can tell the difference between a real issue and a theoretical one, and you know when to hold the line versus when to find a path forward.
• Operational Mindset: Willingness to roll up your sleeves and handle the full spectrum of work at a startup, from high-stakes negotiations to administrative contract management. No task is beneath this role.
• Strong Communication: Able to translate legal concepts into plain language for sales, engineering, and executive audiences. Writes clearly and concisely.
• Education: Law degree (JD, LLB, or equivalent) and active membership in good standing with a relevant bar or law society.
  Additional Nice-to-Haves
• In-House Experience: Prior in-house legal experience at a SaaS, fintech, or data company.
• Financial Services Familiarity: Exposure to capital markets, financial data, or regulated financial services clients and the contracting norms that come with them.
• Privacy & Security: Working knowledge of data privacy frameworks (PIPEDA, GDPR, CCPA) and security compliance regimes (SOC 2).
• Startup Experience: Comfort operating in a small, fast-moving company where priorities shift and structure is built as you go.
• Cross-Border Experience: Familiarity working across Canadian and U.S. legal environments.

Compensation:

• $125,000 - $150,000 salary
• Equity
• Standard Employee Benefits