Director 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

Director of Enterprise Sales   $200,000 USD/year

Description

Enterprise software rarely collapses due to a shortage of customer names—it deteriorates when revenue from existing clients quietly decays. In extended-cycle B2B environments, 70–90% of the following year's income hinges on your ability to renew successfully, drive expansion, and recover at-risk accounts. Forecast drift, poorly structured statements of work, and inconsistent escalation discipline silently erode both profitability and credibility. The outcome: unmet targets, CFO doubt, and clients who view you as interchangeable rather than indispensable.

Our approach is fundamentally different. This is a process-driven commercial framework where rigorous execution outperforms individual heroism. We generate profitable, sustainable revenue from an established Fortune-tier client base through disciplined renewals, targeted expansions, and executive-level escalation management. Commercial rigor is treated as a core deliverable: margin-protected proposals, contracts designed for smooth execution, and quarterly business reviews that genuinely advance product adoption.

This position is not designed for those seeking autonomy without structure, nor is it a place to rely on intuition or superficial pipeline activity. It suits someone energized by forecast precision, margin-preserving deal architecture, tightly drafted SOWs, and executive dialogues that conclude with clear decisions and firm commitments. You will apply genuine GenAI expertise to accelerate analysis and correspondence, demonstrate sound commercial judgment when navigating ambiguity, manage escalations with composure, and possess the coaching capability to refine pricing strategy, deal structure, and negotiation tactics across your team. If your background includes leading 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 currently oversee or have recently managed an enterprise sales organization within SaaS, or 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 a role where your expertise operates free from disorder and command the revenue engine that genuinely determines next year's performance. Apply if you are prepared to demonstrate that structured commercial discipline consistently outperforms optimism.

What you will be doing

  • Leading renewals and expansion initiatives from pipeline development through contract execution
  • Facilitating executive reviews and overseeing escalation management
  • Designing and authorizing commercial proposals and contractual agreements that withstand scrutiny

Key responsibilities

  • Expand enterprise account revenue and retention through rigorous commercial discipline, strategic account oversight, and cohesive customer engagement

Candidate requirements

  • A minimum of 10 years in the IT sector and 5 years within the B2B enterprise software domain
  • No fewer than 5 years managing renewals, expansions, or account development
  • Demonstrated use of LLMs and other GenAI technologies to optimize 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), including compliance-oriented commercial frameworks
  • History of leading sales or account management teams in quota-bearing capacities and mentoring on deal architecture 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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