The startup world is often hailed as a meritocracy – an environment in which ideas and execution reign supreme. But for many women founders, the reality is more complex. From navigating biased investor meetings to balancing societal expectations with business growth, the experience of “founding while female” still carries unique, and often invisible, challenges.
This Women’s Equality Day, we’re handing the mic to female entrepreneurs and businesswomen who’ve built, scaled and survived in a landscape that wasn’t always built for them. Their insights reveal not only the hurdles they’ve faced, but the strategies, communities and moments of resilience that have kept them going.
This isn’t just a conversation about obstacles – rather, it’s a reflection on power, progress and what still needs to change. Whether you’re an aspiring founder or a seasoned investor, their voices offer lessons worth both hearing and acting on.
The Gender Gap Isn’t Just About Funding
Much has been said about the funding gap in startups – women receive less than 3% of venture capital globally – but inequality in entrepreneurship goes far beyond investment. From the early stages of building a business, women often face subtler yet persistent barriers – including being underestimated in meetings, navigating all-male tech spaces or being asked about family plans rather than growth strategies. These are things women face all across the business world.
Now, these biases aren’t always overt, but their cumulative impact is real. Many female founders report having to “over-prove” their competence or temper their ambition to be taken seriously. Even when women secure funding, they’re often steered toward “safer” or “softer” sectors, while riskier ideas are more readily backed when pitched by men.
True, real equality in startups isn’t just about numbers on a cheque, it’s about shifting the culture, language and assumptions that still shape who gets seen, heard and believed, and often, these are things that are inherently subconscious.
Redefining Leadership: How Women Are Changing the Startup Playbook
Female founders are not just breaking into business, they’re reshaping what leadership looks like. Many women are building companies with a different ethos – collaborative cultures, flexible work structures and a focus on long-term impact rather than short-term gain. These aren’t compromises – rather, they’re conscious choices rooted in lived experience.
In contrast to the traditional “move fast and break things” startup mantra, many women-led businesses are prioritising sustainability, transparency and team wellbeing. This doesn’t just make for a healthier workplace – it often results in stronger, more resilient companies.
Yet, these leadership styles are still underrepresented in media narratives and boardrooms alike. As more women rise to leadership roles in tech and entrepreneurship, they’re proving that success doesn’t have to fit a singular mould. They’re not just adapting to the system – they’re rebuilding it on their own terms, and bringing others along with them.
Our Experts
- Deann Evans: Managing Director, EMEA, Shopify
- Sapir Hadad: Executive Director of AI and Innovation, Fiverr
- Meryemm Habibi: Chief Revenue Officer, Bitpace
- Samantha Wessels: President EMEA, Box
- Dr. Andrea Johnson: Chief Information Officer, Pipedrive
- Marni Baker Stein: Chief Content Officer, Coursera
Deann Evans, Managing Director, EMEA, Shopify
“Women’s Equality Day gives us a moment to pause and celebrate the positive impact women in entrepreneurship make, not only creatively but economically, to encourage more women into starting their own journeys. Positively, we’re heading in the right direction: at Shopify, we’ve seen a 44% growth in women-owned businesses since 2007, and Global Entrepreneurship Monitor (GEM) reported one in three high-growth entrepreneurs and nearly two in five export-oriented startups are now led by women. It’s an inspiring testament to the ingenuity and determination women bring to business building.
“Becoming an entrepreneur doesn’t require luck or a background in business. All it takes is ambition. Accessibility, funding, and support, is all vital to make any intention a reality for women entrepreneurs. This means lowering barriers to starting a business with simple, affordable technology; ensuring women have fair access to capital; and fostering strong networks through mentorship and community. Education and skills development are also key, helping women gain confidence in areas like commerce and marketing. Just as important is celebrating and amplifying the stories of women founders to inspire others, and creating initiatives to make entrepreneurship more sustainable. Together, these actions create an ecosystem where women can thrive as entrepreneurs and leaders.”
Sapir Hadad, Executive Director of AI and Innovation, Fiverr
“My journey as an entrepreneur began when I was six years old, selling flowers on the streets of Israel during the holidays. I didn’t realise it then, but standing on a curb with a bunch of bouquets taught me everything I needed to know about resilience, hustle, and believing in your own worth. My father – a real estate entrepreneur – used to tell me, ‘You’re worth seven men.’ That phrase stuck with me, especially as I entered the tech world and began to understand just how necessary that mindset would be.
“Being a woman in tech has never been an easy journey. When I was a pregnant founder pitching investors, the bias was overt in the room. And while we’re seeing more women in this space today, the truth is, there’s still a long road ahead toward equity. My experiences didn’t discourage me – they made me more intentional, and committed to creating space for others.
“At Fiverr, I’m proud to lead our AI Innovation Solution team, building the tools and intelligence that power the next generation of freelancers, and creating the best experience for our clients to identify and collaborate with the right talent. But innovation only matters if it’s accessible. We need to design technology – and the ecosystems around it – with inclusion at the core.
