Earlybird Welcomes Alessandra Mazzilli to the Digital West Investment Team

Embracing Uncertainty & Discomfort as a Precursor to Success

We are delighted to welcome Alessandra Mazzilli to the Digital West Investment Team. Alessandra will combine her educational background in economics, international experiences, and dedication to supporting founders to inform her investment decisions and overall impact at Earlybird.

Learn more about Alessandra through our Q&A below:

1. What experiences have shaped your approach to investing? 💫

I’ve always loved the sense of continuous progress and learning new things, even though it sometimes involves discomfort. It’s a bit of a love-hate relationship, but the alternatives seem too boring to consider!

This resonates with the experience of being a venture capital investor: constantly identifying knowledge gaps, or more simply put, feeling grounded, every day.

Somewhat unconsciously, I embarked on a mission to gather as many diverse international experiences as possible – from high school in the Australian countryside, to the hectic streets of Bangkok, to the intellectual haven of Boston during university. After a brief stint in consulting, I moved to the investment side with a multi-family office. There, I focused on PE & VC tech in the US and EU and helped build their then-nascent EU foodtech vehicle. Fast forward to joining Cavalry Ventures, where I enjoyed working in the early-stage investment space for the past three years, and for the past year, as a Vice President.

Supporting talented founders is a privilege. Few jobs offer the chance to meet such a skilled group of individuals daily; I never take this for granted. I have a special place in my heart for the Italian ecosystem and very much enjoyed creating the ‘Redini in Mano’ event series, designed to bring best practices from abroad to Italian founders. We’ve hosted international speakers who have shared insights on topics ranging from B2B SaaS go-to-market strategies to effective team building. In major VC hubs like London, Berlin, and Paris, many people work in tech or are exposed to it, which isn’t the case in many other regions. Providing exposure to talented and ambitious individuals in more isolated ecosystems is incredibly important to me.

2. How do you evaluate founding teams, and what excites you most about meeting them? 👭

It might sound banal, but one of the qualities I value most is authenticity. I love meeting genuine and transparent founders, as we build a meaningful connection. It’s the best way to establish a relationship that paves the way for an eventual investment and, ensures mutual trust when we get down to business after the investment (aka when the roller coaster ride begins).

Another quality I admire is when founders prioritize their company’s needs above their own. It’s something special to see a founder use “we” when discussing their company, even if they are in the early stages and it’s literally just them. It shows me their deep commitment to their mission and a sense of ownership that goes beyond their individual identity.

Being comfortable with uncertainty is another crucial trait. In today’s rapidly evolving landscape–particularly with AI– defensibility, and value chain positioning may not always be clear. Founders need to be aware of the unknown and quickly devise backup plans for their backup plans.

The most exciting part of meeting founders is the potential to learn from them and support them on the insane journey they somehow willingly decided to embark upon! Their passion and drive are inspiring. Providing help and being a small part of their journey is itself a reward.

3. Why were you keen to join Earlybird, and what are you looking forward to? 🐣

Starting a VC firm is one thing; keeping it running for 27 years is another. Earlybird’s consistent investments show that the firm is not resting on its laurels. Earlybird continues to adapt its investment strategy to ever-changing market conditions while leveraging its longstanding knowledge, track record, and extensive connections built over the years. The firm also built a pan-European approach over the years, with Digital West investments spanning multiple EU regions.

It always comes down to the people. During my time in VC, I’ve interacted with several Earlybird professionals. They are smart, switched on, and down to earth — genuinely nice people who at the same time do not take this job lightly and are ready to put in the effort and go the extra mile.

I’m excited to leverage Earlybird’s incredible history and support the firm with my own network by exploring potential synergies, applying my dedication to discovering exceptional European tech founders, and fostering talent and innovation together.

I also haven’t completely given up on making blazers cool in VC (although perhaps the word ‘cool’ is uncool within itself?). Anyhow, Patagonia, you’ve been warned.

Reach out to Alessandra on LinkedIn to connect or grab a coffee ☕️