Description
The enterprise renewals landscape is evolving. Top performers won't be buried in administrative work—they'll be refining the AI systems that automate it.
This role departs from conventional enterprise renewals positions. You'll manage Trilogy's highest-value customer accounts in partnership with Fiona, our AI-powered renewals agent. Fiona manages preparation, analysis, contract processing, and routine follow-up. Your focus remains on what truly matters: executive engagement, commercial planning, sophisticated negotiations, and the strategic judgment AI cannot yet deliver. Each renewal you complete also trains Fiona to operate with greater independence, strengthening the system through every customer engagement.
Trilogy is constructing an AI-first operational framework across our software businesses. We don't treat AI as an add-on to legacy workflows. We rebuild the workflow with AI at the center and deploy human judgment only where it creates maximum value. In this position, you'll help establish what enterprise renewals become 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 dialogue, views AI as a strategic advantage, and prefers building tomorrow's models over preserving yesterday's, let's talk.
What you will be doing
- Manage executive relationships and commercial discussions for critical enterprise renewal portfolios, including sophisticated multi-year contracts exceeding seven figures.
- Collaborate with Fiona, Trilogy's AI renewals agent, leveraging your expertise and customer insights to systematically enhance its capabilities and independence.
- Evaluate customer health indicators, usage patterns, commercial records, and risk factors to proactively secure successful renewal outcomes.
- Leverage Salesforce and AI-powered workflows to keep forecasts current, surface renewal risks promptly, and focus intervention where human judgment delivers the highest return.
- Convert insights from customer interactions into scalable enhancements that increase the effectiveness of the renewals infrastructure over time.
What you will NOT be doing
- Handling manual renewal documentation, tracking approvals, or executing repetitive administrative tasks.
- Overseeing high-volume transactional renewals or small and mid-sized business accounts.
- Prospecting for new customers or working under a conventional commission-based sales quota.
- Developing production-grade software or constructing AI models from scratch.
- Building and managing a large renewals team rather than directly shaping the most critical customer results.
Key responsibilities
Manage Trilogy's highest-priority enterprise renewals while driving continuous improvements to the AI infrastructure that supports elevated retention, operational efficiency, and progressively autonomous renewal execution.
Candidate requirements
- Direct experience managing enterprise renewals or retention for B2B software clients with accounts generating at least $100K in annual recurring revenue.
- Documented accountability for quarterly retention or Net Revenue Retention objectives, consistently delivering at least 90% NRR or comparable performance over multiple quarters.
- Personal leadership of sophisticated, multi-year enterprise renewals with values of $1M or greater.
- Practical experience deploying AI-enabled or agentic tools in enterprise renewals, customer success, or enterprise sales environments.
- Proficient use of Salesforce or equivalent CRM platforms, including renewal forecasting, risk assessment, and pipeline oversight.
- Outstanding executive communication, commercial negotiation, and relationship stewardship capabilities.
- Able to operate effectively in a global, fully remote setting.
Nice to have
- Experience refining AI prompts, workflows, or decision logic informed by customer engagement data.
- Prior work in enterprise SaaS, cloud software, or subscription technology sectors.
- Track record of integrating data from contracts, customer health metrics, support interactions, and product usage to inform renewal tactics.
- Proven systems thinking with experience optimizing repeatable commercial workflows through automation.
Applying for a role? Here’s what to expect.
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