Women in Tech: 5 Takeaways from Women Founders and Execs

Over the past several years, companies have increasingly invested in diversity and inclusion initiatives, taking steps toward creating more equitable workplaces. At Pacaso, we've made it a priority to build those values into our culture from day one. In recognition of International Women’s Day on March 8, Pacaso invited three amazing women leaders in tech to share their experiences and insights as executives, innovators and entrepreneurs:

Leah Solivan, general partner at Fuel Capital and founder of TaskRabbit
Lara Cumberland, VP M&A Integration and Cross-Company Strategic Initiatives at Facebook
Jana Messerschmidt, founding partner of #ANGELS, partner at Lightspeed Ventures and former Twitter executive

Here are 5 takeaways from the discussion.

It bears repeating: Representation matters

The panelists reflect on the importance of learning from women in STEM: “I grew up in a small town in Massachusetts with no exposure to technology, computers or entrepreneurship, but I always loved math, and all my math teachers in school were women. I ended up going to a women’s college, where I fell in love with computer science and learned about engineering. I then worked at IBM, which was very male dominated, and I think my experiences of learning from and with women helped give me the confidence to succeed. Even by the time I founded TaskRabbit in 2008 there weren't a lot of female CEOs for me to look to as role models. I really believe in the phrase “representation matters” — it’s hard to be what you can’t see.”“I studied engineering because I loved gadgets. When I went to college, I thought I was good at math and science, and I was curious about how computers worked — that’s how I landed on computer science as a major. I was lucky, because I had several female professors even though my major was only 3% women at the time. I think that made it easier to imagine a career in engineering.”

Women are leading the change — and bringing each other along

How the panelists see women influencing corporate structures and opportunities:“I think the most important thing we can do as women in leadership roles is to prop up our female colleagues and look at who we are hiring. Companies need to take the issue of equity seriously, but if women are taking the lead by looking at the opportunities they can give other women, that’s a powerful movement.”“I co-founded #ANGELS with five other female executives from Twitter. We saw male colleagues starting to angel invest and wondered why we weren’t in the same deal flow as our male peers. We’re focused on getting more women and diversity onto cap tables so wealth generation isn’t all going to the same people. We each make our own investing decisions but leverage our collective networks and knowledge. There’s a lot of trust and camaraderie, and we try to build everyone in the group up.”“Women in tech have gotten more organized, and there are more opportunities to come together and support each other. It used to feel like there was only one spot for a woman — there wasn’t room for everyone, so it was more competitive. Now, it’s more about bringing other women along with you and sharing opportunities.”"Women are much more vocal and brave now, especially younger generations. I see young millennial and Gen Z women standing up and holding people accountable for the way they view or treat women in the workplace, and that’s awesome.”

Find your allies and mentors

How advocates and mentors shaped the panelists’ careers:“It’s still important to have the advocacy and allyship of men, especially those in leadership roles. Many of the big moments in my career were marked by men who advocated for me. I think it’s really valuable to bring men into these conversations — even the most enlightened men learn a lot from these kinds of discussions.” “When I founded Taskrabbit, I had never been a manager before. I was introduced to the CEO of Zipcar, and he became my ally and mentor. He took me under his wing and let me and my tiny team work out of their office for the first year. I got to see him be a CEO and effective leader everyday. It was such a gift to me as a young entrepreneur and it helped me develop my own leadership style. When you need support, it’s important to be really clear about where you want to go and find advocates who will mentor or sponsor you. It can be intimidating, but being clear about your direction, even if it might change, will get you further. Pick something and try it on and see where it takes you because it might open other doors.”

Life isn’t perfectly balanced, and that’s OK

The panelists’ perspective on work-life balance:“There are times when I’m super leaned in and focused, but I think of balance over the long term, not everyday, because that doesn’t feel realistic. The most important thing for me to learn was self compassion — and not just as a working mom. Women are bad at this in general, and you need to give yourself a break. Whether it’s your job or your kids, at times it gets easier, then harder, then easier. Expecting those waves helps.” “I don't get too caught up in balancing day to day because I know I’m not. I look at what I did this week, last month — then I know I've carved out time for my kids, family, work and other priorities. I actually do this very systematically with color coding on my calendar. I set it up so I can see, ‘Here’s a chunk of work time, here’s when I’m going to pick up my daughter from school or take my kids to the zoo.’ If I look back on my week and I have enough green, the color for the family, then I feel pretty good about myself.”

Passion and authenticity are your superpowers

Why bringing your passion and true self to work pays off:“Whether you’re an individual contributor or an entrepreneur, I think the most important thing you can bring to your work is passion. I was really passionate about TaskRabbit’s mission, and that attracted people to the company who were aligned with our values. That solidified our culture and helped me develop authentically as a leader. As an investor, I want to know the founder’s story and understand why they are purpose-built for that company. No matter what business you’re building, you’re going to hit walls, and you’ll have to figure out how to break them down and run through them. Passion gives you the energy and power to do that. For ICs, find the areas you’re passionate about contributing to — the places where you add the right value — and apply your special skills to that work. "As a leader, it's important to be authentic if you want employees to feel excited about the work. A lot of companies put aspirational values out there but don’t live up to them. Ask yourself if you’re living your values — they should reflect who you actually are, not who you want to be.”“Early in my career, I was very young for the industry I was in, and I was often the only woman, so I thought I needed to contort myself into this person I didn’t even recognize. When it got too exhausting and I finally decided to show up as me, there was a dramatic shift in the support I started getting and the trajectory of my career. Ignore what you think people expect you to be. It’s too heavy of a weight to carry around. I also encourage people to focus less on their title and more on the impact and value they bring to the company. If you’re focused on being the best, you’ll end up on the right trajectory, and the title will come along.”

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International Women’s Day panel: 5 takeaways from inspiring women in tech