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Commercial Counsel Location: Remote, USA Department: Legal & Compliance   About Syllo Syllo is defining the Litigation AI category. We are the first unified platform designed to autonomously manage the entire litigation lifecycle end-to-end. Founded in 2019 by a team of litigators and engineers, Syllo enables legal teams to securely harness the power of AI across any matter, regardless of complexity or scale. Our technology supports Fortune 500 companies and AmLaw 200 firms managing their most complex litigation portfolios. Awarded ILTA Transformative Project of the Year and ALM eDiscovery Technology of the Year for 2026, we are the market leader in enterprise-grade litigation AI. Backed by top-tier VCs, we are at a clear inflection point — the team has doubled in the last six months and growth is accelerating.   About the role Join the team building Syllo’s commercial legal function. This role is Syllo's first dedicated commercial counsel.  Your will be responsible for negotiating MSAs and NDAs, managing our sales contract coordinator, and building the playbooks that let our commercial legal motion scale alongside our sales pipeline. You will work directly with enterprise customers that include AmLaw 200 law firms and Fortune 500 legal departments, many with sophisticated in-house teams of their own. Because this is a founding hire in a new legal function, the role rewards range. Contracting is the core, but the work extends into intellectual property and data privacy, both inside our agreements and beyond them. You’ll have the opportunity to tackle issues relating to privacy and GDPR, AI regulations, and the intersection between professional responsibility and AI.  We are looking for someone who is excited to build a department, not just fill a seat, and who treats an unfamiliar problem as something to learn rather than something to route elsewhere. We are looking for a commercial attorney who has owned negotiations, not just reviewed contracts. Someone who understands how enterprise software deals are structured, where the real risk sits, and how to move a redline to close without creating long-term liability.   What you will do Negotiate MSAs and NDAs: Own commercial contract negotiations with enterprise customers from first redline through signature. Handle IP in agreements and protect Syllo's IP: Own the IP terms that run through our contracts, and help protect Syllo's intellectual property more broadly as the company grows. Address data privacy in contracts and support compliance: Own the data privacy provisions that a litigation SaaS product demands, and help the Data Security team interpret the statutory rules and regulations that shape our obligations. Build playbooks: Create and maintain negotiation playbooks, standard positions, and pre-approved fallback language that let the team move faster without escalating everything. Manage Contract Administration: Oversee contract management processes and ensure we are aware of key milestones and renewals. Advise the GTM team: Serve as the legal partner for Sales and CS. Available, direct, and commercial in orientation. Develop strategy on legal issues involving AI: Evaluate new models and AI technologies from a legal perspective, guide our responses to new AI regulation, and help educate legal organizations regarding the opportunities and risks involving AI. Identify legal risk: Spot the provisions that create real exposure and distinguish them from the ones that do not. Not everything needs to be a fight.   What you bring MSA and NDA negotiation depth: You have owned the negotiation, not just reviewed the output. You can describe the provisions you pushed on, gave on, and held. Legal tech and AI contract awareness: You understand the risk landscape of AI-powered SaaS in a legal data context, including data ownership, model training restrictions,