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.