Vice President 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

Vice President of Enterprise Sales   $200,000 USD/year

Description

Most enterprise software collapses not from a shortage of customer names, but from revenue quietly eroding within accounts already secured. In complex B2B environments, 70–90% of the coming year's income hinges on renewal strength, expansion discipline, and rescue execution. Forecast drift, poorly structured statements of work, and weak escalation protocols silently destroy margin and credibility. The outcome: plans that miss, CFOs who doubt, and clients who view you as interchangeable rather than indispensable.

Our approach is different. We operate a system-driven commercial engine where structured execution outperforms individual heroism. We generate profitable, sustainable revenue from an established Fortune-tier customer base by executing clean renewals, targeted expansions, and controlled executive escalations. Commercial rigor is treated as a core deliverable: proposals designed to preserve margin, contracts structured for seamless delivery, and quarterly business reviews that genuinely advance adoption.

This position is not for those seeking autonomy without accountability, nor is it a refuge for ambiguous pipelines or style over substance. It suits leaders who draw energy from forecast precision, margin-protected deal architecture, tightly defined SOWs, and executive dialogues that conclude with clarity and commitment. You will apply genuine GenAI expertise to accelerate analysis and communication, exercise sound commercial judgment during uncertainty, deploy escalation control that restores confidence, and coach teams to strengthen pricing, structure, and negotiation discipline. If you have led enterprise B2B software sales with accountability for renewals, expansions, multi-year agreements, SLAs, and pricing strategy, this will feel familiar.

If you currently lead or recently led an enterprise sales organization in SaaS, or you 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. Take ownership of a role where your expertise isn't undermined by disorder, and control the mechanism that truly defines next year's performance. Apply if you are prepared to demonstrate that disciplined commercial execution consistently outperforms optimism.

What you will be doing

  • Leading renewals and expansions from pipeline development through contract execution
  • Conducting executive reviews and owning escalation management
  • Designing and approving commercial proposals and agreements built to withstand scrutiny

Key responsibilities

  • Drive enterprise account revenue growth and retention through disciplined commercial execution, strategic account stewardship, and integrated customer engagement

Candidate requirements

  • A minimum of 5 years of experience in B2B enterprise software sales
  • Direct accountability for enterprise revenue results including quota ownership, renewals, or expansions
  • Direct accountability for enterprise accounts with annual contract values of $1M or more
  • Experience working with CRM systems and understanding of Order-to-Cash (O2C) processes
  • Experience leveraging 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.

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.