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 

Not accepting applications on crossover.com at this time.

Description

Ready to revolutionize enterprise sales with AI? We're seeking a strategic sales maverick who can navigate the complex waters of high-stakes enterprise renewals while embracing the power of artificial intelligence to transform traditional sales methodologies.

At Trilogy, we're disrupting the conventional SaaS sales playbook. Forget about chasing arbitrary quotas or playing commission games – we're building something different. As an AI-first organization, we're reimagining enterprise sales through data-driven insights and intelligent automation. Picture yourself wielding cutting-edge AI tools to perfect deal execution while engaging directly with C-suite decision-makers on multi-million dollar contracts.

This role isn't about maintaining the status quo. It's an opportunity to be at the forefront of sales innovation, where you'll combine your enterprise sales expertise with AI-powered insights to drive unprecedented results. You'll enjoy the security of a guaranteed compensation structure, freeing you to focus on what truly matters: mastering the art and science of modern sales execution.

If you're ready to pioneer the future of AI-enhanced enterprise sales while managing a high-value renewals portfolio, we want to hear from you!

What you will be doing

  • Orchestrate strategic conversations with enterprise clients, masterfully articulating value propositions and securing high-value renewals
  • Pioneer and refine next-generation B2B renewals methodologies, leveraging AI to create scalable, data-driven sales frameworks

What you will NOT be doing

  • Prospecting or hunting for new business opportunities
  • Managing transactional, low-dollar renewal operations

Key responsibilities

  • Serve as the strategic quarterback for enterprise account renewals, orchestrating end-to-end processes to maximize revenue retention and minimize customer churn through AI-enhanced engagement strategies

Candidate requirements

  • Geographic requirement: Must be located in the Americas (North or South)
  • Proven track record of 5+ years in enterprise software sales, specifically in account management, renewal sales, or customer success roles with a focus on revenue retention
  • Demonstrated success managing enterprise accounts with annual recurring revenue exceeding $1 million
  • Forward-thinking mindset with the ability to embrace and champion AI-first approaches in daily operations and strategic planning
  • Strong command of modern CRM platforms (Salesforce, HubSpot, etc.)

Meet a successful candidate

Watch Interview
Jeremy Swartz
Jeremy  |  SVP of Sales
South Africa  

As a kid, Jeremy was inspired by colossal rugby players at the top of their game—and wondered if he could play at that level. Thanks to Cros...

Meet Jeremy

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.

Pass Cognitive Aptitude Test.
STEP 1

Pass Cognitive Aptitude Test.

Pass English Proficiency Test.
STEP 2

Pass English Proficiency Test.

Prove Real-World Job & AI Skills.
STEP 3

Prove Real-World Job & AI Skills.

Ace An Interview Or Two.
STEP 4

Ace An Interview Or Two.

Accept Job Offer.
STEP 5

Accept Job Offer.

Frequently asked questions

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The Olympics of work

The Olympics of work

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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.