Rubén Caballero: Another adventure and loving it!

Black and white photo of Rubén Caballero

A year ago, Rubén Caballero decided it was time. He had built an impressive career for himself in Silicon Valley but wanted to devote more time to his family. So, he rode off into the sunset. 

“I wanted to take some time to enjoy being with my family,” he smiles. “Life goes very fast.” 

At first, he served on several boards for a few companies and spent a lot of time enjoying outdoor activities between California and Montréal. Then, Caballero met with some people from Microsoft — and the topic of conversation was not at all what he was expecting. 

“Initially, I met with Satya [Nadella], Scott Guthrie, and other great leaders including Alex [Kipman],” he says of Microsoft’s lead developer on HoloLens. “One of the things I noticed right away is that we would barely talk about work. Instead, we would talk about empathy, people, and making great things to help this world.”  

Empathy sure sounds like a strange word to bring up when discussing the possibility of joining a multinational technology company. But it was this awareness of “empathy,” and a second career focused on it, that instilled in Caballero the same kind of excitement that drove him in his younger days. 

Empathy leads to innovation  

“The empathy came in questions like, ‘How can we help this world?’” explains Caballero. “How can we make this place better as humans? That, to me, was inspiring and exciting.” 

Caballero had built his career at Apple, beginning in 2004 at the start of a practically mythical run for the company. He was one of the founding leaders of the iPhone hardware design team and later expanded his role to include the design of iPad, Apple Watch, Air Pods, and all other hardware products. He also founded the Wireless Design & Technology development department and oversaw teams of engineers who built all the systems inside iPhones, iPads, and Macs. He performed groundbreaking work in the name of enabling humans to do more. Now, here was the chance to do it again.
Two women in manufacturing plant using Microsoft Hololens 2 for assembly. Contains hologram scenario. Contains hologram. Contextual imagery.

“Having that human touch when you build devices is just simply magical; that’s something I enjoy,” he recalls. “Being able to design a device that people love to use and then make it a part of their day-to-day, is a blessing.” 

Seeing a possible symmetry between opportunities, Caballero recalls that he accepted the position of corporate vice president of engineering for devices and technology after talking with Satya Nadella about Microsoft’s mission of empowering others. 

“Microsoft is focused on making others look cool, not the other way around,” Caballero explains. “After I learned that, I was sold.”  

A natural process

Caballero was hired in March 2020 to join Microsoft’s mixed reality and AI division. Since then, he has been focusing on HoloLens and other special projects aiming to revolutionize the field — a mindset he knows all too well. 

“There were about three or four of us fortunate enough to design the first iPhone with Steve Jobs,” he recalls. “It’s never about the technology when you’re designing a project. It’s about how you can transform, innovate, and change people’s behavior.”
To do that, you must dream of alternate realities, ones that could change our lives for the better. Sometimes, those realities are virtual ones. 

“On a video call, you and I are talking through a 2D box, which is not natural,” he observes. “Imagine if right now you and I could, instead, be sitting in San Francisco, having a glass of wine? We could do that virtually.” 

At a time when so many of us are spending our days staring at a screen, engaged in work calls for hours at a time, Caballero says he’s inspired to find a better way. 

“Imagine that we’re wearing these glasses, these wearables,” he says. “And we’re sitting down together, drinking from our glasses, and everything around us is like we’re in San Francisco. I would see your avatar, you’d see mine. That’s the natural conversation, the natural process of talking to each other — you may think its science fiction, but if I told you ten years ago, we’d be having a conversation through a piece of glass, you’d think I was crazy!”  

“This next step of using HoloLens and having a 3-dimensional view around you is magical,” he adds. “It’s the future.” 

Cherishing the journey
Group of architects collaborating on a building render. Contains hologram scenario. Contextual imagery.
Caballero firmly believes that the future is virtual. One of the reasons he joined Microsoft is because he believes that the company is on track to get there first.

“I think Microsoft is ahead, and ahead of its time,” he explains. “I tip my hat to the team because they have been driving this forward for many years. The hockey stick will be kicking off here, not in the next ten years but the next four or five.”  

Caballero loves making such predictions because he truly relishes the journey as much as the arrival. Born in Santiago, Chile, his whole family fled during the 1972-1973 civil war relocating to Montréal, Québec and had to start a new life, from scratch. Young Rubén had to learn French — the language he would later take all his engineering classes — and then learned English in his early twenties.

“In 2000, my wife got a job offer here in the Valley and we decided to drive here from Québec, where we just got married. This trip was our honeymoon,” he says smiling, remembering that he instantly fell in love with the area climate, which is like where he grew up in the south of Santiago. “We had this beat-up little car, a white Miata, which we still have actually, and we didn’t have a dime. We drove it out west and started our life here.”

Caballero’s penchant for adventure and building with empathy played a large part in why he was eager to start anew at Microsoft. HoloLens represents the chance to employ empathy as it transforms reality; for Caballero, it’s a chance to, once again, channel the possibilities of Silicon Valley, with a new adventure laid out before him. 

“I love starting from scratch,” he smiles. “It proves to me that we can do anything we want if we truly put our minds to it. It is all about people, teamwork, collaboration and pursuing a dream!” 

If you’re interested in joining Caballero’s team and working on our HoloLens product, opportunities can be found here: