🎂 Selina Tobaccowala & Jen Taylor Fireside Chat

Hi, I'm Jen Taylor, Chief Product Officer at Cloudflare, and I am thrilled to be with you here today with Selina Tobaccowala, who is currently the Chief Digital Officer and focused on healthcare and wellness, but has a long and storied career as an entrepreneur and a technology and product leader here across the valley, and actually globally in the work that you did in Europe.

Thank you so much, Selina, for making time to join us today.

Thank you for having me. So Selina, one of the reasons you and I were chatting a little bit, and one of the reasons we're doing a lot of these fireside chats is really in celebration of our 10-year anniversary and sort of reflecting back on sort of the last 10 years in the Internet.

But I kind of want to push that kind of to the side and actually start really understanding a little bit from you.

I mean, your career, you've had such an interesting and diverse career.

I want to go kind of all the way into the Wayback Machine and really talk with you about really your first foray into technology, which was eVite.

Can you talk to us a little bit about sort of the inspiration for eVite and the vision that you had as you were starting off there?

So I wish I could tell you it was some grand vision we had that we were starting the company.

But Al and I, my co-founder, we were still at Stanford, we were in school, and we were surrounded by all of these companies.

The Internet was booming, and we were surrounded by all of these companies starting.

You had Excite, Yahoo, it wasn't quite yet Google, but all of this technology and people starting to figure out how you can use technology to make things available on the Internet.

And so we were at the time just building different products, trying different things out, and got the idea for eVite really to try to just help people get together.

I had an indoor soccer team, and we wanted to help get it organized.

And it was more of that than it was anything that we had this grand vision for electronic invitations.

Well, and it's just, it's fascinating.

So I was an early eVite user, I actually worked at Excite, so you and I share some kind of common history in that.

But the thing that was really fascinating to me, if I think back at that time, was so much of the vision at that moment of how we would experience the Internet was basically kind of really just digitizing content and making content more accessible.

Like, how did you think about kind of taking that to the next level and enabling people to really actually use this technology to connect?

And that's, to me, what I've always been passionate about with technology is how do you use technology to bring people together in that real world or make real decisions with survey money or go to a concert with Ticketmaster, try to exercise with OpenFit.

And so what we saw was, at that time in history, it was almost completely about content.

It was getting access to content.

And obviously, that trend has stayed with people getting access to movies, music, everything digitally.

But it was also starting to turn to be about communication.

So there was the messengers, email, obviously, was suddenly booming.

Everybody was suddenly got access to email. And so that's really what we saw.

We saw this opportunity where you suddenly have this ability to make more efficient communication.

And that's what, when we thought about Evite, which is when you suddenly got over three, four or five people and trying to get them together, it was a super inefficient process.

It's just, I mean, it's interesting if I step back and think about it, because now I'm like, well, obviously, like, I would just text them, right?

Or like, I could have liquid plans with people because I can make a plan and I could change it.

But it was different at that point. Like, when Evite started, like, I didn't have a cell phone.

No. People had some of those brick car phones, but that's about it.

But like, those were only for, like, the high rollers.

It's not like I was, like, parking that in the back pocket of my jeans, my skinny jeans and, like, you know, getting ready to head out as a hipster on my single speed bike.

But how did you guys approach that? I mean, how did you sort of kind of help users kind of catch that fire and maybe overcome some of their apprehensions in thinking about or even conceiving of using this technology in this way?

So one thing that we were very passionate about from the beginning, from a product development perspective, was around A-B testing.

And how did we actually get, and the whole focus was around how we got somebody into the top of the funnel to actually create an invitation.

And then that was going out to an average, at the time it was 19 people.

And how did we turn that person who was a recipient back into a creator?

And we tested everything. And I'll tell you a very funny story, which now, with all privacy going on, but you had, you know, there was no problem with, like, displaying everyone's emails.

So you'd have all the emails go out.

