Three Maternity Leaves at Early-Stage Startups

How it was with different companies, roles, and experiences

From 2013 to 2024, I took three very different maternity leaves, all at early-stage startups. You might be surprised to hear the phrases “maternity leave” and “early-stage startup” in the same sentence. Early-stage startups often conjure up images that don’t seem compatible with having a baby, caring for young kids, or having family responsibilities. As I’ve just returned to work part-time after this third maternity leave, I thought I’d take some time to reflect on how these three maternity leaves have been similar or different.

2013 - Baby A

Before I went on leave, Medium (previously The Obvious Corporation) had about 15 employees. When I told people I was pregnant, there was no official parental leave policy, but I was told it was in the works. Thankfully, it was a generous one (especially for the company size), as they had borrowed heavily from Google’s leave policy. If I remember correctly, it was about 20 weeks paid.

To the best of my foggy recollection, I took about 4 weeks off before my due date, and returned part-time 3 days a week around when I was 8-9 weeks postpartum. I took the remainder of my leave working part-time. At the time, the mix of baby days and work days (with interaction with real adults) was a welcome relief. Now that I am over 10 years older and working entirely remotely, I can’t believe I commuted from San Mateo to downtown SF 3 days a week while still in what people call “the fourth trimester.”

During that time, Medium’s engineering team — once a handful of people I knew well, and who knew me well — had doubled. As I returned 3 days a week, I kept my head down and tried to use my limited time to just get my engineering work done. While I was driving key features and leading projects before I went on leave, I found it hard to find my footing working part-time and with new hires enthusiastic to make their mark. It probably also didn’t help that I started back at work almost the same time a slew of college students started their summer internships. It felt like my work took at least a half-year to year-long step backwards before I built back up to the level of seniority and respect I had on the team before my leave. 

While the amount of leave I took was quite generous, I didn’t feel that supported as I ramped back up. Also notably, at the time, Medium the company was running on Holacracy, and I didn’t really officially have a manager (this was later worked into the company’s model). 

At the time, I really wanted to take on more leadership roles, and I learned the hard way that putting your head down and doing the work you’re assigned is a surefire way to get more work assigned to you, not a successful path to leadership. I remember breaking down and crying during one coaching session, as I wondered aloud why it seemed like everyone else but me had been asked to take on leadership roles (tech lead, people lead, project lead, etc).

Also due to the small company size (didn’t meet legal requirements for a dedicated pumping space) and an office where all the rooms had floor-to-ceiling glass walls, the space I was directed to pump was the handicap stall in the bathroom, where the company added an armchair and side table. I would pull an extension cord from the counter, across the bathroom to the stall. I stored my milk in the main company fridge.

What went well:

• The amount of leave was very generous for such a small company, and I particularly appreciated the option to take my leave part-time.

• Before my leave, I looked forward every week to the Wednesday in-office yoga class. Nadia, the instructor, was super thoughtful in making adjustments for pre-natal yoga for me. It was the best my body felt every week.

• I brought my baby (and ex-husband) to the company’s meditation retreat. It was lovely to be able to spend time with teammates and bring my baby as well.

• Company growth - while this was related to a lot of the ways I felt unsupported, if I had to choose between a company where nothing really happens in the few months you’re out on parental leave, and a company where lots of things change because stuff is happening, I’ll always choose the latter.

What I would have done differently:

• Spent more time re-building relationships with former coworkers and new coworkers, even at the expense of less engineering work done.

• Requested that they frost one of the conference rooms’ glass walls, or set up a small room divider so that I could book a conference room and pump with privacy, not in the bathroom.

• Advocated more for myself during my part-time transition back. When I expressed dissatisfaction, I was met with an attitude of “well, it’s only a few more months that you’re part-time” rather than a genuine interest and desire to make things better.

2015 - Baby J

Medium was an entirely different company by this point, arguably no longer an early-stage startup. The engineering team was probably closer to 50 engineers. I was no longer an IC. By the time I went on leave, I was managing 10-15 engineers, leading engineering for product teams, and still coding. 

When I returned to work (also about 8-9 weeks postpartum), it was straightforward enough to return 2-3 days a week and just pick up people management responsibilities. People and team management work (mostly consisting of team meetings and 1:1s with direct reports) was much more conducive to a workday split up by numerous pumping breaks.

The other major difference was that I had a good manager who slotted me right back in where I was before I left for leave and kept offering me opportunities for growth. He didn’t assume that because I was having a baby that I’d want to coast while I was pregnant, and then half-ass it when I was back. I worked with him at two other companies after Medium.

The pumping situation was much better (and more hygienic). By that point, Medium had grown and moved offices and had a quite nice (and legally required) lactation room, complete with a mini-fridge, sink, hospital-grade pump, and comfy armchair.

While my work experience was quite positive, I remember the realities of two young kids being quite overwhelming. The lack of a break on the weekends, packing lunches in the morning and handling two drop-offs by foot before taking the Bart into work, the long commute daily from Berkeley to SF and back… When people talk about burn out, I imagine long hours and unreasonable work expectations, but because my work was going well, I didn’t realize that the combination of work and life together were burning me out.

