Sales & Business Development Representative
Weekday AI · Boston, MA
- Base
- Not disclosed
- OTE
- Not disclosed
- Quota attainment
- Not disclosed
- Posted
- 12mo 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 Weekday AI's careers page
The job
- Who you'd sell to
- Still reading the posting. Check back within the hour.
- Where deals come from
- A mix. Some leads come to you, some you find yourself.
The Braun Read
Ask hard questionsToo much is left unsaid. Make them answer before you invest.
- Pay
- No pay listed at all.
- Transparency
- Says nothing about quota, attainment, deal size, territory or sales cycle.
- Time on market
- Open 361 days. Ask why it's been hard to fill.
- Company hiring
- 10 sales roles open, hiring at a steady pace.
Red lights
None spotted.
Yellow lights
- Open 90+ days. This role has been posted for three months or more. Ask why it's been hard to fill, and whether anyone left it.
Green lights
- SDR or inbound support. You won't be building all of your own pipeline from zero.
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.
This role has been open a while. What's made it hard to fill?
The answer tells you what candidates saw that made them walk.
- 2.
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.
- 3.
What percentage of reps on the team have been here more than 18 months?
Tenure shows whether people stay long enough to get paid.
- 4.
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.
- 5.
Who sits with reps and reviews calls each week?
Coaching is often what's behind a good or bad attainment number.
- 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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