Enterprise Sales Director
$200,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

Worldwide
Semi-flexible schedule
Fully-remote
full-time (40 hrs/week)
Long-term role

Enterprise Sales Director   $200,000 USD/year

Description

If you're a proven enterprise sales or customer success professional who excels at high-stakes negotiations, engages comfortably with senior executives, and is ready to master AI-enhanced sales execution, this role offers a unique opportunity. You'll take ownership of the renewals pipeline for high-value enterprise accounts, conduct direct conversations with decision-makers, and close multi-million-dollar contracts.

Trilogy is not a conventional SaaS sales organization with arbitrary quotas, commission structures, or excessive management layers. We are an AI-first organization redefining enterprise sales: optimizing deal execution, risk evaluation, and stakeholder engagement through AI-powered insights. You'll join a team that operates with speed, iterates continuously, and applies AI to remove inefficiencies, enabling you to concentrate on activities that actually close 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 uncertainty of variable payouts.

This is not a passive renewals oversight position. It's a hands-on, execution-focused role where you'll manage a renewals pipeline, identify key economic buyers, address objections, and drive contract renewals with precision. You won't be supervising a team or spending time in endless internal meetings. You'll be directly engaged, 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 engagements with key customers, aligning on value delivery, addressing objections, and securing renewals
  • Establish and refine structured B2B renewals playbooks, AI-enhanced sales strategies, and frameworks designed to maximize retention and revenue

What you will NOT be doing

  • Pursuing new logo sales or prospecting for new leads
  • Processing high-volume, low-value renewals

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 reducing 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 complete 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

  • Demonstrated 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

Meet a successful candidate

Watch Interview
Najeeha Humayun
Najeeha  |  AI-First Strategic Sales Specialist
Switzerland

Who says you have to choose between building a family and building an epic career? Najeeha didn’t. After pivoting from finance to tech, she ...

Meet Najeeha

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