I still remember one of our top winning A-B tests was we had a little link underneath your email, and it said, want to see your name here instead.

And that got people to register, which got them into our database, which got them into our CRM to start emailing them.

But it was, even then, there was this view of, like, I want to show up right on the Internet.

And so it was just, it was a fun thing.

But really, right from the beginning, with us from a business perspective, because there were a lot of essentially copycats, there was literally called invite me to see you there.

And what made Evite stand out, I believe, was really because we took that product iteration and focus on our funnel to grow the fastest.

It's so interesting now, because I think about how we do product development.

Well, it's like, of course, you A-B test, but I can imagine at that time, it must have, people must have been like, wait, you can roll this out differently, you can create these variants.

And that was something, there wasn't any tools for it.

You know, we were, and we were, you know, trying in the eyes, I still remember, we'd like split people by their like user ID token.

And, you know, it was all those things versus there was no Optimizely or Google Optimize or anything available to you.

Yeah, yeah. Wow, that's amazing. And then so, what are, like, you talked about kind of overcoming some of the challenges of sort of the A-B testing and stuff like that.

What were some of the key technical hurdles that you guys overcame as a product development and organization?

So back then, you would, as you, you couldn't imagine that we had, everyone had this one big Oracle database.

And so everything was dependent on that. And I'll never, I'll never forget when the entire database went down on eBay.

And, you know, you had BackUs, but everyone was racing around trying to get a backup.

And, you know, people are calling and being like, where's my invitation?

My party's about to get started.

Nobody knows where to go. And so, you know, it was, it was, and at the time, even there was no cloud, right?

So physically, when we physically would go to this, to these cages, stack and rack the servers.

And when we sold the business to IAC, I literally went and unplugged half the machines, shipped them.

And then I flew down, unpacked the machines, re -racked half of them in LA.

And, you know, it was just a totally different environment.

And you look at, you know, the penetration of cloud today, it's just unbelievable.

It makes things so much easier.

It's so funny. You were like the first real virtual machine container service, right?

You're deploying the container in Southern California. Yeah. That's hilarious.

Okay. So then, so then kind of transitioning from, from eBay to your experience at IAC and Ticketmaster.

So, so, I mean, again, like you're seeing a place now where like, you're starting to see the Internet sort of pick up, but you're also dealing in a world and you're also dealing in, in a region of the world that are, that is slightly different.

What, what, what shifted between your time at Evite and your time at IAC and Ticketmaster?

Well, I think one of the most fascinating things about Ticketmaster from a technology perspective is the peaks and valleys you experience, especially the peaks are really unlike any other business.

Because when, you know, at the time when Michael Jackson went on sale, you know, you would get just so many people queuing up for it.

And you would get a huge amount of bots that were focused on trying to essentially the digital brokers.

It was one of the first places where you had all of this traffic coming that we were trying to manage.

And then meanwhile, you had a really interesting marketing challenge where you had, you know, these long running shows like a Chitty Chitty Bang Bang that you're trying to figure out, figure out how do you, you know, use data science and algorithms to generate demand for those shows.

Right. So you start targeting the right people. So from a technology perspective, Ticketmaster is just a fascinating place to work.

And being abroad, like in Europe, you know, one of the biggest, you know, learnings that we had was just how quickly the Internet was becoming global.

I mean, if you look at that change in the last two decades, I mean, there was, I mean, even now you look at the top companies, you know, you have ByteDance, you have WeChat, you know, you have all these international businesses that are suddenly, you know, huge proliferation.

But even then you started to see that was the huge transition where you just started to see that the expectation of product and technology was to be built globally and on a global infrastructure.

And that was a really fun thing to learn and to experience.

So, but back to sort of the image of you plugging in boxes and boxes and flying them to LA.

How did you guys tackle that challenge of scale and global scale and the peaks and the valleys at Ticketmaster?

So we also for a long time had lots of data centers.

It was one of the biggest investments that we made.

