From operations and accounting to AI-native product leadership.

I started out auditing public companies’ books in 2009. I spent the decade after that at Caesarstone, first in national accounts and then running a commercial line I’d built, with the P&L on it. Product came after that. What carried over wasn’t a method. It was the habit of asking what a decision costs, what it returns, and who it’s actually for.

How I got here.

Every system we ran at Caesarstone came out of a P&L I owned. Nothing got bought without saying what we’d stop doing to pay for it.

I started in public accounting in Denver: two years of financial statement audits and 10-K work for public companies. I moved to Caesarstone as a staff accountant in 2011, into national accounts a year later, and in 2017 was asked to build a managed services line that didn’t exist yet.

That line became a $50M business and a department of thirty. I owned the P&L on it: pricing, margin, headcount, the software we ran on, and the quarterly decision about what not to fund. The expensive mistakes weren’t execution mistakes. They were the things we scoped wrong at the start and then paid for all year.

I moved into product at Exclusive Resorts in 2022 and was promoted twice, to Director and then to Senior Director across Exclusive Resorts, Inspirato and onefinestay after the acquisition: a team of PMs to manage, and my own products still to carry.

In September 2026 I joined Virtuoso, the global luxury travel agency network, as Director, Network Products. I lead the product portfolio for Virtuoso’s supplier Partners: hotels, cruise lines and the rest of the network that sells through its advisors.

The finance background still does most of the work. It shows up when I’m sizing a business case, arguing about pricing, or telling a room what we’re not going to build.

  1. Sep 2026 — Present

    Director, Network Products

    Virtuoso

  2. Mar 2026 — Sep 2026

    Senior Director of Product Management

    Exclusive Resorts · Exclusive Collective

  3. Jan 2024 — Mar 2026

    Director of Product Management

    Exclusive Resorts

  4. Jul 2022 — Jan 2024

    Product Manager

    Exclusive Resorts

  5. Jun 2017 — Jul 2022

    Director of Managed Services

    Caesarstone US

  6. Sep 2012 — Jun 2017

    National Accounts Manager

    Caesarstone US

  7. Aug 2011 — Oct 2012

    Staff Accountant

    Caesarstone US (NASDAQ: CSTE)

  8. Sep 2009 — Aug 2011

    Audit Staff

    Ehrhardt Keefe Steiner & Hottman (now Plante Moran)

David Masterson

B.S. Accounting & Finance

University of Northern Colorado; Dean’s List, Beta Alpha Psi. The degree behind the finance background. Twenty product, AI and cloud certifications since 2020. I started them two years before the pivot, to close the gaps I knew I had, and kept going after.

Full record on the resume

I take pictures when I ride.

Denver, CO. When the laptop’s closed: long days on a gravel or mountain bike in the Rockies, training Brazilian jiu-jitsu, and traveling and camping with family and friends. Most of the photos on this page came from those rides.

A gravel bike leaning in spring cottonwoods along the Front Range
A freight train crossing the plains east of the Front Range