Are you an enterprise sales or customer success pro who thrives in high-stakes negotiations, enjoys engaging senior executives, and wants to master AI-driven sales execution? If so, here's a role where you can own the renewals pipeline for high-value enterprise clients, leading direct conversations with decision-makers, and securing multi-million-dollar contracts. At Trilogy, we're not running a traditional SaaS sales org with arbitrary quotas, commission games, or bloated layers of management. We’re an AI-first company that’s rewriting how enterprise sales works: optimizing deal execution, risk assessment, and stakeholder engagement with AI-powered insights. You’ll be part of a team that moves fast, iterates constantly, and leverages AI to eliminate inefficiencies, so you can focus on what actually closes deals. Instead of chasing commissions, you’ll have the stability of a guaranteed comp plan, allowing you to sharpen your sales craft without the stress of unpredictable payouts. This is not a cushy renewals overseer job. It’s a hands-on, execution-driven position where you’ll be responsible for managing a renewals pipeline, identifying key economic buyers, overcoming objections,



and driving contract renewals with precision. You won’t be babysitting a team or wasting time in endless internal meetings. You’ll be on the front lines, negotiating high-value renewals and ensuring long-term customer retention. If you want to shape the future of AI-driven sales while owning high-impact deals, What You Will Be Doing Lead high-touch conversations with key customers, aligning on value, overcoming objections, and winning renewals Define and continuously improve structured B2B renewals playbooks, AI-driven sales strategies, and frameworks to maximize retention and revenue What You Won’t Be Doing This role draws a clear line around two things Senior Customer Success Managers often find themselves pulled into elsewhere: New logo sales or hunting for current leads High volume, low value renewal processing Senior Customer Success Manager Key Responsibilities Own the entire renewals process for high-value enterprise accounts, serving as the primary point of contact, with the goal of retaining revenue and minimizing churn Basic Requirements 8+ years of experience in a CSM or

📌 Senior Customer Success Manager, Trilogy (Remote) - $200,000/Year Usd (Toronto)
🏢 Crossover
📍 Toronto