|

Product leadership,
grounded in business.
Judgment is the scarce resource.

Building software keeps getting cheaper; knowing what’s worth building is the job. My judgment comes from a decade running a business — and five years shipping platforms, portals, and AI in production.

David Masterson
$50M
Business line built from
zero at Caesarstone
Promoted in 4 years
at Exclusive Resorts
20
AI & product
certifications

§ 01

Platform thinking.
Business judgment.

Five years of product work — a year as internal PM on Caesarstone’s operations platform, then four shipping across travel, luxury, and hospitality — with the bias of someone who’s owned a P&L. Member portals, core platform rebuilds, mobile apps, booking systems, and AI in production.

Platform & API Products

Led the ground-up rebuild of Exclusive Resorts’ core reservation platform and own the Member Portal — the company’s largest tech investment.

GraphQLAPI Strategy

AI Product Work

Built an AI trip recommendation tool, itinerary builder, member profile summarizer, and conversational chat agent at Exclusive Resorts — production releases and active betas.

LLMsGenerative AI

Multi-Brand Product Org

Player-coach across Exclusive Resorts, Inspirato, and onefinestay post-acquisition — building shared product processes and tooling from scratch while staying hands-on as IC PM across all three public sites.

Team LeadershipMulti-brand

Business & Finance Background

B.S. Accounting & Finance, University of Northern Colorado. Started in public accounting. Nearly a decade at Caesarstone running P&L — from National Accounts Manager to Director of a 30+ person department. I evaluate product decisions the way a GM evaluates a business unit.

P&L OwnershipROI Modeling