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 

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

Head of Enterprise Sales   $200,000 USD/year

Description

Most enterprise software companies don't fail from a shortage of customer names—they fail because the revenue from those customers quietly erodes over time. In 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 accounts. Forecast drift, poorly structured statements of work, and inadequate escalation discipline silently destroy margin and erode customer confidence. The outcome: missed targets, finance team doubt, and clients who view you as interchangeable rather than indispensable.

Our approach is fundamentally different. We operate a systems-driven commercial framework where rigorous execution outperforms individual heroics. We generate profitable, sustainable revenue from an established Fortune-tier customer base through disciplined renewals, targeted expansion opportunities, and executive-level escalation management. Commercial infrastructure receives the same attention as product: margin-protected proposals, delivery-ready contracts, and quarterly business reviews that genuinely drive adoption forward.

This position is not about unstructured autonomy, nor is it a place to rely on intuition or superficial pipeline metrics. It's designed for someone energized by forecast precision, margin-preserving deal architecture, well-defined SOWs, and executive dialogues that conclude with mutual clarity and firm commitments. You'll apply genuine GenAI capabilities to accelerate analysis and stakeholder communication, exercise sound commercial judgment when circumstances are unclear, manage escalations with composure and control, and develop the team's skills in pricing strategy, deal structuring, and negotiation tactics. If you've led enterprise B2B software sales with accountability for renewals, expansions, multi-year agreements, SLAs, and pricing models, this environment will be familiar territory.

If you're currently leading or 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 foundation in rigorous pipeline discipline, let's connect. Take ownership of a role where your expertise operates without disruption, and control the revenue engine that truly determines next year's performance. Apply if you're prepared to demonstrate that disciplined commercial execution outperforms optimism consistently.

What you will be doing

  • Leading renewals and expansion deals from pipeline stage through signed agreements
  • Conducting executive-level reviews and owning escalation management
  • Designing and approving commercial proposals and contract terms that withstand scrutiny

Key responsibilities

  • Grow enterprise account revenue and retention rates through rigorous commercial execution, strategic account oversight, and integrated customer engagement

Candidate requirements

  • Minimum 5 years of experience in B2B enterprise software sales
  • Direct accountability for enterprise revenue results including quota attainment, renewals, or expansions
  • Direct accountability for enterprise accounts valued at $1M+ in annual contract value
  • Demonstrated experience with CRM platforms and working knowledge of Order-to-Cash (O2C) workflows
  • Proven experience leveraging LLMs and other GenAI technologies to optimize work processes

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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Cognitive 
aptitude test.

Prove real-world 
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Interview with the hiring manager.
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Interview with the hiring manager.

Accept job offer.
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Accept job offer.

Pass
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STEP 5

Pass
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