Cloudflare TV

Legends of Tech

Presented by Chris Georgellis, Sierra Dasso
Originally aired on 

A weekly podcast where Chris Georgellis, on the Customer Development Team, interviews people across the tech industry. From veterans, to hall of famers, day to day tech industry people as well up and comers. Get to know them as individuals, find out what drives them, how they got into tech, and what they see now.

This week's guest: Sierra Dasso


Transcript (Beta)

Hello everyone, welcome to Legends of Tech on Cloudflare TV. Today we have an awesome guest.

She's a teacher, she's worked for companies like ADP, Google and now at Cloudflare.

She has a pet puppy and she studied psychology and business. Please welcome Sierra.

Hello, how's it going? Doing well, enjoying life in Sydney. It's beautiful here.

Great, well thanks for joining today. I've been looking forward to this session all week.

So, like all things, how you been? How's life treating you, I guess in today's circumstances?

Honestly, I spent a lot of my time feeling grateful, right?

Grateful to working at Cloudflare, grateful to work near the beach.

Grateful that restrictions here in Sydney aren't too intense and that people are pretty, you know, aggressive with following the rules and staying safe.

So, I've been just happy with what we have.

That's great. Well, it's good to hear you're in high spirits and, you know, obviously being in Sydney, we're not as locked down as our brethren down in Victoria.

So, it's always good. So, like all things, I actually, you know, I was doing a bit of, you know, background searching, not stalking, just doing a bit of searching.

I've noticed a bit of, you know, some really interesting paths.

But, you know, I guess from, you know, for the viewers here, I'd love to hear how did you actually get into the tech industry and what was your path to where you are today?

Yeah, good question. So, how far do you want me to go back on why I was interested in tech?

I can go far. You can go as far as you want.

Okay. So, I suppose I always knew I wanted to work in Silicon Valley. I thought it was going to be for industrial organizational psychology.

So, I thought that I was going to work in a team at a company like Google, innovate new ways for people to work, to improve their life experience at the job, improve their productivity.

I was going to do research and study making employees happier and healthier and more productive.

That's what I thought my life was going to be. So, I always knew I wanted to work in tech in Silicon Valley, mainly because it was the most innovative employment sort of scenario.

So, that's where it got started. After graduating with a psychology degree, I realized that research is really boring and you don't engage with other people.

So, I found that it was a lot of alone time and not as interesting as I imagined, but that you can actually make a larger impact by dealing with people.

So, that's really where it started. Fantastic. So, look, in terms of where you grew up, is Silicon Valley, I guess, is that what everyone talks about growing up as a kid or when you're in high school when you're studying?

Do all roads lead to Silicon Valley? I think so. Yeah. So, I grew up near Berkeley in California and San Francisco, especially as a younger person, was attractive.

However, it really felt like that's where big skyscrapers were, right?

Corporate offices were in San Francisco. Well-established companies, but the new, exciting, innovative, progressive companies were all in Silicon Valley.

And I knew that that really aligned with what I wanted to be a part of more.

And so, yeah.

So, depending if you were on that path of risk and new and exciting, then yeah, Silicon Valley was really the only direction to go.

Way to go. That's great. So, tell me, how did you actually get your first job within the tech sector?

What was the path and how did you find your way into your first role?

Yeah. So, use my relationships, right?

I knew I wanted to get into technology and I would say my first technology job would be Google.

So, using my network and expanding to who I knew that was at Google and, you know, it was really colleagues, right?

Not manager. But just to understand the role and understand what role was a good fit for me.

Sales was really what made sense. It's also what all of my previous experience had been in sales, even though Google is not really known for being a sales company.

So, I did lots of research on understanding what I should apply to and when.

So, understanding that there is even headcount. There's many, many job listings and half of them aren't real.

And it's very painful. Google gets, you know, tens of thousands of applications probably every single day.

I don't know how many. But they review and accept very few.

So, you really need to have the right timing and have some insight.

And so, I used that and got my first role at Google selling AdWords.

So, advertising. Okay, great. That's awesome. So, you know, always from afar because, you know, Google for us, especially being here in Australia, was such a far thing.

But you heard all these stories. Pinball machines, scooters, free lunches, you know, take a nap whenever you feel like.

