Jay Whitehead is a serial entrepreneur with 17 launches and 5 exits in media, IT and fundraising. He credits being fired from the TV internship and job he got as a UCLA undergrad for his journey into Silicon Valley-style entrepreneurship. In 1982 he started with J. Walter Thompson Advertising San Francisco on the HP personal computer account. Then he moved to Chiat Day Advertising on Apple Computer, where he worked with Steve Jobs on launch of Mac’s predecessor, the Lisa.
The PC gigs led to stints leading sales at computer publications CRN and PC Magazine. And in 1988 Jay co-founded UPSIDE Magazine, the first magazine covering VC-backed tech companies, which was acquired by PC World founder David Bunnell.
"My UCLA experience gave me the most valuable commodity known to man: Confidence."
From covering technology, Jay acquired an affinity for tech companies re-inventing human resources and employee services, and became VP Sales for Ultimate Software (NASDAQ: ULTI), and filled the same role for TriNet (NYSE: TNET). Building on those experiences, in 1996 he launched and raised $20 million as CEO of EmployeeService.com, the first web-based HR services company.
In 2002, with his wife Anne-Sophie, Jay founded HRO Today, the media voice of the global human resources outsourcing market. The company’s online, print and conference media companies were acquired by LRP Publications and SharedXpertise Media for a total of $15 million. He then created Corporate Responsibility Magazine, bought by SharedXpertise for seven figures.
After roles helping to finance and scale IT-based companies as diverse as Montreal-based Rideau Recognition, New York City-based Major League Hacking, and Paris-based PeopleDoc, Jay became CEO of Boston fundraising startup TicketsForCharity.com, which raised over $10 million for charities with a pioneering donation-with-purchase model.
“What I learned at UCLA was that emotional intelligence punches above its weight in market value," Jay recalled. At UCLA, emotional IQ is most-often gained via extracurricular activities. That’s why, as often as possible, I help young Bruins take advantage of internships, sports and co-op programs.”
In 2016, based on Anne-Sophie’s 15 years running a large NJ-based youth sports league, Jay co-founded League Network PBC, which has raised over $1 million in investor capital to address the underserved $3 billion youth sports fundraising market.
"While I’ve given my share in Alumni contributions, I think that my contribution to UCLA Ventures will be much more important to help fellow Bruins take risks on new ventures."