Crossover
Enterprise Renewals Executive, Trilogy (Remote) - $200,000/year USD
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If you're a seasoned enterprise sales or customer success professional who excels in high-stakes negotiations, engages comfortably with C-level executives, and is ready to leverage AI-driven sales methodologies, this opportunity offers ownership of a high-value enterprise renewals pipeline, direct access to decision-makers, and responsibility for closing multi-million-dollar agreements.
Trilogy operates differently from conventional SaaS sales organizations—we've eliminated arbitrary quotas, commission volatility, and excessive management overhead. As an AI-first organization, we're fundamentally transforming enterprise sales: refining deal execution, assessing risk intelligently, and optimizing stakeholder engagement through AI-powered analytics. You'll join a team that operates with speed, iterates relentlessly, and applies AI to remove inefficiencies, enabling you to concentrate on activities that truly drive closures. Rather than chasing variable commissions, you'll benefit from a guaranteed compensation structure, giving you the freedom to refine your sales expertise without the anxiety of fluctuating earnings.
This role is not a passive renewals oversight position. It's a hands-on, execution-focused responsibility where you'll manage a renewals pipeline, pinpoint critical economic buyers, address objections head-on, and execute contract renewals with surgical precision. You won't be managing teams or sitting through endless internal status meetings. You'll be directly negotiating high-value renewals and safeguarding long-term customer retention.
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If you're ready to influence the evolution of AI-powered sales while taking ownership of high-impact transactions, submit your application today!
What You Will Be Doing
- Drive high-touch engagements with strategic customers, aligning on delivered value, addressing objections, and securing renewals
- Develop and refine structured B2B renewals playbooks, AI-enhanced sales methodologies, and operational frameworks designed to optimize retention and revenue outcomes
What You Won’t Be Doing
- Pursuing new logo acquisition or prospecting for net-new business
- Managing high-volume, low-complexity renewal transactions
Enterprise Renewals Executive Key Responsibilities
- Assume full accountability for the renewals lifecycle across high-value enterprise accounts, acting as the principal relationship owner, with the objective of preserving revenue and reducing churn
Basic 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 Requirements
- Demonstrated success renewing sophisticated, high-value B2B software (SaaS and on-prem) and associated services with large enterprise organizations
- Background selling multiple product lines across diverse verticals or business units
- Proficiency in selling value-added services and premium offerings based on business outcomes rather than pricing
- Practical application of AI tools to enhance quality and productivity of customer-facing deliverables
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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-5529-GB-London-EnterpriseRene
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