Description
The enterprise renewals landscape is shifting. Top performers no longer chase administrative tasks—they focus on training the AI systems that automate them.
This is not a conventional enterprise renewals position. You will manage Trilogy's highest-value customer accounts while collaborating with Fiona, our AI-powered renewals agent. Fiona manages preparation, analysis, contract processes, and routine follow-ups. Your focus is on the interactions that demand human judgment: executive-level alignment, commercial planning, sophisticated negotiations, and decisions AI cannot yet make. Each renewal you complete simultaneously 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 companies. We do not treat AI as an add-on to enhance productivity within legacy workflows. Instead, we rebuild the workflow around AI and deploy human expertise exclusively where it delivers maximum value. In this position, you will help establish what enterprise renewals become in an AI-native organization while safeguarding millions in recurring revenue from strategic enterprise accounts.
If you are a seasoned enterprise renewals professional who excels in executive dialogue, views AI as a capability accelerator, and prefers building tomorrow's model over maintaining yesterday's, we want to speak with you.
What you will be doing
- Manage executive-level relationships and commercial negotiations for Trilogy's most valuable enterprise renewal accounts, including sophisticated multi-year contracts exceeding seven figures.
- Collaborate with Fiona, Trilogy's AI renewals agent, applying your expertise and customer insights to systematically enhance its capabilities and operational independence.
- Evaluate customer health indicators, product adoption patterns, commercial history, and enterprise risk to proactively secure successful renewal outcomes.
- Leverage Salesforce and AI-powered workflows to ensure forecast accuracy, detect renewal risks ahead of time, and allocate human involvement where it generates maximum strategic impact.
- Convert insights from customer interactions into scalable system enhancements that strengthen renewals performance across the portfolio.
What you will NOT be doing
- Preparing renewal documentation manually, tracking approvals, or executing repetitive administrative processes.
- Handling high-volume transactional renewals or small and mid-market accounts.
- Prospecting for new customer acquisitions or working toward a traditional quota-based sales compensation model.
- Developing production-level software code or building AI models from scratch.
- Managing a sizable renewals team rather than directly shaping outcomes with the most critical accounts.
Key responsibilities
Take ownership of Trilogy's highest-priority enterprise renewals while systematically refining the AI infrastructure that drives superior retention, operational efficiency, and progressively autonomous renewal execution.
Candidate requirements
- Direct experience owning 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 goals, consistently delivering at least 90% NRR or comparable performance over multiple quarters.
- Track record of personally managing complex, multi-year enterprise renewals with contract values of $1M or greater.
- Practical experience deploying AI-enabled or agentic systems in enterprise renewals, customer success, or enterprise sales environments.
- Proficient Salesforce or equivalent CRM expertise, 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 work setting.
Nice to have
- Experience refining AI prompts, operational workflows, or business logic informed by customer engagement outcomes.
- Professional background in enterprise SaaS, cloud software platforms, or subscription-based technology sectors.
- Ability to integrate data from contracts, customer health metrics, support interactions, and product usage analytics to inform renewal strategy.
- Proven systems-thinking mindset and a history of enhancing scalable commercial processes through intelligent automation.
Applying for a role? Here’s what to expect.
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