Recently, I did a little experiment. I asked DALLE to ‘Give me an image of a tech CEO’. It gave me two photos of a smartly-dressed young, white man in a corporate office setting.

Then I tried regenerating the image to see if it would give me a tech CEO of a different gender (or colour).

After regenerating the image 18 times -and getting pretty much the same result every time – I gave up…

According to AI, the ‘tech CEO’ is young, white, and male.

Why? Because he is.

US Census data from 2022 revealed that only 17% of tech CEOs are female. According to the World Economic Forum’s 2022 Global Gender Gap report – women represent just 36.9% of leadership roles.

Again…Why?

Maybe because it’s harder for them. 78% of women in tech report feeling like they must work harder than male coworkers to prove themselves [Source: Trustradius, 2021].

And yet – even when they work harder – they get paid less. Sometimes – a lot less:

While in 2023 women in CEO roles earned “only” $14,000 less than men on average, in 2020 the gap was over $45,000 (nearly a third -31% – less!). Why? This could be explained by the fact that it was women, more often than men, who had to step down and work part-time to take care of stay-at-home children during the pandemic.

Also – a study by Paychex from December 2018 found that 33% of women in technology have considered changing careers because of male colleagues.

I wanted to learn more about what challenges are deterring women from entering leadership career paths in tech.

So I talked to several female leaders in SaaS – about their experience with breaking into leadership positions in tech startups – what challenges they’ve faced, and how they managed to overcome them.

Keep reading to learn from the inspiring stories* of:

• Melissa Kwan – CEO and founder of ewebinar
• Alice de Courcy – Group Chief Marketing Officer at Cognism
• Maja Voje – Best-selling Author of GTM Strategist, Go-To-Market Advisor & Mentor to +400 tech startups inc. Fortune 500 companies
• Laura Erdem – Senior Sales Manager at Dreamdata
• Else van der Berg – Interim Product Lead, Advisor and Coach
• Frida Ahrenby – CMO at Rillion, CMO to Watch 2024, Board Member and Tech & Start-up Advisor
• Oana Manolache – Founder & CEO at Sequel.io
• Sima Banijamali – Sr. Product Manager @ Microsoft & Top Product Management Voice
• Olga Mykhoparkina – CEO & Founder of Quoleady

*Quotes have been lightly edited for clarity

When did you get into tech? What’s your story?

Melissa Kwan: “I quit my job in SAP and wanted to start a company that uses technology. I worked as a real estate agent and for SAP, so I combined the two and built a tech company for real estate agents. It was an iPad interactive brochure and sales tool for sales centres. That turned into an agency because everyone wanted their version customized. This got me into real estate tech and led to my next company – Base.io – an open-house check-in. I run that company for 4 years (bootstrapped) and got acquired in 2019. I was doing all the demos myself, so that led to my next company – ewebinar – so I could run the demos on autopilot.”

Alice de Courcy: “I got into tech by accident, I always wanted to be a journalist and wanted to work at Reuters, but was put in the legal department and got into legal tech, from which I moved into a legal tech startup.”

Laura Erdem: “I started working in a call centre when I was at university. Then I got hired at a tech company in Lithuania before I knew what tech even was. I knew nothing about tech. I checked in with them: “guys, you know I can’t do Excel?” That was my perception of tech. But I got hired as a coordinator for resource management, which meant that I had to coordinate very highly technical architects for projects. This was my first job in tech and I was with that company for 7 years – going up in ranks, project management, HR, sales…and two kids that I got at that time.”

Maja Voje : “Inititally, I wanted to be an art historian. But my mum told me: “Maja, you need way too much money to be a tour guide for churches.” I said, “Mother, you’re right” – and I went to the economics faculty and studied marketing. But I was initially afraid to enter tech because I couldn’t code, and I was never particularly good at maths, so I thought I couldn’t do that. So I had a bit of an imposter syndrome – just from applying, that I can contribute something to tech companies.”

