Crossover
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in executive-level dialogue, views AI as an amplifier of impact, and seeks to architect the future rather than preserve outdated methods, we should speak.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 Won’t 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. Enterprise Retention Manager 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. Basic 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 Requirements 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. About Trilogy Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career in leaps and bounds. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you! Working with us This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic. Crossover Job Code: LJ-5834-PH-COUNTRY-EnterpriseRete
Crossover
