Description
The enterprise renewals function is in transition. Top performers no longer spend time on administrative tasks—they focus on training the AI systems that will handle 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, contract workflows, analysis, and follow-through. Your focus is the conversations that require human judgment: executive engagement, commercial structuring, intricate negotiations, and decisions AI cannot yet make. Each renewal you manage also trains Fiona to operate with greater independence, strengthening the system through every interaction.
Trilogy is constructing an AI-first operational framework across our software businesses. We do not treat AI as an add-on to legacy workflows. Instead, we rebuild the workflow around AI and deploy human expertise exclusively on the highest-impact decisions. In this position, you will help define enterprise renewals in an AI-native environment while safeguarding millions in recurring revenue from strategic enterprise clients.
If you are a seasoned enterprise renewals professional who excels in executive-level dialogue, sees AI as a capability accelerator, and prefers to shape the future rather than preserve outdated practices, we should speak.
What you will be doing
- Manage executive relationships and commercial negotiations for high-value enterprise renewal portfolios, including intricate multi-year deals valued at seven figures.
- Collaborate with Fiona, Trilogy's AI renewals agent, applying your judgment and client interactions to enhance its autonomy and effectiveness over time.
- Assess customer health, usage patterns, commercial history, and business exposure to drive proactive renewal success.
- Leverage Salesforce and AI-powered workflows to sustain accurate renewal forecasts, flag at-risk accounts early, and focus human involvement where it delivers maximum value.
- Convert insights from customer interactions into systematic enhancements that strengthen the renewals process continuously.
What you will NOT be doing
- Manually drafting renewal documents, tracking approvals, or executing repetitive administrative tasks.
- Overseeing high-volume transactional renewals or small and mid-market customer accounts.
- Prospecting for new business or working toward a traditional commission-based sales target.
- Developing production-level software or constructing AI models.
- Managing a large renewals team rather than directly influencing the most critical customer outcomes.
Key responsibilities
Own the most strategic enterprise renewals at Trilogy while driving continuous refinement of the AI infrastructure that supports higher retention, improved efficiency, and progressively autonomous renewal operations.
Candidate requirements
- Direct ownership 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 objectives, 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 deploying AI-enabled or agentic tools in enterprise renewals, customer success, or enterprise sales environments.
- Deep proficiency with Salesforce or equivalent CRM platforms, including renewal forecasting, risk detection, and pipeline oversight.
- Outstanding executive communication, commercial negotiation, and relationship stewardship capabilities.
- Ability to operate effectively in a fully remote, globally distributed team setting.
Nice to have
- Experience refining AI prompts, workflows, or business logic informed by customer engagement outcomes.
- Professional background in enterprise SaaS, cloud-based software, or subscription technology sectors.
- Experience synthesizing data from contracts, customer health metrics, support interactions, and product usage to inform renewal strategies.
- Proven systems thinking with a history of enhancing repeatable commercial workflows through automation initiatives.
Applying for a role? Here’s what to expect.
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