Olga Mykhoparkina: “There was a big boom for tech in the Ukraine so I was curious. I first got into PPC, then SEO, and then I joined a SaaS company – Chanty – where my SaaS journey started.”

Frida Ahrenby : “I started out in sales in the TelCo industry, I started from working in one of the biggest TelCo providers in the Nordics, moving on to product management, then business development, and then a role in marketing and sales again. That took me to the FinTech and then SaaS industry. I started from Bambora here in the Nordics and then moved on to GetAccept.”

Else van der Berg “My move to tech was completely by accident. I was studying law in Berlin, as a Dutch expat. A friend of mine told me there was a call center job in a tech startup for Dutch speakers, and I just fell in love with the fast-paced, exciting environment. I made my way to operations, and then into product.”

Sima Banijamali: “I started in tech in 2009, and in 2010 I moved to Sweden from Iran and started studying. I got my masters in Computer Science and I had different roles since I joined tech companies in 2013, in different roles: product, design, engineering.”

Have you experienced any challenges as a woman in working in tech? If so – what – and how did you overcome them?

Melissa Kwan “I think the problems I experienced as a woman in tech were not typical for tech – they are typical ones that people experience. I look really young – so very naturally people are dismissing what I do and assume I don’t have [the experience] – and don’t take me seriously. People think they can just interject and take over my conversation – just not even acknowledging that I’m there.

I don’t know if that has anything to do with me being a female or looking young or maybe both – but I’m just not getting enough credit for what I do. People just feel they can talk over me… Once at a conference, where I was with David, my life-partner, when everyone was introducing themselves, a guy just skipped me and approached David directly asking “What do you do?”. I think that happens a lot. When you’re a woman, they don’t think you do anything, you’re just accompanying the men, the founder, and they just talk directly to the men.

It’s a challenge because when you’re constantly not being taken seriously, you start to question yourself. You might feel like you need to act differently, or speak differently – because you want people to notice you.

But while I recognized these as challenges because of who I am – I never let it get to me…as much I guess. But coming to e-webinar – I knew I didn’t want to be the face of the company. Because you don’t know what you don’t know. I don’t know if being a woman means that my last startup didn’t grow as fast, or I couldn’t raise money -I had discussions with my previous co-founder about it – I told him “I always felt like I wasn’t able to do my job as well as a CEO because I was a woman.” He never made me feel that was and told me I was crazy…but again, you don’t know what you don’t know. So coming to e-webinar – I thought I don’t know if being a woman held me back – so I’m going to build a product that can be sold 100% through the internet so nobody would know I’m a founder. Ironically, when we run out of leads – I had to founder-led marketing.”

I guess I never fully overcame those things…but I focused on producing a really good product that delivered value. And I just let the product speak for itself. I have to say most of these challenges came up only in real life and I feel I don’t experience them as much as other people do.”

Alice de Courcy: “I definitely had to change the way I behave and operate in order to be respected at times. I approached the challenge of proving myself by pretty much consistently working harder and longer through much of my career. […]

Now, as a new mum – it has forced me to find more balance. I very much would assume that anyone would know more than me. When I understood that under a lot of that bravado was often a lot of hot air, and not much more – I became a lot more confident. And now I trust myself and my work so much more, and I don’t need to be the loudest voice in the room to be heard. And I got the respect through actions as opposed to any other way.’

Laura Erdem: “I wouldn’t say these are challenges or that the challenges for men and women are different, but sometimes perceptions of these challenges are wrong: I figured out only as I was leaving Gardner that I was hired not only because I was good but also because it was very nice to have diversity in a team. All my colleagues were man in their 40s in blue shirts. The feedback I got when I was leaving was “we hired you because as a diversity”. Not cool.

