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Lisa Conn is Gigi's mom and the co-founder and CEO of Gatheround, an interactive video meeting platform that brings teams together to learn, innovate, and connect.

Lisa's background is as a community organizer and community builder; she started her career as a political organizer with the Obama campaign, then worked on immigration policy reform with FWD.us. From there, she contributed to the MIT Media Lab's landmark scientific analysis of ideological polarization on X (then Twitter) and went on to lead work at Meta on programs to reduce polarization and extremism on the Facebook platform. She earned her MBA from MIT and her BA from NYU.

Lisa lives in Los Angeles with her daughter Gigi, her husband Joe, and their senior dog Henry. Outside of work and parenting, Lisa is interested in interiors, fashion, and politics. She sits on the Board of Directors of the education non-profit Facing History and Ourselves and is a contributor to Forbes.com.

Hi Lisa, thank you so much for joining us. Can you start by introducing yourself? 

I’m Lisa Conn. I'm the co-founder and CEO of Gatheround. We are a video meeting platform that brings people together and builds culture. I’m also, very importantly, the mother to a 13-month-old little girl named Gigi, who's just the best. 

In terms of my career journey, I could talk about this for the next 30 minutes. My background is in community organizing and community building. I worked at Facebook, where I led their work to reduce polarization and extremism on the platform.

I was previously at the MIT Media Lab, and I started my career doing political organizing

At what stage in your career did you find out that you were pregnant?

I found out I was pregnant almost as early as possible.  I was one of those obsessive test takers —  I would squint and look at the faint lines. I was co-founder and COO of Gatheround at the time. We were fundraising. We were hiring. It was an extremely high growth period. And so this big news came along at a time when I knew I needed to figure out balance. 

It wasn't exactly the ideal time. It was very much wanted, and we put a lot of effort into it happening. But I knew that I would need to figure out boundaries. I had her right before taking over as CEO.

How did you approach telling your team and then instilling some of those boundaries during this high growth time? 

Pregnancy is so strange because you don't tell anyone in that first trimester. And that's the time when you feel the worst, but you're not showing, and nobody knows. I was so sick. I would just wake up, be sick, and then fake it and pretend that I was fine. 

We were fundraising in my first trimester. We have these pitches, and moments before pitching, I would be throwing up in the bathroom or just trying to eat fistfuls of saltine crackers just to settle my stomach. 

Because I didn't tell the team for the first trimester and we’re remote, I decided to be a little bit dramatic and wait to tell them until we were at an in-person offsite. When I was 26 or 27 weeks pregnant, we did an in-person offsite with the entire company. This was 2022, so we hadn't seen each other in person in a while because of COVID! 

I showed up that day with a very tight dress on and the big belly. I  surprised everyone with the news, which was really, really fun. We're a very tight-knit team. People were emotional and excited and treated it as if it was a sibling or a relative of theirs making this big announcement.

I love that. That is so fun. How did you go about planning for maternity leave?

I was the first woman at the company to have a baby. And it was really important to me to set an example of taking maternity leave and planning for it well. We're a startup. We didn't have a policy yet. So, the first thing I did was write a policy. 

In some ways, it was really helpful for me to write a policy and be the first to use it, because it allowed me to have a lot of empathy for who was going to be on the receiving end. We included things like equal leave for all new parents regardless of gender and equal leave for adopted children and gestational birth, and settled on a 12-week policy. I knew that I might not want to take those full 12 weeks in order, and I wanted to have the option for people to do it in two parts. 

So, I basically wrote this policy for myself but for everyone, which allowed the policy to be very human and empathetic. That was the first thing that I did. 

I put together a far too complex maternity leave plan that I've since shared with other girlfriends who are founders. If anyone listening wants it, let me know! Email me, and I will send it to you because it's actually a really nice template.

I had a general set of policies, and then I had a little chart that was information on how and when I wanted to be reached. For example, if we were going to make a big hiring decision or a big company decision, I wanted people to contact me. It's my company; these are things I need to know.  If people needed a password or something, I was fine with a quick text. 

