Jay: Hey, guys. This week we have Anna and Gillian, and we are doing a special feature on Women in Tech, and this is during the week of RISE for July 2018. It’s an exciting week. We have thousands of people — entrepreneurs and startup founders and investors — from all over the world coming to Hong Kong. So it’s a very special time near and dear to my heart because I’ve been to every single one of them since they started here. And so we have a very, very good, lucky, fortunate opportunity to interview two guests today. Anna, and Gillian, welcome to the show. I’m very excited to have both of you.

Anna: Thanks so much, Jay. Great to be here.

Gillian: Thank you.

Jay: I’d like to start off with just a quick background introduction. Anna, you can start and maybe give us a little bit of overview of the conference and such, and then we can move to Gillian, and you can, obviously, give us some of your professional background as well.

Anna: Great. Hi, guys. I’m Anna, and I’m content marketing director at Web Summit. RISE comes from the company behind Web Summit, the event, that started back in 2010. It’s been a pretty crazy time for me there. I’ve been there for now about three and a half years. So I was lucky enough to be at the first iteration of RISE back in 2015. Back then, I think it was only about a thousand attendees. And now, this July, we’re looking at welcoming 15,000 to Hong Kong, which is just amazing.

It all started with Web Summit about seven years ago, and it’s really become so much more than a tech conference now. Working in the media marketing space, one of my favorite quotes that describes the event is “Where the future goes to be born.” And I think that really sums it up pretty nicely. We’re so excited to, obviously, be working with Booking.com again at RISE. We partnered with them last year as well, which, I guess, we’ll talk about a little bit later. But especially with Gillian and working with them really closely on our Women in Tech initiative. So it’s great to be here.

Jay: That’s very exciting. And the background of Web Summit is just incredible. It’s my understanding that it was basically Paddy and the handful of people that just started it. It wasn’t necessarily a large organization funding it or anything behind it. It just kind of grew virally. Is that right?

Anna: Yeah, absolutely. It’s a nice Irish success story as well. I think we were speaking just now, but everyone is kind of really surprised that there is this little company — we’re about 180 employees now in Ireland — running these conferences around the world. And Paddy started it like seven years ago from his couch, and it’s so funny hearing him talk about what it was like. We’re getting to the stage where we’re inviting these amazing speakers. Like this year, we’ve got some amazing names joining us. It’s quite humbling, I suppose, as well, to have been with the company for so long, to see it on its journey.

Jay: Absolutely. Fantastic. Thanks for the intro. Gillian, maybe you could give you a little bit of introduction yourself. You’re obviously one of the most successful women in tech today and a CEO of a large corporation. Please give us some of your background and share that with the audience.

Gillian: Yeah. Very good. Thank you very much. I have a background in the hospitality industry. So very early on, I already realized how complicated it was to bring customers from all over the world into properties. So when the internet came, I got really fascinated as to how this could actually improve finding and booking accommodations. So in 2002, I decided to join this startup called Bookings.nl at that time, because I really believe I got fascinated by how this could change this problem.

I’ve been with the company since. I’ve seen this company grow from a few people to now — we have over 17,000 working for Booking — from a few properties to now we have over 1.7 million properties listed on Booking. Basically, Booking has grown into one of the largest e-commerce companies in the world. And if you think about how international booking is, we operate in over 230 countries and territories. We have 200 offices in 70 countries. And our mission is to empower people to experience the world. And you also see, in that sense, Booking evolving from hotels into 30 categories which we offer to customers today, into offering more and more services in travel.

Jay: That’s fantastic.

Gillian: I always say — talking about the Web Summit — that I wish, when we were a startup, that we would have had Web Summits at that time because I think it’s very helpful to companies that are getting started.

Jay: That’s actually true. It’s always hats off to the web 1.0-type companies that have actually survived and made it and thrived into, now, very, very mature companies. Being an entrepreneur and building companies is always hard, regardless, but I feel like it’s quite a bit easier now because of the tools that are available and social media and the internet and this sort of thing. It’s easier to scale up.