What went well:

• Still a generous policy with flexible part-time options

• Much improved pumping experience

• Way better role fit for returning to work part-time

• Most importantly, strong support from my manager (thanks Dan!)

What I would have done differently:

• Spoken up at home about what wasn’t working for me with juggling work, a commute, and two kids

• Being more aggressive in carving out space for myself. 

2024 - Baby K

This latest maternity leave is again at a small startup (Productable), but this time instead of being a mid-level IC engineer, I’m the VP of Engineering. The company is entirely distributed. I’m currently working part-time and have 2 days a week where I’m using up the remainder of my leave.

Working remotely is a game-changer. My pregnancy was pretty rough and not having to commute in and out of SF and inhale car fumes and cigarette smoke while experiencing nausea and vomiting was huge. While I dealing with the worst of pregnancy fatigue, I was able to sneak in naps in the comfort of my own bed, rather than hide out in Medium’s nap pods (yes I know this is also quite a tech company privilege). Also Baby A and J are now 8 and 11, so not having small kids made this pregnancy and maternity leave vastly different from my second.

The paid leave policy for this company is shorter than Medium’s was, though it worked out about the same for me. The official policy is 9 weeks full-time and then 25 days part-time (during which you need to be back 2 days a week). I ended up taking two “unpaid” weeks before my due date, which were partially paid through California paid disability (thanks California!), and then 9 weeks, and now I’m making my way through the remaining 25 days while working part-time.

Although the leave policy is quite a bit shorter than Medium’s, it ended up feeling quite similar in length because I had previously returned part-time around 8-9 weeks.

Working remotely means I can take a break between meetings to nurse, or just turn off video or tilt up my laptop camera and nurse Baby K during meetings, both of which are far more convenient than transporting a pump, pumping, washing pump parts, and packing pump parts. 

The company changed a lot while I was out on leave, but having experienced this before, I had let go of any expectations of what I would return to. I planned the transition and wrote up a handoff doc to the best of my ability, told my product counterpart that he didn’t have to worry about stepping on my toes and to do whatever he felt made sense while I was out, and fully disconnected for 11-12 weeks (9 weeks company leave + 2 weeks unpaid California leave + a few days company holiday).

Being in a leadership role has also given me a lot of autonomy in defining how I want to take my leave and what I want to work on. Some combination of the role I’m in and also just having learned things the hard way and being more determined to take care of myself, I’ve felt empowered to just share what I want first. My leave plan, days I’m working, what I want to focus on. Since I’ve been back 2 days a week, I’ve been very focused on hiring, and that’s been a good well-scoped chunk of work for me to work.

What went well:

• Not having expectations of what I came back to. A lot can happen in 2-3 months at small startups, and a lot did!

• Remote work - this has been the gentlest last few weeks of pregnancy and transition back into work. I still marvel at how I was handling commuting, kids, pregnancy, and return to work with my older kids.

I’m not sure what I would have done differently. Overall, I feel pretty proud about how I’ve shown up for myself and for my work this time around, over 11 years since my first maternity leave.

Of course, I wish the United States had better parental leave policies at the federal level, and parents didn’t have to be at the whims of the companies that employ them. It is absurd that not only do parents get so little paid leave (if they get any at all), but that they also need to so closely plan their career transitions around their tenure at companies.

---

I can understand why many parents, especially moms, opt to work at larger companies during those years that they take parental leave. But it is possible to take parental leave at smaller companies. My three leaves were all very different and hopefully sharing my experience is helpful to others.

Before I went on leave a few months ago, I advocated within the company to increase the part-time leave from 15 days to 25 days. Understandably, at such a small company, increasing full-time paid leave can be challenging — in some cases, one person represents a whole function, and it’s hard to shuffle people around or hire folks in to help fill gaps for a longer period of time. But providing the option for part-time leave is something that smaller companies are able to offer, and after my few maternity leaves, I truly believe it’s a win-win for the company and parent. It reduces the time that someone is completely out of office, while also easing the transition back to work for the parent. I don’t know if this is true anymore, but I’ve also heard that at many large companies, HR requires you to take your leave in at least week-long chunks. I’ve really appreciated the option to return “earlier” but work part-time for all three of my leaves.

Whether you’re at a startup or a larger company, if you have leave coming up, here are some things to think about:

• Consider a part-time ramp-up. If your company offers a certain number of weeks of paid leave, ask if you can return early but take the last few weeks of leave on a part-time basis.

• Speak up for what you want and need. Figure out what would work best for you, write it up, and present it. I’ve been surprised by how little pushback or adjustments there have been to what I have proposed.

• If you are in a position to do so, advocate at your company for better leave policies for everyone. Think about flexible benefits you can offer that meet the company’s constraints. I recently read about a company that offered 4 day work-weeks for parents until the baby’s first birthday. What an amazing benefit — and I imagine the impact on retention to be significant as well.