3299: How Oyster HR Is Using AI to Redefine Employment Infrastructure

Tech Talks Daily

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5d ago 26:33

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When I last spoke with Tony Jamous in November 2020, we were navigating the early days of a remote-first world. The shift was sudden and widespread, but what followed was even more transformative.

In this episode of Tech Talks Daily, I reconnect with Tony to explore how the world of work has changed and how Oyster has grown from an ambitious startup into a B Corp-certified unicorn focused on enabling global employment at scale.

Tony is the CEO and founder of Oyster, a company built on the belief that where you live should never limit where you work. We discussed the journey from pandemic-driven remote work to today’s distributed models, the growing need for location-independent hiring, and how AI is now being embedded into every layer of global workforce management. Oyster is helping businesses hire across 180 countries with just a few clicks, solving compliance, payroll, and benefits challenges without the traditional roadblocks.

During our conversation, Tony broke down what it means to build a mission-driven company and why measuring impact matters. More than 40 percent of employees hired through Oyster now come from emerging markets. That shift is not just a statistic. It reflects real people gaining access to economic opportunities they were previously excluded from. Stories like Christina in the Philippines, who now works from home and spends more time with her children, highlight the human impact of Oyster’s platform.

We also talked about Oyster’s recent Series D funding round and how the company is shifting from high-growth to sustainable profitability. AI is a big part of that evolution. From internal operations to customer support, automation is being used to reduce friction and let people focus on work that matters. For Tony, leadership now means focusing on vision and values while letting AI handle repetitive tasks.

What does the future look like when the world becomes one talent pool? This episode offers a grounded, forward-looking take on what happens when mission, technology, and global opportunity intersect.

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