Leslie Pitterson is a corporate affairs and communications executive who began her career as a UN correspondent and has since led teams at Morgan Stanley, Google and Microsoft. Today, she is Head of Corporate Communications at Block, the company behind Cash App, Square and Afterpay. In her role, Leslie leads communications across investor, policy, community and talent audiences as the organization recenters around intelligence. We spoke with her about helping teams navigate AI transformation, the emotional journey beneath this shift and how our definition of “knowledge work” is evolving.
Most conversations are still focused on mechanics: what needs to be automated, what models are we using, what does our tech stack look like, what should token usage look like? Those are important questions but they're incomplete. We've been at this for over two years now at Block, from building our own agentic harness to leveraging frontier models to ship faster for our customers and sellers. The adoption has gone beyond our development teams to being part of our broader internal culture: in the first few months of this year, production code changes made by non-engineers rose nearly 60%.
Communicating through a shift like that means being able to bring together both the technical and the personal. When a tool can suddenly perform part of a job that someone spent years learning, that person isn't just being asked to change a process. They may be questioning their expertise, their place in the organization. Sometimes the thing that made them feel valuable for most of their career. So yes, this is a tech transformation but it's also an emotional one for most employees.
Something my therapist said to me years ago has always stayed with me: people often function within organizations the way we first learned to function in our family unit. Once you realize that, you start seeing archetypes in the people we work with: the caretaker, the fixer, the prover, the mediator, so on.
Those roles can become part of how we understand ourselves. Intelligence tools disrupt a lot of those identities. I went from working on the team responsible for Microsoft’s early investments in the frontier labs and then came to Block as the company was beginning to build the organization around these tools. Regardless of the organization or the phase it’s in, there are universals: for some employees, the transformation is going to feel freeing. For others, it can feel destabilizing. If you’re suddenly in an era where more people can discover and synthesize information, being the person who holds the information is no longer as powerful as it used to be. What’s often described as resistance to a tool often isn’t really about the tool. It’s about people trying to protect an identity they’ve known for most of their lives.
We need to be more curious about what people believe they’re losing, even when it’s uncomfortable to sit with. Some roles will be permanently changed, and we should be real about that. A lot of change management language has become almost mad lib: here is the new tool/process/task and here’s how this will make us smarter/faster/efficient and here are the adoption/engagement/usage metrics we’re using to measure success. But to drive actual change in our orgs and with our people, we have to get past vanity data or traditional comms. It means standing up learning programs across different levels of aptitude and allowing people to self-identify where they are in the transformation. It means building custom roadmaps by function that are centered around the specific use cases that the team sees as relevant vs anchoring on building individual tools where the primary goal is flowing information upwards.
People are having a range of experiences and questions, and those end up being among the biggest factors in whether or not these transformations work. Leaders have to understand where their people are before they can design an integrated plan.
Depends on what we mean by knowledge. If we mean collecting information and turning it into a draft, that work is changing. But other forms of knowledge are becoming more important.
For a lot of people who came up in environments that weren’t built with us in mind, we’ve always known the tension of being both invisible and hyper-visible. But if you were able to be still enough, you learned to pay attention: to how power moves through an organization, what isn’t being said, who has influence, who believes they do. You had to observe and process all those things in addition to the content of your work because you had to, because those things mattered more acutely to your ability to navigate.
There’s an inherent context layer many of us have built for years while navigating these organizations as outsiders. I used to experience that as hyper-vigilance but I see it more as an advantage now. This feels like a glimmer moment for the noticers, for people more prone to absorb first, speak last. When you bring those traits together with fluency on these tools, it can open up a different kind of impact, a different model for what leadership can look like. We all could use more of that now.
