How Shiv Gupta Became an Ad-Tech Entrepreneur

Shiv Gupta is widely considered an early ad-tech guru, founding ad-tech education firm U of Digital to help tech workers be more savvy at their jobs. The platform reaches employees at 44 companies including Yahoo, Pinterest, Nielsen and FreeWheel to teach the nuts and bolts of programmatic advertising. U of Digital's newsletter, which is a primer of the biggest ad-tech news of the week, reaches more than 7,000 subscribers. But Gupta started his career not particularly interested or knowledgeable about advertising at all. Be open to new avenues A little more than 15 years ago, Gupta took an Advertising.com operations job, hoping to do something interesting on the business side of tech. In this role, he discovered a pleasant challenge in programmatic advertising. “Technology's always changing. It's confusing," he said. "I love kind of dissecting that, and then helping other people understand that." Gupta eventually moved to a sales job to work more directly with clients, where his passion for programmatic advertising became a valuable asset. “They say that the best salespeople are the best teachers, right?” he said. “Because they take information that's complex, they distill it down into easy-to-understand terms, and that makes the buyer comfortable and want to work with somebody.” Find your niche Eventually, Gupta took on the role of vice president of sales at ad-tech firm Criteo. Those years in sales, plus teaching ad-tech courses at Johns Hopkins University, Santa Clara University and University of California, Davis, led Gupta to discover a gap in the market. “The industry, I think, treats learning and development a lot of times like it's a checkbox, like, ‘Oh, I trained the people on the thing. Let's move on with our life,’” he said. “Most salespeople hate training, and they get thrown a ton of training all the time.” U of Digital, which Gupta founded in 2018, aims to move professional development away from perfunctory modules and turn it into something entertaining and inspiring—more TED Talk or MasterClass than webinar. Pivot the model That doesn't mean there weren't challenges. Like many other businesses, U of Digital pivoted quickly to a virtual model at the beginning of the Covid-19 pandemic, which was once anathema to its mission. “We were really scared; we're like, 'This is going to kill the business,'” Gupta said. But the decision ended up helping U of Digital—more than 90% of its trainings are remote, which Gupta said gives the firm more room to grow. Today, U of Digital, a fully bootstrapped business, has $2.5 million in annual recurring revenue, which has been doubling roughly every year since the company's founding, Gupta said. But some of the best proof of its success is hearing from salespeople who say they’re able to not just talk about a product, but also tell a story. “I've captured so many anecdotes over the years where people figure out how to be more consultative in the sales process and help the marketer understand the bigger picture, and in that, the client's like, 'Great. I'm into this,'” Gupta said. Work history Shiv Gupta started his career in operations at digital marketing firm Advertising.com in 2007. In 2010, he moved to a sales role, where he was promoted to lead an enterprise sales team after three years. He became a sales director for AOL, Advertising.com's parent company, for the Eastern U.S. region in 2015. In 2016, Gupta moved to Criteo, where he was vp of sales.

Lessons Learned

Shiv Gupta Embraced Education to Become an Ad-Tech Entrepreneur

The U of Digital founder on taking a more personal approach to tech sales

Catherine Perloff

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Catherine Perloff