Musings on Parental Leave as a Startup CEO

My wife and I are expecting our second child this week, and I start my paternity leave today.

Instawork recently rolled out our leave policy based on the fact that we had 6 employees become parents this year: birth/adoptive parents receive 100% of their base salary for up to 3 months, and parenting partners receive 100% of their base salary for up to 2 months. Our parental leave policy applies to all Instawork employees around the country.

I'd like to share my reflections on why I'm taking paternity leave and what I learned (which I will write when I return to the office), for a few reasons. In talking to other founders and start-up execs, especially men, it became apparent that lots of people (including me!) were confused or had questions around how to set and take parental leave. Also, many CEOs couldn't quite understand how to prioritize investing in leave relative to other benefits their companies could offer.

My journey as a parent: I co-founded Instawork around the same time our daughter was born, nearly 5 years ago. Shortly after her birth, Instawork joined YC in the summer class of 2015. Between the demands of getting an early-stage start-up off the ground, and taking advantage of the generous support of extended family (which we were very fortunate to have), I was not as physically present as I could have been. As my wife and I prepared to have our second child this year, I reflected on what I had learned during my dual journey as a founder and parent. Starting a company and starting a family are clearly different transitions, but they share some similarities: both require long hours and sleepless nights but ultimately bring a great deal of joy in creating something life-changing.

Work-life harmony: During interviews, I tell candidates that start-ups require mental and material sacrifices that will be shared both by them and their families. For this reason, I'll often take candidates out to dinner with our families so we can spend time getting to know each other. Families and partners are also welcome in the office anytime and included in our celebrations. The path to maintaining team loyalty and satisfaction in a start-up requires reciprocal commitment and excitement between families and the company. We want Instawork to be an attractive place to work for everyone, regardless of whether they have families. This is in the spirit of what Jeff Bezos calls "work-life harmony."

Why parental leave matters: Like many start-ups, working at Instawork is demanding. Late-night texts or untimely fire drills come up, especially in a business like ours where our users need us the most on weekends. It's an expectation we share openly during the interview process. There are many other places to work that offer more attractive benefits than we do, such as a robust snack program or chefs onsite cooking fresh meals every day. But we decided to prioritize Instawork's leave policy, and we hope it sets a precedent for other start-ups. Becoming a parent is transformative, and responsible companies should encourage their employees to take time to be fully present during this transition. It was important to me and our leadership team to ensure our leave policy reflected this perspective.

How we set our policy: When iterating on our leave policy, we surveyed similarly situated companies in the Bay Area. We also spoke with our team (especially parents-to-be) and their families. Importantly, we wanted to have a consistent policy for all of our team members around the country, regardless of what their state laws dictate. We also allow employees to split their leave however it works best for them and their families.

My leave plan: My wife and I decided I would divide my leave, taking a month now, and the remainder later next year. Leaving the office for an extended period of time admittedly made me nervous early on. Consequently, I started planning over a month ago, distributing responsibility for key tasks and projects (e.g. All-Hands, partnerships, recruiting) to various individuals across the company. I also checked in with each member of our board to update them on the business. A task that seemed initially difficult — delegating many of my CEO duties — felt very manageable with good planning and loyal and trustworthy colleagues.

I will plan on checking email once a day, but will not dial into meetings or go to the office. I acknowledge that being on email is not being fully disconnected; in reality, there is no single model for what leave looks like, especially for start-up founders. The silver lining is that there is opportunity for each individual to devise their own path based on what works best for them, their families, and teams.

Although letting go of the day-to-day is not easy, I'm proud to have a team who I am confident will step-up and shine, giving me the much-needed time to make new memories with my growing family (not to mention, re-learn and perfect the arduous task of swaddling!).

Note: I will update this section in a month when I am back in the office with some observations and learnings from my time away.

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