Job Specifications
Location: Remote – EST | some travel to customer locations and internal meetings as needed
Employees: 50|Team Size: 5
Industry: SaaS
Reports To: CEO
We’re looking for a hands-on enterprise sales leader to drive and expand our U.S. enterprise revenue motion. Reporting directly to the CEO, this person will oversee a team of Account Executives, own day-to-day sales execution, and help build strategic plans to win and grow large enterprise accounts.
This role fits a performance-driven sales manager who excels in a fast-paced growth environment, understand enterprise complex IT ecosystems, and can mentor sellers through complex, multi-stakeholder deals.
Most Important Responsibilities
Lead, manage, and develop a team of Account Executives, ensuring consistent execution against pipeline generation and revenue goals.
Work closely with CEO to maintain alignment between daily execution and broader commercial strategy.
Track team and individual performance, delivering coaching, feedback, and process improvements to strengthen outcomes.
Review and strengthen key enterprise account strategies, including deal planning, stakeholder mapping, and execution approach.
Coach sellers on enterprise sales fundamentals including discovery, value-driven positioning, qualification, and advancing opportunities through a defined sales process.
Step in as an executive sponsor on high-value or strategic opportunities to support deal progression and close.
Partner cross-functionally with Pre-Sales, Marketing, and Customer Success to ensure customer needs are reflected in messaging, positioning, and go-to-market execution.
Build and reinforce a culture of accountability, ownership, collaboration, and continuous improvement.
What you can bring to the table to impact this role, team, and organization:
3+ years of experience leading enterprise Sales teams with a demonstrated record of meeting ro exceeding revenue goals.
Direct enterprise selling experience in complex, consultative, multi-threaded deal cycles with enterprise technology domains; IT infrastructure, cloud platforms, DevOps, and/or security solutions.
Experience in high-growth, scaling organizations – able to operate strategically while staying actively involved in execution.
Strong people leadership skills with a track record of developing sellers in account planning, value-based selling, and deal management.
A driven, metric-oriented leadership style balanced with a collaborative and supportive team approach.
Compensation: $275K - $330K total compensation + equity options
About the Company
At Cypress, we deliver top talent to your doorstep. Our nationwide reach and industry expertise help us precision-match candidates, saving you time and frustration. Our experts specialize in placing highly qualified employees, ensuring a perfect fit that not only boosts individual career paths but also enhances organizational productivity.
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