Crossover
Enterprise Renewals Lead, Trilogy (Remote) - $200,000/year USD
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The future of enterprise renewals is here.
The best professionals won't waste time on administrative tasks—they'll dedicate their energy to refining the AI systems that handle them.
This role breaks from conventional enterprise renewals positions. You'll manage Trilogy's highest-value customer accounts while collaborating with Fiona, our AI-powered renewals agent. Fiona manages preparation, analytical work, contract processing, and follow-through. Your focus: the interactions that demand human insight—executive engagement, commercial planning, intricate negotiations, and strategic judgment that remains beyond AI's current reach. Each renewal you complete simultaneously trains Fiona toward greater independence, strengthening the platform through every customer touchpoint.
Trilogy is constructing an AI-first operational framework throughout our software business. AI isn't merely a productivity enhancement added to legacy workflows. We reconstruct processes with AI at the center, preserving human expertise exclusively for maximum-impact decisions. In this position, you'll help architect what enterprise renewals become in an AI-centered environment while safeguarding millions in recurring revenue from strategic enterprise accounts.
If you're a seasoned enterprise renewals professional who excels in executive dialogue, views AI as a capability accelerator, and seeks to construct tomorrow's model rather than preserve yesterday's, we want to speak with you.
What You Will Be Doing
- Manage executive relationships and commercial discussions for high-stakes enterprise renewal portfolios, encompassing sophisticated seven-figure, multi-year contracts.
- Collaborate with Fiona, Trilogy's AI renewals agent, applying your expertise and customer insights to systematically enhance its capabilities and self-sufficiency.
- Evaluate customer vitality, usage patterns, commercial records, and organizational risk to proactively secure positive renewal results.
- Leverage Salesforce and AI-powered processes to sustain precise forecasting, surface renewal vulnerabilities early, and concentrate intervention where human judgment delivers maximum value.
- Convert insights from customer interactions into systematic enhancements that strengthen renewals operations progressively.
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What You Won’t Be Doing
- Generating renewal documents manually, tracking down approvals, or executing routine administrative tasks.
- Overseeing high-volume transactional renewal pipelines or SMB customer segments.
- Pursuing new customer acquisition or managing traditional commission-based sales targets.
- Developing production-level code or constructing AI algorithms.
- Building out a large renewals team rather than directly shaping critical customer outcomes.
Enterprise Renewals Lead Key Responsibilities
- Manage Trilogy's highest-priority enterprise renewals while systematically advancing the AI infrastructure that drives superior retention, operational efficiency, and progressively autonomous renewal capabilities.
Basic Requirements
- Direct experience managing enterprise renewals or retention for B2B software clients with account values of at least $100K in annual recurring revenue.
- Documented ownership of quarterly retention or Net Revenue Retention objectives, reliably delivering at least 90% NRR or comparable performance across several quarters.
- Direct responsibility for complex, multi-year enterprise renewals valued at $1M or greater.
- Practical experience applying AI-enabled or agentic platforms within enterprise renewals, customer success, or enterprise sales operations.
- Substantial Salesforce or equivalent CRM expertise, encompassing renewal forecasting, risk detection, and pipeline oversight.
- Outstanding executive communication, commercial negotiation, and relationship stewardship capabilities.
- Prepared to operate internationally in a completely remote setting.
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Nice-to-have Requirements
- Experience refining AI prompts, operational workflows, or decision logic informed by customer engagement patterns.
- History in enterprise SaaS, cloud-based software, or subscription technology organizations.
- Experience synthesizing contract data, customer health metrics, support interactions, and usage analytics to inform renewal approaches.
- Proven systems orientation and history of enhancing scalable commercial workflows through automation.
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-5834-GB-COUNTRY-EnterpriseRene.003
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