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Enterprise Account Executive Midwest - AI Security Start-Up - Paying up to $360,

StealthWatch, Chicago, IL, United States


Enterprise Account Executive – Midwest – AI Security Start‑Up – OTE $360,000 + equity Location:

Midwest, USA (Remote)

StealthWatch is partnering with one of the most exciting AI‑driven security start‑ups in the market today. Backed by top‑tier investors and led by proven security leaders, they’re scaling fast and looking for their

first sales hire on the ground in the Midwest . This is a rare opportunity to join at the foundation stage, own a key region, and make a direct impact on the company’s growth trajectory.

What You’ll Be Doing

Hunt and close

enterprise and mid‑market logos

across the Midwest.

Drive new business opportunities, working directly with leadership to shape GTM strategy.

Build pipeline, run the full sales cycle, and exceed ambitious revenue targets.

Position cutting‑edge

AI security technology

that’s already gaining strong market traction.

What We’re Looking For

Proven track record in

cybersecurity sales

– must‑have.

Experience in

start‑up / early‑stage environments , comfortable building territory from scratch.

Strong hunter mentality with consistent overachievement against quota.

Ability to sell into both

enterprise and mid‑market customers .

Why This Role?

Founding regional role

– huge scope and influence.

Game‑changing AI security tech

with a unique value proposition.

$360K OTE + equity

– competitive comp with upside.

High‑growth environment

with serious career acceleration potential.

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