Sales Development Representative - Summer 2027 Graduates (Boston)
Datadog · Boston, MA
- Base
- $50K
- OTE
- Not disclosed
- Quota attainment
- Not disclosed
- Posted
- Yesterday
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 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
More Developer & IT tools companies →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.
- Pipeline
- Mostly self-sourced. Great if you like outbound, rough if you don't.
- 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.
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 percentage of reps on the team have been here more than 18 months?
Tenure shows whether people stay long enough to get paid.
- 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.
Who sits with reps and reviews calls each week?
Coaching is often what's behind a good or bad attainment number.
- 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.
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.
Josh's top five questions for any sales interview →
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The role
Entry-level outbound SDR role for Datadog in Boston. You'll cold call and email IT and technology prospects to qualify them and book discovery meetings for the sales team.
New Logo · Outbound
Selling motion
Who you're selling to
- Buyer:
- IT and technology innovatorsIn their words: “help IT and Technology innovators across markets recognize Datadog’s impact in their digital transformation and migration to the cloud”
- Industry:
- IT and technologyIn their words: “help IT and Technology innovators across markets”
Pipeline expectations
Compensation
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.