In Their Own Words: Female Founders and CEOs Discuss the Discourse That’s Missing (and Hitting) the Mark

This year’s International Women’s Day theme is “Inspire Inclusion” — a call to recognize the unique perspectives and contributions of women from all walks of life, in all facets of life, including the innovation economy.

Why does representation matter when it comes to startups? Because diversity in experience and perspective leads to better, more innovative solutions that work for more people in more places. Why else? Because women have and continue to gain more purchasing power than ever. Their preferences and spending habits quite literally move industries and economies.

Despite this, venture capital funding continues to miss the gender parity mark, with the gap between all-women and all-men-founded teams becoming even more pronounced amid a broader investment slowdown. A brighter spot: Funding going to startups with at least one female founder ticked up to 26.1% of allocated capital in 2023 (compared to 18.2% in 2022). Still, investors, media, and the tech community tend to fall into familiar tropes, approaching female founders and CEOs with downside-focused lines of questioning that perpetuate the precedent.

So this year, we revisited the idea we explored last year, asking women leading transformative startups across logistics, healthtech, fintech, and climate where they want to steer the “female founder” dialogue. Here’s what they had to say.

“As a female leader in STEM, I want to be asked smart questions about where technologies are headed, and how I’m leading my company and team through one of the greatest technological advancements in our lifetime.”

The CEO: Amena Ali

The Company She Leads: Optoro, a reverse logistics technology platform that uses data science and real-time decision-making automation to improve returns for customers, retailers, and the planet.

The Questions Amena Wishes She Were Asked Less: “‘Why don’t you just demand that everyone comes to the office each and every day?’ Alas, COVID has changed the work paradigm forever, it seems. When people can Zoom into a call from nearly anywhere, and teams are distributed, you have to find a different way to build culture and collaboration. While I understand there are different considerations across individual businesses and industries, the pandemic taught us to be more nimble, adapt to change, and most importantly, find multiple ways to connect with each other. Effective leadership requires embracing what has changed and building upon it.”

The Questions She Wishes She Were Asked More: “‘In a world where AI is emergent and becoming capable, how do we adapt to and leverage this seismic change? What skills do our leaders and teams need to not just be effective, but more fulfilled and satisfied?’ This report from LinkedIn on the most in-demand skills has me reflecting on what is quintessentially human and what could now easily be machine-dominant. Communication, empathy, and critical thought have never been more important, with AI rising and teams working in a distributed and remote manner. As a female leader in STEM, I want to be asked smart questions about where technologies are headed, and how I’m leading my company and team through one of the greatest technological advancements in our lifetime.”

“Women CEOs often find themselves fielding inquiries primarily focused on risk aversion, perpetually having to pivot answers to address concerns about stability and caution.”

The CEO: Traci Keen

The Company She Leads: Mate Fertility, the healthtech company creating access to robust, affordable fertility treatment solutions, from IVF to genetic testing.

The Questions Traci Wishes She Were Asked Less: “I wish I were asked fewer questions that center around risk management rather than growth opportunities. Women CEOs often find themselves fielding inquiries primarily focused on risk aversion, perpetually having to pivot answers to address concerns about stability and caution. However, research consistently shows that companies led by women outperform those led by men in terms of shareholder value enhancement. Shifting the narrative to focus more on growth-oriented questions not only aligns with the proven success of female CEOs but also allows for a more holistic exploration of the strategies and innovations driving our company forward at Mate Fertility.”

The Questions She Wishes She Were Asked More: “I would welcome more inquiries about how intersectionality influences my approach to leadership as a female / LGBTQ+ CEO. Intersectionality, the interconnected nature of various forms of discrimination, is fundamental to understanding the complexities of our business landscape at Mate Fertility. I believe that embracing intersectionality enables me to develop more holistic solutions that resonate with a diverse range of individuals. By considering the intersections of gender, sexuality, and other dimensions of diversity, I can better address the unique challenges and opportunities within the fertility industry and maximize upside potential for the company and the communities we serve.”

“I’ve always seen myself as a founder. So when I’m asked questions that imply being a female founder is different, it’s challenging for me to respond.”

The Founder: Einat Steklov

The Company She Leads: Kashable, the fintech equipping working America with a better way to tackle costly debt and cover unexpected expenses during times of financial hardship.

The Questions Einat Wishes She Were Asked Less: “I’d prefer to be asked fewer questions that solely focus on gender. Regardless of gender, I’ve always seen myself as a founder. So when I’m asked questions that imply being a female founder is different, it’s challenging for me to respond. I’d rather discuss my skills, experiences, and what my company has achieved.”

The Questions She Wishes She Were Asked More: “I wish I were asked more about my personal journey as a founder, beyond just the business aspects. I’d like to share more about my growth and development as a leader, not just my accomplishments. Delving into my journey would provide a deeper understanding of how I’ve evolved throughout my entrepreneurial endeavors and contribute to a narrative that encourages other founders, especially female founders, to have confidence in their direction, decisions, and leadership abilities, paving the way for us all to thrive!”

“Building a company is a marathon, not a sprint — and with so little funding going to female founders, it’s critical that we talk openly about being overwhelmed, stress management, and support to keep women in the game.”

The Founder: Anna Robertson

The Company She Leads: The Cool Down, the mainstream media hub of content, commerce, and climate experts dedicated to creating a sustainable future by connecting consumers to cleaner solutions.

The Questions Anna Wishes She Were Asked Less: “‘What was your most embarrassing moment?’ Let’s drop the silly questions and focus on substance — I’d rather talk about my experience, my mentors, my vision, or yes, how I balance being a great mom to two young kids while juggling a demanding career instead of recalling a moment when I wasn’t at my finest.”

The Questions She Wishes She Were Asked More: “‘How do you avoid burnout?’ It’s a challenge facing all founders — but especially women, because, if we’re being honest, women are the ones who often carry more of the workload at home, in addition to running and growing their businesses. Building a company is a marathon, not a sprint — and with so little funding going to female founders, it’s critical that we talk openly about being overwhelmed, stress management, and support to keep women in the game.”

“It’s assumed male leaders prioritize the business and the rest is taken care of. Adrianne and I are two proud mothers, but we’re also two multi-faceted humans who can juggle a variety of priorities and excel at them, too.”

The Founder: Elaine Purcell

The Company She Leads: Oula, the healthtech startup redesigning maternity care with a midwifery-first, team-based model that dramatically improves patient satisfaction while delivering better outcomes.

The Questions Adrianne Wishes She Were Asked Less: “‘How do you do it all?’ This most often means, ‘How do you raise a family and build a successful company at the same time?’ It’s assumed male leaders prioritize the business and the rest is taken care of. Adrianne and I are two proud mothers, but we’re also two multi-faceted humans who can juggle a variety of priorities and excel at them, too.”

The Questions She Wishes She Were Asked More: “So often questions focus on the challenges women face in male-dominated fields. Instead, I’d love to hear what we are doing to entice more women to take the leap to become founders. What are we doing to increase the odds of women getting funded?”