Sometimes I feel like being a woman in tech is an additional power because you might get into places only because they felt like…they didn’t have enough diversity. Working in sales is tough. It’s not easy, it’s complex, it’s long hours, it’s a lot of hassle – so that’s why we don’t have that many women there. We have to juggle family and work, very demanding work with very long hours…it’s 11 pm and I’m making this video because otherwise it wouldn’t happen. You have to *make* time – for family, friends hobbies…”

Maja: “When I pursued my third tech job, which was like 10-12 years ago. My official title was the ‘COO’ but on Fridays, I made pancakes for the developers. When they had that idea of me cleaning the dishes because I was a woman…I said “no! everyone clean their own cups!”.

Olga: “I’ve never experienced challenges or discrimination as a woman in tech. The only time when I experienced women objectification was when I got a comment from a former friend on LinkedIn that we do the outreach from the profiles of beautiful ladies on purpose because apparently, it improves the reply rate…that comment got me super-furious. The we are ladies are hiring are great professionals and not hired for their looks. And yes, of course, they are beautiful, and they are from Eastern Europe – but it doesn’t give you the right to give comments like that and to blame someone they got the promotion because of their looks.”

Frida: “I have 3 kids. I had the first two when I was working in my first job in the telco industry. I’m quite lucky that being born and raised in Sweden – there are quite high standards in terms of not only maternity leave, but also the paternity leave – and it’s quite generous in terms of how company and the government support it. My first company really supported me and my children, and also my husband was supported in this respect. So in that sense – I come from a background where I pretty much expected things to be that way. And that sets my expectations and how I approach having children and what happens to my role and my career when I have children. In my mind, it shouldn’t change. And that’s also how I go about it when setting expectations as a manager. So to answer the questions if I experienced any challenges – not necessarily with the companies I’ve been at. The challenges have affected my husband more than me.

The Nordic way of things has formed me and made me not settle for less – I have this way of expecting things to be equal. That we should be expecting the same – and I wouldn’t have it any other way. The opportunities should be the same.”

Else: “Yeah absolutely. There are very few women in leadership positions and there is a reason for that – it’s not random. And I felt it *very* strongly when I was working in FinTech. It was my first role as a Head of Product so I was *young*. I was in my mid-to-late twenties, and I was female, and I was a foreigner. And all of a sudden I was doing a lot of projects with banks – so I was stepping into a lot of rooms with German men in their 60s working for a bank. So when I was stepping into the room everyone was thinking “What is she doing here? Is she going to be making the tea?”

And every time they were asking a question, they were asking it to my boss. But he would always pass it on to me. He was my wingman. But he had to do this. Otherwise, they would never ever turn to me. So I felt it quite strongly there. It was a very old-fashioned industry, I was often thinking “why are you doing this to yourself?!” because it was just such a struggle to constantly have to prove yourself – just because you have a slight accent, you’re female and you’re much younger. So I actually switched to a different industry where the average age was a bit lower, so the only thing I had to struggle with was being a woman.”

Sima: “Yes. Especially as an expat woman – there are three buckets. The first one is the inclusiveness and feeling like your opinion matters (as much as the locals’) and the fact that as a woman you might not get that much slack in terms of performance – so you would have to perform at your absolute best most of the time, whereas with men – they get more freedom on making mistakes.”

Have you ever experienced discrimination in workplace due to your gender or family situation?

Melissa: “See, this is the problem. That I don’t know what I don’t know, and that so many things are normalized – like the way that a man speaks to me in a certain way is no different that what other men speak like to me. So it’s become my everyday life.”

I was trying to raise money in the past…I tried to pitch probably around 20 VCs, and in one of the meetings one of the investors asked me: “are you married?” I thought “oh that’s a weird question” but I said “No, I’m not married.” and he said: “Oh that’s good. Because that would never work out” – and what he meant by that was that “It would never work out because you would be then focused on your relationship.

I didn’t think about it at that time but afterwards I thought “oh that’s actually an inappropriate question.”

