Description
The enterprise renewals function is evolving. Top performers will no longer spend their time on administrative tasks—they'll focus on refining the AI systems that automate them.
This is not a conventional renewals position. You will be responsible for Trilogy's highest-value customer accounts while collaborating with Fiona, our AI-powered renewals agent. Fiona manages preparation work, analytical tasks, contract administration, and routine follow-up. You manage what truly matters: executive engagement, commercial decision-making, intricate negotiations, and the strategic judgment AI cannot yet deliver. Each renewal you execute simultaneously trains Fiona to operate with greater independence, enhancing system intelligence with every customer touchpoint.
Trilogy is engineering an AI-first operational framework throughout our software portfolio. AI is not viewed as an add-on productivity enhancement. We reconstruct processes with AI at the core, reserving human intervention for decisions of maximum strategic value. In this capacity, you will help establish the blueprint for enterprise renewals in an AI-driven era while safeguarding millions in annual 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 capability, and seeks to architect the future rather than preserve legacy models, we invite your application.
What you will be doing
- Take ownership of executive-level relationships and commercial discussions for high-value enterprise renewal portfolios, including sophisticated multi-year agreements exceeding seven figures.
- Collaborate with Fiona, Trilogy's AI renewals agent, leveraging your strategic judgment and customer insights to systematically enhance its capabilities and operational autonomy.
- Evaluate customer health indicators, product adoption patterns, commercial history, and business risk factors to proactively secure positive renewal outcomes.
- Leverage Salesforce and AI-powered workflow systems to ensure forecast accuracy, detect renewal vulnerabilities early, and concentrate human expertise where it delivers maximum value.
- Translate insights from customer interactions into scalable system enhancements that strengthen the renewals operation over time.
What you will NOT be doing
- Handling manual renewal documentation, tracking approvals, or executing repetitive administrative functions.
- Overseeing high-volume transactional renewals or small and medium business accounts.
- Pursuing new customer acquisition or managing a traditional quota-based sales pipeline.
- 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
Take ownership of Trilogy's highest-priority enterprise renewals while driving continuous improvement in the AI infrastructure that supports superior retention performance, operational efficiency, and progressively autonomous renewal execution.
Candidate requirements
- Direct experience owning enterprise renewals or retention for B2B software clients with accounts representing at least $100K in annual recurring revenue.
- Documented ownership of quarterly retention or Net Revenue Retention metrics, consistently delivering at least 90% NRR or comparable performance across multiple quarters.
- Personal track record leading complex, multi-year enterprise renewals with values of $1M or greater.
- Practical experience deploying AI-enabled or agentic systems in enterprise renewals, customer success, or enterprise sales environments.
- Substantial Salesforce or equivalent CRM proficiency, including renewal forecasting, risk detection, and pipeline oversight.
- Outstanding executive communication, commercial negotiation, and relationship stewardship capabilities.
- Ability to operate effectively in a global, fully remote work structure.
Nice to have
- Experience refining AI prompts, workflows, or business logic based on real-world customer engagement.
- Professional background in enterprise SaaS, cloud software, or subscription technology sectors.
- Ability to synthesize data from contracts, customer health metrics, support interactions, and product usage to inform renewal strategies.
- Proven systems orientation and history of enhancing repeatable commercial workflows through automation.
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.