Description
If you're an enterprise sales or customer success professional who excels in high-stakes negotiations, thrives when engaging senior executives, and is ready to master AI-driven sales execution, this role offers you the opportunity to own the renewals pipeline for high-value enterprise clients. You'll lead direct conversations with decision-makers and secure multi-million-dollar contracts.
Trilogy is not a traditional SaaS sales organization with arbitrary quotas, commission games, or bloated management hierarchies. We are an AI-first company redefining enterprise sales through optimized deal execution, risk assessment, and stakeholder engagement powered by AI-driven insights. You'll join a team that moves quickly, iterates continuously, and uses AI to eliminate inefficiencies—enabling you to concentrate on what truly closes deals. Rather than chasing commissions, you'll benefit from the stability of a guaranteed compensation plan, freeing you to refine your sales expertise without the burden of unpredictable payouts.
This is not an easy renewals oversight position. It's a hands-on, execution-focused role where you'll manage a renewals pipeline, identify key economic buyers, overcome objections, and drive contract renewals with precision. You won't be managing a team or spending time in endless internal meetings. You'll be on the front lines, negotiating high-value renewals and ensuring sustained customer retention.
If you're ready to shape the future of AI-driven sales while owning high-impact deals, apply now!
What you will be doing
- Conduct high-touch conversations with key customers, aligning on value delivery, addressing objections, and securing renewals
- Develop and refine structured B2B renewals playbooks, AI-enhanced sales strategies, and frameworks designed to maximize retention and revenue
What you will NOT be doing
- New logo acquisition or prospecting for new leads
- High volume, low value transactional renewal processing
Key responsibilities
- Take full ownership of the renewals process for high-value enterprise accounts, acting as the primary point of contact, with the objective 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
- Proven 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 based on business benefit rather than price
- Hands-on use of ChatGPT or Claude to enhance 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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