Description
The enterprise renewals function is evolving. Top performers will no longer dedicate their time to administrative tasks—they'll focus on refining the AI systems that automate them.
This role is distinct from conventional enterprise renewals positions. You'll be responsible for Trilogy's highest-value customer accounts while collaborating with Fiona, our AI renewals agent. Fiona manages preparation, analysis, contract processing, and follow-through. Your focus is on the interactions that require human judgment: executive engagement, commercial planning, intricate negotiations, and strategic decisions that AI cannot yet make. Each renewal you manage simultaneously trains Fiona to operate more independently, enhancing the system's intelligence with every customer engagement.
Trilogy is constructing an AI-first operational framework across our software portfolio. We don't treat AI as a supplementary productivity add-on to legacy workflows. Instead, we rebuild the workflow around AI capabilities and reserve human involvement for the most critical decisions. In this position, you'll help establish what enterprise renewals should look like in an AI-driven environment while safeguarding millions of dollars 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 amplifier, and prefers building tomorrow's systems rather than protecting yesterday's, we want to speak with you.
What you will be doing
- Take ownership of executive-level relationships and commercial discussions for high-value enterprise renewal portfolios, including intricate seven-figure, multi-year contracts.
- 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 background, and business exposure to proactively secure successful renewal results.
- Leverage Salesforce and AI-powered workflows to ensure forecast accuracy, surface renewal risks promptly, and focus intervention where human judgment delivers maximum value.
- Convert insights from customer interactions into scalable enhancements that strengthen the renewals engine over time.
What you will NOT be doing
- Manually generating renewal documentation, tracking approvals, or executing repetitive clerical tasks.
- Handling high-volume transactional renewals or small-to-midsize business accounts.
- Prospecting for new business or working toward a traditional commission-based sales quota.
- Developing production code or constructing AI models.
- Overseeing a large renewals team rather than directly influencing the most critical customer results.
Key responsibilities
Take full ownership of Trilogy's most strategic enterprise renewals while systematically advancing the AI infrastructure that drives improved 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 ownership of quarterly retention or Net Revenue Retention metrics, consistently delivering at least 90% NRR or comparable performance across multiple quarters.
- Personal experience leading complex, multi-year enterprise renewals with a value of $1M or greater.
- Practical experience applying AI-enabled or agentic technologies within enterprise renewals, customer success, or enterprise sales processes.
- Solid Salesforce or equivalent CRM proficiency, including renewal forecasting, risk detection, and pipeline oversight.
- Outstanding executive communication, commercial negotiation, and relationship stewardship capabilities.
- Able to operate effectively in a fully remote, global work environment.
Nice to have
- Experience refining AI prompts, workflows, or operational logic informed by customer engagement.
- History in enterprise SaaS, cloud infrastructure, or subscription-driven technology sectors.
- Experience synthesizing insights from contracts, customer health metrics, support data, and usage analytics to inform renewal tactics.
- Proven systems thinking and a history of enhancing scalable commercial workflows through automation.
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