What’s the nature of Design when it comes to organizations, employees, and culture?

What if we treated internal systems like products…and employees like customers (gasp!)? In this issue, I spoke with my good friend and former colleague, Stephanie Knabe, Director of Business and Org Capability at BILL, about designing performance, culture, and leadership systems from the inside out. From lo-fi prototypes to failed AI pilots, Stephanie shares what it really takes to build people systems that scale without losing their human core.

If you’ve ever wondered how to design for growth (from the inside out), navigate change, or bring clarity to messy org dynamics, this one’s for you. Because culture isn’t declared. It’s designed, tested, and lived. Every single day.

In this issue/episode:

Read on for my main takeaways from our conversation. 🎧 And…listen to the recording of our full conversation on the Design Shift podcast on Spotify and Apple and the Design Shift YouTube channel.

— Justin Lokitz

Like a lot of people who have heard of or interfaced with org designers, before speaking with Stephanie, I had this mental model of org designers constantly messing with org charts and other HR-related tools to help shape a (mostly) hierarchical corporate organization. However, I now know that it is a totally faulty mental model.

Org design, like the kind that Stephanie does, is NOT just an exercise of moving chess pieces (people) on the board. Rather, Stephanie and her peers are designers writ large, who design the way people work together, across systems, teams, technologies, and time.

As Director of Business and Org Capability at BILL, a 2,000+ person fintech company navigating hypergrowth and executive transition, Stephanie leads the design of people systems that support performance, leadership, and scale. Like just about any designer I have ever spoken with, her approach blends systems thinking, human-centered design, and practical experimentation (i.e., prototyping)…treating internal processes like products, and employees like customers (i.e., HUGE lightbulb moment for me).

And in a moment where AI is reshaping how we think about work itself, her design lens is more relevant than ever.

Stephanie didn’t start in tech. Her journey began in international development, working with Population Services International (PSI) to increase access to healthcare in low-infrastructure environments across Africa and Asia. There, she learned that complex systems don’t get fixed with big plans; they evolve through experimentation, behavior change, and feedback loops. Sound familiar?

“Population Services International was using the systems of marketing, the systems of behavior change, to pull people into use of services and save lives,” she explains. “How do you get those services? How do you get those materials? Amazing stories of how they made that happen across lots of different cultures and places.”

That mindset stuck with her.

At BILL, she brings the same systems thinking to internal HR and org challenges. One recent example (of many): rethinking how the company gives and receives performance feedback.

“We were asked by our chief people officer to change how we do our performance management system,” she says. “So I actually got a chance to use that prototyping skill by just putting out: here's three different options of if you were to have a review or give feedback to different peers, what would you want the questions to be?”

The test was deliberately lo-fi. Just a Word doc. But the results were powerful.

“I got a chance to interview over 20 some different leaders across our business. And that evolved into: how are we thinking about launching feedback at the end of the month? How are we creating this bigger system that has all these different touchpoints that doesn't seem so overwhelming, but more of a continuous loop?”

Not every prototype lands. One version—a mini 30-day review cycle using AI agents to generate summaries—flopped.

“It was a bit of a fail. We didn’t really make it through the pilot. People were just kind of like, 'meh.' But it was a huge takeaway for us. Even though it felt like a failure, we learned: people want it in the system. Don’t make me do all this other work on the side. I'm busy.”

To me, this speaks volumes! Not only does this totally change how I’ve thought of org design for a loooong time, but it cements org design as Design (with a big D) for internal people and processes.

That’s the essence of how Stephanie works. Try things quickly. Listen closely. Treat failure as fast feedback. That’s design, full stop.

Having worked in and with some of the world’s largest organizations in the past, I can honestly say, we need more Stephanies.

It’s a natural question these days to ask people about what they’re doing (and feeling) when it comes to AI. Funny enough, I didn’t even have to ask Stephanie. She came right out and explained that she and her team are actively experimenting with AI inside the people function, but they’re not handing over the reins.

