Braun Board

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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The Braun Read

Worth a look

Solid 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. 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. 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. 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. 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. 5.

    Who sits with reps and reviews calls each week?

    Coaching is often what's behind a good or bad attainment number.

  6. 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. 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. 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. 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.

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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

Not stated in the posting.

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

Not stated in the posting.

Compensation

$250K OTE

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.

Full posting
ABOUT SPEAKEASY Speakeasy began in the developer tooling space by building a toolchain for powering API developer experience. With the rise of AI and since the launch of MCP, we have expanded into helping teams build, secure, observe, and distribute AI tools across their organization with the Speakeasy AI Control Plane. Our customers today include leading tech companies and fortune 100 enterprises such as Mistral AI, Vercel, PlanetScale, Verizon, and Docusign. We were founded in 2021 and have already hit important revenue milestones. We have raised funding from top-notch VC and angel investors who share our vision, and have significant runway remaining. Our team is split between San Francisco and London, with offices in both locations. We work best together in person. This role is based in our San Francisco office four days a week, with one day remote. We meet up and spend a week together roughly every quarter. ABOUT THE ROLE As an Account Executive, you will drive adoption of our newest product, the Speakeasy AI Control Plane, and help shape the future of AI adoption, security, and governance across the enterprise. You'll own the full sales cycle from qualified opportunity through close. You'll work with mid-market and enterprise buyers navigating the shift to AI-native workflows, helping them understand how the Control Plane fits into their stack and securely accelerates AI rollout across their organization. You'll run discovery, lead demos, negotiate contracts, and close deals. But this isn't just a closing role. You'll partner closely with GTM, product, and marketing to sharpen how we position, what resonates, and where the market is moving. This is an early sales hire and you'll have a direct hand in building our playbook, not just running it. The ideal candidate is a self-starter and strong relationship builder who gets energy from learning a new market, building strategy around it, and identifying opportunities in a category that is not yet fully defined. ABOUT YOU - 3–5+ years of full-cycle B2B SaaS sales experience, consistently meeting or exceeding quota - Experience selling technical, developer-adjacent or infrastructure products — you don't need to write code, but you can hold your own in a technical conversation - Strong discovery and qualification instincts — you lead with the customer's problem, not the pitch - Demonstrated ability to independently build and advance C-suite and SVP relationships, and manage multi-quarter sales cycles involving technical evaluations and enterprise procurement - Experience managing a pipeline of 15–30 active opportunities, excellent forecasting discipline and CRM hygiene WHO WE’RE LOOKING FOR Our ideal candidate: - High ownership and autonomy: you figure out what needs to happen and make it happen without waiting to be told. - Comfortable operating without a fully built playbook: the market, messaging, and process are still being shaped, and you see that as a feature, not a bug. - Naturally brings customer signal back to the business: You don't just close deals, you surface patterns from the field that sharpen how product, marketing, and leadership think about the market. - Respects how we operate and raises the bar: we are ambitious, passionate about what we do, and seek to be exceptional. If you are looking for a place to clock in and out, we are likely not a good fit for you. BENEFITS - Salary ~ $250K OTE - Generous equity - Competitive pay - 100% employer-covered medical, dental, and vision insurance - 401(k) plan - Unlimited PTO - Lunch provided in office from some of the best restaurants in San Francisco! - Annual off-sites with the entire team (previous locations: 2024 - Lisbon, 2025 - Mexico City, 2026 - Madrid!) - Work with a fun, collaborative, ambitious team Excited to learn more? Get in touch with us at jobs@speakeasyapi.dev. We look forward to hearing from you!
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