Account Executive
Speakeasy · San Francisco, CA
- Base
- Not disclosed
- OTE
- $250K
- Quota attainment
- Not disclosed
- Posted
- 6mo 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 Speakeasy's careers page
What Speakeasy sells
One place to build and secure AI tools
A big company wants its workers to use AI tools, but it is hard to know which ones are safe or who is using them. Speakeasy gives teams one place to build, secure, watch, and share their AI tools. That lets the whole company roll out AI without losing control of it.
In plain English, from their own job posts. Something wrong? Tell us
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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
- Shares 1 of 5: quota, attainment, deal size, territory, sales cycle.
- Pipeline
- Doesn't say where pipeline comes from. Ask.
- Time on market
- Open 183 days. Ask why it's been hard to fill.
- Company hiring
- This is their only open sales role.
Red flags
None spotted.
Worth asking about
- 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 flags
- Publishes OTE. It tells you the on-target earnings up front. Most postings don't.
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.
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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The role
Sell the Speakeasy AI Control Plane, a platform for building, securing, and governing AI tools, to mid-market and enterprise buyers. You run full-cycle deals, from discovery and demos to contract negotiation.
Enterprise
Selling motion
Who you're selling to
- Buyer:
- Not stated in the posting.Ask: “Who's the economic buyer, and who else is in the deal?”
- Industry:
- Technology companiesIn their words: “Our customers today include leading tech companies and fortune 100 enterprises such as Mistral AI, Vercel, PlanetScale, Verizon, and Docusign.”
- Company size:
- Enterprise
Pipeline expectations
Compensation
What is not disclosed
This posting doesn't tell you:
- Base salary
- Quota size
- Quota attainment
- Average deal size
- Territory
The questions above cover the big ones.