No Priors Ep. 44 | With Former Square CEO Alyssa Henry

(music plays) Hi, listeners, and welcome to another episode of No Priors. This week we're joined by Elissa Henry, who recently retired from being long-time CEO of Square within Block. Before that, she was the vice president of AWS, running, amongst other things, the storage products or the digital storage bucket for the world. And before AWS, she ran order management software at Amazon, and started her tech career at Microsoft. She remains on the boards of Intel and Confluent, and was previously on the board of Unity. I'm a huge admirer of Elissa's leadership. Welcome, Elissa.

Great to be here.

Let us start by talking about Square. You led there for almost a decade through enormous growth. Was there a single moment that most defined your experience?

I don't know if there is a single moment that most defined, although there were, there were a ton of different moments. Obviously, we were known as the little white reader company and the farmer markets payments company when I joined. Cash App wasn't really a thing. You know, Tidal wasn't even a thought. Crypto wasn't a thing. Um, the Square business transformed from that little white reader into, um, you know, a much larger business serving, um, businesses of many, many different sizes, from still the smallest to also, you know, large stadiums and multinational companies. So, the moment that really was... I don't know if it was most defining, but one of the, the... I still tear up a little bit about it, is actually the day we IPO'd, and what was so exciting about that was, you know, if you looked at the sign that was outside the New York Stock Exchange, it was covered with just the logos of all these small businesses, right? And, and the, the note was, you know, "The neighborhood is going public." And I think that really kinda sums up, you know, just the mission-driven, purpose-driven organization that Square and Block is, and was, and, um, and just the impact that the company has had on just countless, um, small businesses, helping them, give them the tools and the technology that, in many ways, had only been previously available to, you know, the likes of Amazon and Walmarts of the world.

It's funny, I was a early investor in Square, a small one, and then I, um, worked at Twitter, so I worked with Jack in two very different contexts. The way that he ran the, the two businesses was radically different, right? I think, um, it's everything from the org structure, where Square was always more sort of GM/business unit almost driven, versus Twitter, which was always sort of functionally oriented or, you know, often functionally oriented. Um, how did, how did your career shift over time? Because I think you started off more on sort of platform and technology, and then you took over a big business area, and I'm a little bit curious about that evolution and how you went from being somebody who's done a variety of things, they're more product and engineering driven, to somebody who's really running a whole business area.