Crossover
Enterprise Renewals Lead, Trilogy (Remote) - $200,000/year USD
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The enterprise renewals function is evolving. Top performers no longer spend time on administrative tasks—they focus on training the AI that automates them.
This role is unlike conventional enterprise renewals positions. You will manage Trilogy's highest-value client relationships while collaborating with Fiona, our AI-powered renewals agent. Fiona manages preparation, analysis, contract processing, and follow-through. Your focus is on what matters most: executive engagement, commercial tactics, intricate negotiations, and the judgment AI cannot yet deliver. Each renewal you manage simultaneously trains Fiona to operate more independently, strengthening the system through each customer engagement.
Trilogy is constructing an AI-first operational framework across our software companies. AI isn't treated as a supplementary productivity feature layered onto legacy workflows. We restructure the workflow around AI capabilities and allocate human judgment to the most critical decisions. In this position, you will help establish what enterprise renewals mean in an AI-driven environment while safeguarding millions in recurring revenue from strategic enterprise accounts.
If you are a seasoned enterprise renewals professional who excels in executive dialogue, views AI as an amplifier of capability, and prefers building the future to preserving the status quo, we want to speak with you.
What You Will Be Doing
- Manage executive-level relationships and commercial discussions for high-stakes enterprise renewal portfolios, including sophisticated seven-figure, multi-year contracts.
- Collaborate with Fiona, Trilogy's AI renewals agent, applying your expertise and customer insights to iteratively enhance its capabilities and independence.
- Evaluate customer health indicators, product adoption patterns, commercial background, and business exposure to proactively secure positive renewal results.
- Leverage Salesforce and AI-integrated workflows to ensure forecast accuracy, detect renewal vulnerabilities early, and focus intervention where human judgment delivers maximum value.
- Convert insights from customer interactions into scalable enhancements that strengthen the renewals operation over time.
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What You Won’t Be Doing
- Preparing renewal documentation by hand, tracking down approvals, or executing repetitive clerical tasks.
- Overseeing high-volume transactional renewals or small and mid-market customer accounts.
- Prospecting for new business or working toward a conventional commission-based sales target.
- Developing production-grade software or constructing AI models.
- Running a large renewals team rather than directly shaping the most critical customer results.
Enterprise Renewals Lead Key Responsibilities
- Manage Trilogy's highest-priority enterprise renewals while iteratively refining the AI infrastructure that drives improved retention, operational efficiency, and progressively autonomous renewal execution.
Basic Requirements
- Direct experience managing enterprise renewals or retention for B2B software clients with accounts generating at least $100K in annual recurring revenue.
- Demonstrated accountability for quarterly retention or Net Revenue Retention metrics, consistently delivering at least 90% NRR or comparable performance across multiple quarters.
- Direct involvement in leading sophisticated, multi-year enterprise renewals valued at $1M or higher.
- Practical experience with AI-powered or agentic tools within enterprise renewals, customer success, or enterprise sales operations.
- Solid proficiency with Salesforce or similar CRM platforms, including renewal forecasting, risk detection, and pipeline oversight.
- Outstanding executive communication, commercial negotiation, and relationship stewardship capabilities.
- Able to operate effectively across global time zones in a fully remote setting.
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Nice-to-have Requirements
- Experience refining AI prompts, workflows, or decision logic informed by customer engagement patterns.
- Professional history in enterprise SaaS, cloud-based software, or subscription technology sectors.
- Experience synthesizing data from contracts, customer health metrics, support interactions, and product usage to inform renewal approaches.
- Proven systems-oriented mindset and history of enhancing repeatable 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
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