Description
Enterprise renewals are changing. The best people won't spend their days chasing paperwork—they'll spend them shaping the AI that replaces it.
This isn't a traditional enterprise renewals role. You'll own Trilogy's most valuable customer relationships while working alongside Fiona, our AI renewals agent. Fiona handles the preparation, analysis, contract workflows, and follow-up. You handle the conversations that matter: executive alignment, commercial strategy, complex negotiations, and the judgment that AI can't yet replicate. Every renewal you lead also teaches Fiona to become more autonomous, making the system smarter with every customer interaction.
At Trilogy, we're building an AI-first operating model across our software portfolio. We don't see AI as a productivity tool bolted onto existing processes. We redesign the process around AI and reserve human expertise for the highest-value decisions. In this role, you'll help define what enterprise renewals look like in an AI-first world while protecting millions of dollars in recurring revenue across strategic enterprise customers.
If you're an experienced enterprise renewals leader who thrives in executive conversations, embraces AI as a force multiplier, and wants to build the future instead of defending the past, we'd like to meet you.
What you will be doing
- Own executive relationships and commercial negotiations for high-value enterprise renewal accounts, including complex seven-figure, multi-year agreements.
- Partner with Fiona, Trilogy's AI renewals agent, using your judgment and customer interactions to continuously improve its performance and autonomy.
- Analyze customer health, product usage, commercial history, and business risk to proactively drive successful renewal outcomes.
- Use Salesforce and AI-driven workflows to maintain accurate forecasts, identify renewal risks early, and prioritize intervention where human expertise creates the greatest impact.
- Turn lessons from customer engagements into repeatable improvements that make the renewals system more effective over time.
What you will NOT be doing
- Manually preparing renewal paperwork, chasing approvals, or performing repetitive administrative work.
- Managing high-volume transactional renewals or SMB accounts.
- Hunting for new logos or carrying a traditional commission-driven sales quota.
- Writing production software or building AI models.
- Leading a large renewals organization instead of personally influencing the most important customer outcomes.
Key responsibilities
Candidate requirements
- Experience directly owning enterprise renewals or retention for B2B software customers with accounts worth at least $100K in annual recurring revenue.
- Proven ownership of quarterly retention or Net Revenue Retention targets, consistently achieving at least 90% NRR or equivalent results across multiple quarters.
- Experience personally leading complex, multi-year enterprise renewals valued at $1M or more.
- Hands-on experience using AI-enabled or agentic systems within enterprise renewals, customer success, or enterprise sales workflows.
- Strong Salesforce or comparable CRM experience, including renewal forecasting, risk identification, and pipeline management.
- Exceptional executive communication, commercial negotiation, and relationship management skills.
- Comfortable working globally in a fully remote environment.
- Able to maintain consistent working hours overlapping 9:00am to 5:00pm US Central Time, regardless of your location.
Nice to have
- Experience improving AI prompts, workflows, or business rules based on customer interactions.
- Background in enterprise SaaS, cloud software, or subscription-based technology businesses.
- Experience using data from contracts, customer health, support, and product usage to drive renewal strategy.
- Demonstrated systems thinking and a track record of improving repeatable commercial processes through automation.
You will be working for
Meet a successful candidate
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
School sucks. So we’re fixing it.
The education Olympics
It’s hard to qualify – on purpose. High standards mean every educator, leader and EdTech builder is at the top of their game.
Salary without side gigs
Top performers earn what they’re worth. Six-figure education roles aren’t fantasy here – they’re the baseline for excellence.
Skills make the grade
Skills carry more weight that resumes here. Demonstrate learning mastery, AI fluency and passion for what’s next. That’s what counts.
Join America’s largest community of 
AI-first education leaders.
