Braun Board

Enterprise Security Sales Specialist

Datadog · Chicago, IL

Base
$124K–$165K
OTE
Not disclosed
Quota attainment
Not disclosed
Posted
5d ago

Why it matters: OTE tells you what you could earn. Attainment tells you how realistic it is.

Ask: “What percentage of fully ramped reps hit quota last year?”

Still open · checked 2h agoon Datadog's careers page

What Datadog sells

Monitoring and security software for cloud apps

When a company runs its apps in the cloud, someone has to keep watch on how they perform and whether they're safe. The problem is, complex security and performance issues are hard to explain in plain words, and even harder to tie to what they mean for the business. Datadog's observability and security software shows how cloud systems are running and where the risks are, so teams can explain the results in clear, measurable terms.

In plain English, from their own job posts. Something wrong? Tell us

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The Braun Read

Ask hard questions

Too much is left unsaid. Make them answer before you invest.

Pay
Base is listed but not OTE. Ask what the variable is and how many people hit it.
Transparency
Says nothing about quota, attainment, deal size, territory or sales cycle.
Pipeline
A mix of self-sourced pipeline and inbound or SDR help.
Time on market
Open 5 days.
Company hiring
44 sales roles open, hiring at a steady pace. Ask how many reps they hired last year and how many are still there.

Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

  1. 1.

    What percentage of fully ramped reps hit quota last year?

    OTE is what you could earn. This is how likely you are to earn it.

  2. 2.

    What percentage of reps on the team have been here more than 18 months?

    Tenure shows whether people stay long enough to get paid.

  3. 3.

    Has the comp plan changed in the last 12 to 18 months? What changed?

    A plan that changes every year means the goalposts keep moving.

  4. 4.

    Who sits with reps and reviews calls each week?

    Coaching is often what's behind a good or bad attainment number.

  5. 5.

    What's the OTE, and what did the median rep earn last year?

    Base is what you're guaranteed. OTE and the median show the upside.

  6. 6.

    Why is this role open? Did someone leave, or is it new?

    New headcount is growth. A replacement means someone left. Ask why.

When the offer comes

Save these for later. They land better once they've said yes to you.

  1. 1.

    Can I see the full comp plan in writing, including clawbacks and accelerators?

    What's in writing is what gets paid. Read it before you sign.

  2. 2.

    Can I see the actual comp distribution for the team last year, not just the OTE?

    The spread shows what most reps really take home. OTE is just the target.

  3. 3.

    I'd be walking away from earned commission to join. Is there room for a sign-on bonus to help cover that?

    Leaving money behind is a fair reason to ask. The worst answer is no.

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The role

Sell Datadog's Security platform (Cloud SIEM, CSPM, CWPP) to CISOs and SecOps leaders at enterprise accounts. Co-sell with Enterprise AEs and partners on new logos and expansion.

Enterprise · Mixed

Selling motion

Mixed

Who you're selling to

Buyer:
CISOs, security architects and SecOps teamsIn their words: “Evangelize Datadog’s security story to security leaders (CISO, Security Architects, SecOps)”
Company size:
Enterprise

Pipeline expectations

A mix of self-sourced pipeline and inbound / SDR support.

Compensation

$124K–$165K base

What is not disclosed

This posting doesn't tell you:

  • OTE
  • Quota size
  • Quota attainment
  • Average deal size
  • Territory
  • Sales cycle length

The questions above cover the big ones.

Full posting
As a Security Sales Specialist, you'll partner with Enterprise Account Executives to drive adoption of Datadog’s Security platform across key accounts. This is a high-impact role focused on positioning our Security solutions (Cloud SIEM, Cloud Workload Security, CSPM, and more) into new and existing customers—expanding our footprint and helping customers modernize their security stack in 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: - Act as the subject matter expert (SME) for Datadog Security products across a targeted account patch - Collaborate closely with Enterprise AEs to support net new logo acquisition and expansion in strategic accounts - Own and drive the security sales cycle from discovery to technical close, working closely with Sales Engineers - Evangelize Datadog’s security story to security leaders (CISO, Security Architects, SecOps) - Work cross-functionally with Datadog's partner, channel, and alliance teams to drive joint go-to-market motions - Co-sell effectively with AEs and partners, contributing to deal strategy, solution alignment, and stakeholder engagement - Stay informed on security trends and competitive offerings to differentiate Datadog Who You Are: - Proven success selling into security buyers (CISO, SecOps, GRC, etc.) - Experience co-selling in a matrixed environment, supporting or partnering with AEs and cross-functional teams - Strong understanding of the partner/channel sales model, including how to navigate and influence joint selling motions - Familiarity with modern security solutions such as SIEM, CSPM, CWPP, container/Kubernetes security - Ability to build strong relationships with internal stakeholders, partners, and customer technical teams 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. 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: $124,000-$165,000 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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