Crossover
Enterprise Renewals Lead, Trilogy (Remote) - $200,000/year USD
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The renewals landscape for enterprise software is evolving. Top performers are no longer consumed by administrative overhead—they're shaping the AI systems that automate it.
This is not a conventional enterprise renewals position. You will manage Trilogy's highest-value customer accounts while collaborating with Fiona, our AI-powered renewals agent. Fiona manages preparation tasks, analytical work, contract processes, and routine follow-ups. Your focus will be on high-impact activities: executive-level alignment, strategic commercial decisions, intricate negotiations, and the critical thinking AI cannot yet deliver. Each renewal you oversee also trains Fiona to operate with greater independence, refining the system through every customer engagement.
Trilogy is building an AI-first operational framework across our software businesses. We don't treat AI as an add-on to enhance legacy workflows. We architect processes from the ground up around AI capabilities and deploy human judgment where it creates maximum value. In this position, you'll help establish what enterprise renewals should look like in an AI-driven environment while safeguarding millions in recurring revenue from strategic enterprise clients.
If you're a seasoned enterprise renewals professional who excels in executive-level dialogue, views AI as an enabler of scale, and wants to construct the future rather than preserve the status quo, we want to speak with you.
What You Will Be Doing
- Manage executive-level relationships and commercial negotiations for enterprise renewal accounts of significant value, including complex multi-year deals worth seven figures.
- Collaborate with Fiona, Trilogy's AI renewals agent, applying your expertise and customer insights to continually enhance its capabilities and operational independence.
- Evaluate customer health indicators, usage patterns, commercial background, and business exposure to drive proactive renewal success.
- Leverage Salesforce and AI-powered workflows to ensure forecast accuracy, surface renewal risks early, and focus intervention efforts where human judgment delivers the highest return.
- Translate insights from customer interactions into systematic enhancements that strengthen the renewals operation over time.
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What You Won’t Be Doing
- Preparing renewal documents manually, tracking down approvals, or handling repetitive administrative tasks.
- Overseeing high-volume transactional renewals or small and mid-market accounts.
- Prospecting for new business or working under a traditional sales quota structure with commission-driven compensation.
- Developing production-level software code or designing AI models.
- Building or managing a large renewals team rather than directly shaping the most critical customer outcomes.
Enterprise Renewals Lead Key Responsibilities
- Own Trilogy's highest-priority enterprise renewals while driving continuous improvement of the AI infrastructure that supports superior retention, operational efficiency, and progressively autonomous renewal workflows.
Basic Requirements
- Direct experience owning enterprise renewals or retention responsibilities for B2B software customers 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.
- Proven track record personally managing complex, multi-year enterprise renewals with contract values of $1M or greater.
- Practical experience working with AI-enabled or agentic platforms in enterprise renewals, customer success, or enterprise sales environments.
- Solid proficiency with Salesforce or similar CRM systems, including renewal forecasting, risk detection, and pipeline oversight.
- Outstanding executive communication abilities, commercial negotiation expertise, and relationship-building competence.
- Ability to operate effectively in a fully remote, globally distributed work setting.
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Nice-to-have Requirements
- Experience refining AI prompts, workflows, or business logic informed by customer engagement patterns.
- Professional background in enterprise SaaS, cloud software platforms, or subscription technology companies.
- Experience synthesizing data from contracts, customer health metrics, support interactions, and product usage to inform renewal approaches.
- Strong systems-oriented thinking and a history of enhancing scalable commercial operations through automation initiatives.
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.002
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