Sierra has been investing in Artificial Intelligence for the last 10 years, and in the generative AI space for the last 3 years, well before it became mainstream. We invested in companies like Quillbot (acq by CourseHero) and Modulate. With the latest advancements, we are excited to see this space flourish in 2023. The infrastructure layer is maturing rapidly, making way for new application opportunities and will turbocharge all aspects of Enterprise Software.

Vertical SaaS is another area of interest as software built for specific industries are going to continue to expand its reach into all verticals. There is a lot of value to unlock, and sometimes the toughest verticals have the most amazing SaaS companies that grow out of it. Data and Security continue to boom and now they are becoming nation-state-level investments. Infrastructure to support this boom is of great interest to us and we continue to invest aggressively in the sub-vertical.

I think it is important for founders to be resourceful when trying to connect with a VC. Cold outbound is always going to be challenging because, these days, most VCs openly share their email. That typically translates to a flood of inbound pitches.

As a founder navigating and extending the network, you is key. Go to meetups, reconnect with past colleagues, and find inroads to get warm introductions. This also shows hustle, which is a key attribute to be a successful entrepreneur.

I like a “prepared” mindset entrepreneur who has done their work on their target customer, the market dynamics, their competition, and me. Ie its important to have done your work on if the VC you’re pitching is the right fit from a sector and temperament standpoint.