But then, you know, that's, I guess, the perception from external.

But when you actually started there, what was it like?

Was the hype that I was feeling the same in there? Was it actually like that?

Well, yes and no. Yes, there are pinball machines. There are indoor golfing.

There's beer on tap. There are nap pods and massage chairs. There's actually a masseuse there that you can sign up for once a week.

All of that, you know, unlimited food, all that's very real.

And it's very there. I think the part that I didn't really consider ahead of time is how competitive everything is and the drive for perfection.

And what I mean by that is sometimes there's lots of underemployment, right?

So, there are, it's so competitive that anyone will take any role that they can get.

So, you may have someone who's been a director and had incredible experience, but they're actually, you know, reviewing the video content on YouTube, right?

So, and that's an extreme. But you find these people who are highly talented doing jobs that don't use their talent, but still the competition to be really successful in that role is really taxing.

So, yes, it is really wonderful and I loved working there.

The intelligent other people that I was around was incredible.

I found a lot of people were really underutilized. Yeah, right.

So, what was it like, like, you know, coming from a, with your background and transitioning into Google, you know, did you have a lot of base understanding of things that transferred into the role or did you have to learn things from scratch?

What was the, what was that process like? Yeah. So, sales is the same no matter, you know, what you're selling in regards to human behavior, right?

Well, it can be different, but there's a lot of similarities.

So, I got to take that with me on human behavior and helping people make decisions and solving challenges and things like that.

Learning all of the technology of AdWords and learning the value and learning the proposition that we were putting forward was absolutely new.

I think the, a lot of it was also learning how to work within Google and get things solved.

So, I had been a bit more, you know, individual contributor, but then once I moved towards Google, the solution was very multi-channel, right?

So, you needed strong relationships in all of these different departments in order to solve a problem for a customer.

So, that was a really new thing and one that was so important into my success.

One of the challenges at the beginning, once I got that figured out, started being more successful.

Yeah. Fantastic. And you spent, how long were you at Google for?

Three, four years? How was your time? No, a year and a half.

Yeah. So, a year and a half. Yeah, it was a short period. I think mainly for the lack of upward opportunity.

So, I had looked at other roles. I had actually really wanted to move away from advertising.

Advertising is a wonderful industry, but you sell something that you want to be true.

You sell something and you try to make it true in regards to results for the customer.

I wanted to move into technology where you sell something that works.

You sell something because the customer can actually use it for their business and it delivers immediately, right?

So, I wanted to work for GCP. I interviewed there and basically, I didn't have enough experience, right?

I had no experience in infrastructure technology. So, I looked at the company that Google had invested the most in and that was Cloudflare.

They had invested almost $100 million into Cloudflare and I assumed that GCP would know a good company in the industry.

I learned a lot about Cloudflare, decided to get my experience there in order to go back to GCP eventually and realized that I think I won the lottery here and I'll be staying at Cloudflare and not making a change.

But that was the original transition there and why the stint at Google was sort of short.

Yeah, right. Fair enough. So, for you, Cloudflare was – you saw Cloudflare as a stepping stone to get some experience and go back to Google.

Yeah, I know. It's not really fair for Cloudflare, but I think they've got me hooked.

I mean, look, absolutely. So, you've made the change to Cloudflare.

So, what was it like going into Cloudflare? What was the transition like and were the companies similar in terms of culture or things like that?

What was it like for you?

Yeah, gosh. A lot of differences, right? So, you're going from Google, which I think, I don't know, 50 ,000 employees, maybe more, but even in Mountain View, there's over 20,000 employees and vendors and contractors and stuff, right?

So, you're going from this gigantic organization to one with 400 employees, right, at the time.

The sales team was also small and it was very scrappy, right, in the sense that this was a hunter role.

A lot of people didn't know who Cloudflare was.

At Google, everyone knew how I was. Everyone answered my call and met with me, and I was rejecting customers just as often as selling to them.

So, at Cloudflare, it was a huge transition to make our brand known and to find customers that really wanted something like our solution to solve their infrastructure challenges.

And I was also junior, right? So, I didn't have inbound liens.

I didn't have a BDR. So, it was a very hard role, but really rewarding. So, I found certain industries that no one else was targeting and targeted those and found some success from the outskirts, I suppose.

