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Datadog

Director, Enterprise Sales

USARemotePosted 2 weeks ago

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Job type
Full-time
Work mode
Remote
Level
Director
Department
Sales
Experience
5+ years experience
Posted
Sep 14, 2026

About the role

Our Director, Enterprise Sales will provide strategy, mentorship, and guidance for a team of Enterprise Sales Executives who are responsible for driving new business through the full sales cycle.

What You’ll Do:

  • Manage, hire, train and ramp a team of Enterprise Sales Executives responsible for new and expansion bookings
  • Achieve annual Enterprise bookings quota with monthly and quarterly targets
  • Develop and manage Enterprise Sales Executives on productivity metrics such as deal size, win rate, and forecast accuracy as well as how to lead a customer through a proactive sales cycle
  • Coach Sales Executives through building executive relationships with Named Enterprise accounts in their territories and through complex Enterprise deals and negotiations
  • Shape the direction of the go-to market strategy and execution for your region
  • Work collaboratively with Marketing, Product and Success to build targeted messaging and collateral, and mapping a customer journey for the specific business needs of your region
  • Conduct weekly forecast meetings
  • Support direct reports by participating and leading in client and prospect meetings. Engaging other corporate resources as required

Who You Are:

  • Experienced in managing a high performing Enterprise Sales team for a B2B technology company
  • A strong relationship builder with 5+ years of overall Enterprise sales experience working with Fortune 1000 companies
  • Confident in managing complex sales processes with multiple stakeholders and negotiations with pricing based on business value, legal and procurement
  • Knowledgeable in selling to C-level executives in the IT space
  • Experienced in setting quotas and managing people against those quotas
  • Passionate about coaching others with a successful track record as an individual contributor and can share relevant and complex closing experience with a growing team
  • Role requires regular travel to client sites, within your area and other regions, using various modes of transportation (car, train, air), depending on business needs

Benefits and Growth:

  • High income earning opportunities based on self performance
  • New hire stock equity (RSU) and employee stock purchase plan (ESPP)
  • Continuous professional development, product training, and career pathing
  • Sales training in MEDDIC and Command of the Message
  • Intra-departmental mentor and buddy program for in-house networking
  • An inclusive company culture, opportunity to join our Community Guilds
  • Generous and competitive medical benefits package
  • Retirement savings match
  • Pet adoption and insurance program