Jordan Dea-Mattson: Indeed Singapore Product Center Rise, Navigating Tech Layoffs & Healing Career Trauma – E558

“And the first big responsibility I had was I was put on the team that built the first time Apple changed its processor. Now, Apple’s changed its processor multiple times—the latest being the Apple Silicon we’re all aware of. This was the shift from the Motorola 68K to the PowerPC processor, and I was part of that team. That’s actually how I ended up coming to Singapore, because we were going out and telling developers about this globally. So, first time I came to Singapore was just around the time the North-South Line opened up. That’s when I met my friend Raymond, who for the next—what, almost 20 years—kept saying, ‘Jordan, you should come to Singapore.’ And we stayed in touch. Raymond was a local developer here in Singapore; I supported him over time. And then, from there, things moved in ’99. So I was there, actually, the night Steve Jobs came back in ’96. It was a very interesting and fun event.” - Jordan Dea-Mattson, Veteran Tech Leader

“The most important lesson I ever learned from Steve Jobs—and that’s the power of saying no. Because saying no lets you focus, and focus lets you do great things. When Steve came back, the product line was just this nightmare—hardware products, niches, and everything. And Steve just went and sliced right through it to a model they have today, which is: good, better, best. You look at the product line—there’s always a good, better, best. A very simple approach. And it really makes it easy for people to understand what they should pick.” - Jordan Dea-Mattson, Veteran Tech Leader

“In ’96, Apple was on the ropes. Earlier that year, there had been ‘Death of an American Icon’—the Black Apple cover on Businessweek. And it was scary. Apple was within, I think, 90 days of running out of cash. The technical strategy—there had been this thing called Copeland—there had been all these different strategies, and none of them were yielding fruit. None of them were working. And so the decision was made: Gil Amelio, who had come in as the CEO, and Ellen Hancock, who was the CTO, decided, ‘We’re going to go buy a new operating system.’” - Jordan Dea-Mattson, Veteran Tech Leader

Jordan Dea-Mattson, a veteran tech leader, and Jeremy Au discussed how Jordan built developer tools at Apple and went on to lead engineering teams at Adobe and Indeed. They explored how he witnessed Apple’s transformation under Steve Jobs, the often unseen dynamics behind major tech layoffs, and what it takes to grow and scale high-performing teams in Southeast Asia. Jordan also shared how he led the rapid expansion of Indeed Singapore, navigated its unexpected closure, and helped his team transition. He also opens up about overcoming personal trauma, leading with integrity, and why real bravery means acting in the face of fear.