Commercial Counsel

About the Role

We’re hiring a Commercial Counsel to specialize in commercial contracting and go-to-market negotiations. In this hands‑on, high-visibility role you’ll advise Sales, Customer Success, Partnerships, and senior leadership on complex customer and partner agreements, own negotiation strategy for high-value deals, and establish standard terms, delegation thresholds, and efficient, risk-calibrated contracting workflows.

We are looking for a specialist with strong commercial judgment, deep SaaS/B2B and technology contracting experience, and the ability to translate legal risk into pragmatic business options.

• Act as the primary legal advisor to GTM and executive leaders on customer, partner, including MSAs, SOWs, and enterprise procurement contracts
• Lead negotiation of complex, high-value commercial deals and define negotiation strategy to balance speed, growth and legal risk
• Draft and redline standard templates and negotiation playbooks for Sales and Rev Ops; maintain a delegation matrix and exception approval workflows
• Own service delivery and uptime terms: draft and negotiate SLAs, SLOs, service credits, incident management, change control and remedies tied to service levels, and ensure alignment with SRE/Product on feasibility and operational risk
• Counsel on data processing, privacy, security, and cross-border data transfer clauses in commercial contracts in partnership with Security and Privacy teams
• Provide legal guidance on vendor and procurement agreements, including cloud service, subcontractor and third-party integration contracts
• Support HR on employment and contractor matters, including employment agreements, independent contractor agreements, equity plans, terminations, restrictive covenants, immigration/relocation and employment law compliance across Canada and the US
• Build and maintain contract lifecycle and legal operations capabilities - turnaround SLAs for redlines, approval flows, standard clauses, and training for commercial teams
• Surface commercial risk trends, produce concise reporting and guidance on recurring negotiation points, and work cross-functionally to remediate systemic risk
• Provide timely, practical legal advice in a fast-paced environment and help the business scale while protecting company interests

• 3+ years' post-qualification experience in commercial and technology contracts, ideally in‑house at a SaaS or tech company
• Demonstrated experience negotiating enterprise MSAs, SOWs and partner agreements, and handling high-value, complex commercial deals
• Practical experience drafting and negotiating SLAs, SLOs, and service delivery terms and working closely with our Engineering and GTM leadership on operationally-driven contract terms
• Experience advising on employment law issues, drafting employment and contractor agreements, and supporting HR on compliance across Canada and the US
• Strong commercial judgment and the ability to present tradeoffs and clear recommendations to non‑lawyers and senior leaders
• Excellent drafting and negotiation skills, with an emphasis on clear, business-oriented drafting rather than legalese
• Familiarity with privacy and security controls (SOC2, GDPR, PIPEDA, DORA, ISO 27001) and an ability to collaborate with technical teams on feasible contractual commitments
• Strong stakeholder management skills: comfortable influencing Sales, Product, Security, Finance and HR

• Competitive compensation and early equity in a fast-growing, venture-backed company
• Comprehensive medical, dental, and vision coverage
• 3 weeks of vacation, plus unlimited sick and mental health days, and a company-wide end-of-year shutdown to recharge
• $500 stipend for home office setup
• Unlimited token usage and access to AI tools
• A fast-moving, high-impact environment where your leadership and ideas directly shape the future of the company

Rootly is an equal opportunity employer. We aim to create an environment where every team member at Rootly feels like they belong so they can have a greater impact on our business and customers. We do not discriminate on the basis of race, religion, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.