Jess Jackson’s journey into venture capital isn’t your usual! From beginnings in hospitality to becoming a respected voice in the industry, her path is a testament to adaptability, authenticity, and challenging the status quo.
In a field long dominated by uniform backgrounds, Jess represents a new kind of VC investor – one who embraces diverse perspectives and breaks down barriers rather than conforming to them.
We sat down with Jess to talk about her work in VC and what advice she’d give anyone interested in working in venture capital investment.
What inspired you to pursue a career in venture capital?
Honestly, I didn’t set out with a clear plan. After university, I had no idea what I wanted to do. I started working in hospitality, which I believe should be mandatory – it teaches you incredible people skills. My career really took off when a recruiter called about a graduate scheme in health tech. I thought, “Why not?” and jumped in. It was all about seizing opportunities and being open to new experiences.
Your career path seems quite unconventional. How did you transition into investment?
It was definitely not a straight line! After working in health tech and then a family office, I found myself at a crossroads. I was offered two roles at a growth company – one operational, one in investment. The investment role just felt right. At GC Angels, I quickly grew the portfolio from 8 to 33 investments, with a focus on diversity. I went from not knowing what venture capital was to becoming an integral part of the ecosystem.
What were the biggest challenges you faced breaking into this industry?
As a woman in venture capital, the landscape was intimidating. Everyone looked the same – white men in blue suits with finance degrees. I didn’t see people who looked like me or came from my background. Walking into rooms, you’d get those side-eye looks that made you feel like an outsider. But I learned to own my unique perspective and build relationships based on authenticity.
How has being a woman shaped your perspective as a VC?
I think it’s given me a significant advantage. Authenticity is key. When I’m on panels or speaking with founders, I bring a genuine perspective that challenges traditional norms. I can speak candidly about investing in women-led businesses and bring a different viewpoint to the table. It’s not about fitting into an existing mould, but creating space for diverse voices.
Who were some of your mentors or influential figures?
I was incredibly inspired by Helen and Jordan from Lifted Ventures. I remember attending an event before I even started at GC Angels, and seeing them speak so confidently made me think, “This is where I want to be.” Women like Charlotte Ashton, Vic Stewart, and Liz Scott have been incredibly generous with their time and advice, showing me different ways to navigate the industry.
What advice would you give to women looking to enter venture capital?
Be persistent and creative. The VC landscape is challenging right now, with fewer opportunities and tighter funding. But don’t get discouraged. Look into incubators, accelerators, angel groups, and pre-seed funds. Every experience is valuable – hospitality, tech, operations – it all builds your skill set. There’s no single path into VC, so focus on building a diverse, well-rounded profile.
Any final thoughts for aspiring women in venture capital?
Embrace your uniqueness. Don’t try to fit into a predefined mould. Your different perspective is your strength. Be confident, build relationships, and never stop learning. The ecosystem is always evolving, and there’s space for those willing to challenge the status quo.
Jess’s story is a powerful reminder that there’s no one-size-fits-all route to success in venture capital. By embracing the unexpected, staying authentic, and continuously growing, women can carve out their own space – and redefine what it means to belong in VC.
Jess will be running a workshop for aspiring women VCs as part of the Athena VC festival, 13 May at Nexus in Leeds.
The workshop is ideal for any woman, from any background who is thinking about entering a career in Venture Capital in the next two to three years.
Sign up for your ticket for this exciting workshop here: https://liftedventures.co.uk/athena-vc-festival-2025/