We had in Europe, we had a huge data center in Amsterdam and Ireland. And I was responsible for all of that.

And it was, and again, we had massive, you know, cages of equipment.

And we were, we were really innovating in terms of using global network routing at the time to split traffic between the different international data centers.

And then, but it was still, you know, you didn't have this advantage of that, of, you know, the, there was, there was the beginnings of CDNs, you know, where you start to get at least some of the fresh content.

But if you think about something like a show or inventory, it's very difficult to use that because the, you know, the rate of change of the seat map is, is immediate.

Yeah. Well, and also, yeah, just thinking about that, the, the importance of pushing that, that data out and having it be very, very current and, and the freshness of it.

And it was interesting because we created this whole queuing system and, and I had recently, that Cloudflare created a product around that as well.

We're still, we're in the early, we have early access out now in waiting room.

And it's one of those products where I was like, really, people want this from us.

And it's been amazing to me to see, I think the response we're seeing in the market, because I do think there is this challenge of how do you, as, as, as somebody who's running an application, anticipate and manage kind of the peaks and the valleys and, and how do you do it in a way that is really cost effective, right?

Because you could build up kind of endless origin capacity, but that's going to kill you on your cloud bill or your, your servers or whatever you decide you want to run it on.

But, but a waiting room enables you to create a, a much more kind of civilized experience.

And it's also more fair, you know, that, that makes sure that it's not just the person who has the most number of machines or anything like that.

You're actually getting people into a fair queue, which was important.

So how did you approach that challenge?

So it was a huge amount of infrastructure we put in place at Ticketmaster.

I don't know if it's still there today, but we built out essentially a waiting room, a huge queuing system where people would get put in, they'd get their number in the queue, and we would be, and we'd release people in a queue as the inventory, as people were getting through checkout.

And then eventually, you know, and what it also allowed us to do is add more shows in the background.

So that if, if the shows were selling out, we had backup shows that we'd quickly add an ad to see, so they'd add more nights on.

Oh, interesting. So there was this collaboration with the people running, using kind of the real-time data of what you're seeing.

And we're on the phone with the promoter. And they're like, Of course you're on the phone.

We had a night, we had a night. So. There's a venue available.

Somebody call the venue. It was a great, it was a really good, it was, from a technology perspective, it's, it's a fascinating, it was a fascinating learning experience.

That's amazing. And then, and then, and then you shifted, right?

And then you, you moved over to, to SurveyMonkey. Talk to me a little bit about, about that shift for you and sort of what drew you to SurveyMonkey.

Absolutely.

So, so the shift was really both a personal and professional decision. So I was in London, happened to meet a wonderful gentleman over there.

Yeah. And, and, but we wanted to start a family and I was traveling about 60 to 70% of the time because I was responsible for 11 different markets across Europe.

And so it really wasn't feasible.

And so, and I also wanted to get something back to something smaller and innovative.

And, and so I started, you know, looking at Silicon Valley and there was just so much opportunity, but what drew me to SurveyMonkey and what I, what draws me and what I look at across my career is really a focus of three things.

The first is always people.

And the late Dave Goldberg was a magnificent gentleman. He was our CEO at SurveyMonkey.

And right from the moment I met him, I was inspired by him.

So leadership style, the way he was going to grow the company. The second for me is always about the mission of the company.

And that's what I was saying for, I like working on products that are helping people in the real world.

And with SurveyMonkey, our mission at the time was to help people make better decisions with data.

And so it's like to listen to people's opinions, right? So if you think about, I had spent so much of my career on quantitative analysis, and this was adding that element of qualitative, right?

So how do you not just understand what's happening, but the why it's happening across all different disciplines, employee feedback, consumer feedback, schools, nonprofits, you know, the use cases are just fabulous at SurveyMonkey.

And, and then the third factor for me is always like, what am I going to learn?