I ended up doing eight weeks immediately postpartum, and then I did another month at the end of the year, which was in line with our policy. 

I'm so glad that I did it that way. I wanted to lead by example for everyone on the team who might be thinking about having children, and show, whether you're a founder or brand-new, we value time with our children and take our policy seriously. I was able to model that.

That's incredible. You came back, and then you had a photo go viral, which is wild. How did that all go down?

Yeah, it was really fascinating and complicated and beautiful, actually. I use LinkedIn like most professionals do. And usually, when you have a role change, you announce it on LinkedIn.I decided to do that—to let my network know that I was back from maternity leave and that I had taken on this new role as CEO.

My husband had just snapped this photo of me sitting at my desk nursing the baby. I was at my computer about to join a call, but she was hungry. So, I nursed her while I was leading a video meeting on Gatheround. 

When I was writing the post announcing my role, I started reflecting on how grateful I was that remote work made it possible for me to be a CEO and a new mom and still have some balance. So I thought, “I’ll share this photo. This is what it’s like.” 

And again, it's just my life. It’s messy, it’s genuine. I posted it and signed off and didn't really think anything of it. And very, very quickly, it started to go viral. I've never experienced that before, and it’s a strange feeling. It wasn't supposed to be this big statement, but it ended up really resonating with people. 

There were thousands of comments, and I read every single one. There were some from people who were early in their careers and thinking about how they might balance parenthood or motherhood and a career. They shared how much it meant to them to see this example.  Then, there were many people who were later in their careers and were sad about their lack of choices. 

There were a lot of parents who had made sacrifices for their careers. And that was really heartbreaking and sad. And then, of course, it's the internet. There was quite a bit of misogyny and hate, but there was a lot more enthusiasm. I opened up our careers portal, and we had hundreds of resumes from people who saw the values in my post and voted with their CVs to apply to work at Gatheround. 

This was a time when a lot of layoffs in tech were happening. I initially thought these applications were from people impacted by layoffs, but it was mostly people who were employed, who were perhaps being asked to return to office, and who wanted to devote their talents to a company that valued the flexibility in where and how you work.

At the time, our company was making an educated guess and a value-based bet on remote work. Our company primarily sells to and supports companies that choose to offer flexible hybrid work to their employees. The public response to this image really reinforced to me how right we were and how right we are that people want remote and flexible work options. Parents and caretakers of all kinds want flexibility. 

It was a great reminder of what we're fighting for.  It was just my life, my home, and my story, but it tapped into something that people were so passionate about.

Why is this such a game-changer for parents and people in general?

We can start with the data because I find that a lot of the data is really interesting. There are a number of different sources and studies that look into remote work and its impact. 

The 2022 Women in the Workplace report from McKinsey and LeanIn found that nine out of 10 women want to work remotely all or part of the time. That's why I tend to use the word flexible because flexible encompasses both of these things. 89% of American workers agree that mothers in leadership roles bring out the best in their employees. 

When we look at these two facts, and then we see that only about 25% of C-suite executives are women. And only 25% or so of top managers identify as mothers. There’s a disconnect here that has been building for decades. 

I can share anecdotal evidence from my own experience and the experience of many of our customers that remote and flexible work is helping to close a very major gap here. And why is that? Well, when I became a parent, my 24 hours in the day suddenly seemed like a lot fewer hours. 

When you have children, the opportunity cost of your time is so much higher. Any hour or minute you spend away from your kids has to be worth it. And that doesn't mean we need to be productive all the time. Time away might be a bath or a little extra sleep, or time at work. All of that is worth it. 

What I can tell you is that time sitting in traffic is not good for you. It's not good for your child. It's not good for your company. It just doesn't quite make sense. 

I recently did a LinkedIn live with some folks at Gusto and Nick Bloom, a Stanford researcher doing fantastic research about remote work. And one of the things that they found was that people, men and women, between 30 and 44, are the most likely to take advantage of remote work.

Why is this? Again, the story points to people who are working parents who want to use their time efficiently and well and have fulfilling lives. The commute and sitting in the interruption factory of an office is just not consistent with that formula.

