Jeff Aragon | Enterprise Sales Leader, Healthcare and Payer Markets
Case Studies

How I close enterprise deals.

Three anonymized case studies, each one a different operating pattern: tactical entry to coalition close, commodity RFP to category-defining platform, and technical-symptom to revenue-infrastructure reframe. Each one is the same discipline applied to a different shape of opportunity.

Healthcare Payer · Coalition Close

$249K Entry to ~$10M Three-Year TCV | Incumbent Displaced

Large Southern California public health authority. The largest enterprise sale of my career. A tactical Medicaid Redetermination entry below the $250K RFP threshold expanded into a $10M three-year transformation through deeper discovery and coalition orchestration.

$249K Entry deal
~$10M Total contract value
~40x Expansion
Displaced Dominant incumbent
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Healthcare Payer · Layer 4 Reframe

$200K Commodity RFP to $1.4M ARR | Continuity-of-Care Reframe

Northern California Medi-Cal managed care plan. A commoditized notification-vendor RFP reframed mid-cycle into a continuity-of-care platform during active wildfire season. Three of four incumbents were eliminated at Forecast Gate 2 because they could not quantify Layer 4 severity.

$200K Commodity RFP
$1.4M ARR Final contract
7x Expansion
3 of 4 Incumbents eliminated
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Healthcare Provider · Category Expansion

$30K OCR Buy to $1.6M ARR | Revenue-Infrastructure Reframe

Large national radiology provider. A $30K commodity OCR procurement reframed as revenue infrastructure through five-layer discovery, observed live from inside the Center of Excellence. The incumbent patient-engagement vendor was displaced despite shared board members with the buyer.

$30K Entry buy
$1.6M ARR Final contract
53x Expansion
Displaced Incumbent vendor
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