Position SummaryTipalti's Commercial Legal Team is adding a Senior Commercial Counsel to its Toronto office. You'll be heavily relied on by a tight, high-autonomy team that treats AI as infrastructure, not novelty. Your practice will span both sides of the commercial deal sheet, and your influence will extend well beyond contract negotiation into how this team operates and evolves.
This role reports to the Director, Commercial, within a team of three. You'll get structured ramp-up time, the tools and training you need to operate at full speed, and the support to build real confidence in Tipalti's products, business, and regulatory landscape before we turn up the volume.
In this role, you will be responsible for:- Own the Sales-Side Pipeline. You'll negotiate and close the Tipalti Services Agreement, along with order forms, schedules, SOWs, partner and alliance agreements, and channel deals. You'll handle security questionnaire escalations, privacy and DPA negotiations, and commercial and contractual inquiries from sophisticated international buyers, managing each from first markup to signature with minimal oversight.
- Drive Vendor-Side Contracting. You'll lead commercial contracting of Tipalti's vendor engagements, coordinating risk reviews with internal teams. Software agreements are the bread and butter, but you'll also handle accounting, professional services, marketing, consulting, events, and other operational agreements. You'll participate in vendor due diligence and the procurement-led intake process while coaching the procurement team and other teams on contracting processes and workflow improvements.
- Advise the Business Directly. You'll be a primary commercial legal point of contact for stakeholders across sales, customer success, procurement, finance, marketing, security, and go-to-market teams in every time zone Tipalti operates in. Customer retention, dispute resolution, commercial regulatory and compliance: you'll field these and drive them to resolution.
- Shape the Contracting Playbook. You'll help reengineer how the commercial legal team operates, from templatizing agreements to building AI-powered workflows. Within your first quarter, you'll own key segments of the contracting pipeline and begin contributing to the team's AI integration roadmap.
- Use AI Like a Boss. You'll calibrate its use to the risk profile and complexity of each matter, applying professional judgment to every output. We need someone who already uses AI, understands its limitations, and knows how to right-size it across contract types.
- Run Your Own Book. You'll carry a full portfolio of matters and exercise independent judgment on risk, deal structure, and escalation. You'll communicate directly with opposing counsel, business leaders, and cross-functional partners, handling matters from intake to close.
About you - You hold a common-law law degree (J.D., LL.B., or equivalent) and are in good standing with the Law Society of Ontario. We are open to other Canadian jurisdictions or US-qualified counsel.
- You have 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.
- You are genuinely enthusiastic about AI tools and legal technology, and your willingness to teach others matches your own skill.
- You communicate directly and collaboratively, and you're built for a team that stays tightly connected.
- Your judgment on sensitive matters is independent, your attention to detail is sharp, and your comfort managing volume in a fast-moving environment is proven.
Our benefits package includes:- Hybrid working model that requires you to be in office Monday, Tuesday, and Thursday
- Competitive salary and equity
- Matching RRSP
- Extended benefits, Employee Assistance Program, life insurance, AD&D, LTD
- Maternity, Paternity and Fertility Treatment benefits
- 15 days of PTO
- Subsidized lunch on office days
- Dog friendly office
- Fresh fruit, snacks & drinks in office
- Conveniently located close to transit
- Phone/internet allowance
- Regular company-wide social events
- Multiple ERG groups celebrating our diversity and creating an inclusive culture
Base Salary Range: $147,000 - $183,000 CAD annually.
The compensation information, above, reflects our reasonable expectation for this role based on several factors, including current market conditions. Final compensation will be determined through individual assessment of experience, skills, qualifications, and other job-relevant factors. Actual offers may vary within or, only in exceptional circumstances, outside the stated range based on the candidate's unique qualifications and our comprehensive evaluation process. We are committed to equitable compensation practices in compliance with applicable employment laws.
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