Anna, maybe you can talk a little bit about, through the Women in Tech initiative, it’s obviously a very important subject, especially at this point in time and history. I think it’s something that is very poignant. So maybe you can tell us a little bit about the initiative. How did you come up with this? What are you doing from a conference standpoint to promote this?

Anna: Absolutely. It kind of all launched in 2015. We kind of labeled it our Commitment to Change program. It started as just trying to increase female participation at all of our events. From a personal standpoint, I’m a woman; I’m working in tech; and I’m working for a startup conference. I certainly, over the years, have been acutely that female participation in the tech sector, it just continues to be a significant issue. We’ve, obviously, managed to come some way. I think it’s not as exclusive as it used to be, but we still have an awful long way to go. So we’re in the third year now, and I think it’s just over 45,000 tickets that we’ve issued to female attendees across the globe. It’s been amazing to see it come the whole way through and to even meet some of the amazing women that decide to come and take a chance and pay for the tickets and come to the event.

For me, I think what’s great is looking at the data. To put it in context, I think the average for tech industry events, the female to male ratio is usually about 20% speakers. So last year and for the previous two years, our male-to-female gender ratio for attendees was 42 to 58, and then the percentage of women speakers rose to over 35% across all of our stages last year. It’s definitely not equal, but we really hope it’s a small step in the right direction. It’s exciting to see that progress and hear from all these incredible women speakers — whether they’re a speaker or investor or even a startup or a marketing manager sitting in an office in New York and putting themselves out there and coming along to the event.

Jay: What specifically at the conferences? Maybe we can use RISE as an example. What are some of the specific… Is there a special stage? What are some of the specific initiatives, specific to RISE, that allows you to get that ratio up of both speakers and attendees?

Anna: Definitely. So I think, for my team, from the marketing standpoint, one of the most important parts of this is our Facebook community. We’re just over 10,000 in our Facebook community. We’re actively involved in that every day. That’s something that we’re able to test ideas out with so we can talk directly to our community and say, “You’ve got a ticket. You’re coming along to the event. What do you want?” Or, “What would help you?”

A lot of the time, the feedback is that they just want to meet other women or they want to meet someone that they can be inspired by. It’s very… You don’t really think… I’m in the conference industry, so I forget it sometimes. But it can be quite daunting going along to an event and not knowing anyone and taking the time off work and having to justify it to your boss or whatever it is. So we really try and partner with companies like Booking.com on the initiative and think, how can we introduce women to each other?

So one of the main things last year at Web Summit was our Mentor Hours program. So that was where women — and startups in general — got to book prescheduled 15-minute meetings and get advice and find a mentor. Gillian herself was a mentor, which is kind of insane when you think about it. You turn up, and you’re able to chat and get advice from someone who has done it all before.

Jay: That’s absolutely incredible.

Anna: Yeah, it’s great.

Jay: It sounds like these initiatives are actually working and gaining very good traction. That data is basically proof of concept. Thank you for sharing that.

Gillian, on your side, as someone that has been a woman leader in tech for most of your career, how have you seen the tech industry and just the corporate world in general? How has it evolved? Obviously, there is still a lot of shortcoming that the industry has, but I’m sure it’s getting better because there are more places that people can speak their voice and initiatives such as Women in Tech and this sort of thing. Maybe you could walk us through your experience coming up in the early days and how it’s changed, hopefully for the better now.

Gillian: I always say that if you think about my history in Booking, I’ve always been very lucky because, basically, the culture that we’ve built at Booking has been a very diverse culture from the start, and that really has helped me. And I’ve had many mentors within Booking that really gave me the confidence to try lots of new things, to make mistakes, and to learn from those. And that’s how I grew within the business and actually — if I think back — has enabled me to get into this position, which, maybe when I started at Booking, would never have thought that that was feasible. So that also shows that mentorships are quite crucial, I think, in people’s careers and making sure that people feel confident in making these types of steps.

