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Enterprise Sales Executive - Healthcare AI Systems

Dark Deck Shell Co. /Medical
Chicago, IL Full Time
POSTED ON 10/23/2025 CLOSED ON 12/23/2025

What are the responsibilities and job description for the Enterprise Sales Executive - Healthcare AI Systems position at Dark Deck Shell Co. /Medical?

Enterprise Sales Executive - AI Clinical Decision Support Platform

We're selling a $500K-$1.2M/year AI system (DarkDeck) to hospital systems - NOT a SaaS subscription, but enterprise licensing deals with 2-12 month sales cycles.

REALITY CHECK:

You'll be selling to hospital CMOs, CFOs, and procurement committees
Average deal: $500K-$1.2M initial ongoing licensing
Sales cycle: 2-12 months (procurement, compliance, IT security reviews)
You need to understand: HIPAA, clinical workflows, hospital budgets
80% video calls, 20% on-site demos/contract negotiations
WHAT YOU'LL DO:

Cold outreach to hospital C-suite (CMO, CFO, CIO)
Navigate procurement committees and compliance requirements
Demo AI medical decision support system to clinical staff
Handle objections about data security, HIPAA, liability
Close 6-figure enterprise licensing deals
IDEAL CANDIDATE:

3 years selling B2B enterprise software ($100K deals)
Healthcare/hospital technology sales experience preferred
Comfortable with long sales cycles and complex stakeholder management
Can explain AI/ML to non-technical hospital administrators
Track record closing enterprise deals (not SMB/SaaS)
COMPENSATION (Draw Against Commission):

Monthly Draw: $4,000-$6,000/month ($48K-$72K annually)
Commission: 12% of contract value
Draw is recoverable from commission earnings
Realistic Year 1 Earnings: $120K-$250K (if you close 2-3 hospitals)
Year 2 Earnings: $200K-$500K (if you close 4-6 hospitals)
EARNINGS EXAMPLES:

Close 2 hospitals at $600K each = $144K total ($72K draw $72K commission)
Close 3 hospitals at $800K each = $288K total ($72K draw $216K commission)
Close 5 hospitals at $700K each = $420K total ($72K draw $348K commission)
WHY DRAW STRUCTURE:
We're early-stage with limited runway. The draw covers your basics during long hospital sales cycles (6-12 months). Higher commission rate (12% vs. industry 5-10%) compensates for lower base. This is for entrepreneurial sellers who can handle uncertainty for significant upside.

TRAVEL REQUIREMENTS:

20-30% travel (approximately 1 week per month)
Quarterly on-site hospital visits for demos and stakeholder meetings
Contract signing trips (when closing 6-figure deals)
Annual conferences (HIMSS, healthcare IT events)
Regional territory coverage (specify based on your location)
NOT A FIT IF:

You've only done SMB/SaaS sales (different game)
You need fast wins (hospital deals take 6 months minimum)
You're uncomfortable with procurement bureaucracy
You can't handle 6-12 months of $4K-$6K monthly income before first commission hits

Salary : $1,200 - $500,000

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