Learning is Never Boring

I’ve been fortunate in my career in that I’ve been able to work on products and services that are evolving the way people work and what’s possible for businesses. The path that got me to venture capital is one of successive experiences that have helped me develop a deeper understanding not only of products, customers, markets, and businesses, but also the leadership and teams necessary to make impact. And that experience is full of new endeavors - first internet product shipped at Microsoft, a series of 1.0 products and initiatives everywhere I have worked, and work to shift strategy and businesses at all scales.

Every role I’ve had has offered me a “land and expand” mode of learning and leading. As an engineer and product leader at Microsoft, I was given the latitude to develop a keen sense of the what and the how of product development. What is a meaningful product to create? How do you sequence its construction and bring it to market, especially when you’re building something as massive as an entire suite of data services for the cloud?

At SAP, I was challenged to think globally and to approach customers as a partner, not as a vendor. This mindset helps in meeting the customer where they are. Understanding what’s possible in internal product development is table stakes. Understanding external forces — customer needs, emerging innovations, and competitor advantages — is a business’s differentiator and key to continued growth.

When I joined the team at Dropbox, a company far earlier on in its life cycle than the two I’d worked at previously, I was exposed to a newer approach to product and brand building. Deliver value first and users will self-select; brand awareness and affinity can grow organically. Dropbox had done an incredible job pioneering the freemium business model to create a virtuous cycle: deliver value that attracts customers who will sing your praises, attract more users and convert to paying. 

Now after over two decades into an operational career, I am putting myself in a position of needing to climb a totally different learning curve. Learning often begins for me by asking questions. Some of the initial things I’m thinking about —

How does the next generation of productivity software shape up? Can we be thoughtful about how we work as part of designing this new toolset? And what functional areas will see the greatest impact from innovation here?

Where will the next iteration of business models take us? We’ve gone from selling shelfware to licensing services to embracing a bottom-up freemium approach. What’s next?

What will data transform next in business operations? How will product truth be better leveraged in how a business not just operates, but partners and plans? How can the day-to-day activities of a workforce lead to a better way of understanding an organization’s talent, its culture, values and diversity?

As an investor, I am enthusiastic to meet entrepreneurs who are asking questions similar to these, especially in areas that might have a direct impact on how we’re working today and how we will accomplish work in the future. 

This is the first time in a while where I have walked into a job and know the people better than the specifics of the work. While I am new as a investing professional, I am not new to the General Catalyst team. I’ve been super fortunate to get to know them over the last several years and really excited about the learning, impact and scale this work will bring!

Happy New Year!