I think if you think about women in technology and what I’ve seen over time, I do think that it has become more transparent. In the beginning, I think the problem was there as well, but it was not so visible. I think today it’s quite clear. There’s lots of data around what is happening. So that’s a good thing. At least we know how big the gap still is today. I do think — and that’s also something that we see in data that still, today, there is a big, big gap. In Europe, you see only 30% of the 7 million people working in Europe’s digital sector are basically working in technology roles. So it’s still have much underrepresented.

Jay: You mentioned coming up and the culture at Booking.com. So currently at Booking.com what are some of the initiative that you have within your organization? Do you offer in-house mentorship or even external mentorship-type programs for women that are aspiring to be involved in the technology industry?

Gillian: Yeah. We’ve done lots of initiatives internally, but we also learned that we need to also help externally. And so internally, I think what has helped us a lot is looking very good at data, to truly understand what is happening. You will learn that there are very small things that you can change which will actually improve to bring more women in technical roles, even in your recruitment process, promotional processes. So that’s something at Booking, and every time, we’ll go through again to make sure there is no pay gap and these type of activities.

Then we do mentorship programs internally and also, as has been clear, together with the Web Summit and other conferences externally as well. But we should also realize that the biggest problem sits, I think, with girls in age 12 to 17, because that’s when we have the biggest drop off, because they don’t make choices in certain types of study. And that’s also why Booking has decided to sponsor scholarships. And we do that together with Oxford and Delft. We give away scholarships, 40 scholarships to women. So this is something that we’ve done.

And then we do the Tech Playmaker Awards because we’ve also learned that it’s very important that there are role models, and that women see these role models as well. So we have the Tech Playmaker Awards internally, but we also do it externally, really, to showcase women that have changed industries and companies. And that is something that we started off this year. We had the first Playmaker Awards. And that’s something that we are continuing to do. So there’s lots of investments we’re doing both internally but also outside of Booking.com.

Also, because we’re a leading technology company coming out of Europe, we also take it very seriously that we need to play a bit role in this topic.

Jay: Yeah. That’s absolutely important. Gillian, you bring up a good point. A lot of people are much more focused on the here and now, and you brought up a good point about the early years when a young woman is developing. The choices she makes of what to study and what career path, that essentially is the seed that gets planted that will drive her career in the future. It’s sort of breaking down those barriers and the traditional silos. That is all relevant. Absolutely. So I think it’s very important, and it’s great that you guys are out there doing this sort of thing.

I also think that one of the issues that I see being in this part of the region is there are a lot of cultural nuances here in Asia. I am Asian, but I’m from the West. I’m from America. So I’ve lived here since 2005, and when I moved here, I noticed certain things. And so I think that Asia does have a lot of room for improvement as well when it comes to encouraging women in the workplace and empowering women to take more leadership roles.

As far as… This is a general question for both of you, Anna and Gillian, what would you say is the number one issue that might not be discussed or is not being talked about right now, whether it be large organizations or maybe startups? Is there anything that you can pinpoint and say if people just did this or talked about this more, it would dramatically change or improve the struggles that some women in tech have?

Anna: I think for me, the whole dialog around things getting better with time… I’m talking about women and how many women are working in your company and the ratio. I think that saying things will get better with time hasn’t really proved itself as a strategy. And I think going back to what Gillian mentioned about just looking at the data, what really stands out for me is there are still over 5% of the Fortune 500 that have female CEOs. I think in 1995, we were at about 0%. So we really haven’t made that much progress. Systemic bias is clearly a huge problem, and I think it’s simple. We had Sarah Friar of Square speak at our event last week in Dublin. She put it quite nicely where she just said people ask her for advice and how can our companies do better. And startups were coming up to her saying, “What’s the secret?”

And she was saying, “Why don’t you just recognize that diversity is essential?” There is so much research out there saying that by having a more diverse leadership team or having females on your board or on your leadership team, your company will do better. And your company will think more; it will be more innovative and all these different advantages. So it’s really just saying times up and for companies to start taking notes of this. Like Booking.com has so many different initiatives that they’re working on. Instead of being shy about it, maybe it’s time now to take a stand on something. If your company is 80% male, maybe just look to only hire women. Maybe that might seem a little bit aggressive, but I think, at this point, something needs to be done instead of saying, “It will get better. It takes time.”