So, very, very different, but a lot more rewarding being able to make a lot more impact and having a lot more freedom, all things I appreciate.

That's great. That's good to hear. So, you joined Cloudflare.

You're having a good time. So, what made you decide to make the jump to DownUnder?

Yeah, yeah. So, I guess I knew that I wanted to live internationally. I knew I wanted to work internationally.

I didn't really care where or how or when it happened.

I just knew that I had to, right? So, even when I started at Cloudflare, it was one thing that was really important that they had all these international offices that they had in London and Singapore and all these places.

And I knew I wanted to prove myself in San Francisco and take that to another country.

One day, Aliza Knotts came to the San Francisco office and did sort of a talk about her career and what she's doing as head of APAC.

And I emailed her after and said, I have to work for you.

So, you know, it was really by her recommendation. I thought I would be working in Singapore.

What a challenge, how different it would be, huge culture shock, and I would learn so much.

And Aliza knew better and she said, you need to go and live and work in Australia and you will love it and you'll be successful.

And it couldn't have been more true. So, she really sort of guided that.

Fantastic. So, how was it once you jumped on a plane and came here? What was it like?

I guess, were there similarities between your approach? What was the learning curve like in terms of the culture and the customers here?

Yeah. Good question.

I would say things are pretty similar in the sense that we're solving the same challenges, we're engaging with the same individuals.

There are cultural differences, but if anything, they're more welcoming and more interested in discussion.

I think the biggest difference in the market here is that there's less competition, there's less incumbent solutions.

So, we really get to walk in with a new customer and take some sometimes legacy solutions or solutions they've had for a long time and say, here's how we do it better.

And solving that and creating such a big step for the customer, one, takes a lot of education and more time.

So, that was new for me. So, longer sales cycle, but a better reason for them to buy.

So, we're making more impact for that customer versus just pushing out an incumbent, which was an okay solution and we have a better one, right?

We're introducing a more progressive solution for them, which is really quite cool.

And I love that everyone agrees to have a coffee with me. I love that when I ask, people want to have a beer or have a coffee and don't find that as intrusive or time consuming as in the United States.

There's really that, I don't know, aversion to going out and having a good time.

Yeah, well, that's good.

We are pretty laid back here. But I guess, in terms of, I guess, your approach, you went into Cloudflare, you had to build out, I guess, a different perspective and you went and attacked markets that no one was attacking.

What approach did you take here in ANZ when you rocked up?

Yeah, okay. I think that my first approach was more traditional to Cloudflare.

So, Cloudflare traditionally does very well in SaaS solutions.

We do very well in Internet -first companies.

And that was so saturated in the U.S. and the San Francisco market and what I was working before.

But here, it wasn't. And so, taking that industry that we are so well -placed to solve challenges for was really my focus.

And I got significant response there. So, in the States, I went for crypto and sometimes unusual content, right, because no one was reaching out to those customers.

But here, the traditional use case of Cloudflare, our core solution was not already saturated with a different competitor.

Yeah, that's great. And what do you love about living in Sydney?

I love the beaches. I love that I live within two minutes of the dog beach.

And I really love the people. People are really just happy and healthy and want to live life and have some work-life balance, which is really beautiful.

Everyone that I've met, whether there's so many expats, but also all the Aussies, everyone's been just quite great.

So, yeah, the people and the beaches.

That's great. So, did you know that we had great beaches and great people before you came across?

Honestly, I didn't know anything about Australia. It's almost embarrassing how little I knew about Australia before I agreed to come here.

I knew about kangaroos.

I'd seen some pictures of the Opera House, but I really didn't know anything.

And you know what, I think I knew that it would be good. And I knew I would find a way to make it great.

But I didn't really know much at all. And I guess coming here, was there anything that came out of left field?

Was there something that you just didn't think that was here or were there any surprises when you did come to Australia?

Any surprises? If you don't expect anything, then nothing is a surprise.

It's all been, everything's been, I guess, a good surprise as you've learned and discovered more about the country.

Yeah, absolutely. I rented a van, took the puppy.

We drove to Byron Bay and really explored the country and got to see tons of places in between.

So yeah, it's just been, it's been constantly surprised with new and beautiful places.

