About this role.
Datadog is hiring a Director of Enterprise Sales to lead, hire, coach, and scale a team of Enterprise Sales Executives serving named enterprise accounts. The role owns annual bookings performance, forecasting rigor, sales productivity metrics, and complex enterprise deal execution. It partners closely with Marketing, Product, and Customer Success to shape regional go-to-market strategy and customer messaging. This is a hybrid/remote Texas-based leadership role requiring regular travel to client sites and experience selling B2B technology to Fortune 1000 and C-level IT stakeholders.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
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Sample interview questions
I establish clear stage-exit criteria, inspect deal health weekly, compare rep forecasts with objective pipeline evidence, and coach managers and sellers on risks early. I also track forecast variance by rep and segment to identify whether issues stem from qualification, deal strategy, or pipeline coverage.
I begin by mapping the buying committee, decision process, business pain, technical requirements, procurement path, and competitive risks. I then help the seller create a mutual action plan, build executive alignment, quantify value, and assign clear next steps and owners for each stakeholder.
I would monitor bookings attainment, pipeline coverage, pipeline creation, win rate, average deal size, sales-cycle length, stage conversion, forecast accuracy, expansion contribution, and rep ramp progress. I use the metrics together rather than in isolation to diagnose performance and prioritize coaching.
I would share field intelligence on target-account pain points, objections, competitive patterns, and conversion gaps. Together, we would develop segment-specific messaging, account campaigns, proof points, and customer journey plans that improve demand generation, sales execution, and retention.
I maintain disciplined operating rhythms for current-quarter execution while investing continuously in hiring, onboarding, coaching, and repeatable playbooks. Strong near-term results come from focused deal support, but sustainable performance requires building seller capability and a healthy future pipeline.
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. Actual 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:
$158,000—$210,000 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.
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