I’ve spent the last three years of my career working at two different technology startups in San Francisco, CA. The vast majority of that time I spent at Snapdocs, a real estate technology company led by Aaron King and backed by leading investors like Sequoia and F-Prime Capital. I helped create and launch a new product, close a massive enterprise partnership, and build out our Customer Success (post-sales) team. There were ups and downs, but overall I loved my time at Snapdocs – what we accomplished and how I grew.
More recently, I’ve spent three months at Zeplin, a design handoff tool that makes it much easier for designers and front-end developers to collaborate. I joined the company because I was super-impressed with its scale – 3 million plus users, thousands of companies, and incredible revenue – without ever raising a Series A! Inspired by the passion and commitment of the founders I’ve spent time with, I am now ready to venture out on my own. I am leaving Zeplin in order to pursue my own dream. What is it you ask? Loosely defined – expression, excellence, and impact.
I want to write, express, explore, and create in a way that is uniquely me. In doing so, I want to find where I can add value in the world. A couple ideas have already come to mind that I want to explore.
First, I am in the process of creating a weekend retreat experience for my closest friends as a beta to explore doing something that I personally love. Retreats have helped me to reflect and grow so much in my life. So far I’ve asked three friends what they need and, as they are all new mothers, what they need right now is support. In my conversations I’ve heard variations on the theme of wanting to not feel like they are making tradeoffs and sacrificing all the time.
Underneath the desires to plan better or make more money without going back to work full time, I sense there is much more there, specifically around reconsidering – what are my values? What are my family’s values? Are we living in accordance with those and eschewing anything that’s getting in the way? What are my beliefs about being a mom? Where did they come from? Do I still hold them true? Is there some other belief that would be more supportive of my desire. There is so so much to unpack here.
I would never have thought my first retreat might be about motherhood, a topic that I have no familiarity with, but the more that I think about it the more that it might be perfect for three reasons. First, I am a researcher at heart and I have the time that my new mother friends do not have to research and come back to the group with ideas for the issues they are facing. Second, I believe there is something deeper going on here and feel like I could bring that perspective and value to the group. Yes, I want to serve stated needs, but maybe there is something deeper and more foundational to resolve first. Finally, I want to be a mother and raise my family in a very intentional way. This feels like the perfect start to following that desire.
Second, I have been highly critical – though admittedly silent up until this point – of today’s women’s movements within business and technology. I’m seeing very insidious things like higher bonus referral rates for women for the exact same role and recruiting demands that we “keep looking for a woman”. I’m also seeing less insidious things that I am starting to question nonetheless. I see women’s groups talk incessantly about the “gender wage gap” or being “mansplained to”. Overall, a lot of what I am seeing has a tone of – “this is ours, give it to us.” This is a highly masculine approach. To fight, to battle, to push, to yell – these are not the most effective ways for women to create better work environments, earn money, and achieve their dreams. There is something special about being a woman and it is the ability to literally and figuratively create. It is in our ability to attract. To dream bigger and consider all perspectives.
I am curious to see if I can create a space for women who want to achieve their personal dreams by working within a corporation or building a startup but want to do so from a feminine – not feminist – perspective. I admit that I was not great at doing this in my corporate life – I demanded way more than I attracted. However, I now realize that this because I was not living in alignment with my values. I was selling myself short, getting frustrated, and then lashing out.
What if there were a space where woman could have honest conversations about their desires, talents, perspectives, and challenges in a forum that didn’t automatically bias to a progressive or feminist perspective but instead to a individual and feminine one?
Do you know someone who might be interested in this topic? I’d love to hear from them at kayleigh.okeefe@gmail.com.