Allison Whalen — From Wall Street to parental leave expert and CEO

Allison Whalen left coveted roles on Wall Street to move into the startup tech world and eventually become a CEO and Founder of Parentaly. We talk about the difficulty of pivoting away from a job you love and how becoming a mom made Allison a better leader.

Q&A

How did you start your career? And how did you execute your early career pivots? 

I started off in investment banking, and realized I didn’t like it, but I wasn't ready to step off the finance path. So then I went to private equity for two years in a role where I focused on emerging markets, which was an interest of mine. I realized at the end of those two years that I still didn’t enjoy the finance experience in general. But I really didn’t know what I wanted to do.  

Instead of finding another job right away, I quit and I took a year and moved to Colombia to volunteer for Shakira’s foundation Pies Descalzos, which builds and runs schools in high poverty areas. I then won a fellowship to move to San Francisco and work in education for a year. What I realized at the end of that fellowship year was that while I was passionate about education being one of the most important investments society can make – my skill set wasn’t aligned to actually working in education. In other words: there’s a difference between believing in something as a worthwhile problem to solve, and being able to personally add value and solve that problem. I wasn't adding any value because my role was in operations and I wasn’t very good at that work. I didn't think that I could be that useful because I wasn’t teaching. I found that very frustrating. 

After that fellowship year I went to business school and started to think more critically about what I wanted to do professionally. I ended up working for a year and a half for an investor in Europe who had successfully exited some companies within the money transfer space and was starting up a different business. I helped him get that off the ground. But similar to my previous work in finance, I found that that role was too removed from the underlying business because I was working on the investor side and not in the operating company.

And so finally from there, I spent a lot of time recruiting and landed at Managed by Q, a facilities tech startup. That’s where I ended up staying for four years and that’s where I felt like it was the best experience that I’ve ever had, it was exactly what I wanted. 

What did you love about your time at Managed by Q?

I joined very early on in the company and so I was able to see different stages of growth and play many different roles. I'd never done anything entrepreneurial in my life. I didn't even take a class on it in business school because I hadn't grown up around entrepreneurial people. I didn't know any entrepreneurs, I was never exposed to that world. I assumed that I wasn't going to be good at it. But what I found is that I was one of the most aggressive risk takers – and I mean that in a good way - at the company. All of a sudden I was like wait, I'm really loving this. And I'm actually good at it. 

You’re now a CEO & Co-Founder of Parentaly, a company improving the parental leave experience for corporate employees. How did you make the pivot to startup Founder?

The whole idea for Parentaly was born while I was at Managed by Q. During that time I had my first child. And it was just such a shocking experience to have a child and go on maternity leave and try to return to work successfully – without any role models or playbooks on how to take three months off of work. Particularly in a really high stress, fast moving environment where I had direct reports. I had this obsession with my experience of becoming a parent and how that transition could have been better. In hindsight I realized there were so many things that I wish someone had told me to do – how to plan for my leave, questions to ask, expectations to set, goals to renegotiate, professional development to plan for my direct reports, things like that. And I thought, oh my gosh, this is a major, major problem. 

That's where I started to plant the seed for Parentaly. I realized this is a real problem that everyone experiences who has a child. There are no other companies focused on what we are focused on, which is business planning and career coaching within the context of parental leave. Other companies are more focused on parenting advice and medical support within the context of parental leave. We wanted to focus on the career aspect of how to do this right, and better, and more successfully. 

My cofounder and I thought, is there any way that we can spin this up while we're still working? So we worked on it super slowly over about a nine month period. We would work on it late at night during the week, a few hours here and there. We put together the first version of our content, hired a career coach to deliver the curriculum, and completed our pilot while we were still employed. We were able to pilot the business without really taking any risk. It cost us money, but that was it. We ran the pilot and the feedback was phenomenal. 

So you started as a side hustle. What pushed you to go full-time?

I would actually reframe it as – we built and piloted the first version of our business without quitting our day jobs. We didn’t intend to monetize the business as a side hustle, but we wanted to de-risk the business so that at the moment in time that we quit to focus on the business fulltime, we would be ready to sell and work with clients right away.  

For the pilot we sent a few emails out to friends and we said “Hey we have this idea, it's a combination between an ecourse and 1 on 1 executive coaching, to help women who are pregnant plan for their maternity leave and return to work. Here's a link for people to sign up.” We hoped to get 10 women to sign up. But within four days we had 35 women. So we knew that this had strong appeal to women who were pregnant and focused on their careers.

