Enterprise Sales Executive, Trilogy (Remote) - $200,000/year USD

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 opportunity 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. You'll join a team that operates with speed, iterates relentlessly, and harnesses AI to remove inefficiencies, enabling you to concentrate on what truly drives closures. 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. This is not a passive renewals oversight position. 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 won't be supervising a team or spending hours in redundant internal meetings. You'll be directly engaged, negotiating high-value renewals and ensuring sustained customer retention. If you're ready to influence the future of AI-driven sales while owning high-impact transactions, apply today! What You Will Be Doing 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 What You Won’t Be Doing Pursuing new logo acquisition or prospecting for net-new leads Managing high-volume, low-value renewal transactions 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 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 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 Comfort selling value-added services and premium tiers based on business benefit rather than price Practical experience using ChatGPT or Claude to enhance the quality and efficiency 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 new 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. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you! 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 www.crossover.com/help-and-faqs for more details on this topic. Crossover Job Code: LJ-5529-CA-Toronto-EnterpriseSale1

Own the full renewals lifecycle for high-value enterprise accounts to preserve revenue and reduce churn. Design and refine AI-enhanced sales methodologies and B2B renewals playbooks to optimize retention.

Requires 8+ years of experience in CSM or account management for enterprise SaaS/Cloud products, including closing deals over $100K. Must be proficient in English, experienced with AI tools, and able to work U.S. business hours.

Identified from the job description. Confirm important requirements above.

• Enterprise Sales
• Customer Success Management
• Contract Negotiation
• Account Management
• Renewals Pipeline Management
• C-level Engagement
• AI-powered Sales Execution
• B2B Sales
• Churn Reduction
• Stakeholder Engagement
• Value Proposition Design
• Strategic Customer Engagement

• Sales
• Customer Service & Support
• Software
• Technology
• Management & Leadership

Minimum experience

10+ years

Apply by

Sep 11, 2026

Posting language

English

Working hours

40 hours per week

Location requirements

Country, Toronto, Ontario, Canada

Seniority

Director