What changes would you like to see in how we support women in the workforce, in addition to flexible work options?

I think about flexible work, not just in terms of where we work but also when we work. I am a big believer in strong goals and clear goals. That and a culture of trust enables all of these policies to work and to make sense. The combination of setting clear goals, establishing success, and having goals and visions for what success looks like, plus building a really strong culture where people understand each other and feel connected as human beings, enables people to do their best work regardless of the where and the when.

At Gatheround, we're 100% remote. We have people all over the world. We can't all be sitting at a computer together or sitting in a conference room all the time. We have very clear company goals and company objectives that we report on every single week. And if it takes someone 10 hours that week to accomplish their goal, fabulous. If it takes someone longer than that to accomplish their goal, that's okay, too. 

I try to model, for example, if I have a doctor's appointment, head-down time, or the morning routine with my baby — it’s on my calendar and it's public. My team sees that I can hit our goals and succeed and lead the team in an effective way and also still be a human being who does other things with my life and with my time. I wish that we supported parents and anyone, really, with not just flexibility in where we work but also flexibility in when and how we work.

So, the first year postpartum is super tough. It's also like super tough to run a startup. What's it like to tackle both of those things at the same time? What types of things have you been learning?

The biggest thing that I've learned is that you have to do fewer things and do them well. For years my husband and I have done an offsite every June where we establish priorities for our lives together for the year ahead. Typically,  we pick three categories, and then we explicitly name everything else that is not a priority. 

A category might be family, health, career, friends, hobbies, or home, for example. When we had our baby, we had to say, I don't think we can prioritize three things. I think we have to pick two. So we chose work and family and even narrowly defined family as our immediate family. 

What that has meant is that my best friends of many, many years, unless they are going to come over and help with bedtime, we’re probably not going to see each other that much. And that's temporary, and that's okay. They're not going anywhere long-term. It meant that hobbies were not a priority. What hobbies? Sleep is my hobby.

I've had to focus on doing fewer things and trying to do them well. That's one big thing that I've learned. 

The other is, I'm such a perfectionist. I've been this way since I was tiny, and I've had to define perfection differently for myself. If you're holding a bunch of balls and you know you can't carry them all, learn which of those balls are made of rubber and can bounce and be fine and which of those balls are made of glass, and if they fall, they're gonna break, and then you're gonna have to pick up the pieces. You have to decide you're going to let some of those balls drop instead of defining perfection as holding all of the balls perfectly. 

The third thing that I have learned is how to ask for help and accept help. If you are someone who is a new parent or about to be a new parent, and you have friends who are offering to do a meal train where they bring you food, just say yes. If they haven't offered, ask someone to do it. 

You might think like I did—I can order takeout, I can order food, I don't need it, but getting help and getting that muscle of accepting and asking for help is absolutely essential in those first few months and years. 

These are things that make me sane as a person but also make me a good CEO. Leading the team to do fewer things, helping the team recognize which balls you can drop and which ones you can't, and asking for help, I think, are just good habits for leaders in general.

Do you have any advice that you could give employers as a leader and a recent mother in better-supporting women preparing to go on maternity leave and when they return?

I think we've established in this conversation that enabling people to work flexibly is essential. So, let's just assume that we're all in agreement about that. So then the question is, how do you enable that while still maintaining a successful company? And there's really interesting research about this. The Gusto work-from-home research, the Stanford group analysis, found that companies that have strong cultures and are remote or hybrid perform better across all key performance metrics than those that don't. 

I think that the culture piece is really important. Building a culture of trust, where people understand each other and feel connected to each other, enables you to have a workforce that is flexible and remote without sacrificing productivity. 

I think the best way to support parents, potential parents, and really any kind of caretaker is by building and investing in culture. Caretakers of all kinds need support. Many people do caretaking work that might be invisible, including elder care or care for other family and friends. There might not be a policy for that the way there is a parental leave policy. Building a strong foundation of trust, understanding, and empathy is the safety net when you don’t have a policy, or it might be the thing that signals it’s time to build one. 

My advice is to invest in your culture; even if it doesn't seem immediately important, it’s everything.