Enterprise Account Executive
Middesk · Hybrid · New York, NY
Full health. Just posted.
New Business: you win brand-new customers.
- Base
- Not disclosed
- OTE
- $300K–$330K
- Quota attainment
- Not disclosed
- Posted
- 5h 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 Middesk's careers page
The job
- What you'd do
- Find and win new customers among big finance apps, lenders and online marketplaces, selling software that confirms companies are who they say they are. You'll do much of your own prospecting.
- What you'd sell
Business identity checks for banks and fintechs
When a bank signs up a new business customer, it has to confirm the company is real and who runs it, usually by digging through records. The problem is, slow checks hold up sign-ups, and one missed detail can mean risk. Middesk checks business details against trusted data, so banks approve customers faster and catch risk early.
In plain English, from their own job posts. Something wrong? Tell me · More Security companies →
- Who you'd sell to
- Fintechs, lenders, marketplaces and B2B platforms at big companiesIn their words: “You'll partner with some of the most innovative fintechs, lenders, marketplaces, and B2B platforms, helping them build trust into critical customer workflows.”
- Where deals come from
- Mostly you. Expect a lot of outbound: cold calls, emails and LinkedIn.
The Braun Read
Worth a lookSolid on the basics. Use the first call to fill in the gaps.
- Pay
- OTE is listed. Ask what the base is.
- Transparency
- Says nothing about quota, attainment, deal size, territory or sales cycle.
- Time on market
- Brand new.
- Company hiring
- Ramping up: posted 5 sales roles in the last 30 days.
Red lights
None spotted.
Green lights
- Publishes OTE. It tells you the on-target earnings up front. Most postings don't.
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 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 base, and how is the rest paid out?
OTE without a base doesn't tell you what you can count on.
- 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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