Crossover
Enterprise Renewals Lead, Trilogy (Remote) - $200,000/year USD
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The enterprise renewals function is evolving. Top performers will dedicate their time to refining the AI that automates routine work, not performing it themselves.
This role departs from conventional enterprise renewals. You'll manage Trilogy's highest-value customer accounts while collaborating with Fiona, our AI renewals agent. Fiona manages preparation, data analysis, contract processing, and routine follow-up. Your focus is the interactions that demand human judgment: executive engagement, commercial structuring, sophisticated negotiations, and decisions AI cannot yet make. Each renewal you oversee also trains Fiona toward greater independence, strengthening the system with every engagement.
Trilogy is constructing an AI-first operational framework across our software companies. AI isn't a layer we add to legacy workflows—we rebuild the workflow around AI and deploy human judgment only where it creates the greatest value. In this position, you'll help establish what enterprise renewals become in an AI-driven organization while safeguarding millions in recurring revenue from strategic enterprise accounts.
If you're a proven enterprise renewals leader who excels in executive dialogue, views AI as a multiplier of capability, and prefers building the future to protecting the status quo, let's talk.
What You Will Be Doing
- Manage executive relationships and commercial negotiations for enterprise renewal accounts of significant value, including multi-year agreements exceeding seven figures.
- Collaborate with Fiona, Trilogy's AI renewals agent, applying your judgment and customer insight to refine its capabilities and expand its autonomy.
- Assess customer health indicators, usage patterns, commercial history, and risk exposure to drive proactive renewal success.
- Leverage Salesforce and AI-enabled workflows to sustain precise forecasts, surface renewal risks promptly, and concentrate your effort where human expertise delivers maximum impact.
- 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 documentation manually, tracking down approvals, or executing repetitive administrative tasks.
- Handling high-volume transactional renewals or small and mid-market accounts.
- Pursuing new customer acquisition or operating under a conventional commission-based sales quota.
- Developing production code or constructing AI models.
- Overseeing a large renewals team rather than directly influencing the most critical customer outcomes.
Enterprise Renewals Lead Key Responsibilities
- Take ownership of Trilogy's most critical enterprise renewals while iteratively strengthening the AI infrastructure that drives superior retention, operational efficiency, and progressively autonomous renewal execution.
Basic Requirements
- Direct experience owning enterprise renewals or retention for B2B software accounts generating at least $100K in annual recurring revenue.
- Documented ownership of quarterly retention or Net Revenue Retention objectives, consistently delivering at least 90% NRR or comparable performance across multiple quarters.
- Direct responsibility for leading complex, multi-year enterprise renewals with a value of $1M or greater.
- Practical experience working with AI-enabled or agentic systems in enterprise renewals, customer success, or enterprise sales contexts.
- Proficiency with Salesforce or equivalent CRM platforms, including renewal forecasting, risk detection, and pipeline oversight.
- Outstanding executive communication, commercial negotiation, and relationship stewardship capabilities.
- Ability to operate effectively in a global, fully remote setting.
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Nice-to-have Requirements
- Experience refining AI prompts, workflows, or business logic informed by customer engagement outcomes.
- Professional history in enterprise SaaS, cloud-based software, or subscription technology sectors.
- Ability to leverage data from contracts, customer health metrics, support activity, and product usage to inform renewal strategy.
- Proven systems thinking and a history of enhancing repeatable commercial processes 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.001
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