Exploring intrapreneurship culture

Issue #58: Why the hardest word to spell is so crucial to product innovation

Nearly a year ago, Apple removed the Remote app from its App Store as it introduced the Siri remote. Since most of the remote functionality was now integrated with iOS, Apple felt there wasn’t a need for an app. Alan Cannistraro, the former Apple engineer who created the app, shared his reflections on Twitter about his experience in bringing it to life. For one of the largest companies in the world, many were surprised to learn the first iOS app in the App Store (internally) was an idea developed by one person. Cannistraro often says that Apple works more like a startup and the story of the Remote app is a prime example of that entrepreneurial spirit coming to life. I had the opportunity to work with Cannistraro and consider him a good friend and mentor. Our time collaborating together fueled the idea of always operating like a startup at growing companies.

Intrapreneurship was first coined by Gifford Pinchot III in 1978 and described as "dreamers who do." As the name eludes, intrapreneurship is someone operating like an entrepreneur or founder within a more established company. The best companies constantly reinvent themselves before it becomes too late. It's hard to fathom now, but when Netflix decided to do away with DVDs and focus on streaming services, it was seen as a bad move by many analysts. Once known as Square Cash, this product initiative started as being able to email people payments and evolved into Cash App—a standalone brand and business success within Square.

At the early startup stage, you're the one moving fast and innovating—almost out of survival. If you're fortunate to find product-market fit (PMF), you’re now focusing on growth, market expansion, and continued product development. Suddenly, emerging competitors are able to move faster than you. It's like seeing a speedboat move past larger ships. You want to be the battleship that can deploy small boat operations, being both nimble and supported by the scale. Larger companies need continuous innovators, and this is where intrapreneurship comes in.

Before going back to management at One Medical, I was a lead product designer as an individual contributor. My time at One Medical was a place where intrapreneurship and service design was strongly encouraged. In addition to my core responsibilities with the product area team, I spent time working with other product managers, ops leaders, and people in the company to explore strategies of where we can go next. I don't think anyone ever asked me to do it. I invited myself to the party and nobody ever asked any questions about why I was there. When I'd have coffee 1:1s with colleagues, I'd pull out prototypes I built on my iPhone to share with them; asking them to play around and get reactions. We’d sketch ideas together on paper or the whiteboard and I’d have them walk me through their business problems.

I began building a portfolio of opportunities. They were one-pagers of different ideas we could explore based on the problem and business opportunity. This eventually became a product vision book that helped us build our product roadmap.

Identifying these opportunities internally was not my primary job. It was something out of my passion for it I did in addition to my day job—my internal side hustle. Through hackathons and small brainstorm sessions, some of these were prioritized on the product roadmap and provided clarity on how we'd explore it.

Intrapreneurial Attributes

Not everyone has the entrepreneurial spirit, and that's okay. It’s not something everyone wants to do. Companies need a diverse set of skills and people excelling at what they do best. I'm frequently asked what the common traits and attributes people who have a knack for intrapreneurially work have. These are the five that come to mind.

Thrive in the ambiguity

When you embark on exploring new innovations that people haven't thought of, it's going to be ambiguous. Nobody is going to tell you what to do because there is nobody to do so. When you can take mysterious areas and start making sense of the fog, opportunities emerge.

Ruthless in iteration

There is a finite amount of time to explore new products and services, and the time to iterate is life-or-death on the projects. People who know how to iterate fast on a concept do well in this space. This is where you want to be an optimalist over being a perfectionist.

Inspire through storytelling

Storytelling is one of the most critical skills of a designer. Great storytellers develop concepts, frame the problem and opportunity, articulate their design decisions, and inspire. If you're going to work as an entrepreneur within a company, you need to get really good at selling and pitching; almost like you're raising money for your startup, because, in a way, you are.

Business acumen

We can cover an entire issue on business acumen. Roughly stated, this is the combination of knowledge, skill, and ability in the business. People who understand the business and are aware of stakeholders get things done. Those who do well in intrapreneurship are research-driven and analytical. They understand the business and find gaps that become opportunities. Most importantly, they have strong relationships with people all over the business to bring it all together.


This might be the most important one. Intrapreneurship isn't for the faint of heart. It requires grit, scrappiness, and a desire to do it. Any initiative with intrapreneurship in mind will come with a lot of skepticism, and that's the point. When you are looking for completely new opportunities the company isn't focused on, it's going to come with a lot of questions. I pitched dozens of initiatives at One Medical, and only a handful was greenlit, but those that survived became very high-impact services.

Unleashing the intrapreneurial spirit

Culture is what people do when they're not told what to do. Whether you're a full-time employee, founder, or freelancer, find something you can pick up and run with. It's working within the constraints of the business but requires going a little rogue too. Innovation isn't always about the frosted glass studios where nobody knows what is being designed, it's building publicly at your company and sharing ideas. I believe that the entrepreneurial spirit is a mindset and culture—one that can be applied within a company.

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