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 

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

Director of Enterprise Sales   $200,000 USD/year

Description

Most enterprise software fails not from lack of customer logos, but from silent revenue erosion within accounts already won. In extended B2B sales cycles, 70–90% of your next fiscal year's revenue depends on renewal quality, expansion execution, and timely intervention. Forecast drift, poorly structured statements of work, and inadequate escalation protocols quietly destroy margins and erode customer confidence. The outcome: missed targets, finance team doubt, and clients who view you as interchangeable rather than indispensable.

Our approach is fundamentally different. We operate a system-driven commercial framework where structured discipline consistently outperforms individual heroics. We build sustainable, profitable growth from an established enterprise customer base through rigorous renewal management, targeted expansion strategies, and executive-level escalation oversight. Commercial architecture is treated as strategic infrastructure: margin-protected proposals, contracts designed for operational clarity, and quarterly business reviews that genuinely drive product adoption.

This position is not designed for those seeking autonomy without accountability, nor is it a refuge for vague pipeline theater or aesthetic metrics. It's built for leaders who derive satisfaction from forecast precision, margin-preserving deal architecture, tightly scoped SOWs, and executive dialogues that conclude with mutual clarity and firm commitments. You'll apply genuine GenAI capabilities to accelerate analytical work and stakeholder communication, exercise strong commercial judgment in uncertain situations, manage escalations with composure and control, and develop team capabilities in pricing strategy, deal structuring, and negotiation technique. If your background includes leading B2B enterprise software sales with direct accountability for renewals, expansions, multi-year agreements, service-level commitments, and pricing strategy, this environment will feel immediately familiar.

If you're currently running or have recently managed an enterprise sales organization within 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 disciplined pipeline discipline, let's connect. Enter a role where operational rigor isn't compromised by disorder, and take ownership of the revenue engine that truly defines your next year's performance. Apply if you're prepared to demonstrate that structured commercial execution reliably outperforms optimism.

What you will be doing

  • Leading renewals and expansion initiatives from pipeline development through contract execution
  • Conducting executive business reviews and owning escalation management
  • Designing and approving commercial proposals and contract terms that maintain integrity under scrutiny

Key responsibilities

  • Expand enterprise account revenue and improve retention rates through rigorous commercial discipline, strategic account stewardship, and frictionless customer alignment

Candidate requirements

  • Minimum 5 years of experience in enterprise B2B software sales
  • Proven accountability for enterprise revenue results including quota attainment, renewals, or expansion targets
  • Direct management experience with enterprise accounts carrying $1M+ in annual contract value
  • Operational proficiency with CRM platforms and working knowledge of Order-to-Cash (O2C) workflows
  • Demonstrated use of LLMs and other GenAI technologies to optimize work processes

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.

Accept job offer.
STEP 6

Accept job offer.

Pass
proctored test.
STEP 5

Pass
proctored test.

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.