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 quick, 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 High-touch customer conversations are the core of this role — 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 New logo sales or hunting for new leads High volume, low value renewal processing Enterprise Sales Executive 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

📌 Enterprise Sales Executive, Trilogy (Remote) - $200,000/Year Usd (Toronto)
🏢 Crossover
📍 Toronto