Kaidi Ruusalepp needs no introduction. We had recently connected with the CEO and Founder of Funderbeam and co-author of the Estonian Digital Signatures Act back in 2000 on the important lessons she has learnt through her fascinating journey.

What was also interesting to us about Kaidi was the fact that she is among the few women who have raised to power and position in the startup world. Curious to know more about that journey, we connected with her for a conversation.

Find the first part of the two-part series here.

Sandhya: How has your entrepreneurial journey, specifically as a female startup founder, been so far? Has the fact of being a woman in a primarily male-dominated startup world posed any hurdles?

Kaidi: My journey started in 1996 when I joined as the first IT lawyer for the Estonian government. And with this, I started to build my connections and network in the industry. Later, I worked with securities trading and the financial sectors, served as the CEO of Central Securities Depository and the CEO of NASDAQ Tallinn.

During those years, I had to go through invisible glass ceilings and work hard to let people know that it doesn’t matter that I’m a woman. Yes, I AM a young woman from Estonia. But I can run the business and take risks.

So, when I started Funderbeam, my CV was strong enough to overcome any professional barriers. Now a new barrier has arose — being a mother. For example when I was raising the funds for the company, the questions VC’s (mainly men) asked were not just about our company. It was more like:

“You’re a mother?”

I’d say, “yes.”

“You have small children?”

“Yes.”

“How do you run a company then?”

This was a new level of bias!

Sandhya: Wow. Something completely unrelated to your work. Do you think they ask these questions to men?

Kaidi: I have discussed this with men and they say that sometimes they do. But for me it seems to be a standard: how do you manage kids and a company?

Not just VCs, even when I go out to attend social events like receptions and business meetings, every time I get asked, “Do you have family? Do you have children?” And when I say, “Yes I have two kids,” then, instead of discussing the business, people tend to discuss the kids and how they do at schools and what schools they go to, etc.

Sandhya: Do you see this more in Estonia or in Singapore or any specific place?

Kaidi: Oh, it’s everywhere!

Sandhya: Speaking of Estonia, it is a very forward-looking country. It’s one of the first digital countries in the world. So, does that give you an advantage?

Kaidi: It does give an advantage. You gain massive trust by saying you come from Estonia. But it has no impact on those biases towards being a female, a mother and being in this industry. But Estonia as a brand helps me a lot.

Sandhya: A big section of society perceives women as soft or non-risk-taking. Do you think this prevents women from pursuing their dream careers? Do we limit ourselves because of societal pressures?

Kaidi: In a way, yes. That’s one thing.

The second is the trust network around us. Women are the ones who primarily take care of the kids. In Singapore, there is a help/care network which is not the case elsewhere. In Europe, you depend on your own family. So, it’s not just about society but also who helps us out with our kids.

Sandhya: Was this a reason for the move from Estonia to Singapore?

Kaidi: No. We still don’t have anybody helping us. It’s just me and my husband who take care of the kids. The move to Singapore was purely a business decision. Singapore is looking towards the future and bringing in new business models. But, I must admit that Singapore being a very safe country with very strong schools made the decision to move here with the family much easier.

Sandhya: Do you see any differences in the way these two societies- Singapore and Estonia- operate with respect to women?

Kaidi: Yeah, I think in Singapore I meet more women in high positions. Ladies are ladies in the system. They are not forced to behave like men to be taken seriously. And to my surprise, so many VCs are women and so are the board members of big banks. It’s not like women are filling the H.R. or operations department. They are filling the top positions in large businesses. That’s different in Singapore. In Estonia, the businesses are run by men. And then the soft and support areas are run by women.

Sandhya: You mentioned that you and your husband share the responsibility of taking care of the kids. Husbands playing an equal part is sadly a non-traditional path in our society, although this is changing. So, tell us more about how this plays out in your family.

Kaidi: A marriage never works when one partner is dominating and the other is just supporting. For me, marriage has been a partnership. So, a partnership means that in this relationship you can be who you want to be. And you let your partner be who he or she wants to be.

When my husband was managing his own business, and travelling around the world, I supported him. And now when I am running my business, he’s there to support me.

We are raising the kids to be quite independent too. Here in Singapore, they come and go on foot, manage their own activities and help us when cooking food, buying the groceries etc.

Sometimes, when I travel for business and have an opportunity to take the kids with me, I show them what I do and why I need to travel. That helps the kids to see the larger picture and I can explain business, technology and global life to them.