And it was really interesting opportunity because I was the 18th employee, but yet it was doing $20 million of revenue already with an extremely high EBITDA.

There was a huge opportunity to globalize the business. There was a huge opportunity to build new products.

And so, you know, across the six and a half years, we grew the revenue 200 million, grew the team, and it was just a really fun experience to scale that business.

Yeah. I mean, it's amazing. I think for myself, and I can imagine almost everybody who's listening today has taken a survey on SurveyMonkey.

I was using SurveyMonkey as an intern in 2001. And it's just, it's one of those products that has become such a fabric of the way we capture and share information.

And the diversity, like for me, as a product leader, one of the things that I always find really interesting is the diversity of problems to which you can apply the solution and the flexibility of the product.

Well, and the fact that everybody's voice gets heard. Like if you think about in that, you know, when you think about diversity and inclusion, unfortunately, it's often the loudest voice, the squeakiest wheel.

And what that survey allows you to do is let people's voices be heard who aren't, who aren't, who are not always willing to raise their hand or speak the loudest, right?

Yeah. And from a tech perspective, it was really interesting because it was a completely very, it was like, it was not a super modern system.

It was like one single database.net.

There wasn't even necessarily a backup. And so we got to modernize the whole platform.

We moved everything to Python. We moved everything into virtual, into the cloud, you know, with all the containers.

And it was just, it was a really fun experience to also redo the tech stack while we were growing the business.

So there are a couple of, there are a couple of different directions I want to go on here because I'm like, oh that, and that, and that, and that.

So just, I mean, just to your moment there on the transformation of the tech stack, like going back to sort of Evite and again, that image of you plugging and plugging and stuff like that.

And then kind of being a part of this moment that I think so many people today are actually still in the moment of, right?

Which is transforming their infrastructure to containers, to cloud and stuff like that.

You guys were really on the forefront of some of that.

What are some of the kind of early challenges that you guys faced in that?

And how did you kind of, how'd you decide to bite the bullet to do it?

Because there must've been a moment of sort of risk and reward in there.

So the biggest first thing we were doing was we knew we wanted to do a platform rebuild.

And a lot of that was actually about hiring talent, you know?

So we, it had been, you know, a .NET shop from Portland and we were, we were kind of going to take, kind of do SurveyMonkey 2.0 here in Silicon Valley.

And I did a lot of research on what's the best place we can find talent.

And it was at the time, you know, this was 2009, 2010. It was really around, you know, Python and moving, you know, moving to more open source database structures, starting to think about, as you said, starting to think about virtualization and starting to think about really, you know, DevOps wasn't really a word yet.

No, it wasn't. It wasn't a thing. No, it wasn't. But it was starting to think about how do you create more productivity among your engineering team?

It was a transition period.

You know, I think it was, it was five, six years for us to get the platform fully migrated, both from a technology perspective, getting everything into the cloud.

And so it was, it was quite a, it was quite a process.

Yeah. Yeah. And it's, it's one of those things as a, as a, as a product leader, you know, I think a lot about the importance of these sort of platform transformations, but the need to change, you know, the metaphor you always use is like changing the engine of the airplane sort of mid flight.

Like, I mean, how did you get, how did you think about structuring that such that it was basically kind of a non-issue for your users?

So, you know, the most important thing also is to just continuing to drive the business value.

And so, so how do you tie the technology projects that need to be done to actually also delivering financial and business results?

So for example, one of the first things that we did is that the business was completely us -based and there was just massive opportunity to internationalize.

So the first thing we needed to do was rebuild the entire system for commerce, right?

To just take payments so that we could take national currency, international payments.

And so what we did is, is that we did it, you know, started building out the microservices, you know, area by area of the product.

And as we were doing that, it was also building in the functionality we needed to drive the business forward.

And by the time I left, it was about, it was, it was almost half and half in terms of the track from U.S.

versus international. And that, so that led to quite a bit of growth.