“We're exploring this around performance conversations where it's like: I can't remember what I did six months ago, but that's our review period. So how can something go through all my different documents and help me remember shout-outs or different things that I've worked on?”

That kind of assist is welcome…and it feels like a really fertile use case, especially for orgs that only perform reviews 1-2 times/year. But full automation? That’s where the limits become clear, especially in a human-driven org/

“Sometimes people want to use AI to avoid hard things or avoid conversations. And that's actually what's uniquely human. Where we can have that contextual understanding and respond to facial expressions… to deliver a more human, empathetic message.”

She frames the challenge not as a tech problem, but a design one: what should be human, and what can be delegated to machines?

“It's really fascinating,” she says. “You're like, okay, lots of people are like: it's gonna change the world, it's gonna make everything easy. But where's the human in the loop?”

Part of our conversation veered into the idea that AI agents could even be thought of as junior employees and/or team members, as part of agentic workflows. These could potentially be managed by anyone on any team. And…while Stephanie sees potential for org design to expand into agent orchestration, the questions remain:

“So what does it give you? If it creates more time, more time on what? How do you distinguish that importance?”

She also warns about misplaced trust. One of her first real experiences with hallucinations came through a meeting summary tool.

“I was looking back at a conversation, and I was like, I don't remember that theme coming up. I looked at my notes—not a single word of it. The AI totally inserted that in there. And you can really get into some crazy themes about like truth, what's real, perception…”

The message: use the tools. But stay awake…and keep. Designing. For. Humans.

As her title suggests, Stephanie’s scope spans both business and organizational capability. That means working with everyone from frontline managers to executive teams, designing leadership off-sites, team rituals, and strategic communication.

“My role really spans that whole gamut from our executive leaders to that frontline builder,” she says. “How are they thinking about learning and growing in their job?”

What ties it all together is culture. Not in the abstract, but in lived behaviors.

“We’re actually doing an exercise around values and culture. Our Chief People Officer came in and asked people about culture, and it was like: I got a million different answers. Every person, it was something different. So now we’re asking: what is that core experience? How do we articulate it?”

Stephanie thinks of culture as a system of shared stories, habits, and expectations. Her work is to make it visible, repeatable, and real.

“How do we have that show up in all these different touchpoints—our existing employee programs and future-facing ones too? Imagine the best-case scenario. Imagine the worst-case scenario. How does all of that play out in the messaging, the systems, the experience?”

She draws a direct line between leadership development and cultural consistency. In one session for aspiring managers, she told them to treat their growth like a design experiment. HUGE learning alert!

“Make yourself your own design experiment. Learn different things, put yourself in experiences where you can fail, learn, and apply it forward.”

Because at the end of the day, Stephanie, like all of us, is a designer. Of systems, of culture, and of possibility.

“It’s all how you tell your story and frame your experience. And there are companies that are searching for that. They want that in their company and their company culture.”

As I mentioned above, Stephanie and I go way back. We’ve been in the innovation trenches together, working with giant clients, on giant projects, with giant challenges (and opportunities). So, it was only natural that once I stopped recording, we kept talking.

One of the things we dug deeper into was this idea of culture. This is something that Stephanie is a master at and is truly passionate about. In hindsight, I wish I had asked more about culture design and her experiences therein. Alas, I did not…at least not while recording.

That being said, the part of our conversation that did veer into culture design territory was rich, and swirled around culture building, strategy design, and execution…which must go hand in hand in hand.

To me, one of the clearest representations of how this works in the real world — and one that Stephanie agreed with as well — is this diagram, created by the innovation consulting company, XPlane…

To me, this diagram, and really everything I learned from Stephanie (which was a lot), is the essence of (big D) Design. What’s more, while I have for a long time thought about employee experience (EX) as yet another design challenge/opportunity, it was never so clear as when Stephanie was explaining it.

And…it immediately reminds me of the often-used Charles Eames quote, when he was asked by a French reporter, "What are the boundaries of Design?". To which he replied…

Want more? Connect with Stephanie and tell her Justin sent you!

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