Lessons Learned From a Founder-CEO’s Short Maternity Leave
Updated: Sep 26
I signed a ~$2 million term sheet from the triage bed, forwarded it to my legal team, and then gave birth
This article was originally published to Medium.
A “maternity leave plan” is an oxymoron; bodies and babies don’t follow timelines. While I knew this in theory, it became painfully clear when, at a routine OB visit, my doctor told me that my fluid levels were dangerously low and I needed to be induced immediately. It would be pointless to tell him — and my placenta — that “immediately” wasn’t the right time. Though the thought did cross my mind.
Instead, I texted my husband to grab our things and meet me at the hospital, and then proceeded to waddle the half-block there. Alone on the triage bed, I scanned my inbox for an email from DocuSign. Our lead investors had sent a term sheet for ~$2 million in additional capital the night before, and I needed to sign it before I was too far along in labor to care. I signed, forwarded it to our legal team, and let my co-founder know that I was passing her the baton. While things were quiet and I waited for my husband to find parking, I wrapped up a few other tasks, and gave birth to a perfect little boy.
My team sent baby Aloha shirts and carbs, not passive-aggressive emails.
Since writing about fundraising and running a high-growth startup while pregnant, I’ve received a steady stream of messages from women who are navigating their own pregnancies and experiences as new moms. Because of widespread remote work policies during the pandemic, many women now have a choice of when to share their news and, like me, most choose to delay as long as possible. Reasons for not disclosing a pregnancy can be personal or professional, and the professional ones make a lot of sense: Capital available to women is already small, and declining. Because hustle culture is celebrated, having the additional duties of motherhood can make women founders appear less ambitious and committed. We know from research that no similar fatherhood penalty applies.
Because navigating pregnancy and parental leave as a founder is a relatively rare experience, advice can be hard to come by. I’m cautious of giving it since pregnancy is personal, but as I reflect on my parental leave and first months as a mom working outside the home (or rather, a mom working in her son’s nursery since I live in a New York apartment), there are several things I wish I’d known.
These “lessons,” said lightly, are about navigating work postpartum and pertain to my privileged position as someone who has a job that’s relatively easy to navigate remotely. The pressure to return to work too soon is powerful, complicated, and real. I returned after several weeks on my own volition, and honestly, that may not reflect well on me and definitely doesn’t reflect well on capitalism. But it’s what I chose to do, and given so many people are also navigating parenthood in startups, I’ll share what I’ve learned so far. Said another way: These lessons are for navigating the world of tech as it is, not as it should be.
Appreciate those who self-select off your team
When I started fundraising for my company Ethena, I had VCs ask if I were pregnant and convey in all manner of words and actions that they were not interested in backing women founders. Had they been on our cap table when I did finally get and stay pregnant, they would have been so hard to work with. I’m grateful that we didn’t hide our values, emphasizing that we want to build a company where parents can thrive in order to chase investors, advisors, and team members who would have been completely wrong for us. Said another way: My team sent baby Aloha shirts and carbs, not passive-aggressive emails.
Perhaps most significantly, our lead investor, GSV, knew that I was eight months pregnant when they offered us additional capital. Early on, Deborah, the partner we work closely with, told us that she’s seen women founders consistently underpay themselves, and I happen to think that part of the reason they provided us additional funding was to ensure I could continue being a great CEO as a new mom. Yes, it was also because we’d landed several large enterprise deals in a matter of weeks and got to product-market fit with our lean team, but their “founder friendly” stance meant being genuinely supportive of my big life change.
Embrace letting go
At the outset, being a founder means doing it all. Initially, I played many of the roles we’ve now hired great people to do. Because those responsibilities were mine in the past, it was hard for me to let go of them, and sometimes I’d find myself editing something that really didn’t need my eyes. Maternity leave forced me to let go because I physically couldn’t hang on.
A decision-making framework is far better than a rigid set of rules.
Ideally I wouldn’t have needed to push out a small human to learn that lesson, but I’m nevertheless grateful for the intervention. Now that I’m back at work, the time I would have spent living in workstreams I now devote to coaching and giving feedback to my direct reports, planning for quarters instead of weeks, and recruiting, all tasks that are much higher value than micromanaging.
When I sat down to write my maternity leave plan, I initially thought back to my time in the military. I envisioned a detailed document that had a variety of scenarios and corresponding actions: If, for example, a large enterprise comes inbound while I’m gone, do X. I quickly realized that this document would be 20+ pages and still wouldn’t capture all the scenarios my team would navigate without me. A decision-making framework is far better than a rigid set of rules.
Netflix is both an Ethena customer and a company whose culture I deeply admire. I was reading Netflix CEO Reed Hastings and business professor Erin Meyer’s book No Rules Rules during my third trimester, and I used the principles of trust and transparency discussed in that book when writing my maternity plan. It ended up fitting on a single page that began with: “You’ll be supported for taking the initiative and making the best call you can in the moment. With my being gone, you aren’t lacking permission to make decisions, just the context I may have regarding the issue.”
To ensure my team could get that context, I discussed with each of my direct reports who they could turn to, including my co-founder and our advisors. My maternity leave plan is not what I expect of my team members, and I wrote about the challenge of being the first to take maternity leave as the CEO for Inc.
It’s okay to want to work
When friends find out how long I took off, they usually express their sympathies that the leave time wasn’t longer. While I understand their intention, I feel pressure to hide that I really did want to come back. Sure, ideally I would have had a few more weeks, but I missed interacting with adults, and the excitement of winning a deal, working through a problem, and leading a team.
Truthfully, the first hour of the day with my baby boy feels magical. By hour six, I’m blasting podcasts as he screams in my ear, since I need something to feed my mind and he seems unaware of my presence. I was so grateful when I read Emily Oster describe the diminishing marginal value she gets from childcare. It felt like someone yelling a secret from their balcony — if she admits to feeling this way, maybe I’m not a horrible monster mom for feeling it too. The daily challenges of motherhood and work are enough and I can do without the guilt.
Don’t sacrifice your health
What scares me most about my experience is thinking back to that routine appointment where I learned that something had gone wrong. Each doctor’s appointment was at least an hour of my day and, toward the end, I got annoyed with their frequency. I felt like I had so much work to fit in before my due date, and briefly considered skipping my last appointment. I figured it would be another quick ultrasound that would tell me everything was fine.
Because it’s easy to feel like every minute must be optimized, I can easily see a world in which I gave in to that pressure at the expense of my health. As I hear my baby boy sucking down a bottle in the other room, I’m so glad I didn’t.