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 recent 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 account management role at a software/SaaS/Cloud products company serving Enterprise clients Experience managing the entire renewal cycle — client engagement, value proposition, negotiation, managing paper process, and closing deals worth $100K+ Fluent English, with strong verbal and written proficiency Experience using AI tools in a professional setting Must be able to work during U.S. business hours Nice-to-have Requirements Track record renewing complex, high-value B2B software (SaaS and on-prem) and related services with large enterprises Experience selling multiple products across different verticals or business units Comfort selling value-added services and premium tiers on business benefit rather than price Hands-on use of ChatGPT or Claude to raise the quality and throughput of customer-facing work About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, innovating new technology, and incubating recent businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs.

Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career in leaps and bounds. Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult for more details on this topic.

📌 Senior Customer Success Manager, Trilogy (Remote) (Calgary)
🏢 Crossover
📍 Calgary