Description
The nature of enterprise renewals is shifting. The strongest performers won't allocate their time to administrative tasks—they'll focus on refining the AI systems designed to 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 work, data analysis, contract execution, and follow-through. Your focus remains on high-impact activities: executive engagement, commercial planning, intricate negotiations, and judgment calls that AI cannot yet perform. Each renewal you oversee contributes to Fiona's learning, increasing her autonomy and enhancing system intelligence through every customer touchpoint.
Trilogy is constructing an AI-first operational model throughout our software portfolio. We do not view AI as an add-on productivity feature layered over legacy workflows. We rebuild the workflow around AI capabilities and deploy human expertise exclusively for the most critical decisions. In this position, you will help establish what enterprise renewals mean in an AI-native environment while safeguarding millions in recurring revenue from strategic enterprise accounts.
If you are a seasoned enterprise renewals professional who excels in executive-level dialogue, views AI as an amplifier of impact, and seeks to architect the future rather than preserve outdated methods, we should speak.
What you will be doing
- Manage executive relationships and lead commercial negotiations for enterprise renewal accounts of significant value, including complex agreements exceeding seven figures and spanning multiple years.
- Collaborate with Fiona, Trilogy's AI renewals agent, leveraging your expertise and customer insights to continuously enhance its capabilities and operational independence.
- Evaluate customer health indicators, product utilization patterns, commercial history, and business exposure to proactively secure positive renewal outcomes.
- Leverage Salesforce and AI-powered workflows to ensure forecast accuracy, detect renewal risks promptly, and focus intervention efforts where human judgment delivers maximum value.
- Convert insights from customer interactions into systematic enhancements that strengthen the renewals process over time.
What you will NOT be doing
- Preparing renewal documentation by hand, tracking approvals manually, or executing repetitive administrative tasks.
- Overseeing high-volume transactional renewals or small to mid-market accounts.
- Pursuing new customer acquisition or fulfilling a traditional commission-based sales quota.
- Developing production-level software or constructing AI models.
- Building or managing a large renewals team rather than directly influencing the most critical customer relationships.
Key responsibilities
Own the most strategic enterprise renewals at Trilogy while driving continuous improvement of the AI infrastructure that supports higher retention rates, 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 goals, consistently delivering at least 90% NRR or equivalent performance across multiple quarters.
- Personal ownership of complex, multi-year enterprise renewals with a value of $1M or greater.
- Practical experience working with AI-enabled or agentic systems in enterprise renewals, customer success, or enterprise sales environments.
- Proficient use of Salesforce or equivalent CRM platforms, including renewal forecasting, risk detection, and pipeline oversight.
- Outstanding executive communication, commercial negotiation, and relationship stewardship capabilities.
- Capable of operating effectively in a fully remote, global setting.
Nice to have
- Experience refining AI prompts, workflows, or operational rules informed by customer engagement data.
- Professional history in enterprise SaaS, cloud software, or subscription-driven technology sectors.
- Experience synthesizing data from contracts, customer health metrics, support tickets, and product usage to inform renewal strategy.
- Proven systems thinking ability and a history of enhancing repeatable commercial workflows through automation initiatives.
Applying for a role? Here’s what to expect.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
Chat-style
screening interview.
Cognitive 
aptitude test.
Prove real-world 
job skills.
Interview with the hiring manager.
Pass
proctored test.
Accept job offer.
Frequently asked questions
Reviews
Meet some people who've landed similar jobs
Recruitment sucks. So we’re fixing it.
The Olympics of work
It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.
Premium pay for premium talent
Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.
Shortlist by skills, not bias
We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.
Join the world's largest community of 
AI-first remote workers.