At the same point in time, Managed by Q was acquired by WeWork. I was debating quitting to focus on Parentaly because I knew it was a massive problem that no one was working on. But then, when Managed by Q got acquired, I got a promotion and I got a new job that I really liked. So we put the business on hold – until – WeWork announced that they were going to sell Managed by Q. 

That was the push that I needed to get me to go all-in on this business. I left WeWork on a Tuesday and started working fulltime on Parentaly on Wednesday. 

Many entrepreneurs I talk to wait to go “all in” until they are forced to. A layoff, for example. Why not jump sooner? 

I really liked what I was doing. I was still very engaged when we were acquired by WeWork. I got moved into a new role and I recruited some people to come and work on my team. I felt like I had never been surrounded by better people. I got such enjoyment out of working with my team on a day-to-day basis. And that is really what kept me from quitting.

We briefly looked into the idea, can we launch Parentaly without me quitting? I even reached out to a woman who used to work for me and we were in early discussions about hiring her to be a sales rep and start promoting the business. But I was really uncomfortable because I thought, You don't start a business and pay someone else to get it off the ground. I knew I should be doing it. I was anxious. It was a weird and fortunate experience where I was so happy at Managed by Q, but also had this other thing that was wildly unrelated to my day job that I was also obsessed with. How do you choose?

You had made a big leap earlier in your career, leaving finance to volunteer in Colombia. Was that jump easier to make?

I think the career changes were just very different, but neither was necessarily easier. When I moved to Colombia I was leaving a job that I knew was not my future, something that I knew I wanted to move away from. But it was scary because I didn’t know where I was going, even though I was actively looking to make a change. Still – everyone around me told me it was the biggest mistake to leave finance. “You’re never going to get back into finance again. How do you recover? And you’re not even taking a job, you’re going to be unemployed and go live in Colombia?” But for some reason, I thought, I just don’t believe that I can’t pick another thing again. I don’t believe that I can’t take a year off and get back into things. 

With the leap from Managed by Q / WeWork to Parentaly, I felt pulled between two great options. I wasn’t running away from a job to find the next thing, I was debating between two different but exciting opportunities which is incredibly fortunate. So I felt great relief when that decision was made for me.

You’re an expert on career and parental leave. Not only as CEO of Parentaly, but also in your personal story. How did you navigate your career journey while pregnant?

When I was pregnant for the first time, it was the most insecure I had been in my entire career, which was weird because I was already recognized as being successful at Managed by Q. I had turned around the city of Chicago, I’d already launched one of our largest businesses, I was on the leadership team. 

And yet, something about being pregnant was turning me into the most insecure I’d ever been. I was trying to figure out why. And I think it was because I didn't hear stories of positivity, where a woman had a child and became better at work. I was surrounded by everyone asking, “Oh, are you going to come back to work?” I had a lot of concern about how to manage it. 

But the biggest change after having a child was that I became sick of the inefficient work and tedious tasks. Becoming a mother made me so much better at my job. I was much more direct, much more productive, much more effective. It allowed me to be even more successful – but also I worked way less. I was so happy because I spent plenty of time at home. Anytime my son was sick and I had to stay home I could do it. I was able to manage things really well.

Luckily I was in a position in a career that was good. But a lot of the time before women go on leave, there are problems already in their jobs. And the second you have a kid, you’re not going to tolerate those problems anymore. Society gets it wrong. They think, oh you have a kid and the woman changes. No. The problems at work were already bothering women before. It’s just now their bar is so high, they think it’s not worth it anymore to tolerate those problems. 

In our Parentaly programs we have women identify the things at work that bother them. We try to identify those things early on and work with women to ask, how do we create more of an ideal role for you to come back to work in? Because stepping out of work for three months makes you realize what you miss – and what you don’t miss. 

We both believe it’s important to see and hear other women’s stories. Tell me about the importance of celebrating stories of women returning to work.

Yes! Even before Parentaly, I wanted to hear stories of what you never hear – stories of women having children and coming back better than ever. I was really hungry for that. Everything I was hearing was about how 43% of women quit after having children. And I really did not want to quit! I looked around at my peers – women in leadership, getting promoted rapidly after having children. Why don’t we hear those stories? 

There's so much content for women about how to scale back and find your balance. It's not that balance is bad, but when I was pregnant with my first child I was in a state of mind where I refused to believe I had to take a step back to get it. And I still believe that. Yes, it looks different, and I work fewer hours. But I was better at my job after I got into the rhythm of taking care of my son. I wish someone would write something that showcased more of those success stories.

Allison is sharing more positive stories of women’s return-to-work experience here. To learn more about how Parentaly can help improve the parental leave experience at your company, you can reach Allison at info@parentaly.com. 

*Q&A has been edited for brevity and clarity.