Description
The enterprise renewals landscape is evolving. Top performers no longer spend their time managing paperwork—they focus on guiding the AI systems that automate it.
This role departs from conventional enterprise renewals work. You will manage Trilogy's highest-value customer accounts while collaborating with Fiona, our AI renewals agent. Fiona executes the preparation, analysis, contract processing, and follow-through. Your focus remains on the interactions that truly matter: executive-level alignment, commercial planning, sophisticated negotiations, and the strategic judgment AI cannot yet deliver. Each renewal you complete also trains Fiona toward greater autonomy, strengthening the system through every customer engagement.
Trilogy is constructing an AI-first operational model throughout our software portfolio. We view AI not as a bolt-on productivity enhancement but as the foundation around which we rebuild processes, reserving human expertise exclusively for the most critical decisions. In this position, you will help establish what enterprise renewals should become in an AI-driven environment while safeguarding millions in recurring revenue across strategic enterprise accounts.
If you are a seasoned enterprise renewals professional who excels in executive-level dialogue, views AI as a strategic enabler, and seeks to architect the future rather than preserve the past, we would like to speak with you.
What you will be doing
- Lead executive relationships and commercial negotiations for Trilogy's most valuable enterprise renewal accounts, including sophisticated seven-figure, multi-year contracts.
- Collaborate with Fiona, Trilogy's AI renewals agent, applying your judgment and customer insights to systematically enhance its capabilities and autonomy.
- Evaluate customer health metrics, product adoption, commercial history, and risk factors to proactively secure successful renewal outcomes.
- Leverage Salesforce and AI-powered workflows to sustain accurate forecasting, detect renewal risks at early stages, and focus intervention where human judgment delivers maximum value.
- Convert insights from customer interactions into scalable enhancements that elevate renewals system effectiveness over time.
What you will NOT be doing
- Preparing renewal documentation manually, tracking approvals, or executing repetitive administrative tasks.
- Overseeing high-volume transactional renewals or SMB customer portfolios.
- Pursuing new customer acquisition or working toward traditional commission-based sales quotas.
- Developing production software or constructing AI models.
- Managing a large renewals team rather than directly influencing the most critical customer outcomes.
Key responsibilities
Lead Trilogy's highest-priority enterprise renewals while systematically refining the AI infrastructure that drives improved retention, operational efficiency, and progressively autonomous renewal execution.
Candidate requirements
- Direct experience owning enterprise renewals or retention for B2B software customers with accounts representing 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.
- Personal leadership of complex, multi-year enterprise renewals valued at $1M or greater.
- Practical experience deploying AI-enabled or agentic systems within enterprise renewals, customer success, or enterprise sales operations.
- Extensive Salesforce or equivalent CRM proficiency, including renewal forecasting, risk detection, and pipeline oversight.
- Superior executive communication, commercial negotiation, and relationship stewardship capabilities.
- Ability to operate effectively in a fully remote, global work environment.
Nice to have
- Experience refining AI prompts, workflows, or business logic based on customer engagement data.
- Professional history in enterprise SaaS, cloud software, or subscription-based technology sectors.
- Experience synthesizing data from contracts, customer health indicators, support interactions, and product usage to inform renewal strategy.
- Proven systems thinking and a history of enhancing repeatable commercial workflows through automation.
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