As fintech companies grow, legal complexity rarely increases in a straight line. New products bring new obligations. Regulators increase scrutiny. Customers raise new expectations. What starts as a payments platform can quickly become a business operating across lending, music, bitcoin, and financial services. For legal teams, the challenge is not just identifying risk. It is about helping the business understand which risks matter and how to move forward.
At Block Inc., David Cannon has seen that challenge evolve firsthand. Block grew from its roots as Square into a portfolio including Cash App, Afterpay, TIDAL, Bitkey, and Proto. All share a mission: increase access to the global economy and drive economic empowerment.
As Litigation Counsel, David handles a wide range of matters at Block. “They’re really varied. Some matters involve large regulatory investigations and litigation. Others are partner disputes or customer issues. They can be small, but they’re never dull.”
The role has grown with the business. When David first joined Square, the legal team supported a much smaller company. He has watched Block expand into consumer finance, lending, investing, music, and bitcoin. Growth brought opportunity, but also new legal scrutiny.
David recalls the difference between the company he joined and the one he advises today: “I remember handling our first deposition. It felt like a big deal at the time. As the company expanded during the pandemic, everything changed. Now, as a financial services provider at scale, we see far more investigations and litigation.”
As Block’s footprint grew, legal questions became broader and more frequent. For David, though, the core task stayed the same: understand what happened, evaluate the facts, and find the best path forward.
Scale changes everything
Block’s businesses operate in very different worlds. A dispute about TIDAL’s music platform brings up different issues than one about Cash App, merchant payments, lending, or bitcoin. David finds that variety shapes how he works: “You must take each case as it comes and evaluate it on its own merits. Then you develop the strategy to advise your client and, hopefully, reach a good outcome. It’s fascinating. You’re working on different things all the time.”
Variety alone does not make the role challenging. The harder question is determining how legal teams should respond as new products, technologies, and regulatory expectations emerge. For David, that starts with changing how lawyers think about risk itself.
Finding real risk
Supporting innovation means recognizing that not every risk requires action. “Litigators can always find a risk, and there are always risks. The key is to know which ones are real. It’s easy to say no, but you’ve got to be realistic about whether that’s really warranted, or whether you can tell the business there’s a risk here, but it’s not a big one.”
The question is not whether uncertainty exists. In a company operating across multiple regulated industries, it always does. The challenge is deciding how to respond to it. Legal teams cannot eliminate uncertainty, but they can help the business understand it.
Balancing caution and progress matters at a company focused on economic empowerment. Block’s purpose is to help individuals, businesses, artists, and others access and benefit from the economy. For David, that mission comes to life when disagreements happen. “We can never get cynical. There’s a real person on the other side of a dispute. Maybe the problem is theirs, maybe it’s ours, but you always want to find a solution that works for everyone and remember where they’re coming from.”
Understanding people is just one part of resolving disputes. The other is anticipating how a disagreement might play out. David’s early trial experience still shapes how he approaches cases today. “It’s helpful and fundamental at the outset to realize that, while it’s rare for something to actually go to trial, ultimately, that’s where it might end up. So, you need to think early on: what would it look like if that’s where we land?” That mindset shapes every decision, from strategy and negotiations to resource allocation.”
Judgment matters
The habit of looking beyond the immediate issue has followed David throughout his career. Raised in Montana, he moved to California to attend UC Berkeley before earning his law degree from UC Law San Francisco. Long before he became an in-house lawyer, he was drawn to litigation for reasons that had nothing to do with the law itself. “I’ve always had a bent toward history, and litigation in a way is history. It’s researching what happened, getting to know the personalities, learning the stories, and then building the arguments.”
That interest led him into private practice, where he spent years building a litigation career and eventually became a partner. It also made him pay attention when colleagues began leaving law firms for in-house positions. “They told me about the advantages of working directly with the business, having very direct responsibility for both handling matters and advising the business. It changes your perspective. You just get a better view of everything going on in the business. If you’re at a law firm and handling specific litigation, you try to know the broader picture of what’s happening with the business and how that might affect your strategy. But when you’re in-house, you’re much more in touch with that broader set of factors that may affect your strategy.”
The closer David moved to the business, the clearer it became that relationships matter. “Part of it is having good relationships with the teams that advise on new products, so that they will bring you in. You can take a look and let them know of any risks that you see. And when you are looking at a new product, finding the risks, advising the business of what you think those risks are, but being realistic about how high the risk is.”
For David, spotting risk is only part of the job. The business values solutions. “If you can come up with ideas for mitigating risk, that is always hugely helpful.” David brings that same instinct to his work with other teams. “If something comes up and someone is frustrated with another team, I say, hey, we want to be good partners here because one day we might need these folks and we want them to come to us and ask for our perspective.”
While the facts of a disagreement may stay familiar, everything else can shift across borders. “In the UK, there’s the ombudsman process. The procedure is very different from what we’re used to in the US, so we really need to rely on local counsel to walk us through that process. I have a dispute in France right now, and the process is very different, so we need to rely on local counsel to assist.”
That reliance on human judgment is not limited to disputes or jurisdiction. Whether he is working with product teams, business leaders, or local counsel abroad, David’s approach depends on expertise, context, and relationships. Those are also the qualities he believes will be hardest to replicate as AI becomes more deeply embedded in legal work.
Looking ahead, David is watching one big development: AI that could reshape nearly every aspect of legal practice. What interests him most isn’t what AI can automate today, but what might remain beyond its reach. “We’re all using AI tools now for research, writing, and as a thought partner. I think it is hugely helpful but wonder how much more it can do. There’s a lot of feel in what we do in litigation. There’s a lot of assessing what the other side is like, what outcome they want, whether it’s realistic and whether they’re rational, and then formulating the best strategy based on those and a host of other factors. Can AI do all of that? We’ll see.”
Whether AI ultimately changes the practice of law remains an open question. For David, however, some things still cannot be learned from a screen, a deposition transcript, or a regulatory inquiry.
Outside of work, David skis, mountain bikes, hikes, backpacks, and plays tennis. “I like to get outdoors when I can to refresh and regain perspective.”
For a lawyer whose days are spent helping Block navigate complexity, the principle is surprisingly simple: understand the terrain, stay grounded, and only then decide what comes next.
Gibson, Dunn & Crutcher LLP
David is the ideal client partner. He has a great feel for strategy and tactics, sees around corners, and sidesteps potential problems before they develop. Efficient, practical, and business-focused, he is a strong leader who helps everyone around him give their best. We’re proud to call him a client and friend