I think the nature here is my hobby on the weekend. You know, how do I explore something new and beautiful in New South Wales?

Well, at the moment in New South Wales.

So yeah, I think those have been kind of where I find some surprises.

That's great. Actually, we do have a question. I think it's about, I'm just going to hit play.

Just give me a second. This is Jason. I'm calling from San Francisco.

My question is for Sierra. I heard Chris mention that you've got a new puppy.

I'd like to hear all about it. What's his favorite toy? Did it devour his favorite toy and you had to get a new favorite toy?

What breed is it? All that stuff.

So looking forward to hearing about it. Yeah, I did. I got a COVID puppy. His name is Leo.

He's a Cocker Spaniel and his favorite toy is probably my hand. He loves chewing on my fingers.

We try to make sure he doesn't, but especially as a puppy, he has those little needle teeth and all he wanted to do is chew on people.

So we've got a number of other toys.

I guess the squeakers are the worst, but we're trying to teach him how to play fetch.

It is a slow process. He likes to hide the ball instead of bring it back.

So we'll try to find out as he grows up what his favorite toy should be.

Right. Well, thanks for the question, Jason. It's awesome. So look, in terms of what motivates you, I guess what gets you out of bed every day and what helps get you into action and motivated to kick ass in our world?

Yeah, yeah. I suppose I'm definitely motivated to kick ass.

I think that there is just an overall drive to take on things that are impossible.

Looking at our goals as a team, looking at my own goals, it sort of seems daunting, especially when I arrived here, right?

So the goal that I had in San Francisco and the goal that I had here was about double, more than double, almost.

Yeah. So it looked impossible from the outside and just killing it anyway is what excites me.

And I do love my customers, maybe too much.

I love working with them. I love that there's that strong relationship and trust.

So, you know, getting up to deliver really is a big part of that.

Deliver for my team and deliver for my customers and myself. You know, the pride that you feel from achieving something that's difficult.

That's great. That's fantastic.

So you studied psychology. Have you, I guess, you know, studied psychology.

Has that helped you, I guess, in context of what you're doing today?

Yeah. Well, unfortunately, my dad tells me that I use my psychology degree for evil, right?

So I don't think it's that true.

I mean, he's sort of implying that, you know, I learned human behavior and then now I'm in sales.

But, you know, I think that you can use it for good.

Understanding what someone is saying between the lines can help you really, you know, and get them to open up and get them to tell you what their real challenges or what their real hesitations are or whether they're not interested at all.

If you can't understand who you're talking to, because everyone communicates differently and you don't connect with them, nothing's going to be achieved.

You want to build a new project with someone.

And if you don't understand each other and can't help them see your position, then you don't get anywhere.

So, yes, my psychology degree does help to understand, you know, human behavior.

But I hope that I am entrusted and use it only for good.

I mean, look, it's good. I mean, at the end of the day, we're in a we're in a business where we're dealing with people and everyone's their own individual, everyone with their own needs.

Yes, there's a technology element, but at the end of the day, it's people, different people.

And, you know, if you can read someone and you can help someone, I guess that's the key part.

But yeah, maybe your dad's saying you can use it for evil, but it's also possible.

Yeah. Well, you know, you got to you got to you got to find a middle ground and you got to you know, you got to trust.

I don't think anyone's getting tricked here.

You know, these are CTOs. I'm not going to be able to manipulate them to buy hundreds of thousands of dollars of Cloudflare.

Right. So what's your advice for people, I guess, you know, that are in a similar position to you or, you know, looking to get into, I guess, into the tech sector?

You know, it's always a daunting thing for some people, especially if they've studied something and then they've gone, all right, what do I do now?

But, you know, you've gone through, you've studied, you know, you threw yourself into Google.

Now you're here in Australia. You know, what sort of advice do you have for, I guess, for the up and comers or people that are coming through the industry?

Yeah. One of the main things that helps me is ignoring all the reasons that I can't do something.

Purely ignoring them and doing it anyway.

Right. So, I mean, there are very few females in a role like my own.

And there might be a number of reasons that you might think a woman wouldn't be able to do this role or engage with all male buyers.

Right. Almost all male buyers.

Right. So, or, you know, being a woman, leaving your own country and your family and living alone.

