Director, Enterprise Sales

Datadog; United States; Hybrid; USD 150,000 - 200,000; Full time

Benefits offered by this job

RSU & ESPP

Dev & training

Sales training MEDDIC

Mentor program

Inclusive culture / Community Guilds

Medical benefits

401(k) match

Pet insurance

Job summary

Datadog is seeking a Director of Enterprise Sales to lead a team of Enterprise Sales Executives driving new business and expansion across Fortune 1000 accounts. You will mentor, hire, train, and ramp the team while guiding them through complex multi-stakeholder deals and executive engagements to achieve quarterly and annual bookings targets.

You will shape regional GTM strategy, collaborate with Marketing, Product and Success to tailor messaging, and oversee weekly forecast meetings.

Qualifications

• Experience leading a high‑performing Enterprise Sales team.
• 5+ years in Enterprise sales with Fortune 1000 clients.
• Able to navigate complex multi-stakeholder deals and procurement.
• Proven track record of closing large deals with executive sponsorship.
• Willingness to travel as needed.

Responsibilities

• Manage, hire, train and ramp a team of Enterprise Sales Executives.
• Achieve annual Enterprise bookings quota with monthly/quarterly targets.
• Develop and manage productivity metrics (deal size, win rate, forecast).
• Coach executives on executive relationships and complex negotiations.
• Shape go‑to‑market strategy and regional execution.
• Collaborate with Marketing, Product and Success on messaging and journey mapping.
• Conduct weekly forecast meetings.
• Support direct reports in client meetings and resource engagement.

Skills

Enterprise sales

Leadership

C-level selling

Forecasting

Relationship building

Job description

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
• 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

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

Datadog offers a competitive salary and equity package, and may include variable compensation. Active compensation is based on factors such as the candidate's skills, qualifications, and experience. In addition, Datadog offers a wide range of best in class, comprehensive and inclusive employee benefits for this role including healthcare, dental, parental planning, and mental health benefits, a 401(k) plan and match, paid time off, fitness reimbursements, and a discounted employee stock purchase plan.

The reasonably estimated yearly salary for this role at Datadog is:

$150,000—$200,000 USD

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.