So what I always, you know, my thought process is that just doing tech projects, you know, it doesn't drive the business, but if you actually tie, okay, we're, as we're doing this, we're going to think about what actual business value can drive, the customer value we can drive.

Then when you release it, even if it has some of those bugs or it has some of the, a little bit of hair on the ball for the customer, they're a little bit more forgiving.

And so that's kind of the way that we were thinking about it and why it took us a little while to get it done.

Yeah. Well, as you move, move at the rate that you can, I want to come back to something you were saying a moment ago about the importance of, of tools like SurveyMonkey in really ensuring that everybody's voice is heard.

Right. And, and a lot of what we talk about today from a product perspective is really thinking about how do you build for, for sort of diversity and inclusion?

Was this an intentional decision on the part of, of the team and, and how did the team talk about it?

How did you guys think about sort of the, this kind of quintessential, like to me, it's like, this is really a key part of the essence of the product.

It really was. And it was something that was really important to Dave actually, right from the beginning.

You know, and part of what, when he was recruiting me, I still remember that was part of the conversation, which is that what we have the ability to do is help people make decisions with the best data and a broad set of that data.

And it's not. And so we always made sure that when we were thinking about user testing, when we were thinking about usability testing, that it was that broad swath of the customer because you wanted people across all different segments to actually have that, that opinion.

And the thing is, is, you know, so much shows, especially when you think about women, when you think about people of color that, you know, they're not always willing to stand up in the room and make their voice the loudest.

So I think that collecting data in a way that can be anonymized, collecting data in a way that lets people have a thoughtful versus always off the cuff.

Right. I mean, that when you start thinking about, you know, that was, that is a good thing about SurveyMonkey.

And what it also provide with a product we built when we were there was a benchmarking product, which also gave you comparatives, right?

Because if you don't know, you know, we ask all these questions about now, like people are starting to ask all these, you know, D&I questions, but if you don't know where you rack and stank against other people, you don't know if you're doing well or not.

Yeah.

Yeah. That's amazing. And then I want to make sure we get a chance to talk about Gixxo because Gixxo is so cool.

So, so, so then the shift from, from SurveyMonkey to, to doing your own thing again, to Gixxo, talk a little bit about that shift, that inspiration, like talk about that moment.

So the unfortunate inspiration for the, for the product for me and wanting to think about health and wellness was Dave passing.

So, you know, he was 47 with two young kids. I was, I think, 38 at the time with two young kids.

And I started to think about, you know, for me I wanted to think about how, again, how can we use technology to help people from a health perspective?

And it just so happened that my co-founder from Evite also at the time, he had really gotten back into running and, and he was open to do a new thing and he's brilliant.

And we worked together super well. And so we teamed back up and the thing that we saw in the health and wellness market is that the solutions that were working well were very targeted at the wealthy.

So you had the, the Barry's Bootcamp, the SoulCycles, the Pelotons of the world.

And these were great products.

You know, you went to Barry's Bootcamp and it was super engaging and you really had a good experience, but it's $30 a class.

It's only on the coasts. And it takes an hour over an hour of time.

And so we had the vision was, could you use technology to democratize access to these amazing trainers and to that experience?

So great music, great trainers, a good class where you're just driving through it.

And that's what we built with. We built it originally with Gixxo.

We recently got acquired. It's now OpenFit. But we, we built essentially live trainers who are sitting in front of large monitors.

You have the option whether to either turn your camera on or they're monitoring a walk or run outside, and they're giving you real-time feedback about how you're doing real-time encouragement, you know, correcting your form.

And there's this awesome music playing in the background.

And so we tried to say is, could we give people who either don't have an hour and a half, aren't intimidated to go to the gym?

Like I hadn't gotten in a while and I certainly didn't, you know, walking into the SoulCycle class, I was like, oh my God, I'm doing this for market research.

And that's all, you know.

Loose-fitting clothing. I'm wearing loose-fitting clothing, loose-fitting clothing.

