Enterprise Sales Executive
$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 Executive   $200,000 USD/year

Description

Are you a seasoned enterprise sales or customer success professional who excels in high-stakes negotiations, relishes engaging C-level executives, and is ready to master AI-powered sales execution? If that describes you, this role offers the opportunity to own the renewals pipeline for high-value enterprise accounts, lead direct dialogue with decision-makers, and close multi-million-dollar contracts.

Trilogy is not your typical SaaS sales organization with arbitrary quotas, commission schemes, or excessive management layers. We are an AI-first enterprise redefining how enterprise sales operates: refining deal execution, risk evaluation, and stakeholder engagement through AI-driven insights. You'll join a team that operates with speed, iterates relentlessly, and harnesses AI to remove inefficiencies, enabling you to concentrate on what truly drives closures. Rather than chasing variable commissions, you'll benefit from the security of a guaranteed compensation structure, freeing you to refine your sales expertise without the uncertainty of fluctuating 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 critical economic buyers, address objections, and execute contract renewals with precision. You won't be supervising a team or spending hours in redundant internal meetings. You'll be directly engaged, negotiating high-value renewals and ensuring sustained customer retention.

If you're ready to influence the future of AI-driven sales while owning high-impact transactions, apply today!

What you will be doing

  • Conduct high-touch engagements with strategic customers, aligning on value delivery, addressing objections, and securing renewals
  • Design and iteratively refine structured B2B renewals playbooks, AI-enhanced sales methodologies, and frameworks to optimize retention and revenue growth

What you will NOT be doing

  • Pursuing new logo acquisition or prospecting for net-new leads
  • Managing high-volume, low-value renewal transactions

Key responsibilities

  • Take full ownership of the renewals lifecycle for high-value enterprise accounts, acting as the primary relationship owner, with the objective of preserving 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 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
  • Practical experience using ChatGPT or Claude to enhance the quality and efficiency 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

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.
STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Pass
proctored test.
STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

Frequently asked questions

About Crossover

Meet some people who've landed similar jobs

Why Crossover

Recruitment sucks. So we’re fixing it.

The Olympics of work

The Olympics of work

It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.

Premium pay for premium talent

Premium pay for premium talent

Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.

Shortlist by skills, not bias

Shortlist by skills, not bias

We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.

Crossover Logo White
Follow us on
Have a question?

Get answers to common questions using our smart chatbot Crosby.

HELP AND FAQs

Join the world's largest community of  AI first Remote WorkersAI-first remote workers.