Right. There are a number of reasons that would come up, maybe a hundred, right, on why that's not a good idea or why it can't happen.

If you just ignore all of those and look at what you want and determine what you want and go ahead and get it anyway.

Use your relationships. Use other champions.

Leaders like Aliza is a great example. You know, someone that you relate to that is there to help you achieve the things that you think, you know, or others might think is impossible or, you know, a big challenge.

I think that really helps if you just ignore it and don't think about it.

By the time, you know, some time passes, you've achieved a lot.

Because you weren't, you know, afraid. Now, look, it's great advice.

I think, I think it's really important. And you're right. I guess, you know, our industry is very one-sided, very male-dominated.

I remember even when I was studying, there was like, you know, recruitment drives to try to promote women in the industry.

But for whatever reason, it just wouldn't happen. So, you know, it's always good to see people like yourself promote and I guess give people the possibility, you know, the possibilities are there.

It's, you know, don't ignore the, I guess, what may be a thought and actually just go for it and do it.

I mean, I think that's how it should be, which is great. And it's good. And I think you being an advocate, especially within the industry here in Australia is very important.

I think, you know, we need more Sierras in the marketplace. We need more Sierras pushing, I guess, pushing the message.

But it's really good to hear, I guess, that approach, you know, because I think a lot of people, not just women, but just people in general.

Whatever your reason is, whatever your reason is, you can't do something.

Just ignore it. Forget about it. And have you, I guess, by doing that, have you come across anything that's been, like, have you always overcome your challenges or has anything come up where you've gone, geez, I've really taken too much or bitten off too much that I can actually chew?

Yeah, I mean, of course. Right.

But, you know, I would say you fall down, you fail, you know, maybe you don't get paid one quarter, you know, or whatever that might be.

Maybe I, you know, I tried to buy a house, but something went wrong and I didn't spend enough time and I lost that house.

Right. So there are things you're going to fail. But the people that are there to pick you back up, the people that are there to make it okay again is way more than you can imagine.

The fear of something bad happening when it actually happens, you know, a week later, it's not that bad.

Some things have been solved. Yeah, it sucked. But, you know, it doesn't end up mattering in your life.

What ends up mattering is when you risk, when you take that initiative, take on something that's too big to chew, even when you fail, it's still worth it.

That's great. Great advice. And I think, you know, I think a lot of people need to take that approach as well.

So that's, that's brilliant.

Yeah. So I hear on the side, you've also become a bingo host as well. So I'd love to hear a little bit about your bingo hosting process.

Yeah, well, I wonder if any of the bingo hosts are on from last night.

They gave me a bingo guest.

They gave me some encouragement for the interview today. But yeah, Cloudflare, we hosted a whiskey tasting and a bingo night.

So we had a lot of leadership on prospects to Cloudflare, people interested in learning on what we do.

They learned about some whiskey, had some banter and some laughs, and we had a couple of winners on to our bingo game.

So it was definitely a lot of fun. And, you know, I think taking advantage of being remote is great.

You can have more people online, more people on Zoom that you can engage with.

So just a really, really nice experience.

I hope I get to host another one soon. Fantastic. And just for everyone's, it was a COVID safe event.

It was all virtual. High-fiving in a room together playing bingo.

So just for everyone's peace of mind out there. That's fantastic.

Well, Ciara, look, it's been brilliant speaking to you. Obviously, we've been working together now for the last nine months.

And I've learned so much.

Hasn't it been a year? Pardon? I feel like I've known you forever. The baby's come, everything's merged.

So I can't really, I don't know what day it is today.

So I've learned so much about you. So it's just been great to see, I guess, to see you in a different lens outside of the, I guess, you know, we are in the work environment, but it's just good to hear, you know, your story, what you've done.

And I guess, you know, it's good inspiration for others to follow in terms of, you know, having a plan, putting your mind to something and just ignoring what may not happen.

And, you know, just get out there and go for it. Yeah. Right. So again, thanks.

Thank you. I'm hoping that we can have a part two to this conversation.

I've got so much more that I want to ask you, but I guess, you know, we have 30 minute time.

So thank you again for your time. Really appreciate it. Have an awesome Friday.

And to all the viewers out there, thanks for tuning in and we'll see you next week.

See ya's. Thank you, everybody. Bye bye.