Exactly, you know. And, but you know, it's intimidating.

And so how to create a space and a community for people where they can exercise, they can get back to their health, they can think about their wellness, they can start thinking about their nutrition, but it's in a supportive space and also with real connections.

Because the classes are live, we have mothers and daughters that are doing it together.

We have best friends across the country, you know, your sisters.

And that is really exciting, right? Because you're bringing people together to do something, to be active.

Yeah. I think about the, again, from like a product nerd perspective, the, again, sort of the underlying complexity that you had to navigate to build something that was so simple and intuitive and easy to use for people to be able to pick up their phone and basically do a guided run with their mom on the platform.

What are some of the, what are some of the technology challenges that you guys faced in kind of building this platform?

Yeah. So, you know, there's a huge amount of technology challenges in the live class side.

I mean, so if you think about it, like what happens when somebody like goes through a patch where they don't have connectivity, right?

How do you make sure that, that, you know, that as people are sort of, you know, people are different, wifi is different connection.

A lot of what we were trying to figure out was around the connectivity issues.

And then also just the accuracy, like if you're running outside, we use both the GPS, the step counter, and a couple of things off the phone.

But, you know, suddenly you're in San Francisco with large buildings and the GPS is bouncing everywhere.

So how are you normalizing that data?

How are you thinking about, so, you know, you see one pace that's really high, one pace that's really low, but you're trying to give that feedback to the customer in real time, right?

It's not smoothed out over time. So we spent a lot of effort to try to make sure that it was that strong consumer experience on the technology side.

It wasn't necessarily the scale issues because our classes are limited.

So in the sense of like, we only limit, we limit the classes to have about 40 to 45 people in them.

So that the trainer can have, so we didn't have the same scale issues, but it was more about the accuracy because you wanted to give it to that customer.

And the product side, the bigger thing that was a question for us is when people find it really strange, right?

Like what this idea that like somebody was like in your ear and watching you, like, is that going to be something that people were uncomfortable with?

And so what we did is we actually built just a very simple prototype.

I mean, you couldn't even authenticate, you couldn't even register.

It was just like, go into our beta class, test it out.

And we spent the first three or four months building just that prototype and do a whole bunch of product testing and market research.

And then we went and we raised capital because we wanted to validate that first, that business assumption and product assumption and the tech around that live class piece.

Yeah.

And we have just a little over two minutes. So I wanted to make, no, that's good.

No, but so I, but the thing kind of coming back just sort of bookending it to the conversation we had at the beginning about Evite, the thing I thought about a lot when I was using Gixxo was the community.

How, how did you go about building and thinking about and supporting the community and the connectivity within that community and the way that kind of the technology brought the people together?

So for us and for me, one of the most important things around the community was that it was supportive that, you know, we weren't necessarily focused on this already fit customer who wanted to, you know, go out there and be super competitive and pat themselves on the back.

We wanted to make sure that we were there for people.

We had five minute classes, 10 minute classes, 15, 25 minute classes.

So people could fit it in as they went. And it was okay to have, you know, your kid walking through to have your dog in the middle.

Like it created that ability for people to do it in their own space and their own comfort.

And that allowed us to expand in terms of the demographics.

So, you know, if you look at gyms, they're, you know, they're not very inclusive in terms of people of color.

And so it, it allowed our product to create that community.

And that was something that's really, really important to us.

And we focused a lot on the community within live classes and actually now on OpenFit, we're starting to focus also on how we bridge that community between classes.

That is amazing. I want to thank you so much for taking the time today.

It, you know, I'm just, I'm so inspired by, by the work that you've done, by the way that you've built these, these technologies that, that really help bring people together and, and how you've, you've taken the technologies that exist in the moment and pushed them to their boundaries to make those seamless experiences possible.

So thank you so much. It was really great chatting.

Thanks. Nice chatting. All right. Take care. Bye. Bye. Bye.