Jennifer Flanagan
MBA’25J
American
I grew up in Washington, DC, and studied International Economics and French at the University of Notre Dame. There, I developed a deep interest in European history, culture, and policy, which led me to live and work in France and Ireland.
My career has followed both opportunities and evolving interests. I started on a corporate strategy team at a government consulting firm before transitioning into intelligence analysis focused on Francophone Europe and Africa. After a policy fellowship, I was recruited as the first employee and Executive Director at a digital media start-up. Over three years, I helped scale the company into a widely recognised news source for young Americans.
A common thread in my career is working in environments that blend innovation and storytelling. I am drawn to industries that influence how people connect with information and understand the world around them.
Have you witnessed any changes in gender dynamics throughout your career?I intentionally sought a first role with a female leadership team, which shaped my expectations for leadership and collaboration. But as I moved across industries – intelligence, policy, and media – I saw fewer women in senior roles.
The gap became even more apparent when I joined a media start-up as its first employee. As we scaled past 20 employees, I remained the only woman. I watched informal networks form among my male colleagues, where deals were discussed, and decisions were made outside formal meetings. The absence of women in leadership wasn’t intentional, but it was ingrained in how the company operated.
When it came time to hire interns, I advocated for a 50/50 gender split to build a more balanced pipeline of future talent. However, the approach didn’t achieve the desired outcome – we prioritised gender balance without fully aligning with the company’s evolving needs. The challenge wasn’t just representation but how to integrate diversity in a way that also met the organisation’s specific demands.
So how can leaders drive real change? I’ve seen first-hand that it comes from female mentorship, intentional hiring pipelines, and expanding networks to attract a more diverse leadership pool.
But real progress isn’t the result of one initiative or one leader – it requires sustained, structural change across multiple levels of an organisation.
These experiences are part of why I chose to pursue an MBA. I want to learn from peers who have faced similar challenges and explore how organisations can move beyond performative diversity efforts to create real, lasting change.
Can you share a moment when you overcame a challenge related to gender expectations, and how it shaped you?
When I joined a media start-up as the first employee, I took on multiple roles – content creation, operations, and strategy – without defined authority. In a fast-paced, male-dominated environment, I noticed that while my male colleagues confidently made decisions, I often hesitated to assert myself and took on tasks that others overlooked.
I wasn’t alone in this. In conversations with female colleagues and friends, I saw a common pattern – women holding back out of fear of seeming too aggressive or overstepping. I realised I was doing the same, not because I lacked capability, but because I subconsciously prioritised being likeable over taking ownership.
Over time, I learned that leadership doesn’t begin with permission or depend on gender, but comes from taking initiative and letting the best idea win.
I started pushing my ideas forward, setting clearer boundaries, and advocating for my contributions. That shift in mindset gave me the confidence to lead and make an impact. Effective leadership isn’t about gender; it’s about stepping up, taking responsibility, and delivering results.
Are you or your organisation currently taking steps to support and advance gender equity?
I have been so inspired by the women around me at INSEAD.
Their project is focused on breaking the stigma around vaginal health and creating solutions that address a long-overlooked need. These are just a few of the many women I see leading in these spaces – challenging norms, building businesses, and driving real impact. That energises me.
At INSEAD, I’ve tried to be intentional about creating spaces where women can connect and support one another. I naturally gravitate towards sports teams and took on the role of Women’s Development Lead for the Touch Rugby club. I have organised events across both the France and Singapore campuses aimed at bringing women onto the field to learn the game.
I also believe understanding people’s backgrounds is key to breaking down biases and systemic barriers – gender and more.
This belief led me to co-lead OrigINSEAD, a weekly gathering where two students share their personal stories – whether about their origins, pivotal life experiences, or challenges that shaped them. These conversations push past labels and remind us of our shared experiences.
I think it is important for any organisation to create spaces where people – women, men, anyone – feel encouraged to take up space, share their voices, and challenge the status quo.
Can you reflect on the progress made toward gender equity and the work that still needs to be done?
A conversation I find myself having more often with female friends and colleagues is about fertility, parental leave, and career progression. Many of us are thinking about the long-term implications of balancing professional growth with starting a family. Yet, policies around fertility benefits, equal parental leave, and flexible work structures still lag behind.
I see this as one of the biggest steps toward gender equity and want to have more conversations that recognise how starting a family impacts women’s careers – and address the structures that disproportionately place that burden on them. I just came from a policy class on women in the workplace, so I have the data on hand: women still earn, on average, 82 pence for every pound earned by men in the UK (Pew Research, 2023), and the gap widens after having children. Studies show that women’s earnings drop by an average of 30% after becoming mothers, while men’s incomes remain unchanged or even increase (Harvard Business Review, 2022).
This is an important conversation and one where real progress is still needed. Companies and policymakers must go beyond surface-level diversity efforts and invest in family-supportive policies that enable both women and men to thrive in their careers without penalty. Until then, gender equity will remain an unfinished goal.
I recently took a Negotiations class at INSEAD with Professor Eric Uhlmann, who shared his research on gender and negotiations. He noted that while the gender pay gap narrows post-MBA, younger women tend to negotiate less often and advocate less successfully than men. This inspired a project with him to address the gap early by developing negotiation case studies tailored for young women. If anyone is interested in our work, I'd love to connect!
More information about the programme Jennifer attended:
The INSEAD MBA is highly ranked and one of the world's most prestigious programmes for ambitious early to mid-career professionals. The accelerated 10-month curriculum develops successful, thoughtful leaders and entrepreneurs who create value for their organisations and their communities.
Programme benefits:
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