About this role.
Datadog is hiring an Enterprise Federal Sales Executive to develop and close new business with civilian agencies and large enterprise accounts. The role owns territory planning, prospecting, relationship mapping, value-based selling, commercial negotiations, pipeline development, and forecast accuracy. Candidates need at least three years of closing experience, demonstrated success against $1M+ sales goals, and experience selling SaaS, IT infrastructure, or similar technology solutions. This is a hybrid/remote field-sales role requiring significant client travel of up to 70% and strong independent pipeline-generation capability.
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 begin by segmenting accounts by fit, urgency, existing technology environment, and potential business impact. I map buying committees, build multithreaded outreach plans, use relevant customer stories, and maintain a weekly operating cadence that measures activity, meetings, qualified pipeline, and conversion rates.
I use discovery to connect technical capabilities to the customer's operational, financial, and risk-related priorities. I quantify the current cost of the problem, align stakeholders around measurable outcomes, and build a business case that demonstrates why the proposed solution and implementation approach provide a credible return on investment.
In a complex negotiation, I first confirmed the decision criteria and non-negotiables on both sides. I protected value by trading rather than conceding—for example, aligning pricing flexibility with term length, expansion commitments, or implementation milestones—while keeping executive sponsors informed and preserving the long-term relationship.
I qualify opportunities against a consistent methodology, validate compelling events and decision processes directly with customers, and identify gaps in access, technical validation, legal review, and procurement. I update close dates only when customer-verified milestones support them and clearly communicate risk alongside upside.
I avoid treating displacement as a feature comparison. I identify where the incumbent is not supporting strategic outcomes, engage advocates across technical and business teams, create a differentiated proof plan, and establish a mutual action plan that makes the cost and risk of maintaining the status quo visible.
Our Enterprise Federal sales team works with a best-of-breed product that solves real problems for our customers. Sellers follow a well-defined methodology that helps them identify the customer’s unique needs and clearly convey the value of the Datadog product. Whether you’re looking to learn from the best or be the best, the Datadog sales team is dedicated to furthering personal development and team success.
We are searching for an experienced Federal, Civilian Sales Executive that has a real passion for technology and can deliver on bold revenue targets. As we continue to enter into bigger markets, and formalize our support for the Public Sector enterprise segment, this division within Datadog will blaze the path for organizational growth. This is a lucrative opportunity to break into new Civilian Agencies within a rich territory, as well work with accounts who are in a hybrid state and transitioning to the cloud.
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:
- Prospect into large Fortune 1000 companies while running an efficient sales process
- Maintain, build and own specific relationship maps for your territory including existing relationships and aspirational contacts
- Develop a deep comprehension of customer’s business
- Negotiate favorable pricing and business terms with large commercial enterprises by selling value and ROI
- Handle existing customer expectations while expanding reach and depth into assigned territory
- Demonstrate resourcefulness when faced with challenges that defy easy solution
- Have intuitive sense of necessary steps to close business and gain customer validation
- Identify robust set of business drivers behind all opportunities
- Ensure high forecasting accuracy and consistency
Who You Are:
- Someone with 3+ years closing experience (mix of field selling within mid-market and enterprise)
- Driven and have met/exceeded direct sales goals of 1M+ and operated with an average deal size of $100k+
- Able to demonstrate methodology to prospect and build pipeline on your own
- Experienced in working for an innovative tech company (SaaS, IT infrastructure or similar preferred)
- Experienced in selling into large Fortune 1000 companies with the ability to win new logos
- 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
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:
$90,000—$120,000 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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