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Director, Enterprise Sales

Datadog

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Questions you are likely to be asked

  1. Why do you want to join Datadog?
  2. What is your experience with Observability? Tell me one thing you learned the hard way.
  3. How do you find and qualify new leads?
  4. What is your target, and how did you do against it last quarter?
  5. Walk me through a deal you closed, from the first call.

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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.
At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them.
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
  • Able to sit up to 4 hours, traveling to and from client sites
  • Able to travel via auto, train or air up to 70% of the time
Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That’s okay. If you’re passionate about technology and want to grow your skills, we encourage you to apply.
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
Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog.
#LI-Remote
 

About Datadog: 

Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across the technology stack to manage complexity at scale. It brings applications, infrastructure, data, models, and security into one place, using AI to detect and resolve issues before they impact customers. Trusted globally by Fortune 500 companies and high-growth AI leaders, Datadog enables businesses to move faster with clarity and confidence. Learn more about #DatadogLife on Instagram, LinkedIn, and Datadog Learning Center.

Equal Opportunity at Datadog:

Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Here are our Candidate Legal Notices for your reference. 

Datadog endeavors to make our Careers Page accessible to all users. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please complete this form. This form is for accommodation requests only and cannot be used to inquire about the status of applications. 

Privacy and AI Guidelines:

Any information you submit to Datadog as part of your application will be processed in accordance with Datadog’s Applicant and Candidate Privacy Notice. For information on our AI policy, please visit Interviewing at Datadog AI Guidelines.

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Listed on greenhouse · posted 2026-11-11. ApplySarthi collects openings and links to application pages; the role is advertised by Datadog, not by us.