I was lucky enough to work at Square between 2015-2019, before the company was public and way before success was assured. 

Jack is one of the most enigmatic business leaders alive and his superpowers aren’t well understood. Most of the time, they get boiled down into “product sense,” which means he has proven incredibly prescient about the specific types of products that will translate into huge businesses. But this boilerplate judges his skillset based on the outcomes of products he’s been involved in. They don’t describe the inputs that led to his success, namely his personality, process, and way of operating that led to these outcomes. 

Though I didn’t interact with him frequently, seeing Jack build, evolve and innovate was fascinating and I learned a lot. A few of the things that stuck with me:

Product design. Jack is famous for “inventing” both Twitter and Square, and playing a major role in Cash App. While the founding stories are complex, Jack’s talent in product discovery is surprisingly simple. In both cases, and with Cash App, Jack took inspiration from simple human needs paired with elegant product design. The simplicity of these products belies an incredible depth of technical expertise. Jack’s ability to rally technical teams to deliver a very precise, simple user experience is a difficult ability to master. Most product teams quickly encounter complexity and compromise on this, exposing users to complex and confusing product experiences. Perhaps Jack’s greatest skill is editing a product down to the essence required to appeal to large numbers of users.

Feel it early. Inventing new products is hard. Abstract debate and research can only get you so far. But disruptive ideas become totally obvious when you experience and feel them. For Jack, the earlier you design and build your idea, the faster you’ll persuade others, learn, and execution can flow. A product demo with Jack was a Socratic exercise where designers and engineers needed to be ready to justify every decision and defend every detail. At many companies, this is an exercise that leads designers to parade their design sensibilities or engineers to showcase their technical prowess. None of that mattered to Jack. The only lens he viewed the product through was that of the end user. How a product functioned was tablestakes; how it looked was imperative; but how it felt is what he really cared about. Did the gestalt have soul? Would users not only use it but trust it? Would they linger because they felt something? These considerations may sound ephemeral but were at the core of the product development process that led to break-out products.   

Purpose. There were many times at Square when things were dire—a product was going sideways, investors were questioning the strategy, a controversy had taken hold. Jack was always poised, focused on standing by our customers and never betrayed a sense of worry. His ability to unite people around a shared purpose (why Square existed) and mission were remarkable, and, like with all things about Jack, authentic and simple. During my time at Square, the company’s purpose shifted from “Make commerce easy” to “Economic empowerment.” This was prompted in part by the growing family of products — things like Cash App, Capital, and Caviar — that didn’t fit cleanly into the original purpose around Square Reader. Jack reframed the purpose to encapsulate everything. It was around this time that Bitcoin became one of his long-term focus areas, and this expanded purpose helped sow the seeds for a much larger push into crypto in the years that followed. While setting a company’s vision is a core CEO requirement, Jack’s ability to authentically connect and sell these ideas was impressive. At no point did they feel like the output of a consulting project or the groupthink that typically comes out of a corporate retreat. He believed that getting everyone on the same page about why Square exists and why you should come to work were the starting point. Designing a company with clear purpose would lead to products with purpose and soul, and success would follow.

Be yourself. Jack is an introverted, quiet, thoughtful person. His entire persona, from his fashion sense to his speaking style, defies a lot of the traditional stereotypes of a Fortune 500 CEO. Way before this more authentic style of leadership was commonplace, Jack made everyone feel comfortable by being himself.