Head of Legal

Fiscal AI

Head of Legal managing legal responsibilities in a fast-growing financial data company. Oversee contracts, compliance, and legal strategy while collaborating with various departments.

Posted 5/26/2026full-timeToronto • 🇨🇦 CanadaLead💰 CA$125,000 - CA$150,000 per yearWebsite

About the role

Key responsibilities & impact

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.
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.
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.
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.
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.
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.
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.
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

Requirements

What you’ll need

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.
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.

Benefits

Comp & perks

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

commercial contractsSaaS agreementsdata licensing agreementsvendor agreementsenterprise customer agreementscontract managementlegal risk assessmentcorporate governancedata privacy compliancenegotiation

Soft Skills

business judgmentstrong communicationoperational mindsettrusted advisorproblem-solvingadaptabilitycollaborationtrainingclear recommendationspractical advice

Certifications

law degree (JD, LLB)active bar membership