Braun Board

Director, Enterprise Sales

Datadog · San Francisco, CA

Base
$158K–$210K
OTE
Not disclosed
Posted
2d ago

Still open · checked 1h agoon Datadog's careers page

What Datadog sells

Helps teams watch cloud apps for problems

A software team runs its apps on servers in the cloud, and it needs to see what is happening inside them. This product gives the team a clear view of its systems, so it can watch for problems and security risks. The payoff is measurable business results the team can point to.

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
Doesn't say where pipeline comes from. Ask.
Time on market
Brand new.
Company hiring
Ramping up: posted 9 sales roles in the last 30 days. That many open roles can also mean churn. Ask how many reps are still there from last year.

Based only on what the posting says. Flags 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'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.

  3. 3.

    What's the annual quota, and how was it set?

    A quota built from real data is a target. Otherwise it's a hope.

  4. 4.

    Where does pipeline come from: inbound, SDRs, or me?

    Tells you how much of your week is prospecting versus selling.

  5. 5.

    How long is ramp, and what's the quota during it?

    Full quota on day one means you start behind.

  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.

Josh's top five questions for any sales interview →

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The role

Leads a team of Enterprise Sales Executives selling to Fortune 1000 companies, owning new and expansion bookings against an annual quota. The role centers on coaching, forecasting, and regional go-to-market strategy.

Enterprise · Mixed

Selling motion

Mixed

Who you're selling to

Buyer:
C-level executives in ITIn their words: “Knowledgeable in selling to C-level executives in the IT space”
Company size:
Enterprise

Pipeline expectations

Not stated in the posting.

Compensation

$158K–$210K 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
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. 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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