Every era of David's career has compounded into the next — government tradecraft became product expertise, product expertise became executive leadership, and now all of it is pointed at protecting small businesses.
// 2008
Offensive Cyber Operator
David spent 10 years working for the United States government, conducting offensive cyber operations. This is the discipline most security vendors only read about — David lived it, learning firsthand how real adversaries break in.
// 2015
Threat intelligence
David moved into the commercial sector at Mandiant, applying his offensive background to nation-state threat intelligence, eventually running point on the secretive Nucleus project.
// 2018
AI Research Lab
At MITRE, David managed a research lab studying how AI applies to offensive security, leading a team of 40+ researchers. That lab launched CALDERA, the open-source autonomous red team platform now used industry-wide.
// 2020
Founder
David founded his own startup in offensive security, backed by Sequoia, CrowdStrike, and MITRE, where he wrote two Breach and Attack Simulation products from scratch — one of four products he's brought to market from the first line of code.
// 2023
Author
David wrote Irreducibly Complex Systems, the first technical book on continuous offensive security testing. The book was initially published in 2023, with physical copies printed in 2024.
// 2024
Chief Technology Officer
David served as CTO of Praetorian, an offensive security services company, where he also redesigned and rebuilt Chariot, their attack surface management product — his second tour as a CTO.
// 2025
Distinguished Engineer
David joined Rapid7 as a Distinguished Engineer, the company's most senior technical rank, continuing to support security products at scale with a focus on detection and response capabilities.
// 2026
Pink Duck
David founded Pink Duck as a research incubator, building products and services that challenge the status quo. First stop: managed IT services.
