Team Enmasse: Windy, your passion for rock climbing is intriguing. How do you see it reflecting your career path?
Windy Wilkins: Rock climbing has been more than a hobby; it’s been formative and taught me lessons for my life and career. When climbing, every step is a calculated risk, much like the decisions I’ve made professionally. It's about assessing the situation, trusting your instincts, and pushing forward.
In college, climbing provided a community off campus and a physical outlet; a space to push myself and grow. This mindset of facing challenges head-on and the joy of overcoming them has been a constant in my career. Whether I was in Peru or navigating the intricacies of microfinance at Unitus, the lessons from climbing — resilience, focus, and strategic thinking — have always guided me.
Team Enmasse: Can you delve deeper into your transformative experience in Nicaragua and later in Peru?
Windy Wilkins: My trip to Ometepe Island in Nicaragua as a teenager was a pivotal moment. Living with a host family in a rural setting, I saw firsthand the disparities in living conditions. This experience pushed me towards international development. Years later, in Peru, as a recipient of a Fulbright Grant, I delved deeper into this field. In Lima, I worked with nonprofit community development organisations, and in Cusco, with rural workers. These experiences were insightful yet challenging. They taught me the complexities of implementing sustainable changes and the need for culturally sensitive approaches. It was a mix of fulfilment and learning the hard truths about development work.
Team Enmasse: After Peru, you ventured into diverse roles. How did these shape your perspective?
Windy Wilkins: Each role I took on was a stepping stone. At a law firm, I learned about advocacy and justice but realised my heart was in international development work. The Rand Corporation opened my eyes to the impact of policy and research on real-world problems. At Unitus, I found my calling in microfinance. Here, I saw how financial power could change lives, especially in underprivileged communities. Each of these experiences added layers to my understanding of development work, shaping my approach to creating impactful and sustainable change.
Team Enmasse: Your roles at The Gates Foundation and Pivotal Ventures were quite formative. Can you share more about your experiences there, especially working with Melinda French Gates?
Windy Wilkins: Working at The Gates Foundation was an incredible opportunity that provided me the chance to be at the forefront of global development. I was part of a team that tackled the world’s most complex problems, from global health inequity to education reforms. The scope of our projects was vast, and it required an intricate understanding of not just the problems and possible solutions, but also the cultural and regional nuances. One of the most rewarding aspects was seeing lives saved as a result of our work.
Working with Melinda French Gates was particularly inspiring. She's a leader who combines deep empathy with strategic acumen. Melinda has this rare ability to look at complex issues through a human-centric lens. Her focus on gender equality and women’s power had a profound influence on me. She champions the idea that investing in women’s power is key to lifting communities out of poverty. She also lives her values, which is incredibly inspiring.
Team Enmasse: How did your role evolve at Pivotal Ventures?
Windy Wilkins: I joined Pivotal Ventures right at its inception and had the privilege of building the organisation over the eight years I spent there. I had the opportunity to be part of a team that was relentlessly pursuing social progress and breaking down barriers for women and girls. I worked in a variety of roles from communications to partnerships to strategic leadership, all requiring a blend of creativity, collaboration, and strategic thinking. Working closely with Melinda and other leaders, we sought to effectively leverage philanthropy as a tool for systemic change. Our work was always about creating long-term sustainable impact.
And Melinda's leadership style – her clarity of vision, her unwavering commitment to equity, and her ability to inspire those around her – had a lasting impact on me.
Team Enmasse: What were some key takeaways from your time at these organisations?
Windy Wilkins: My time at The Gates Foundation and Pivotal Ventures reinforced my belief in the power of strategic philanthropy and cross-sector collaboration. These experiences taught me that while the challenges in global development are immense, solutions are possible with the right partners, community ownership, approach and resources. I learned the importance of staying grounded in the realities of the people we’re trying to help, while also being bold and innovative in our approaches. These lessons continue to guide me in my current endeavours and shape my vision for the future.
Team Enmasse: How do you approach leadership, especially in building collaborative teams?
Windy Wilkins: Leadership, to me, is about creating an environment where everyone can thrive. It's fostering a space where diverse opinions are valued, and collaboration is encouraged. My role has often been to align different perspectives towards a common goal, which requires patience, process, empathy, and sometimes a bit of humour. In high-stress environments, like those at The Gates Foundation or even at Unitus, keeping the team motivated and optimistic is key. I believe in leading by example, being approachable, and always being ready to roll up my sleeves and work alongside my team.
Team Enmasse: Your global travels have given you unique insights. Could you share a standout experience, particularly from India?
Windy Wilkins: My first trip to India was a mix of awe and heartache. The country's diversity, the vibrant colours, the sheer intensity of life there was overwhelming. I remember being struck by the entrepreneurial energy, the bustling markets, and the ingenuity of people making the most of limited resources. Yet, alongside this vibrancy, there was stark poverty and hardship. This duality was thought-provoking, highlighting the resilience of communities and the urgent need for sustainable development solutions.
Team Enmasse: Let's dive into some fun questions. Can you expand on your desert island choices – books, movies, and companions?
Windy Wilkins: For books, I’d choose ones that offer both escape and reflection. Sapiens by Yuval Noah Harari is a favourite for its deep dive into human history. I’d also pick a fictional work, maybe something light and humorous for balance. The third would be a comprehensive history book, something I could learn from and ponder over. For movies - well, I’m a mother of two energetic young kids so I rarely have the time! But I did watch Barbie this year and loved how Greta Gerwig took on a cultural phenomenon and created a savvy narrative about patriarchy. As for companions, Martin Luther King Jr.’s insights on activism, Trevor Noah’s humour and unique life experiences, and Melinda French Gates' wisdom in balancing personal and professional life would make for enlightening companionship.
Team Enmasse: Finally, what would be your first meal back in Seattle after the island adventure?
Windy Wilkins: Coming back to Seattle, the first thing I’d crave is the comfort of my mother’s cooking. Her seafood pasta has always been a family favourite. It’s not just about the meal but the feeling of being home, surrounded by loved ones. That sense of belonging and warmth is irreplaceable.
Team Enmasse: Windy, it’s been an absolute pleasure. Your journey is a testament to the power of passion and perseverance. Thank you for sharing it with us.
Windy Wilkins: Thank you. It’s always refreshing to reflect on the experiences that shape us.