Jay: Absolutely. Gillian, any thoughts?

Gillian: Absolutely. I think the first step is, if you think about women in leadership roles, it’s very difficult, I think, if we only try to fix that problem on the level itself, because there’s just not enough women to choose from. So we need to really solve this problem bottom up, which also means that companies need to take ownership over it. Everybody looks at governments, but I think, how can governments solve a bottom-up problem? It sits in development of women within companies from the lowest level and making sure that women make it up to the top.

For me, it’s quite crucial that companies now really start to make this part of their values. I think if every company includes this in their values, I think that’s a big step because then it’s in your values. So then you need to report on your values. You will check if everything is happening according to your values. You will evaluate managers to see if they act according to the values, etc. Then I think you can really drive a cultural change, which, in my opinion, is what needs to happen. So this will be something that I always push for and talk about.

And it’s hard work. Companies think they do one thing, and then they think I have addressed the issue or I have done something. It’s hard work. And it sits everywhere, and it also means every year, again, you need to make sure that you look at data and see where you can make improvements.

And it won’t change overnight, but I think if everybody will make these steps, I think eventually we will make a change.

Jay: Definitely.

Anna: Definitely.

Jay: I absolutely agree with that. It’s not a one-and-done type thing. You have to keep at it. An organization moves like a supertanker. So it’s a very slow, gradual move, but within time and without dropping the ball, if you keep after it, then I think real change can be enacted.

Anna, let’s jump quickly back to RISE. I don’t know if you have this off the top of your head, but do you actually know how many female speakers you guys have for this specific conference? Sorry, I didn’t mean to catch you off guard.

Anna: No, no worries. We always announce our figures — that means every type of identity, so investors, speakers, attendees, and all the different places they’re coming from — on the first day of events. So stay tuned for that. I will say that we do still have some Women in Tech tickets available. They’re all gone, unfortunately, for Web Summit, but we do have some left. There’s been quite a high uptake, which is great to see, especially us being an Irish conference, and we’re still trying to figure out this whole Asian market. The URL is just riseconf.com/women-in-tech. And you can apply. And I really would encourage anyone listening that is interested in this space, to come along and, as well, don’t feel daunted by it. We have an app. We have the Facebook group I mentioned about. I’ll be there as well. We can go and grab coffee. It would really be great to see as many people, especially from Hong Kong, there as we can.

Jay: So just to clarify. If you go to riseconf.com/women-in-tech, you have basically…is it a special program if you’re a female founder or investor?

Anna: Exactly. You don’t necessarily have to be a female founder or investor. You could be working. As I said, it’s not really just about tech anymore. We’ve got lots of different conferences there. Whether you’re in marketing, whether you’re in fintech, finance, whatever it is, apply or just reach out to me either at anna@WebSummit.com, and we can sort something out.

Jay: Fantastic. And you have allocated an allotment of tickets specifically for women in tech. Is that right?

Anna: Exactly. So for RISE, we have 4,000 tickets that were just for women in tech.

Jay: That’s awesome. So for all of the women listening in that are interested in this, please head on over to riseconf.com. We’ll have it all linked up in the show notes. And Gillian, you will be also attending RISE. Is that correct?

Gillian: No, I’ll be attending the Web Summit in Lisbon.

Jay: The Web Summit. Right. Is there anything on your runway in 2018 or maybe in 2019, anything that you’re excited about that you’re working on directly at Booking.com that you’d want to share with our listeners? And this could be for the company itself or specifically for your initiatives helping women in tech.

Gillian: So I spoke a lot about women in tech, so maybe it’s nice to speak a little bit more about Booking.com because there is also a lot happening in our business, especially the work you see that we’re doing in homes. So have 5 million homes, apartments, and other unique places to stay, which we are expanding all over the world. And then if you think about Booking and the products that we’re innovating into, you see we’re more and more thinking about the end-to-end trip of customers. So you will see now that Booking is offering destinations, transportation, or experiences — so what to do — once you arrive. We’ve learned a lot through customer data that customers still need a lot of help when they go on their trip. So you’ll see a lot of innovation happening in this part of our business and in technology as well.

