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 falls short not from insufficient customer acquisition, but from quiet revenue attrition across existing accounts. In B2B environments with extended sales cycles, 70–90% of the following year's revenue depends on renewal excellence, expansion discipline, and churn mitigation. Poor escalation protocols, imprecise statements of work, and inconsistent forecasting silently erode profitability and client confidence. The outcome: missed targets, finance team doubt, and client relationships that feel transactional rather than strategic.

Our approach is different. We operate a process-driven commercial framework where rigorous execution replaces improvisation. We build sustainable, profitable revenue streams from an established Fortune-tier portfolio through methodical renewals, targeted expansions, and executive-level escalation management. Commercial infrastructure receives the same attention as product: margin-protecting proposals, delivery-enabling contracts, and quarterly business reviews that genuinely advance adoption.

This position is not for those seeking autonomy without accountability, nor is it a place for intuition-based forecasting or superficial pipeline metrics. It's designed for leaders who draw satisfaction from forecast precision, margin-disciplined deal architecture, unambiguous SOWs, and executive dialogues that conclude with mutual clarity and firm commitments. You'll leverage authentic GenAI capabilities to accelerate analysis and stakeholder communication, apply sound commercial reasoning in uncertain situations, manage escalations with composure and control, and develop team capability in pricing strategy, deal structure, and negotiation tactics. If you've directed enterprise B2B software sales with accountability for renewals, expansions, multi-year agreements, service-level commitments, and pricing frameworks, this environment will feel familiar.

If you're currently steering or have recently guided an enterprise sales organization within SaaS, or you've advanced through demanding roles such as Sales Director, Regional VP, or Head of Enterprise Accounts after building foundational expertise in disciplined pipeline stewardship, let's connect. Enter a role where operational rigor isn't undermined by disorder, and take ownership of the mechanism that genuinely defines next year's performance. Apply if you're prepared to demonstrate that systematic commercial discipline consistently outperforms optimism.

What you will be doing

  • Leading renewals and expansion initiatives from qualification through contract execution
  • Facilitating executive-level reviews and controlling escalation processes
  • Designing and authorizing commercial proposals and contractual agreements that withstand scrutiny and operational stress

Key responsibilities

  • Expand enterprise account revenue and retention through systematic commercial discipline, strategic account stewardship, and frictionless customer engagement

Candidate requirements

  • Minimum 5 years managing renewals, expansions, or account development within B2B enterprise software
  • Demonstrated use of LLMs and GenAI technologies to optimize operational workflows
  • Track record managing enterprise accounts valued in the multi-million-dollar range
  • Proficiency with CRM platforms and Order-to-Cash (O2C) workflows
  • Background serving regulated industry clients (finance, healthcare, or pharmaceutical sectors), including compliance-centric commercial frameworks
  • Leadership experience directing sales or account management teams in quota-accountable capacities, with emphasis on coaching deal architecture and negotiation strategy

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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