3 Things I Have Learned As A Female, First-Time CEO

Originally published on Forbes.

I’ve been pretty fortunate in my career to not experience much overt sexism. Working in majority-female organizations, mostly in the nonprofit sector, I’ve had amazing female bosses and mentors. Other than the rare uncomfortable moment with a leering male donor, I’ve always felt like I was seen for my talents and hard work. Still, when I was named CEO of Venture for America a few months ago, I wrestled with some imposter syndrome and worried if I would be taken seriously by outsiders in my new role. I’m only a few weeks into the job, but here’s what I’ve learned so far about being a woman in the driver’s seat.


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1) The secret mafia of powerful women that we suspect exists really does

It was a busy summer. I knew I had to finish a strategic plan and hire a COO by the end of August to be ready for my official takeover September 1st. I spent a lot of time in advice-gathering mode, and frankly, I have a hard time not being honest and open about the things I’m worried about in growing and leading the business. But I’ve found that in admitting that I don’t know things, the offers to help have come flooding in – mostly from other women. I’ve been invited to brain trusts of power ladies and had figurative Rolodexes opened wide for me.

Women truly want to see other women succeed and they put in the time to help those that come after them. And they expect nothing in return. I had an incredibly successful former media executive more or less appoint herself to my personal advisory board within an hour of knowing me – and she followed through on every promised introduction and word of advice. On another occasion, over coffee, a female leader with a storied background in technology and government reached over the table, grabbed my hand, and said to me, “You deserve to be here. I’m going to help you get where you need to be.” I couldn’t be more grateful to these women. Knowing I can lean on them for judgment-free advice and timely counsel as I scale our organization gives me incredible confidence.

I’m doing my part to keep paying it forward by personally helping as many of young women who are launching their careers through Venture for America as I can. Twenty years from now, I hope to be able to point to hundreds of young women who made the leap into entrepreneurship because of Venture for America. I’ll be there for them every step of the way.

2) Technology is sexist

As you can imagine, I was pretty excited to share the news of my new gig with friends and family. When I went to text my best friend something like “OMG this is :banana emoji: :banana emoji: :banana emoji: they named me CEO!” I was pretty stunned that the autosuggest feature on my iPhone thought I should replace the acronym “CEO” with this emoji of a mustachioed man wearing a tie: :business man:. I thought it was a fluke so I had my husband and another friend try it on their phones. Same thing. I don’t know if this is a machine learning fail or something Apple specifically coded into their technology, but all I have to say is, seriously?!?!?

Unfortunately this isn’t the first time things like this have happened. Try being the named party on a hotel reservation for two – I have many an email addressed to “Mr. Nelson” confirming my stay. Gender is such a nuanced thing; companies need to find a better way to approach communication to catch up with the times. I have a feeling that with more diverse leaders at the helm, change will come.

3) You have to ask for what you want

Nearly two years ago, VFA’s Founder Andrew Yang and I had a conversation in which he was fretting over finding a successor for the organization. He imagined this person coming from the outside, and having some personal notoriety already. I took a deep breath, looked him square in the face and said “so what you’re saying is you don’t see me in that role?” He was taken aback, stammered a bit, and admitted that he thought I wouldn’t want the job because of the travel and pressure. I told him in no uncertain terms that I did, and we agreed then and there that he would put me into a more public role with the organization. And he did. He sent me in his stead on some speaking engagements and had me write some guest columns he’d been asked to do. Now, he’s my hype man, setting me up to succeed in front of everyone from the VFA Fellows to our very prominent supporters. Without his backing, I wouldn’t have had the credibility I’m able to enjoy from day one, and it is making a huge difference.

I’ve often counseled young people to avoid asking for raises and promotions too quickly, and generally speaking, this is good advice for those starting out in their careers. Despite years in fundraising, where asking people for things, especially money, was my full-time job, I had only rarely advocated for myself. But in this case, I had put in the work. The organization had come to rely on me. But because I wasn’t the obvious second in command based on tenure and hierarchy, it took some creative imagination to see the possibility that I could one day be steering the ship. The act of asking made all the difference, but it was predicated on a foundation of trust between Andrew and me. Unfortunately, many women are penalized for asking, or never ask at all for a myriad of reasons. I feel incredibly fortunate that I was in a position to do so, and want to make sure I’m creating a culture where people can advocate for themselves without fear of retribution.

I’m the first to admit that I am learning on the job. I feel myself stretching and growing each and every day. I’ve had to formulate opinions on issues I might not have had prior experience with – which requires knowing what counsel to seek and when to trust your instincts. I’ve gained access to people and events I didn’t have previously by dint of my title. Work requires switching gears much more quickly, and very rarely entails actually making things. But the emotional labor has increased, because people look to me for clarity and for guidance when things don’t go as planned. Public speaking has become a fairly regular occurrence for me. I’m on the road so much I’ve got more airline status that I know what to do with. It can be a lot to process, but I have an incredible community of people alongside me, building this incredible organization.

Amy Nelson joined Venture for America in 2013 to lead fundraising and external relations, rose to Managing Director in 2016 and became CEO in 2017. As CEO, Amy is focused on making VFA the go-to path for aspiring young entrepreneurs and helping lower the barriers to entrepreneurship for all. This blog post originally appeared on Forbes. Follow Amy on Twitter!

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