Senior Commercial Counsel — AI-Driven Tech Contracts

Tipalti; Toronto; Hybrid; CAD 147,000 - 183,000; Full time

Benefits offered by this job

Hybrid working model

Competitive salary and equity

RRSP matching

Extended benefits

Family benefits (Maternity/Paternity)

15 days PTO

Phone/internet allowance

Office near transit

Job summary

Tipalti is hiring a Senior Commercial Counsel for its Toronto office. You will operate in a small, autonomous team that treats AI as infrastructure, influencing negotiations and internal processes beyond standard contracts.

Your practice spans sales, vendor contracts, and regulatory aspects, reporting to the Director, Commercial. You will guide global transactions, leverage AI to optimize workflows, and shape the contracting playbook while maintaining strong business partnerships across time

Qualifications

• Must hold a common-law law degree and be in good standing with the Law Society.
• 8+ years in commercial technology transactions, ideally with both law firm and in-house software company experience.
• SaaS agreements, DPAs, NDAs, SOWs, and partner agreements are second nature.
• Genuine enthusiasm for AI tools and legal tech, with willingness to teach others.
• Communicate directly and collaboratively in a tightly connected team.
• Judgment on sensitive matters is independent, attention to detail is sharp, and ability to manage volume in a fast-moving environment.

Responsibilities

• Own the Sales-Side Pipeline. Negotiate and close the Tipalti Services Agreement, order forms, schedules, SOWs, partner and alliance agreements, channel deals, privacy and DPA negotiations.
• Drive Vendor-Side Contracting, lead commercial contracting of vendor engagements, review risk, handle software, accounting, professional services and other agreements, coach procurement teams.
• Advise the Business Directly as the primary commercial legal contact for sales, customer success, procurement, finance, marketing, security, and GTM teams across time zones.
• Shape the Contracting Playbook by templatizing agreements and building AI-powered workflows; own segments of the contracting pipeline in early quarters.
• Use AI responsibly, calibrate usage to risk and complexity, and apply professional judgment to outputs.
• Run Your Own Book with independent judgment on risk, deal structure, and escalation; communicate with opposing counsel and business leaders.

Skills

SaaS agreements

DPAs

NDAs

SOWs

Contract negotiation

AI in legal tech

Team collaboration

Independent judgment

Education

Common-law JD / LL.B. or equivalent

Job description

Tipalti is hiring a Senior Commercial Counsel for its Toronto office. You will operate in a small, autonomous team that treats AI as infrastructure, influencing negotiations and internal processes beyond standard contracts.

Your practice spans sales, vendor contracts, and regulatory aspects, reporting to the Director, Commercial. You will guide global transactions, leverage AI to optimize workflows, and shape the contracting playbook while maintaining strong business partnerships across time