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

In enterprise software, failure rarely stems from an insufficient client roster; it stems from silent revenue erosion within the accounts you've already secured. Within long-cycle B2B environments, 70–90% of the following year's revenue hinges on your ability to renew effectively, expand strategically, and recover at-risk contracts. Forecast volatility, poorly structured Statements of Work, and inadequate escalation protocols quietly destroy both margin and credibility. The outcome: unmet targets, CFO distrust, and clients who view you as disposable rather than indispensable.

Our approach is fundamentally different. We operate a system-driven commercial framework in which disciplined execution consistently outperforms individual heroics. We generate profitable, sustainable revenue from an established Fortune-tier customer base by executing flawless renewals, targeted expansions, and executive-grade escalation management. 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 product adoption.

This position is not a "freedom without accountability" opportunity, nor is it a refuge for those who rely on perception or inflated pipeline metrics. It suits someone energized by forecast precision, margin-protective deal architecture, tightly drafted SOWs, and executive dialogues that conclude with clarity and firm commitments. You will apply authentic GenAI expertise to accelerate analysis and communication, exercise sound commercial judgment amid ambiguity, employ escalation techniques that restore confidence, and develop coaching capabilities to refine pricing, structuring, and negotiation across your team. If you have led enterprise B2B software sales with accountability for renewals, expansions, multi-year agreements, SLAs, and pricing strategy, this environment will feel immediately familiar.

If you are currently directing or have recently directed an enterprise sales organization within SaaS, or you have advanced through senior positions such as Sales Director, Regional VP, or Head of Enterprise Accounts following an early career grounded in rigorous pipeline discipline, we want to speak with you. Enter a role where your expertise is not diluted by disorder and take ownership of the revenue engine that truly defines next year's performance. Apply if you are prepared to demonstrate that structured commercial execution outperforms optimism every time.

What you will be doing

  • Leading renewals and expansions from pipeline origination through contract execution
  • Conducting executive reviews and directing escalation resolution
  • Designing and authorizing commercial proposals and contractual agreements that withstand scrutiny

Key responsibilities

  • Grow enterprise account revenue and retention via disciplined commercial execution, strategic account stewardship, and seamless customer integration

Candidate requirements

  • A minimum of 5 years managing renewals, expansions, or account growth within the B2B enterprise software sector
  • Demonstrated experience leveraging LLMs and other GenAI tools to optimize workflows
  • Proven track record managing multi-million-dollar enterprise accounts
  • Hands-on experience with CRM platforms and Order-to-Cash (O2C) workflows
  • Background working with regulated industry clients (finance, healthcare, or pharma), including compliance-oriented commercial frameworks
  • Experience directing sales or account management teams in quota-bearing capacities and mentoring on deal architecture and negotiation

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.