Description
The enterprise renewals function is evolving. Top performers no longer spend their time on administrative tasks—they focus on refining the AI systems that automate them.
This role differs from conventional enterprise renewals positions. You will manage Trilogy's highest-value customer accounts in collaboration with Fiona, our AI-powered renewals agent. Fiona manages preparation, analysis, contract execution, and routine follow-up. Your focus is on what matters most: executive engagement, strategic commercial planning, intricate negotiations, and the critical thinking AI cannot yet perform. Each renewal you oversee also trains Fiona to operate with greater independence, enhancing system intelligence through real customer interactions.
Trilogy is constructing an AI-first operational framework across our software businesses. AI is not treated as an add-on to legacy workflows. We rebuild processes with AI at the core and deploy human expertise where it creates maximum value. In this position, you will help establish the blueprint for enterprise renewals in an AI-driven environment while safeguarding millions in recurring revenue from strategic enterprise clients.
If you are a seasoned enterprise renewals professional who excels in executive dialogue, views AI as an amplifier of capability, and prefers building tomorrow's systems over preserving yesterday's, we should speak.
What you will be doing
- Lead executive engagement and commercial discussions for Trilogy's most valuable enterprise renewal portfolios, including multi-year contracts exceeding seven figures.
- Collaborate with Fiona, our AI renewals agent, applying your expertise and customer insights to enhance its capability and operational independence.
- Evaluate customer health indicators, usage patterns, commercial records, and business exposure to proactively secure successful renewal results.
- Leverage Salesforce and AI-powered tools to keep forecasts current, detect renewal threats early, and concentrate your involvement where human judgment delivers the most value.
- Convert insights from customer interactions into systematic improvements that strengthen the renewals engine over time.
What you will NOT be doing
- Creating renewal documents by hand, tracking down approvals, or handling repetitive clerical tasks.
- Overseeing transactional, high-volume renewals or small and mid-market customer accounts.
- Prospecting for new business or working under a traditional quota-based commission structure.
- Developing production-level software code or constructing AI models.
- Building or managing a large renewals team rather than directly shaping the most critical customer results.
Key responsibilities
Lead Trilogy's highest-priority enterprise renewals while driving continuous enhancement of the AI infrastructure that supports superior 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.
- Demonstrated accountability for quarterly retention or Net Revenue Retention metrics, consistently delivering at least 90% NRR or comparable outcomes over multiple quarters.
- Track record of personally negotiating complex, multi-year enterprise renewals with transaction values of $1M or greater.
- Practical experience working with AI-enabled or agentic platforms in enterprise renewals, customer success, or enterprise sales environments.
- Proficiency with Salesforce or equivalent CRM systems, 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 work setting.
Nice to have
- Experience refining AI prompts, workflows, or operational logic using insights from customer engagements.
- Professional history in enterprise SaaS, cloud infrastructure, or subscription technology sectors.
- Ability to integrate data from contracts, customer health metrics, support interactions, and product telemetry into renewal planning.
- Proven systems-oriented mindset and experience enhancing scalable commercial operations through automation.
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