Block insiders talk about how Jack Dorsey turned Square into a multidimensional financial services giant

On November 19, Block Inc. held its first Investor Day in three years. Jack Dorsey, the company’s cofounder, chief executive, and “Block Head,” took to the stage and summarily posed what many investors and others in the industry were likely thinking. 

“Our business is complicated,” he said. “We want to make it much easier to understand going forward.”

Dorsey—notably clean-shaven—proceeded to summarize the past few years at Block. The company is indeed much more complex now than when it was founded in 2009 as Square, named for the point-of-sale system that was the company’s first product.

Four years ago, it changed its name to Block, a much more fitting moniker given its increasingly multidimensional portfolio, which now includes not only Square but also Cash App, Afterpay, Tidal, Bitkey, and Proto.

For Oakland, California-based Block, the growing pains were real as it has evolved from a single-product company to one that now facilitates payments (and buy-now-pay-later features) for both customers and merchants, has its hands in the crypto space, and even offers a streaming platform for musicians and creators.

The numbers bear it out: After going public in 2015, Block saw its stock price peak in 2021 at more than $270.

Like many other tech companies, Block has seen its shares fall from their pandemic-era highs. The stock is down roughly 26% in 2025 and the company fell short of Wall Street’s projections for its third-quarter earnings in November.

But Block has been making some behind-the-scenes moves over the past few years to right the ship. A major philosophical change, key acquisitions, and a renewed focus on simplicity have Block’s leadership excited about the company’s future.

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A lesson in shape-shifting

Changing from a Square to a Block required fundamental organizational and philosophical shifts, which have been the most important aspect of Block’s evolution. 

“We decided to ‘functionalize’ the company,” says Owen Jennings, Block’s business lead. 

That meant making big internal shuffles and reorganizing how information moved between engineers, designers, sales staff, and executives. It also meant putting “functional leads” into positions where they could be most impactful, whether they were working on product development or sales strategies.

“We dissolved the business units and brought functional leaders to the top who reported directly to Jack,” he says. He adds that the company’s multiple business units were “siloed” and had different goals and models, which were “leading to the wrong outcomes.” 

What became evident was that Block needed to find ways to serve both merchants and customers—using its products to either transact (via Cash App) or process payments (via Square).

“The most obvious [thing] we could bring to the world was connecting the two worlds: consumers and sellers,” Jennings says. “But it wasn’t happening based on the structure we had.

Since the reorganization, “it feels like we’re one massive company,” Jennings adds, but those changes took time to implement.

“Functionalization happened within 18 months,” says Nick Molnar, Block’s sales and marketing lead and the cofounder of Afterpay, who decided to stay with Block when it acquired Afterpay in early 2022. 

Molnar says that while he is a relative Block newbie (Jennings, by contrast, has been at the firm for more than a decade), he’s seen a notable shift at the company. Meanwhile, most people aren’t even seeing the full results yet.

“The back half of this year, you’re seeing the work of the previous 18 months,” he says.

Block’s leaders have also married the “functional” model to the “Rule of 40,” a metric common in the SaaS sector, which says that a company’s growth rate and profit margin should sum up to 40%. 

Amrita Ahuja, Block’s foundational lead, says that prior to instituting the Rule of 40 framework, “the company had expected that we’d advance margins every year—we wanted to share the trade-offs behind long-term growth and profitable long-term growth.”

“So we reoriented the company from the inside out,” she added. “That was really a language we built for the company. It helped us move faster and become more efficient, and ensure investments were going to drive growth.”

The Rule of 40, paired with the new “functional” model, also allowed Block to reorient its larger focus on simplicity—something it had gotten away from over the years as its business and structure have grown more complicated and convoluted.

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Basic building blocks

Ahuja first came to the company as Square’s CFO in 2019. “The thing that was striking to me, working at my first tech company, was the level of trust and transparency,” she says. “There was so much information, and everybody had access to it.”

But, naturally, things get more complicated as a company grows, as Square did when it contended with the pandemic and then morphed into Block.

“Square started with payments, then we built more than 30 products around it,” Ahuja says.

It was a similar situation with Cash App. “The kernel was around social money, peer-to-peer transactions,” she adds. “Now we have built a dozen products around that.”

Over the years, it’s become increasingly important to get back to basics and “focus on the things that mean the most to our customers,” Ahuja says, adding, “We’ve already built a lot of depth and complexity—now it’s about making sure the right product gets surfaced at the right time for customers.”

That is exactly what Block is doing now.

In recent months, Block has announced several new products, including new tools and features under its Square AI suite, Square Bitcoin, and Neighborhoods, a new feature for Cash App, which connects customers with local businesses.

With crypto finding wider adoption and a friendly regulatory framework, and AI being basically everywhere and anywhere, developing and releasing these types of products clearly makes sense for Block.

But Jennings says that Dorsey is not merely jumping on trends for the sake of doing so.

“He’s willing to be patient for a long period of time to the extent that he has conviction, and he’s been proven right many times,” Jennings says of Dorsey, who is also a cofounder of Twitter and, more recently, the competing social media platform Bluesky, although he’s no longer involved in either.

“The power of Jack is that when he comes to the all-hands or presents the company strategy, it’s incredibly simple,” he adds, “and gets to the essence of what we’re trying to do.”

The big question: Will it all pay off?

A chip off the new Block

Block’s leaders say that the pieces are in place for a sort of corporate renaissance.

“I believe that Block has the ingredients it needs to accelerate its growth, that flows through a really strong, profitable business that’s growing in line with some of the best companies in the world,” says Molnar.

So even as it may seem like the company’s been underachieving—perhaps in terms of sagging stock and recent earnings misses—those on the inside say they are brimming with confidence.

“We’re leading, and will continue to lead,” says Jennings, who is particularly confident about Square Bitcoin, which offers no-fee Bitcoin payments for sellers around the world through its existing point-of-sale systems.

He thinks Block is well-positioned to take advantage of the growing ubiquity of Bitcoin payments in the years ahead.

As for Block’s broader goals? During its Investor Day 2025 presentations, the company’s 2026 guidance showed expectations of nearly $12 billion in gross profit, an increase of 17% year-over-year.

It also released, for the first time, a three-year financial outlook that lays out what Block’s leadership is expecting, a sign that Block is fully grown up out of its startup stage, and that it’s here for the long haul.

By 2028, Block’s outlook shows, the company anticipates gross profit growth will be in the “mid-teens,” and that adjusted earnings per share growth will be somewhere around 30%, and on track for further revenue growth.

That would mark quite a turnaround, but Block executives believe they have the team, product mix, and leadership to persevere—even if it takes some time.

“Jack is very good at knowing when to be patient and impatient,” says Ahuja. “From the first day I joined the company, there was a conversation about what his title should be: CEO or editor? He’s the editor—he’s the person who guides us in how we focus our efforts.”

During his comments at Investor Day, Dorsey echoed Ahuja’s sentiment. “I’ve never felt more confident that we have all the tools, the structure, the team, and the people to prove this out,” he said.

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