Director, Enterprise Sales (SLED)
Datadog · Remote · US
Full health. Just posted.
New Business + Account Growth: you win new customers and grow existing ones.
- Base
- $165K–$220K
- OTE
- Not disclosed
- Posted
- 5h ago
Still open · checked 2h agoon Datadog's careers page
The job
- What you'd do
- Lead a team of sales reps who sell to state and local governments and schools, winning new customers and selling more to existing ones. You'd hire, coach and set targets for them, and travel to client sites.
- What you'd sell
Warns companies the moment their website or app breaks
When a company runs a website or app, somebody has to notice the moment something breaks. The problem is, if they notice late, customers notice first, and engineers end up hunting through many servers to find the cause. Datadog watches your apps and servers in one place, so the team hears about a problem before customers do and can see exactly where it started.
In plain English, from their own job posts. Something wrong? Tell me · More Developer & IT tools companies →
- Who you'd sell to
- Top IT leaders at state, local and education agencies at big companiesIn their words: “Knowledgeable in selling to C-level executives in the IT space”
- Where deals come from
- Not stated in the posting.
The Braun Read
Ask hard questionsToo 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.
- Time on market
- Brand new.
- Company hiring
- 45 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.
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.
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.
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.
Where does pipeline come from: inbound, SDRs, or me?
Tells you how much of your week is prospecting versus selling.
- 5.
How long is ramp, and what's the quota during it?
Full quota on day one means you start behind.
- 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.
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.
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.
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.