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 

Not accepting applications on crossover.com at this time.

Description

Enterprise software rarely collapses due to insufficient client logos; it deteriorates because revenue from acquired accounts quietly decays. In extended B2B cycles, 70–90% of the following year's income hinges on your ability to renew, expand, and recover. Forecast drift, poorly drafted SOWs, and inadequate escalation discipline silently erode both margin and credibility. The outcome: unmet targets, CFO doubt, and clients who view you as a disposable supplier rather than essential infrastructure.

Our approach operates differently. This is a system-driven commercial framework where disciplined execution outperforms individual heroics. We build profitable, sustainable revenue from an established Fortune-tier base through clean renewal processes, targeted expansion efforts, and executive-level escalation management. Commercial rigor is treated as a core deliverable: proposals designed to preserve margin, contracts structured for efficient delivery, and QBRs that genuinely advance adoption.

This position is not a low-structure, high-autonomy arrangement, nor is it a place to rely on instinct or inflated pipeline projections. It suits someone energized by forecast precision, margin-protecting deal architecture, well-defined SOWs, and executive dialogues that conclude with clarity and commitment. You will apply genuine GenAI capabilities to accelerate analysis and communication, exercise sound commercial judgment amid ambiguity, manage escalations with composure, and develop the team's pricing, structuring, and negotiation acumen. If you have led enterprise B2B software sales with accountability for renewals, expansions, multi-year agreements, SLAs, and pricing, this will feel natural.

If you are currently running or have recently managed an enterprise sales organization in SaaS, or you have advanced through roles 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 is not undermined by disorder, and take ownership of the engine that truly determines next year's results. Apply if you are prepared to demonstrate that structured commercial execution surpasses optimism every time.

What you will be doing

  • Leading renewals and expansions from pipeline through final execution
  • Conducting executive reviews and overseeing escalation management
  • Designing and authorizing commercial proposals and contracts built to withstand scrutiny

Key responsibilities

  • Expand enterprise account revenue and retention via disciplined commercial execution, strategic account stewardship, and seamless customer engagement

Candidate requirements

  • Minimum 5 years of experience in B2B enterprise software sales
  • Direct accountability for enterprise revenue metrics including quota responsibility, renewals, or expansions
  • Direct accountability for enterprise accounts with annual contract values of $1M or greater
  • Proficiency 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.