From the Vault · Recorded 2004–2005

The Big Sessions

Conversations that shaped an industry
From the Host

In 2004 and 2005, I sat down with some of the people who were shaping digital media and advertising for a series of candid conversations I called The Big Sessions. Some are still close friends. Some I’ve lost touch with. And some, sadly, have passed away. But every one of them played an integral part in building an industry.

Twenty years later, it felt like the right time to open the vault. I hope you enjoy taking a trip back in time.

— Jon
The Sessions
JB
Joanne Bradford
Former Revenue Leader, Microsoft MSN • Former SVP, Yahoo!
Joanne Bradford led revenue for Microsoft’s MSN — where she received the Bill Gates Chairman’s Award — before joining Yahoo! as Senior Vice President of U.S. Revenue and Market Development. At every stop, she brought a rare talent for building and scaling revenue organizations inside the biggest names in technology and media.

Bradford went on to become Chief Revenue Officer at Demand Media, then served in a senior leadership role at the San Francisco Chronicle’s parent organization, and later joined Pinterest in 2013 to lead its early monetization efforts. She became Chief Operating Officer of SoFi, helping build its profile as a leading fintech brand. Named to the Forbes CMO Next 2018 List and Ad Age’s 100 Most Influential Women in Advertising, Bradford has consistently been at the forefront of revenue innovation across media and technology.
JD
John Durham
CEO, Catalyst S+F • Digital Marketing Pioneer
John Durham was CEO and Managing General Partner of Catalyst S+F, a San Francisco–based marketing consulting firm, and a widely respected figure in digital media. His career spanned over two decades in marketing and advertising, with executive leadership roles at Jumpstart Automotive Media, Carat Fusion — where he spearheaded North American development for the digital marketing division — and earlier positions at Winstar Interactive Media and MapQuest.

Beyond his corporate career, Durham taught marketing at the University of San Francisco for over 25 years, shaping hundreds of students across graduate and undergraduate programs. He was a founder and president of the San Francisco Bay Area Interactive Group (SFBIG), a founding member of The Seller Forum, and a recipient of the ad:tech Industry Achievement Award — a lifetime honor. Known as a master communicator and tireless mentor, he maintained a network of thousands through his legendary “Durhamisms” — thought-provoking ideas shared daily that became a ritual for colleagues and friends alike.
John passed away on November 16, 2021, at the age of 70. He meant the world to so many of us — myself included. His generosity, his energy, and his genuine love for the people in this industry left a mark that doesn’t fade. Donations in John’s memory can be made to St. Jude Children’s Research Hospital.
SF
Sean Finnegan
Digital Advertising Pioneer • Founding Leader of Omnicom Media Group Digital • “The Great Connector”
Sean Finnegan helped shape the rise of digital advertising. Starting at BBDO New York in the early 1990s, he went on to lead OMD Digital at the national level and later became the founding leader of Omnicom Media Group Digital — playing a key role in pushing digital to the center of modern media strategy. He was also a founding member of the Interactive Advertising Bureau’s Agency Advisory Board. He subsequently held senior leadership roles at Starcom MediaVest Group, including Chief Digital Officer, before turning entrepreneur as the founder of C4 Group and later VO Partners.

But those who knew Sean remember something beyond the titles. Often described as “The Great Connector,” he had an extraordinary gift for bringing people together — making introductions, lifting others up, and building relationships that strengthened the entire industry. A Murray State University graduate, devoted father of seven, and longtime champion of the American Advertising Federation, Sean gave generously of his time and energy to support others throughout their careers.
Sean passed away on April 29, 2022, at the age of 50. We miss him — his generosity, his charisma, and the way he made everyone around him feel like they mattered. His legacy lives on through the Sean Finnegan Memorial Scholarship at the American Advertising Federation, and in the countless careers he helped shape along the way.
MF
Matt Freeman
Founder & CEO, Tribal DDB Worldwide
Matt Freeman founded and led Tribal DDB Worldwide, growing it from an idea into a global network of 46 offices in 28 countries — one of the largest and most awarded digital agency networks in the world. During his decade-long stewardship, Tribal DDB won Advertising Age’s Global Agency Network of the Year award, among the first digital agencies to earn that distinction. After departing Tribal DDB, he went on to serve as CEO of Mediabrands Ventures at IPG.

Freeman championed a collaborative, borderless approach to digital advertising that redefined what an interactive agency could be. His vision for a truly global digital network — one built on cooperation across markets rather than top-down mandates — set the template that many agency networks would follow. He is currently a Partner at Fenway Summer and a leader within the Kyu Collective.
TG
Toby Gabriner
CEO, Bitly • Former CEO, AdRoll • Ad Tech Pioneer
Toby Gabriner led Adap.tv from $200K to over $200 million in revenue before its $465 million acquisition by AOL in 2013 — one of several ventures he has built and scaled as a multiple-time CEO in ad tech. Earlier, at Carat Interactive, he created one of the first combined TV and digital units, Carat Fusion, which pioneered cross-platform planning, buying, and measurement.

