Virginia Bassano, VC Investor at Eight Roads | Q and A

Silicon Roundabout
3 min readNov 16, 2022

What were your biggest learnings at Citigroup and DailyInternship?
I would define my Investment Banking and entrepreneurial experiences as complementary. One could expect that the biggest learning from a banking experience would be related to modelling / financial analysis but personally I have learnt how to perform under pressure and prioritise tasks while covering a variety of business models and sub-sectors. On the other hand my experience as entrepreneur was substantially valuable, particularly in the context of my current role as a VC investor, to appreciate that (i) it’s okay to make mistakes: embrace them as a chance to grow and learn and (ii) you can’t be everywhere: the single most important thing you can do as an entrepreneur is to hire the right team and give them space to execute.

What inspired you to become a VC investor and was there a ‘lightbulb’ moment?
Ever since I was a child, I have been fascinated by the positive impact that tech can have on the world. I was initially more focused on the consumer side (e.g. When I was 13 I remember asking a few restaurants in my city to set up a website to help facilitate online deliveries) but over the years I realised that technology can improve not only our personal lives, but also companies’ performance and have an impact on the whole society. I am an extrovert by nature and when I discovered that there was a job allowing me to speak with ambitious entrepreneurs every day, develop your own thesis on a particular sector and contribute to transforming an industry, I went all-in.

What opportunities, threats and risks does the current economic downturn have for the fintech market?
We’ve come from a market that rewarded pure growth to a market which now values efficient growth, and clearly raising funds is becoming more challenging in the current macro-economic context. That being said, the traditional financial system is still inefficient, slow, often built on obsolete technology. Therefore, I believe there continues to be ample opportunity for founders to provide better products and customer experiences, especially in sectors such as B2B FinTech infrastructure, embedded finance, open insurance, payment analytics, climate fintech and so on.

What do you look for particularly in the teams you back?
At Eight Roads we invest $10–30m+ cheques in scale-ups, with the aim of supporting them during the critical steps of international expansion and go-to-marketing scaling. We try to develop relationships with founders well in advance (sometimes even before the seed round) to have the chance to get to know them personally, but also follow how the company develops over time. We look for teams that are hyper ambitious and complementary, with diverse strengths and skillsets; teams that share a common vision while being open to learn and coachable.

What are the biggest mistakes you see from portfolio companies as they begin growth hiring?
It’s easier said than done, but across all stages of growth, there should be a greater focus on mentoring and retaining the best talent. This starts with better understanding their needs. At Eight Roads we recently published a report called “Young Generation in Tech” which looked into what is the experience of the young generation of workers in the tech sector. We surveyed 2,000 20–30-year-old workers across Europe to understand their motivations, what they’re looking for from their roles and their expectations for the future at work. What we discovered is that more than a third of young tech workers (35%) are unhappy in their role, with over half (54%) considering a complete change of career. More than ever, companies need to address issues including career development, progression, remuneration and workplace relationships, if they aim to retain their best talent.

Originally published at



Silicon Roundabout

Silicon Roundabout provides unique and unrivalled access to leading entrepreneurs and VC’s from Europe and the US.