Rethinking How We Work: A Conversation with Justin Watt
Sitting down with Justin Watt felt less like an interview and more like a systems therapy session. He’s one of those rare thinkers who can speak fluently about operational complexity and AI tooling without ever sounding technical for the sake of it. Our conversation peeled back layers of what it means to build a modern team, one that is lean, adaptable, and built to move fast without breaking everything along the way.
We started by exploring something deceptively simple: how most businesses are just pipelines. Sales pipelines. Hiring pipelines. Creative review pipelines. Justin’s framework isn’t about adding tools. It’s about subtracting friction. He shared how his work often starts not with software, but with stakeholder interviews. What do the people closest to the work say is broken? Where are they wasting time? Only then does tech come into the picture.
One idea that stuck with me was his concept of low-lift, high-impact automation. Not the kind that makes flashy dashboards, but the kind that quietly makes your team more effective. Think AI-generated project briefs that eliminate the need for yet another kickoff call. Or pulling brand questionnaires, sales notes, and creative inspiration into one cohesive document to guide your design team. These aren’t futuristic use cases. They’re available right now, if your systems are structured enough to support them.
That’s the caveat Justin kept coming back to. AI is only useful if your data is clean, your processes are sane, and your team is ready to change how they work. It’s not a magic overlay. It’s an opportunity to rethink the foundation.
We also got into the messy middle between automation and collaboration. I asked him if he worries about AI stripping away moments of connection, like a sales-to-service handoff that used to require real dialogue. His answer was honest. Yes, sometimes. But he sees AI as a way to create space for better collaboration, not replace it. Let the machine do the prep work. Let the humans do the thinking.
One of the most compelling parts of our discussion was Justin’s take on AGI. Not from a sci-fi perspective, but through a practical lens. He believes the biggest bottleneck isn’t intelligence or creativity. It’s memory. Until large language models can hold context the way a human brain can, layering past conversations, project details, and team dynamics, we’re not there yet. But that doesn’t mean we should wait. It means we should build systems today that are ready for what’s coming.
We wrapped with a conversation about tools. He’s still bullish on Notion and Airtable, two platforms that manage to balance power and usability, and that integrate well with other parts of the stack. His advice was refreshingly practical. Don’t chase tools with trendy AI features. Use the ones your team already understands, then build bridges between them.
Walking away from this conversation, I felt more convinced than ever that the best DTC brands in the next five years won’t be the ones with the flashiest marketing. They’ll be the ones with the most functional systems. The teams that embrace AI not as a bolt-on, but as a core part of how they operate: from creative development to client onboarding to internal reporting.
Justin reminded me that operations isn’t something you fix once. It’s something you evolve, continuously and intentionally. When done right, it doesn’t constrain creativity. It supports it.
If you’re a founder trying to scale without losing your edge, or a marketer looking for smarter ways to work, this episode will give you a clear starting point.