Commercial Counsel

Rootly

43d

About The Position

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.

Requirements

• 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

Responsibilities

• 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 RevOps; 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

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed