Enterprise renewal positions typically limit you to a single product line and a fixed quota. This role breaks that pattern. You will work with a portfolio of enterprise software products — developing sufficient expertise in each to articulate its value to executive stakeholders — and accelerate your sales capability in months rather than years.

Trilogy measures the caliber of execution, not volume metrics. We do not monitor deal counts or churn rates. Instead, we evaluate preparation quality: whether renewal discussions were thoroughly planned, whether customers clearly understood their available paths forward, and whether your correspondence genuinely advanced the renewal process.

Earnings are salaried, not commission-based. Discounting is not within your authority — pricing remains fixed. Your responsibility is to articulate value with clarity.

You will lead renewal discussions and manage customer communications for enterprise accounts, present AI functionality alongside Platinum and Prime offerings, and direct customers to our Self-Serve Portal. AI integration is operational, not conceptual: you will apply it to opportunity preparation, inbox management, and refinement of outbound messaging.

If you prefer building mastery of a rigorous, consistent sales methodology over chasing a quota, submit your application.

What You Will Be Doing

- Conducting renewal sales discussions with enterprise customers — drawing from Salesforce chance records and AI-produced summaries of current and historical renewals, establishing the agenda, adhering to the call protocol and quality standard, and concluding with a mutually confirmed next step
- Articulating the business case for AI features, Platinum, and Prime, or directing customers toward the Self-Serve Portal to review materials independently
- Composing customer correspondence that progresses the renewal — clear, direct,



aligned with playbook standards and templates, and refined using AI tools
- Executing the Renewals Cadence in full and maintaining Salesforce opportunity documentation with sufficient clarity that any reader can immediately assess renewal status
- Submitting internal requests — quotes, invoices, legal reviews, support tickets, escalations — to ensure customers never need to follow up on commitments you have made

What You Won’t Be Doing

- Pursuing new customer acquisition or lead generation
- Adjusting pricing or offering discounts to secure agreement
- Relationship maintenance calls, goodwill meetings, or satisfaction check-ins

Enterprise Renewals Executive Key Responsibilities Ensure excellence in every renewal interaction and customer communication assigned to your accounts: thoroughly prepared calls, options explained with clarity, outcomes that drive action, and Salesforce documentation that accurately reflects status. Performance is measured against the renewal call quality standard and the AI Opp Cadence Checker report — not against a revenue quota.

Basic Requirements

- 4+ 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+
- Full professional fluency in written and spoken English
- Experience using AI tools in a professional setting




- Must be able to work during U.S. business hours

Nice-to-have Requirements

- Proven success renewing complex, high-value B2B software (SaaS and on-prem) and associated services with large enterprises
- Background managing multiple products across diverse verticals or business units
- Ability to position value-added services and premium tiers based on business impact rather than cost
- Practical experience with ChatGPT or Claude to enhance quality and efficiency of customer-facing deliverables

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 $50 USD/hour, which equates to $100,000 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-3282-CA-COUNTRY-EnterpriseRene

📌 Enterprise Renewals Executive, Trilogy (Remote) (Canada)
🏢 Crossover
📍 Canada