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
Not accepting applications on crossover.com at this time.
Description
Most enterprise software doesn't collapse from a shortage of customer names—it fails when revenue from existing accounts quietly deteriorates. In multi-year B2B environments, 70–90% of the following year's income depends on your ability to renew effectively, expand strategically, and recover at-risk relationships. Forecast drift, poorly drafted statements of work, and inadequate escalation discipline silently destroy both margin and credibility. 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 process-driven commercial framework where rigorous execution outperforms improvisation. We generate sustainable, profitable growth from an established Fortune-tier client base by executing clean renewals, targeted expansions, and controlled executive escalations. Commercial rigor is treated as a core deliverable: margin-protecting proposals, delivery-enabling contracts, and quarterly business reviews that genuinely drive adoption forward.
This position is not a laissez-faire environment, nor is it a refuge for those relying on narrative or speculative pipeline metrics. It suits someone energized by forecast precision, margin-disciplined deal architecture, well-structured SOWs, and executive dialogues that conclude with clarity and firm commitments. You will apply genuine GenAI expertise to accelerate analysis and communication, exercise sound commercial judgment during ambiguity, manage escalations with composure, and coach the team to strengthen pricing, structure, and negotiation discipline. If you have led B2B enterprise software sales with ownership of renewals, expansions, multi-year agreements, SLAs, and pricing strategy, this environment will suit you well.
If you currently lead or recently managed an enterprise sales organization in 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 discipline, we should connect. Enter a role where your expertise is not diluted by disorder, and take ownership of the engine that truly defines next year's performance. Apply if you are prepared to demonstrate that structured commercial execution consistently outperforms optimism.
What you will be doing
- Leading renewals and expansions from early-stage pipeline through contract execution
- Conducting executive business reviews and owning escalation management
- Designing and approving commercial proposals and contracts built to withstand scrutiny
Key responsibilities
- Grow enterprise account revenue and retention via disciplined commercial execution, strategic account ownership, and seamless customer engagement
Candidate requirements
- Minimum 5 years of experience in enterprise B2B software sales
- Direct accountability for enterprise revenue metrics including quota ownership, renewals, or expansions
- Direct accountability for enterprise accounts with annual contract values of $1M or higher
- Hands-on experience with CRM platforms and working knowledge of Order-to-Cash (O2C) workflows
- Demonstrated experience using LLMs and other GenAI technologies to optimize workflows
Applying for a role? Here’s what to expect.
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Cognitive 
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Prove real-world 
job skills.
Interview with the hiring manager.
Pass
proctored test.
Accept job offer.
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