Description
The landscape of enterprise renewals is shifting. Top performers no longer chase administrative tasks—they focus on guiding 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, analytical work, contract processing, and follow-through. Your focus is on the interactions that require human judgment: executive engagement, commercial planning, intricate negotiations, and decisions beyond AI's current capability. Each renewal you guide simultaneously trains Fiona toward greater independence, enhancing system intelligence through every customer engagement.
Trilogy is constructing an AI-first operational framework throughout our software portfolio. We do not treat AI as an add-on to legacy workflows. Instead, we rebuild processes around AI capabilities and deploy human expertise where it generates maximum value. In this position, you will help establish what enterprise renewals should be in an AI-native organization while safeguarding millions in recurring revenue from strategic enterprise clients.
If you are a proven enterprise renewals professional who excels in executive dialogue, views AI as a strategic advantage, and seeks to architect the future rather than preserve outdated models, we should connect.
What you will be doing
- Manage executive-level relationships and commercial discussions for critical enterprise renewal portfolios, including sophisticated multi-year contracts valued in seven figures.
- Collaborate with Fiona, Trilogy's AI renewals agent, leveraging your expertise and customer engagement to refine its capabilities and expand its operational independence.
- Evaluate customer health indicators, usage patterns, transaction history, and business exposure to proactively secure favorable renewal results.
- Leverage Salesforce and AI-enhanced workflows to ensure forecast precision, surface renewal risks promptly, and direct attention where human judgment delivers the most significant outcomes.
- Translate insights from customer interactions into systematic enhancements that strengthen the renewals operation over time.
What you will NOT be doing
- Manually generating renewal documentation, tracking approvals, or executing routine administrative tasks.
- Handling high-volume transactional renewals or small and mid-market customer accounts.
- Pursuing net-new customer acquisition or working under a conventional commission-based sales structure.
- Developing production-level software or constructing AI models from scratch.
- Overseeing a large renewals team rather than directly influencing the most critical customer decisions.
Key responsibilities
Manage Trilogy's most critical enterprise renewals while systematically enhancing the AI infrastructure that drives superior retention, operational efficiency, and progressively autonomous renewal processes.
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 goals, delivering at least 90% NRR or comparable performance across multiple quarters consistently.
- Personal track record leading sophisticated, multi-year enterprise renewals with deal values of $1M or greater.
- Practical experience deploying AI-enabled or agentic tools within enterprise renewals, customer success, or enterprise sales operations.
- Proficient Salesforce or equivalent CRM experience, covering renewal forecasting, risk detection, and pipeline oversight.
- Outstanding executive-level communication, commercial negotiation capabilities, and relationship stewardship skills.
- Able to operate effectively in a fully remote, globally distributed work environment.
Nice to have
- Experience refining AI prompts, operational workflows, or business logic informed by customer engagement outcomes.
- Professional background in enterprise SaaS, cloud-based software, or subscription technology markets.
- Experience synthesizing data from contracts, customer health metrics, support interactions, and product usage to inform renewal approaches.
- Proven systems-oriented thinking with a history of optimizing scalable commercial operations through automation.
Applying for a role? Here’s what to expect.
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