Career Experience

“Victory is winning people over, not defeating others.”

chief technology officer • chief product officer • product engineer

Honored as a Young Global Leader by the World Economic Forum

Highlights

Referred to as a “well-respected Chief Technology Officer” in mainstream media ( The Wall Street Journal , Politico )
Received several prestigious awards for web & mobile app development and infrastructure engineering
Led technology organizations at major media companies including The New York Times, Dow Jones, and Condé Nast
Led development of web & mobile apps and e-commerce for news, media, and publishing
Led scalability and reliability engineering for sites with up to 90+ million monthly unique visitors and over 1 billion monthly page views
Managed annual technology budgets of $150+ million
Supervised staff of 500+ employees

Competencies

Leadership

Influencer: Leads by Example
Collaborator: Brings People Together
Engineer: Solves Problems Innovatively

Domain Expertise

Digital Media & Content Management
Cognitive Science & Social Psychology
Machine Learning & Data Science

Current Roles

Flatiron Software & Snapshot AI

President • November 2024 – Present • New York City

Companies that augment and advance human innovation and software engineering through artificial intelligence. Partners with enterprises to transform their technology operations, combining AI-powered solutions with product development and strategic consulting.

Longevity Workers

CTO Advisor & Co-Founder • November 2024 – Present

Platform connecting experienced professionals with meaningful work opportunities.

TrustGuard AI

Advisor • September 2024 – Present

ScalePost.AI

Founding Technology Advisor • 2024 – Present

Platform that elevates collaboration between media companies and AI developers, unlocking new revenue opportunities and enhancing content strategies for technological advancement.

Corporate Experience

Hearst

Hearst Magazines , Hearst Autos , CDS Global

Chief Product & Technology Officer • February 2022 – December 2023 • New York City Interim CPTO • August 2021 – January 2022

Led product, design, engineering, and technology operations across Hearst’s magazine portfolio, automotive brands, and subscription management services.

The Wall Street Journal , Dow Jones , and News Corp

Deputy CTO, News Corp • March 2019 – May 2020

CTO & Chief Product Officer, The Wall Street Journal • February 2017 – March 2019

Responsible for Product, Design, and Engineering, reporting jointly to the WSJ editor-in-chief and to Dow Jones corporate.

3 years 4 months total • New York City

The New York Times

Chief Technology Officer • June 2012 – June 2015 • New York City

Vice President, Digital Technology • May 2011 – June 2012

Led the successful development and delivery of dozens of acclaimed mobile and web products. Reported jointly to the business and to the editor-in-chief of The New York Times.

4 years 2 months total

Condé Nast and Reddit

Vice President, Digital Technology • June 2007 – May 2011 • New York City & San Francisco

Headed up technology for all of Condé Nast’s U.S. brands
Supervised the Reddit technology and engineering teams

4 years • Read about what we built →

Cox Enterprises : Cox Newspapers

Chief Technology Officer, COXnet (now Cox Media Group ) • June 2004 – May 2007 • Atlanta

Received the Newspaper Association of America’s 20 Under 40 Award during this tenure.

3 years

Knight Ridder

Vice President, Engineering • January 2001 – June 2003 • San Jose

Director, Technology, Northeast US • March 2000 – December 2000

Director, Online Technology, Philadelphia Newspapers • July 1999 – February 2000

Manager, Online Technology • August 1998 – June 1999

Senior Software Engineer • July 1997 – July 1998

Software Engineer • September 1995 – June 1997 • Philadelphia

Led development of Cofax , a leading open-source content management system, and Xmultra , which won the NAA New Media Award. Twice received the Knight Ridder Excellence Award for Technology Innovation.

Knight Ridder was acquired by The McClatchy Company and MediaNews Group.

7 years 10 months total • Read about what we built →

Synthesis Engineering & Open Source

Rajiv practices synthesis engineering , a methodology for human-AI collaboration in building software, and synthesis coding , the craft of writing code in partnership with AI. He develops open-source tools that embody these practices. See more on GitHub .