Why this Microsoft veteran’s next act is AI conferences

Curiosity may have killed the cat…but for Microsoft veteran Stefan Weitz, it opened a lot of doors.

Curiosity is what led Weitz, who described his younger self as the “prototypical ’80s nerd kid” who loved his computer and Dungeon & Dragons, to his first gig outside of college with Andersen Consulting, a premier consulting firm.

“I did that because I like the idea of trying different things,” Weitz told IT Brew. “Part of my problem, honestly, is I love to learn different things, which is great, but also from a career perspective, it can be kind of sketchy, because you kind of bounce around.”

His knack for trying new things is what attracted him to Microsoft after Andersen embedded him in the tech giant as a consultant.

“When I was there, I was sitting in RedWest, which was a new building at the time…I looked around as I was having lunch with these people and said, ‘These are all people like me. They’re all just nerds who really just loved the work and loved the puzzles and loved the challenges,’” Weitz recalled.

After six months, a Microsoft recruiter approached Weitz to make his stay permanent with one line: “You can either stay with the Navy or join the pirates” (Microsoft being the pirates in this analogy).

“That was the pitch that got me over,” Weitz said.

Bada bing. Weitz’s time at Microsoft spanned almost two decades, during which he juggled several titles and opportunities.

“I would basically ingratiate myself with different organizations and then they’d say, ‘Well, okay, just come run it then,’” Weitz said.

One of Weitz’s most notable projects as a Microsoftie: helping launch Microsoft’s Bing search engine, which was designed to compete against Google. Part of the challenge of launching a brand-new search engine was not only the need to build something different from the competition, but also persuade people to try it, he said.

“That was literally building a product that nobody said they wanted and then convincing people they actually wanted it,” Weitz said.

The team ended up producing a “decision engine” designed to help users quickly move past “basic” search to find and utilize the information they needed. “So, if you looked at flights to Boston from Seattle, we would give you all the stuff you’d usually see, but we then have a prediction as to whether or not you should buy it now or wait,” Weitz said.

While Bing’s market share was never able to surpass Google’s, the work that Weitz’s team did had a lasting impact.

“It’s helped a lot with the AI efforts because a lot of the work we did in Bing early days…kind of laid the groundwork for a lot of the work in how AI operates today,” Weitz said.

Post-Microsoft. In 2016, Weitz closed his chapter at Microsoft to focus on his love of building. Since then, he has been up to just about everything under the sun, including running the e-commerce fulfillment solution provider Radial for a few years, co-founding a PTSD treatment company, and starting up a music superfans platform.

“I love to go from zero to one,” Weitz said. “I love to have the idea and then get the thing running, and get it all stood up, and then hand it off to somebody to actually really run it. That’s my throughline there, for sure.”

Weitz’s journey after Microsoft hasn’t followed the traditional playbook of ex-Microsofties, but isn’t out of character for Weitz, according to Matt Wallaert, chief experience officer at outsourcing company Oceans and former Microsoft colleague of Weitz, who said Microsoft employees tend to stay with the company long-term or leave the tech giant to chase roles at similar companies.

“You just don't see that many people who go and do something entrepreneurial and do it really well and dive into that with discipline,” Wallaert said. “Stefan is a really shining example of what it looks like to find a second act that is meaningful and thoughtful.”

Main event. These days, Weitz is known for his event-planning skills. Earlier this year, he tried his hand in the conference industry, co-founding the HumanX conference, an AI-centric conference. Inspiration for the conference came after he noticed some industry leaders’ AI investments remained stagnant, as well as a lack of general-purpose AI gatherings.

“I said, ‘Well, shoot, if we’re relying on enterprises to figure their way through this cacophony of innovation that’s happening every single day, we are going to, at best, under-deliver on the promise of what AI can do,” Weitz said.

The conference’s inaugural year went better than Weitz expected, who said the conference industry is not for the “faint of heart.” Even so, he sees room for improvement for year two, including the type of content the conference will focus on.

“It’s very much more focused on the role of the person, not the industry in which they find themselves,” Weitz said. “We’ll have some that are more geared towards that, but the majority is going to be focusing on the people and the job they have to do.”

As a co-founder of one of the largest AI conferences, he advised young AI talent to remain curious and open to challenges, two of the skills that worked in his favor in his own career.

“That curiosity and that lack of determinism is what’s missing in a lot of young people today, but also is the opportunity for those who identify that to thrive.”