So that’s what I mean by saying that I don’t know if I’ve experienced discrimination – because so much of it is normalized. Maybe now that I’m older I’m more aware of it, but in my 20s or maybe even in my early 30s I wasn’t – and that is a problem of its own.”

Alice de Courcy: “I would say, unintentionally yes – it was just a passing comment but for me, it really impacted me – and it was from an incoming VP of sales who at that time was super-new and didn’t really take time to understand what I do and my impact on the business, and in one of the conversations I was becoming quite uncomfortable with the direction the conversation was taking, which was quite political, and wanted to bring it back down to the work-related professional aspect – and his response was “you’re supposed to be a CMO, not a marketing manager.” And that really hit me and knocked my confidence.”

As a young woman in tech it can be easy to judge so I definitely felt I needed to work harder to prove myself, and I definitely needed to develop a much tougher skin.”

Laura: “I haven’t. But I also live in Denmark – a country that is built for that. In some places you’re not expected to work for more than 37 hours. At Dreamdata you’re not expected to work any longer than it takes you to do your job. So no, I never experienced any discrimination.’

Olga: “I guess I’m lucky because I’ve never experienced discrimination. Some people accuse us of discriminating men because 90% of our agency are female.”

Sima: “When I was in Sweden – and this is what I’ve been hearing from a lot of nationalities – there is a lot of bias around your name. At some point I was working in a company with 14 Swedish men and they forced me to speak Swedish with them, even though they knew I didn’t understand Swedish at that time. Their logic was that “I had to learn”, but it really pushed me into the corner.”

Frida: “I grew up with two brothers. So I’ve sort-of been trained to always make my voice heard growing up. Not saying that it’s always been easy, but most of the time I’ve been quick to raise my hand, put my foot down, or raise my voice when I felt I was being overlook. I’d say I not only had the mindset but also the awareness that the word works like that and when e.g. I entered a room where there were only men – I would raise my voice and make a loud entrance. I have my small tricks that I’ve come to use. I don’t wait to be asked for my opinion, I speak up. Is it right or wrong, should it be like that – I don’t know, probably not. But it works and my voice is taken into consideration. But maybe I have to work a bit harder to be heard. And this is what I teach my reports – to lean in, speak up, and not wait to be asked. This has helped me to progress in my positions in any context.”

Else : “There’s a lot of bias. At some point I also felt my own bias. At some point I was going into a meeting with a Product Leader at a bank and it turned out it was a woman with a Russian accent. And for a second I thought to myself: “Eh, they didn’t sent their best.” And then I realised what I just thought and felt OMG that was me! It was me thinking that! I’m a female with a foreign accent too! We also have a lot of bias towards female traits. Being approachable, asking questions – are traits often associated with being weak. There’s also constantly something we should be doing – smiling more, smiling less – but there’s constantly this bias.”

Sima: “For women, usually, especially if you’re an expat – it can be difficult to gain the trust, more than locals. And usually you need to work a bit harder to prove your skill, to showcase that you are capable of what you’re saying you are.”

Maja: “Some women really have it tough. A friend of mine is working in finance as a compliance manager, and every New Year’s party the guys are literally harassing women. And if you have the guts to do it to your compliance manager – imagine that – you really need to be a Neanderthal. But she said: this is my passion, this is my fight.”

How do you navigate work-life balance, especially in a field as demanding as technology?

Melissa: “I made a very early decision that I didn’t want to be a mother and that made my entrepreneurial journey easier than women who chose a different path than me. I think it’s much easier for women who don’t have children to navigate work-life balance.

I like integrating the two. I don’t like taking time off. I don’t like digital detox. My work is my life. My husband is my co-founder. So we are on the same schedule. We’re going towards the same goals, we have the same fun schedule – which I think is amazing. So I navigate the work-life balance by integrating the two very tightly.”

I think a lot of people are delaying gratification. I’m going to travel, I’m going to get married, I’m going to have kids…after I exit. Unless you figure out how to inegrate work and life in a harmonious way you will never be happy. So stop delaying what brings you joy and try to figure out how to weave those things into your work, especially as a founder. That’s what I’m trying to do now.”

