Director - Sales (Customer Success)
Weekday AI · Remote · US
- Base
- Not disclosed
- OTE
- Not disclosed
- Posted
- 4mo ago
Still open · checked 2h agoon Weekday AI's careers page
The job
- What you'd do
- Sell Analytics, AI, and Data consulting services to enterprise clients by hunting new logos and building CXO relationships, managing deals from prospecting through close. Requires U.S. travel.
- Who you'd sell to
- Still reading the posting. Check back within the hour.
- Where deals come from
- Mostly you. Expect a lot of outbound: cold calls, emails and LinkedIn.
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 149 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
None spotted.
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 are the base and the OTE for this role?
No point investing hours before you know the number.
- 4.
What's the annual quota, and how was it set?
A quota built from real data is a target. Otherwise it's a hope.
- 5.
What share of last year's closed deals did reps source themselves?
Shows how much pipeline you'll have to build on your own.
- 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.