So we have the Booking Assistant, which is a bot we have running to make sure that we give customers answers faster. In travel, there’s still a lot of questions that customers have. It’s not all that straightforward as when you would order a book online. So it’s very important that we provide technology for customers which give them their answers really quickly and that bot is already answering 30% of questions in the English language, which we are expanding.

And then also, something that Booking is very active in is called the Booking Booster, which is basically the work we’re doing in sustainable tourism. Our mission is to empower people to experience the world, but we also find it very important to make sure that the world keeps being worthwhile to be explored. So we basically help, proactively, startups that are active in sustainable tourism with funding and with knowledge. And this is also something that Booking.com is very active in, and that also connects us a lot to the startup world as such, which is a nice connection because it’s connected to our mission and to our business.

Jay: Wow. That’s very exciting. Just quickly, are you guys involved with any of the online booking and travel within the region here, within China, perhaps?

Gillian: Yeah. Booking.com, of course, is a brand that is operating out of Asia and China, ourselves as well. And we have a very close corporation with Ctrip in China. This is a company that we operate very closely with.

Jay: That’s a very good and strategic alignment because, obviously, they’re the largest from out of China. Fantastic.

Thank you both for your time. I just have a couple of questions left as we look to wrap up here. I would like, Anna and Gillian, if you could both each answer this question. As both female entrepreneurs, successful in both of your fields and what you do, what advice, if you could have one piece of advice for aspiring female entrepreneurs coming up within tech or within corporate or just wanting to get out there and maybe rise to a position of power within a corporation, what would that one piece of advice be?

Gillian: For me, I think what I always find the most valuable advice for women is to not be afraid to step out of your comfort zone and to basically not be afraid to make mistakes. So this is something that I always say because that’s how you will learn faster. And I think, especially for female entrepreneurs, this is super important. And I always say also, don’t try to do everything yourself. Make sure that you get the right people around you. And there’s one thing I always say in Booking as well — don’t let failures get into your heart and successes into your head, which has helped me throughout my career in Booking. It reminds you to stay humble.

Jay: Very good advice. Very good advice. Thank you, Gillian. Anna…

Anna: Yeah, I love that. I think it all comes down to what Gillian said. Risk taking and comfort rarely co-exist. And I think, for me, throughout my career, when I’ve been faced with maybe a new job opportunity or promotion, I think I’m not ready just yet. But if I just do this one other thing, then I’ll feel ready. I think you realize that you may never feel ready. So just try and find the courage and welcome change.

And I think, again, it goes back to what we spoke about about finding a mentor. So whatever company you’re in, when you look up and look at the leadership team, you need someone that you can aspire to. Your role model doesn’t necessarily to perfectly fit who you are, but I think you can pull pieces from their experience to make that part of your journey as well.

Jay: Fantastic. Anna, Gillian, then you both so much for your time. It’s been great to hear about both of what you guys are working on. We’re super excited for RISE this week. Anna and Gillian, if you could both just quickly say where is the best place that our audience can find you, follow you, or learn more about what you guys do.

Anna: Absolutely. You can find me on Twitter. It’s just @annaohare. And you can also follow Web Summit and RISE’s accounts there. And as I said, the URL is riseconf.com/women-in-tech. And hopefully I’ll see some of you guys there.

Jay: Awesome. And Gillian?

Gillian: I post regularly on LinkedIn and on Facebook as well. Twitter, I think you have to be always on. That, for me, is more challenging. But these two channels, I use. So that’s where people can read more.

Jay: Fantastic. We will get that all linked up. Thanks once again, Anna and Gillian, for your time. We really appreciate it, and we wish you both the best of luck.

Anna: Thank you so much, Jay.

Gillian: Bye.

Jay: Alright. Thanks so much.

Anna: Brilliant. Take care, guys. Bye.