HealthTech · 0-to-1 Venture
Optimist Health
Direct-to-consumer healthcare platform — operating layer, vendor integrations, and AI-enabled product roadmap from concept to first revenue.
San Diego, CA
Matt Skeffington
COO | CPO | Head of AI Transformation & Enterprise Strategy
I am a chief operator and AI product leader with 15+ years scaling Fortune 100 and startup ventures from ambiguity into governed, revenue-producing enterprises. I bring MBA-level P&L ownership, healthcare technology experience, and a track record of building board-ready operating models across regulated industries.
AI Governance & Enterprise Transformation | P&L Management | Product Strategy | GTM Execution
$1.6B
Extend valuation at scale
12+
Global markets at Amazon
$100M+
Retained risk governed
15+
Years executive leadership
Executive Summary
I define AI product requirements, agentic workflows, model evaluation, human-in-the-loop controls, and PHI-aware governance. I blend Amazon and Boeing leadership with startup execution to build scalable operating models and standard GTM systems.
At Extend, I helped scale the company to a $1.6B valuation, founding six regulated subsidiaries with $100M+ in retained risk. Today, as President & COO of Optimist Health, I oversee corporate direction, capital formation, product delivery, and AI governance for a healthcare venture on track toward a $100M annual budget.
Ventures & Products
Selected work & project highlights
Detailed write-ups on ventures, platforms, and transformations I have led — from healthcare and AI product to regulated insurance at scale.
AI Product · Pont
RecoverEdge
Generative AI product for recovery workflows — requirements, model evaluation, voice-to-text intake, and clinical data pipeline at scale.
FinTech · Regulated Insurance
Extend's Retained Risk Infrastructure
Architected a portfolio of regulated subsidiaries, underwriting analytics, and streaming data pipelines supporting unicorn-scale warranty and risk operations.
AI Product · Contract
Photography Proposal CoPilot
Designed and built an AI proposal copilot that helps photography businesses qualify leads, dynamically price projects based on variables associated with individual requests and draft client-ready proposals with human-in-the-loop controls.
Full write-up in progressMore details
Areas of Expertise
Core capabilities across venture building, regulated industries, and AI-native product development.
- 0-to-1 Venture Building
- HealthTech & FinTech Product Strategy
- AI-Native Workflows & Automation
- Agentic AI Product Development
- Captive Insurance & Reinsurance
- Data Governance & Analytics
- Team Leadership & Mentoring
- Compliance (HIPAA, SOX, GDPR)
- Multi-Entity Corporate Structuring
- Board & Stakeholder Engagement