Description
Are you an enterprise sales or customer success pro who thrives in high-stakes negotiations, enjoys engaging senior executives, and wants to master AI-driven sales execution? If so, here's a role where you can own the renewals pipeline for high-value enterprise clients, leading direct conversations with decision-makers, and securing multi-million-dollar contracts.
At Trilogy, we're not running a traditional SaaS sales org with arbitrary quotas, commission games, or bloated layers of management. We’re an AI-first company that’s rewriting how enterprise sales works: optimizing deal execution, risk assessment, and stakeholder engagement with AI-powered insights. You’ll be part of a team that moves fast, iterates constantly, and leverages AI to eliminate inefficiencies, so you can focus on what actually closes deals. Instead of chasing commissions, you’ll have the stability of a guaranteed comp plan, allowing you to sharpen your sales craft without the stress of unpredictable payouts.
This is not a cushy renewals overseer job. It’s a hands-on, execution-driven position where you’ll be responsible for managing a renewals pipeline, identifying key economic buyers, overcoming objections, and driving contract renewals with precision. You won’t be babysitting a team or wasting time in endless internal meetings. You’ll be on the front lines, negotiating high-value renewals and ensuring long-term customer retention.
If you want to shape the future of AI-driven sales while owning high-impact deals, apply now!
What you will be doing
- Lead high-touch conversations with key customers, aligning on value, overcoming objections, and winning renewals
- Define and continuously improve structured B2B renewals playbooks, AI-driven sales strategies, and frameworks to maximize retention and revenue
What you will NOT be doing
- New logo sales or hunting for new leads
- High volume, low value renewal processing
Key responsibilities
- Own the entire renewals process for high-value enterprise accounts, serving as the primary point of contact, with the goal of retaining revenue and minimizing churn
Candidate requirements
- 8+ years of experience in a CSM or account management role at a software/SaaS/Cloud products company serving Enterprise clients
- Experience managing the entire renewal cycle — client engagement, value proposition, negotiation, managing paper process, and closing deals worth $100K+
- Fluent English, with strong verbal and written proficiency
- Experience using AI tools in a professional setting
- Must be able to work during U.S. business hours
Nice to have
- Track record renewing complex, high-value B2B software (SaaS and on-prem) and related services with large enterprises
- Experience selling multiple products across different verticals or business units
- Comfort selling value-added services and premium tiers on business benefit rather than price
- Hands-on use of ChatGPT or Claude to raise the quality and throughput of customer-facing work
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.
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