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 

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

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

Description

In enterprise software, most failures don't stem from a shortage of customer logos—they occur when revenue from existing clients quietly deteriorates. Within long-cycle B2B environments, between 70% and 90% of the following year's income depends on your ability to renew agreements, drive expansion, and recover at-risk accounts. Forecast drift, poorly constructed statements of work, and inadequate escalation protocols silently damage both profitability and credibility. What follows are unmet targets, CFO doubt, and clients who view you as expendable rather than essential.

Our approach is fundamentally different. We operate a system-driven commercial framework where rigorous execution outperforms individual heroics. We generate profitable, sustainable revenue from an established Fortune-tier customer base by executing clean renewals, targeted expansions, and executive-level escalation management. Commercial infrastructure is treated as a core deliverable: proposals designed to safeguard margin, contracts structured for seamless delivery, and quarterly business reviews that genuinely advance product adoption.

This position is not a high-autonomy role without structure, nor is it an environment where you can rely on superficial metrics or vanity-stage pipelines. It suits someone energized by forecast precision, margin-protected deal architecture, well-defined SOWs, and executive dialogues that conclude with concrete clarity and actionable commitments. You will leverage authentic GenAI capabilities to accelerate analysis and stakeholder communication, apply sound commercial judgment during ambiguous scenarios, deploy escalation control that stabilizes critical situations, and provide coaching that refines pricing discipline, deal structure, and negotiation technique across your team. If you have managed enterprise B2B software sales encompassing renewals, expansions, multi-year agreements, SLAs, and pricing strategy, this role will align with your expertise.

If you currently lead or have recently overseen an enterprise sales organization within SaaS, or if you have advanced through senior positions such as Sales Director, Regional VP, or Head of Enterprise Accounts following an early career grounded in disciplined pipeline oversight, we invite your application. Assume ownership of a role where your professional craft is protected from operational disorder and take command of the mechanism that truly defines next year's performance. Apply if you are prepared to demonstrate that structured commercial execution consistently surpasses optimism.

What you will be doing

  • Leading renewals and expansions from opportunity development through contract execution
  • Conducting executive business reviews and directing escalation management
  • Designing and authorizing commercial proposals and agreements that maintain integrity under scrutiny

Key responsibilities

  • Expand enterprise account revenue and retention by executing disciplined commercial strategies, providing strategic account leadership, and ensuring seamless customer integration

Candidate requirements

  • A minimum of 10 years of experience within the IT industry and 5 years of experience in B2B enterprise software
  • A minimum of 5 years of experience leading renewals, expansions, or account growth initiatives
  • Demonstrated experience applying LLMs and other GenAI tools to optimize workflows
  • Proven track record managing multi-million-dollar enterprise accounts
  • Working knowledge of CRM systems and Order-to-Cash (O2C) processes
  • Experience serving customers in regulated industries (finance, healthcare, or pharma), including compliance-focused commercial frameworks
  • Background leading sales or account management teams in quota-carrying capacities, with coaching expertise in deal structure 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 5

Accept Job Offer.

Pass 
proctored test.
ONE LAST THING

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.