Matt Skeffington / Executive

How I Lead

Leadership Philosophy

I am an operator who turns ambiguity into governed, revenue-producing enterprises. Whether I am standing up a pre-seed healthcare venture or scaling infrastructure across 220 global markets, my approach is the same: define the operating model, align product and capital, build the team, and execute with measurable accountability.

I do not need to write the code to lead technical product development. I define requirements, evaluate tradeoffs with engineering partners, and govern AI systems with the rigor they demand — including model evaluation, human-in-the-loop controls, and PHI-aware compliance frameworks.

Career Arc

Boeing — Technical Program Management & Operations

I started my career resolving critical engineering, supplier, and production challenges on major commercial aircraft programs. I learned to lead cross-functional teams under pressure — eliminating a 24-week manufacturing delay, avoiding a work stoppage through supplier crisis management, and generating $2M+ in program savings by rebalancing team structure.

Amazon — Senior Product Manager

I held three consecutive Senior PM roles building global insurance, payments, and market-expansion infrastructure across millions of customers. I expanded local-currency payments across 220+ markets, established Amazon's global corporate travel insurance program in six weeks, and built configurable regional insurance architecture that cut onboarding friction 80%+ for 1M+ delivery partners across seven countries.

Extend — Principal & Senior Product Manager

I quarterbacked underwriting, risk management, and regulated insurance infrastructure as Extend scaled to unicorn status and a $1.6B valuation. I founded and governed six regulated subsidiaries supporting $100M+ in retained risk, built underwriting analytics for capital visibility, and reduced data processing time and operating cost by 60% while avoiding $25M in locked regulatory capital.

Pont & Optimist Health — COO, Head of Product, President

At Pont, I served as COO and Head of Product, scaling a seed-stage venture from proof of concept into a multi-entity operating model while incubating Optimist Health to independence. I defined generative AI product requirements for RecoverEdge, built an AI-enabled healthcare data pipeline processing 100,000+ patient records, and mentored an engineering intern into a product manager. Today, as President & COO of Optimist Health, I authored the 36-month operating plan, lead product strategy and AI governance, and am guiding the company from concept to first revenue on a path toward a $100M annual budget.

What I Bring to the Table

  • Full P&L ownership and board-ready financial planning across multi-entity corporate structures
  • AI product strategy — requirements, agentic workflows, model evaluation, and governance in regulated environments
  • Go-to-market execution and customer discovery that converts user behavior into prioritized product decisions
  • Deep experience in HealthTech, FinTech, and captive insurance with HIPAA, SOX, and GDPR compliance
  • Team building and mentorship — scaling organizations from 5 to 17+ with clear operating accountability
  • Vendor and partner management across payment processors, EHR systems, labs, pharmacy, and carrier networks

Entrepreneurship

Before Amazon, I co-founded Active Logik in Seattle, bootstrapping a startup that identified a $20M annual opportunity to increase on-street parking revenue for the City of Seattle. I led the DiscoverPark mobile app from concept through a public-private partnership, improving utilization by 20% over 18 months.

Education & Credentials

  • Master of Business Administration (MBA)

    University of Washington — Business Administration and Management

  • Bachelor of Science, Aeronautical Science

    Embry-Riddle Aeronautical University — Cum Laude

  • Generative AI for Product Managers — IBM
  • FAA Certified Flight Instructor
  • Property & Casualty Insurance Producer License

Affiliations

  • Member, Project Management Institute
  • Board Member, Elphie's Animal Alliance
  • Sigma Alpha Epsilon

Earlier in my career, I served as an Air Traffic Control Specialist with Lockheed Martin in Fort Worth, training incoming specialists and representing Lockheed Martin Flight Services at the EAA AirVenture Oshkosh Airshow — grounding my leadership in FAA regulatory discipline and high-stakes operational accountability.