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Director of Sales

Cypress HCM, WorkFromHome, NY, United States


Overview

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, understands enterprise complex IT ecosystems, and can mentor sellers through complex, multi-stakeholder deals.

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 or 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

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