Laura: “This was tough. Really tough. That’s why I’m thankful for my husband who takes the load as well. It’s not easy, but it helps to have a supportive partner.”

Olga: “Work-life balance has been a constant struggle for me. Especially being a founder means everyday stress and I found that unless I find a way to get rid of that extra adrenaline, I burn out really quickly. So exercising is my best friend. As well as some breathing techniques. It’s also important to cut off work in the evenings and on the weekend (although I’m sometimes guilty). And it’s important to separate yourself and the business – because as founders, we think that we are the business. But I learned to separate myself over the years and it makes life a lot easier.”

Did you ever feel like you had to make trade-offs and choose between family/personal life and work? Do you think it’s possible to combine e.g. working in tech startups with family life/motherhood?

Melissa: “I did. And the only time I did was because I was struggling so much that I could barely pay for my own food. I thought that if I worked more I’d have a higher chance to be successful…but to be honest, I didn’t know how to do it differently. There was this hustle culture in New York that if you take time off, you’re lazy. Now I’m building a lifestyle company that puts happiness in front of revenue, and lifestyle ahead of work.”

Alice: “The pressure I put on myself makes the balance really hard. The more we see women in leadership roles the more there will be the support in the industry. Until you’ve experienced it yourself it can be really hard and therefore difficult to make provisions to really make the difference. I say that as a women who – prior to having my child – would be very supportive, but probably in not helpful ways because I didn’t know what it took.”

Laura: “Oh yeah. Every day. I do that *Every*. *Single*. *Day*. And the hardest part of that is when I feel the kids need attention and I have a late meeting, so it’s not like I can do it tomorrow and I can’t say no, so I have to miss e.g. a performance or drawing with the kids. That’s hard.

So if I feel that there are some things that the future me will regret – this is it.

That I had to say no to some things with kids, family – and I said yes to work. But those situations you have to do what’s right.

I have two daughters and sometimes this grows them stronger too – them seeing me work hard, having ambitions, and explaining that to them – rather than me being available to the kids all the time.

It’s definitely possible to combine working in tech with motherhood. And it’s very rewarding as well. But you have to choose right. And you have to choose companies which are both supporting and understanding – because there will be times when you have to say no to some specific travels or meetings to prioritize your family. I’m at the best place possible at DreamData where – if you need to go, you go. So – choose your company wisely. Ambition is good. But choose a company that will appreciate you putting in extra hours. “

Do you think the tech industry could do more to encourage more women to work in tech, without having to make these tradeoffs?

Laura: “Definitely. And may women don’t take on jobs in tech not because it’s not inclusive, but because it’s hard.

And if more and more of us are doing the job we’re doing – and the more we speak with each other – how rewarding it is, how hard it is – then we’re gonna be building a more inclusive environment because the technology we’re building is more inclusive. We’re leading by example. So anyone should be encouraging it more – the husband encouraging his wife to take that job, a girl who feels underqualified – just f*cking take that job.”

Olga: “I would say I never expected the tech industry or any industry to do anything for me. I was working at a startup and raising a 2 year old and it felt like having two jobs. At the same time I can say tech work is pretty perfect for a young mums because you can work from home so when your kid is sick you can do a lot at the same time while working – like the laundry or cooking.”

Else: “Often around our thirties when we are progressing into leadership roles, we have to take step back to look after our child. Sometimes once, sometimes twice, sometimes three times. And even with freelance contracts – even when on paper we’re contracted to work 20 hours and we’re paid for 20 hours, we are expected to work 60 hours. So one needs to be selective. For me, 32 hours is my limit.”

What can help women succeed more at careers in traditionally male-dominated fields such as tech or product management?

