Head 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

Head of Enterprise Sales   $200,000 USD/year

Description

Most enterprise software fails not from insufficient customer acquisition, but from silent revenue decay within accounts already secured. In B2B environments with extended sales cycles, between 70% and 90% of the following year's revenue depends on renewal quality, expansion effectiveness, and timely intervention. Forecast drift, ambiguous statements of work, and poor escalation discipline erode both profitability and credibility. The outcome: unmet targets, finance leadership doubt, and clients who view you as interchangeable rather than indispensable.

Our approach is fundamentally different. We operate a process-driven commercial engine where systematic rigor outperforms individual heroism. We generate sustainable, profitable growth from an established enterprise customer base through structured renewals, targeted expansions, and executive-grade escalation management. Commercial infrastructure is treated as core product: margin-protected proposals, contracts engineered for smooth delivery, and quarterly business reviews that genuinely drive adoption.

This position is not an unstructured autonomy role, nor a place for perception management or inflated pipeline metrics. It's designed for leaders energized by forecast precision, margin-conscious deal architecture, unambiguous SOWs, and executive dialogues that conclude with clarity and commitment. You will apply genuine GenAI capabilities to accelerate insight and communication, deploy sound commercial judgment in uncertain situations, provide escalation leadership that restores confidence, and develop team capability in pricing, structuring, and negotiation. If your background includes leading enterprise B2B software sales with accountability for renewals, expansions, multi-year agreements, SLAs, and pricing frameworks, this environment will be familiar.

If you are currently heading or have recently led an enterprise sales organization in 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 management, let's connect. Take ownership of a role where commercial excellence isn't compromised by disorder, and control the mechanism that truly defines next year's revenue. Apply if you're prepared to demonstrate that rigorous commercial execution consistently outperforms optimism.

What you will be doing

  • Leading renewals and expansions from opportunity identification through contract execution
  • Conducting executive business reviews and directing escalation resolution
  • Designing and authorizing commercial proposals and agreements built to withstand scrutiny

Key responsibilities

  • Expand enterprise account revenue and retention through systematic commercial execution, strategic account stewardship, and frictionless customer integration

Candidate requirements

  • A minimum of 10 years of IT industry experience and 5 years within the B2B enterprise software sector
  • A minimum of 5 years of experience driving renewals, expansions, or account growth initiatives
  • Demonstrated use of LLMs and GenAI tools to optimize workflow efficiency
  • Proven track record managing enterprise accounts valued in the multi-million-dollar range
  • Working knowledge of CRM platforms and Order-to-Cash (O2C) workflows
  • Background serving regulated industry clients (finance, healthcare, or pharma), including compliance-oriented commercial frameworks
  • Leadership experience in sales or account management with quota responsibility and coaching expertise in deal structuring and negotiation

Meet a successful candidate

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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.

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