Senior Account Manager, Trilogy (Remote) - $200,000/year USD
About the role
This opportunity is for an enterprise sales or customer success professional who excels at high-stakes negotiations, engages comfortably with C-level executives, and is ready to master AI-enhanced sales execution. You'll take ownership of the renewals pipeline for high-value enterprise accounts, lead direct discussions with key decision-makers, and close multi-million-dollar agreements. Trilogy isn't a conventional SaaS sales organization with arbitrary targets, commission structures, or excessive management layers. We are an AI-first organization redefining enterprise sales: refining deal execution, risk evaluation, and stakeholder engagement through AI-powered insights. You'll join a team that operates with speed, iterates continuously, and uses AI to remove inefficiencies, enabling you to concentrate on what truly drives 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 uncertainty of fluctuating earnings. This is not a passive renewals oversight role. It's a hands-on, execution-focused position where you'll manage a renewals pipeline, identify critical economic buyers, address objections, and drive contract renewals with precision. You won't be managing a team or wasting hours in internal meetings. Instead, you'll be actively negotiating high-value renewals and ensuring sustained customer retention.
What You Will Be Doing
- Drive high-touch engagements with strategic customers, establishing value alignment, addressing objections, and securing renewals
- Develop and refine structured B2B renewals playbooks, AI-enhanced sales methodologies, and frameworks designed to optimize retention and revenue growth
What You Won't Be Doing
- Pursuing new logo acquisition or prospecting for new leads
- Managing high-volume, low-value renewal transactions
Key Responsibilities
- Take full ownership of the renewals process for high-value enterprise accounts, acting as the main point of contact, 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
- Proven history 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
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.
Pay
$100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. Payment period is weekly.
Schedule
Full-time (40 hours per week), long-term position. Must be able to work during U.S. business hours. Position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record.