Foundations

I want to tell you a story about my co-founder, Carolyn. 

We met at a lousy networking event. You know the kind — trapped at a table with people you don’t know, attempting to participate in a conversation dominated by one overly confident individual around a topic you don’t care about. Having heard one another’s names through mutual friends, we shared an eye roll at the coat check.

Fast forward a year. Carolyn asked me to coffee. After startup small talk, she pitched the idea that would become Chief. 

“You know we’re meeting because I’d like you to be my co-founder,” she asked. 

“You know I’m a mom, right?” I felt obligated to reply. At the time, my son Max was two years old. 

“Yes, and?”

Carolyn never questioned if this would impact my work ethic, capabilities, or qualifications for the role — despite the tremendous time commitment of building an early-stage startup. 

It was Carolyn who introduced me to the concept of cognitive diversity. She was an HBS MBA with a strong operational background. I was a creative thinker with a marketing background. She was flying solo, I was married with a kid. And, like our Chief members — executive women from different roles, industries, and backgrounds — our differences made us stronger. Even when I felt weaker. 

A year later, when we went out to raise our Series A, Carolyn caught on before I did. We pulled up to a VC meeting on Sand Hill Road and I struggled with my first bout of intense nausea. Carolyn didn’t bat an eye. That week, we closed a $22M round of funding — the highest series A raised by women founders in 2019. And one of us was pregnant.

Every parent knows there’s never a right time to have a kid — or in this case, a second. And yet, Carolyn was proud of me for having a second child. “Are you sure this is the right time” was never said or implied. She just asked me to name the kid after her. (Spoiler: I didn’t.) 

Just as Chief entered year two and sped up launching new markets, I dramatically slowed down. My third trimester was painful, and I could barely walk around my apartment, let alone make it downtown to the office. Carolyn invested in better remote working tools, and told the company we better get used to being distributed as our team grew across offices in New York, LA, and Chicago. 

When I went into labor on my due date, I texted Carolyn from the hospital. She reminded me to name the baby after her, and to get off the phone and focus on my family. 

As a co-founder, I didn’t want to take traditional maternity leave this time around. I had a plan.  

I told Carolyn I wanted to stay in sync, and she suggested, or, more accurately, ordered me to take at least four weeks off. She covered for me, kept me in the loop, and never made me feel sidelined or replaceable. A month into mat leave, I started working from home and popped by the office every so often, with the idea of coming back full-time in late March. 

Well, that didn’t happen.

Now, I’m sheltering upstate with my husband and two boys, Max and Sam. I have no childcare, and like so many working parents, I’m drowning. I don’t need to tell you how impossible it is to get work done, tend to an infant, entertain an extroverted four year old, cook, clean, and care for the household. My husband and I try to alternate dedicated work time, but those hours are usually abbreviated with tantrums, spills, and tears. Some of them are mine. I feel exhausted, sad, overwhelmed, and, more than anything else, guilty. 

This was not the plan.

“Do what you need to do. I’m here for you,” Carolyn repeats.  

I couldn’t be more grateful to have a co-founder — and a foundation — like Carolyn Childers. And while I don’t know how I’ll ever thank her, I do know there’s still time for me to change the kid’s name.