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Matt Swann, former CTO of Nubank and experienced technology leader for companies like Booking and Amazon, shares key insights on leading companies through digital transformation. With a focus on setting ambitious long-term goals and fostering a fail-fast culture, Swann emphasizes the importance of driving transformation rather than simply choosing the right tools.

Reflecting on his time at Amazon, Swann highlights the company’s evolution and success due to constant innovation and adaptability. By breaking the company’s architecture into decentralized services through APIs, Amazon aimed to become more agile, scalable, and innovative across its product portfolio. This approach set the stage for identifying long-term visions and goals for the company’s growth.

In his role at Amazon, Swann faced challenges in the global payments division, including poor business growth, slow expansion, and operational inefficiencies. By setting clear priorities and long-term goals, known as “big hairy audacious goals” (BHAGs), Swann was able to drive transformation and refocus the company’s efforts. These BHAGs helped filter out the noise of new technologies and strategies, allowing the team to prioritize effectively.

Swann emphasizes the importance of setting game-changing BHAGs, such as Amazon’s goal to become “Earth’s most customer-centric company.” By establishing objectives and key results (OKRs) that align with these long-term goals, businesses can track progress and hold themselves accountable. However, the most challenging aspect of digital transformation is changing people’s behavior to support these goals and drive lasting change.

To drive cultural transformation, Swann recommends implementing a clear communication plan that embeds company values in rituals and learning moments. By reinforcing these values consistently, employees will internalize them and help drive the culture forward. Building a culture of trust and embracing quick feedback loops is key to fostering innovation and adaptability within a company.

Ultimately, Swann’s experience at Amazon demonstrates the importance of a living culture and continuous innovation for lasting transformation. By aligning people, operations, and architecture, companies can drive forward even as the world evolves. By applying these insights and fostering a culture of trust and innovation, companies can navigate digital transformation successfully and achieve their long-term goals.

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