“On Women’s Equality Day, we’re reminded that progress happens because people choose to push for it. Women deserve a seat at the table, not just in the room.”
Meryemm Habibi, Chief Revenue Officer, Bitpace
“As the Chief Revenue Officer of Bitpace, a company at the heart of fintech and crypto, Women’s Equality Day resonates deeply with me. This day is a powerful reminder of the incredible women who have broken barriers and are now leading the charge in an industry once dominated by men. I see every day how diverse perspectives can challenge the status quo and lead to more inclusive financial solutions.
“However, we can’t celebrate this progress without confronting the data that shows how far we still have to go. Women in fintech and crypto still face a significant leadership gap, often overlooked for top roles despite their expertise. They battle against implicit biases and a culture that sometimes struggles to recognise their value. From the persistent gender pay gap to the “motherhood penalty,” these challenges aren’t just statistics. They are real obstacles that limit potential and stifle the growth of our industry.
“The more women leading this change, the more inclusive, dynamic, and resilient our financial systems will be. In a leadership role, I’m committed to leaving a legacy of inclusivity, collaboration, and trust, proving that when we bring different voices to the table, we can build a financial future that works for everyone. By investing in women, we’re building a more robust and innovative future for fintech and crypto, not just checking the boxes for DEI.”
Samantha Wessels, President EMEA, Box
“This Women’s Equality Day, championing gender parity in emerging technology fields is highly important. Take AI, the pace of change is remarkable. From our report – The State of AI in the Enterprise, 90% of survey respondents are planning to increase AI spending next year, and projections indicate that 25% of business processes will be AI-augmented within three years. AI-related change is bringing so many benefits, and we need to democratise its access for everyone. That means equal pay for women in AI development roles, greater representation in model design and application innovation, and fairer hiring and upskilling strategies across the industry.”
“Diversity of thought is essential to the future success of AI, which is why finding the right people for the job and giving them the confidence to thrive is key. We need individuals who are ready to be comfortable working with AI, and hands-on training is the best way to make it second nature. Gender doesn’t define belonging. Young women need to know they have every right to participate in the AI workshift. We need more women in tech and sales, fields still dominated by men, but hungry for diverse voices and perspectives. If you’ve got the skills, AI literacy and the drive, don’t let bias or self-doubt hold you back. Let your talent shine, great leaders will recognise it, and the right environment will help you thrive.”
Dr. Andrea Johnson, Chief Information Officer, Pipedrive
“When people hear the word “doctor,” only 5% assume that person is a woman. I’ve known this stereotype first-hand, most are surprised to learn I have a PhD in computer science. I used to joke it was in knitting, until I realised that even small jokes can reinforce the stereotype that women don’t belong in tech.
“You can’t aspire to what you can’t see, visibility is vital. If young girls don’t see women thriving in tech, they may be less likely to imagine themselves there. It’s not just about hiring women, it’s about showing them they belong. That means putting more women on stages, on boards and in leadership positions. It also goes far beyond the workplace. It should apply in classrooms, adverts, and the stories we tell about who gets to lead in tech and other male dominated professions.
“At Pipedrive, and through my work with Women in Technology and Science Ireland, I’m committed to opening doors, and keeping them open, so the next generation of tech leaders knows they have a place in this future. Because the future of tech should have room for everyone.”
Marni Baker Stein, Chief Content Officer, Coursera
“As Generative AI continues to transform labour markets, one consistent research finding is that women are significantly less likely to use the technology than men, with Deloitte research suggesting that 43% of British men have used GenAI models – compared to just 28% of UK women. This gendered disparity in usage is also reflected in Coursera’s platform data: in the UK, approximately 68% of enrollments in GenAI courses are from men. Among under-30s, this gap is more pronounced, with men representing 77% of enrolments.
“These disparities are concerning because GenAI fluency will increasingly empower individuals to seize economic and career opportunities. Microsoft’s Work Trend Index 2024 indicates that 71% of employers say they’d rather hire a less experienced candidate with AI skills than a more experienced candidate without them, while a recent Coursera survey of technology leaders finds that 72% of them expect new hires, regardless of their specific role, to understand how generative AI could be applied to their work tasks.
“When women use GenAI less than men, and when women do not access GenAI training at the same rates as men, it increases the risk that they will be unable to unlock the immense economic opportunity that AI promises to create. This is not just a risk for women in technical roles: those best-placed to thrive in the emerging AI economy will be those who understand how to leverage AI to improve their productivity, whether they are in Marketing, Product, Sales, HR, or other core job functions. A world in which fewer women are involved in the production and regulation of AI is also one that threatens to produce models that fail to reflect – and support – the needs of half of the world’s population.
“Ensuring that the UK closes the gender gap in GenAI skills is essential to ensure that the AI economy is an equitable, inclusive one. However, interventions that provide personalized learning support, structured milestones, real-world case studies, and mentorship opportunities have been shown to improve persistence and completion rates among female learners. Building on these best practices, and making concerted efforts to bring them to more of the UK’s female workforce, is imperative to enable all women to upskill, reskill, and thrive in the GenAI economy.”