Gabriner has also served as President and CEO of NextRoll (AdRoll), CEO of MAGNIFI.FM, and held leadership roles at Adzilla and Tribal Fusion, among others. An Occidental College graduate with an MBA and MS in Management Information Systems from Boston University, he currently serves as CEO of Bitly, bringing a rare combination of technical depth and business acumen to every venture he leads.
JJ
Joseph Jaffe
Author • Marketing Strategist • Founder of jaffe, LLC
Joseph Jaffe held senior interactive leadership roles at TBWA\Chiat\Day and OMD USA before founding jaffe, LLC — and along the way became one of the earliest and most vocal advocates for rethinking traditional advertising. His book Life After the 30-Second Spot laid out a bold vision for nontraditional marketing, and he followed it with Join the Conversation, Flip the Funnel, and Built to Suck — each pushing the boundaries of how brands should engage their audiences.

A Senior Fellow at the USC Annenberg Center for the Digital Future, Jaffe consulted for brands including Google, Absolut Vodka, Reuters, MSN, and Kmart. He brought a provocative, forward-looking perspective to the industry at a time when most agencies were still anchored to legacy formats — and his ideas proved prescient as the digital revolution unfolded. He continues to share that perspective as the host of his daily streaming show, The Joseph Jaffe is Not Famous Show.
LK
Larry Kramer
Founder of MarketWatch • First President of CBS Digital Media
Larry Kramer founded MarketWatch in 1997 and grew it into one of the web’s definitive financial news destinations before its acquisition by Dow Jones for over $500 million. He went on to become the first President of CBS Digital Media, helping establish major distribution partnerships with platforms including Google, Amazon, Apple iTunes, Yahoo, and Verizon — creating a new division encompassing online, interactive, and wireless initiatives. He later served as President and Publisher of USA Today from 2012 to 2015.

Before his digital career, Kramer spent nearly a decade as a reporter and editor at The Washington Post, followed by a stint as Executive Editor of the San Francisco Examiner. That combination of editorial instinct and entrepreneurial drive defined his approach to building digital media businesses. He has served on the boards of Gannett, TheStreet, and MDC Partners, and is also the author of C-Scape: Conquer the Forces Changing Business Today.
WM
Wenda Harris Millard
Founding Partner, MediaLink • Former Chief Sales Officer, Yahoo!
Wenda Harris Millard built her career across every major era of the media business — from traditional publishing to the earliest days of digital to the modern landscape. As Chief Sales Officer at Yahoo!, she led the team that grew revenue from $700 million to over $6 billion in six years, widely regarded as one of the top sales organizations in media.

Millard entered the digital world in 1996 as a founding member of the executive team at DoubleClick, where she helped establish the brand and oversee media operations. She later served as co-CEO of Martha Stewart Living Omnimedia before becoming a Founding Partner at MediaLink. A Harvard Business School and Trinity College graduate, she has also served on the boards of Caleres, Inc. and Vroom, and was named one of Advertising Age’s 100 Most Influential Women in Advertising in the Last 100 Years.
PJ
PJ Pereira
Co-Founder & Creative Chairman, Pereira O’Dell • Emmy Award–Winning Creative Leader
PJ Pereira co-founded Pereira O’Dell and built it into one of the most celebrated independent creative agencies in the country, with offices in San Francisco, New York, and São Paulo. Before launching the agency, he worked at AKQA, where he further developed a digital-first creative approach that would become his signature. In just a few years, Pereira O’Dell was producing breakthrough work for clients including Intel, Lego, Skype, Airbnb, and Corona.

In 2013, Pereira received a Daytime Entertainment Emmy for Innovation for the web series The Beauty Inside. He has been named to Ad Age’s “40 Under 40,” Adweek’s Creative 100, and the 4A’s 100 People Who Make Advertising Great. More recently, he co-founded Silverside, an AI innovation lab bringing together startups and leading brands, and took on the role of Chief Creative Officer at Serviceplan Americas. He is also a novelist, writing under the pen name PJ Caldas.
MS
Mark Stewart
VP Global Media, Kraft Foods • Former President, OMD New York
Mark Stewart spent a decade at McCann Worldgroup, where he held the positions of Media Director, Managing Director of Universal McCann North America, and Chief Strategy Officer of Universal McCann Worldwide. He then became President and Managing Director of OMD New York, overseeing all client and business activities for one of the world’s leading media agencies.

At Kraft Foods, Stewart served as Vice President of Global Media, overseeing more than $1 billion in U.S. measured media spend. Named “Media Director of the Year” by both Advertising Age and Adweek, “Media Maven” by Ad Age, and “Global Innovator” by Internationalist Magazine, he also served as Jury President at the Cannes Lions International Advertising Festival. He sits on the Wharton School’s Future of Advertising Global Advisory Board and has served as Chief Strategy Officer of BLOX Digital.
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David Verklin
CEO of Aegis Media Americas • CEO of Carat Americas
David Verklin was CEO of Carat Americas and later Aegis Media Americas, where he grew capitalized media billings to nearly $7 billion and helped advance the free-standing media agency model in the United States and Latin America. He served on the Aegis Group plc board for a decade before its $4.9 billion sale to Dentsu — one of the largest transactions in advertising industry history.

Verklin began his career at Young & Rubicam in New York and later helped create Hal Riney & Partners in San Francisco, one of the country’s most celebrated advertising agencies, first serving as Media Director and later as Managing Director. He went on to found Canoe Ventures, the advanced-advertising joint venture of the major U.S. cable operators, and subsequently served as a Senior Advisor at Boston Consulting Group. A Broadcast and Cable Hall of Fame inductee and member of the American Advertising Federation’s Hall of Achievement, Verklin also authored Watch This, Listen Up, Click Here, a widely used guide to understanding the evolving media landscape.