Director of Enterprise Sales
$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

Most enterprise software doesn't collapse from a lack of marquee clients—it erodes because revenue from existing customers decays quietly. In long-cycle B2B environments, 70–90% of next year's top line is determined by your ability to renew, expand, and recover accounts. Forecast drift, ambiguous SOWs, and poor escalation discipline silently destroy margin and credibility. The outcome: missed targets, CFO doubt, and customers who view you as a disposable supplier rather than essential infrastructure.

Our approach is different. This is a system-driven commercial engine where disciplined execution outperforms individual heroics. We generate profitable, sustainable revenue from an established Fortune-tier base through structured renewals, targeted expansions, and executive-level escalation management. Commercial rigor is treated as a core product: proposals designed to preserve margin, contracts built for clean execution, and QBRs that genuinely advance adoption.

This role is not a low-accountability, high-autonomy opportunity, and it's not a place to coast on optics or phantom pipeline. It's designed for someone who derives energy from forecast precision, margin-protected deal architecture, tight SOWs, and executive dialogues that conclude with clarity and commitment. You'll apply genuine GenAI proficiency to accelerate analysis and communication, exercise sound commercial judgment under ambiguity, manage escalations with composure, and coach the team to refine pricing, structure, and negotiation. If you've led enterprise B2B software sales with direct accountability for renewals, expansions, multi-year agreements, SLAs, and pricing strategy, you'll recognize this environment immediately.

If you're currently running or have recently managed an enterprise sales organization in SaaS, or you've advanced through senior positions such as Sales Director, Regional VP, or Head of Enterprise Accounts following an early career grounded in rigorous pipeline discipline, let's connect. Enter a role where your expertise isn't undermined by disorder, and take ownership of the engine that truly determines next year's revenue. Apply if you're prepared to demonstrate that structured commercial execution outperforms optimism every time.

What you will be doing

  • Leading renewals and expansions from pipeline development through contract signature
  • Conducting executive reviews and overseeing escalations
  • Designing and approving commercial proposals and contracts engineered to withstand scrutiny

Key responsibilities

  • Grow enterprise account revenue and retention through structured commercial execution, strategic account stewardship, and frictionless customer engagement

Candidate requirements

  • Minimum 5 years of experience in B2B enterprise software sales
  • Direct accountability for enterprise revenue performance including quota ownership, renewals, or expansions
  • Direct accountability for enterprise accounts with annual contract values of $1M or more
  • Hands-on experience with CRM platforms and working knowledge of Order-to-Cash (O2C) workflows
  • Demonstrated use of LLMs and other GenAI tools to optimize workflows

Meet a successful candidate

Watch Interview
Andres Ramirez
Andres  |  Senior Account Manager
Netherlands

Globetrotting Andres moved to Amsterdam for love. Thanks to Crossover, that’s only the beginning of the story.

Meet Andres

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.