Are you a seasoned enterprise sales or customer success professional who excels in high-stakes negotiations, relishes engaging C-level executives, and is ready to master AI-powered sales execution? If that describes you, this role offers the prospect to own the renewals pipeline for high-value enterprise accounts, lead direct dialogue with decision-makers, and close multi-million-dollar contracts. Trilogy is not your typical SaaS sales organization with arbitrary quotas, commission schemes, or excessive management layers.

We are an AI-first enterprise redefining how enterprise sales operates: refining deal execution, risk evaluation, and stakeholder engagement through AI-driven insights. Rather than chasing variable commissions, you'll benefit from the security of a guaranteed compensation structure, freeing you to refine your sales expertise without the uncertainty of fluctuating payouts. It's a hands-on, execution-focused role where you'll manage a renewals pipeline, identify critical economic buyers, address objections, and execute contract renewals with precision.

You'll be directly engaged, negotiating high-value renewals and ensuring sustained customer retention. Conduct high-touch engagements with strategic customers, aligning on value delivery, addressing objections, and securing renewals Design and iteratively refine structured B2B renewals playbooks, AI-enhanced sales methodologies,



and frameworks to optimize retention and revenue growth Pursuing new logo acquisition or prospecting for net-new leads Enterprise Sales Executive Key Responsibilities ~ Take full ownership of the renewals lifecycle for high-value enterprise accounts, acting as the primary relationship owner, with the objective of preserving revenue and reducing churn 8+ years of experience in a CSM or account management role at a software/SaaS/Cloud products company serving Enterprise clients ~ Fluent English, with strong verbal and written proficiency ~ Proven 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 Practical experience using ChatGPT or Claude to enhance the quality and efficiency of customer-facing work Hundreds of software businesses run on the Trilogy Business Platform. 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. 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.

📌 Enterprise Sales Executive, Trilogy (Remote) (Vancouver)
🏢 Crossover
📍 Vancouver