Melissa: “Every company should encourage more women to join their company. Because it’s not only about gender balance – it’s a balance of perspective. A lot of times men can’t empathize with women because they don’t know what they go through. So having more women in the workplace allows companies to be more empathetic just like travelling to a different country allows you to become more empathetic towards other cultures. I think encouraging more women to speak up can help.

When people see success that looks like them – then it breaks their idea of what can make them successful.

So if they see a very successful female Fortune 500 CEO speak about their journey, then in their formative years – as a child or a teenager – they can think ‘I can be like that person’. If all they ever see in male-dominated industries is only men talking about their successes, then they won’t be able to identify themselves.”

Alice: “Encourage more women into the field – because that’s the only way how we’re gonna fix that. We need to really support and champion each other.

And hopefully as more and more women do take on this role, and more partners support that – that will bring more recognition and understanding of what women are trying to balance and go through. And hopefully, that will help drive some change as well.”

Laura: “Having examples. Seeing other women do it. And having management who supports you doing it. Even if it’s a male – someone who supports it, who’s inclusively thinking about it. E.g. for us when we were hiring – it was our CTO, who is a man – told us “If we want to attract more women to take that job, we need to rewrite the job description. The language we’re using, the way we write – not the requirements – has to be different for women to apply.

When I talk about my ambitions, my job – I always think about the women who are going behind me. I don’t know who that is but she needs inspiration just like I do – I wanna see somebody who did it before me, and I wanna show the women going behind me – that I can do that, you can do that too. And these types of people we need more of. To support us, to help us climb that ladder.”

Olga: “Flexible work hours are important. Sometimes there’s a school play or a doctor’s visit – and this family life often overlaps and you need to take a lot of things. As an agency founder who employs over 90% of women I’d say we are quite flexible about working hours and results is what matters at the end of the day. So I’d encourage tech founders to provide this flexibility to their teams, but of course do not forget about the KPIs.”

Else: “I think we don’t need to glorify hustle. Go for it if you want, but we don’t need to glorify people who get up at 4 am and celebrate it so much. We can also celebrate the people who don’t do that. On all levels we can maybe normalize smaller workloads. Also leaders who create space for women, introverts etc.”

Sima: “I think women should be getting more support and should be treated more equally in technical roles. I think finding a mentor, someone that has done this job before and has walked this path before so they can help you reduce the mistakes you may make in your career – and they can give you advice on how to move smoother and perhaps faster.

Regardless of your gender – it’s important that you’re evaluated on your performance and skills, and given the chance and opportunity to showcase them.”

Maja: “When some says something stupid, I ask them: ‘how would you feel if someone said something like that to your mother…or sister…or daughter?’”

Or if you yourself feel like you’re being eaten by the impostor syndrome and you feel like you can’t do it…send it to a few of your colleagues and get their opinion…and do it anyway. Nobody’s gonna judge you as much as you will. You should be second-guessing your fears. What’s the worst possible scenario that can happen?

Finally as a team leader – tell your team members you’re proud of them. That you value and appreciate their work, and that you think they are important.”

What do you think is the role of a supportive partner in entrepreneurial success?

Maja: “If it wasn’t for my partner’s support, I don’t think I would be where I am today. So I believe in teamwork, appraisal and support, and I don’t belive I could be where I am without this social network.”

Melissa: “If you don’t have a partner that empathizes with entrepreneurship, it’s gonna be a very hard relationship. Just try to be a sounding board to what they need to do.”

Olga: “It is definitely important to have a supportive partner by your side, and I have mine. Because there will be ups and downs as you grow the business…at the same time I’d recommend to always have your feet on the ground, because your business should not depend on your partner.”

Alice: “Being able to act as a primary caregiver in all capacities. Some days that may be just taking on the household mental load, other times it might be covering for you at home when you’re off on a business trip.”

Laura: “It’s really, really, really important. I wouldn’t be where I am without my partner. My husband is a corner stone of my success as well. Support, taking over when I need it, picking up the kids, when I’m away for a week – I don’t even need to think if they are doing well because I know they do.”