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Episode 8 - Ryan Bonnici

Flying Blind: From Flight Attendant to CMO

4 Key Learnings – Ryan bonnici

How to optimize a “stepping stone” job for future opportunities.

When to take the next leap, and the order he recommends to do it in.

The top 3 things to do when looking at your next career move.

Hear how he went from college student and flight attendance to working at Microsoft by meeting an executive on an international flight he was working.

About this Episode

Ryan has a unique path to rarified air. He started as a flight attendant while still in college as a way to pay the bills and see the world at a young age. He met an executive of Microsoft on a flight one day which launched him into a career in Marketing for some of the worlds largest and fastest growing companies. Now he’s the CMO at G2Crowd, a software reviews site that just raised $50 million in venture funding and seems to be the next big time in B2B tech. Hear story is fun, but also methodical in his ascension into Marketing leadership.

“I think what I’ve done and what I’d recommend other people do, is try and grow and join a mid size company or a bigger company, whereby you’re working under someone that you really admire and is incredibly smart and good at what they do. Because I think that’s really the most important thing. It’s like the learnings that you will get and the autonomy that you’re getting from being able to try different things and new things.”

Ryan Bonnici

Listen to Episode 8 - Ryan Bonnici

Flying Blind: From Flight Attendant to CMO


More on – ryan

Ryan is the CMO of G2 Crowd, but he got his start as a flight attendant for Quantus Airlines, flying around the world and seeing the sights while he was still in college in Sydney, Australia. Got out of college, went straight to Microsoft, Microsoft into Exec Target, which ended up getting acquired by Salesforce, Salesforce over to HubSpot, which then IPO’d, he’s got a wild journey with some really interesting learnings working for some of the biggest companies in the world, and some of the most innovative companies in the world.

Connect with ryan

Products Mentioned

  • The Power of Now by Eckhart Tolle
  • Trust Me, I’m Lying, by Ryan Holiday
  • A Little Life by Hanya Yanagihara
  • Muse Meditation

Max Altschuler:

Welcome to this episode of the career hacking podcast. On today’s episode we have Ryan Bonnici, CMO of G2 Crowd.

This episode is brought to you by Sutra Superfoods.  Sutra is a healthy and beautiful superfoods latte and alternative to coffee. It gives you balanced and natural energy without any caffeine or stimulants. I love Sutra Gold, with Turmeric, Ginger, & Maca root in the mornings. It tastes like a spicy chai. I drink the Sutra Black in the afternoons with activated charcoal and raw cacao, and it tastes like a healthy hot cocoa. It’s beautiful too. It’s great for travel because it comes in stick packs and I can have it easily on planes, trains, and in hotels. And it can be made hot, iced, or even into a smoothie. It’s definitely my new favorite drink. Check it out at sipstura.com. And if you haven’t already, check out my book, “Career Hacking for Millenials.”

Really fun episode for you today. We have Ryan Bonnici here. He’s the CMO of G2 Crowd, but he got his start as a flight attendant for Quantus Airlines, flying around the world and seeing the sights while he was still in college in Sydney, Australia. Got out of college, went straight to Microsoft, Microsoft into Exec Target, which ended up getting acquired by Salesforce, Salesforce over to HubSpot, which then IPO’d, he’s got a wild journey with some really interesting learnings working for some of the biggest companies in the world, and some of the most innovative companies in the world. So we’re really excited to talk to Ryan today. Ryan, thanks for joining us.

Ryan Bonnici:

Thanks Max. It’s great to be here.

Max Altschuler:

So you have a pretty action packed career, if I don’t say so myself. In the marketing space, in the tech space HubSpot, Exact Target, Microsoft, Salesforce, some of the biggest companies in sales technology, and some of the biggest companies in the world today. You’ve been a marketer pretty much all your career starting as a flight attendant though in Australia. We’re really excited to hear your story. So why don’t you tell us a little bit first about what it is that you’re working on right now. You’re the CMO of G2 Crowd. What is that?

Ryan Bonnici:

I’m the CMO of G2 Crowd, it’s my dream job. So I’m very happy. For those of you listening that don’t know about the G2 Crowd, but I’m guessing most of you probably do or have come across our site some point in time, we’re basically the world’s most visited site for software and service technology. So we have millions of people coming to us every month that are looking to buy a new CRM or your marketing automation tool or a new [inaudible 00:02:53] accounting tool. Basically any kind of software that you could need for your business is listed on our site and hundreds of thousands of uses of those different pieces of technology are reviewing the software that they’re using at their business live in real time. So we’ve got this really fascinating data set around the different industries and about the different competitors and who’s growing and who’s slowing and who has customers that love their product and whatnot. So, really fascinating company.

Joined last year and so I’m just still kind of in the thick of things, really Max, and getting a lot of new programs up and running. So, one of the big key areas of focus for me and my team is helping grow our traffic to that website, so getting more and more millions of users coming to our site for their software and service needs. And then I’m also really focused on building a team in marketing to support our sales team. We’re growing incredibly fast and not only on reviews and headcount and revenue, which is really exciting, but really helping support that sale sales to turbocharge sales to 2018 and 2019. [crosstalk 00:04:03]

Max Altschuler:

And it’s a lot like Yelp for buying software, right?

Ryan Bonnici:

A hundred percent. Yeah, if you’re going to a restaurant, you’re not sure where to go, you go on Yelp. If you’re sure about a new job you might be taking for a new company, you go on Glassdoor. If you’re not sure what software services could help your business, you come to G2 Crowd

Max Altschuler:

Awesome. So, that does sound like your dream job, considering that you’ve worked at some of these high profile software companies before joining G2 Crowd, and chief marketing officer at one of the hottest tech companies, especially B to B tech companies in San Francisco for someone, I’d say, what are you early thirties?

Ryan Bonnici:

I’m actually still in my twenties. I’m getting close to that thirty mark. I’m very lucky.

Max Altschuler:

That’s pretty freaking impressive. So I want to know, let’s get into your story, where do you start. You were born and raised in Sydney, Australia. Now you’re living over here in Chicago working for G2 Crowd. So let’s go back to Sydney, university. What’s the starting point for you?

Ryan Bonnici:

So I was one of those very off kids or teenagers that just always knew what they wanted be when they grew up, which is kind of annoying, I think, you know, most people never really know what they want to be and a lot of people, and a lot of my friends still don’t know. But I was just weird to be honest. I was just like, this kid, I remember being in high school and just always knowing I wanted to be CMO. I know that sounds really bizarre, like what kid wants that, but I always said. So I worked really hard at school and through college and I started college, I worked my butt off basically to get into a really good degree at the best uni in Australia and did my first year there and kind of was getting burnt out to be honest. I’d worked really hard at school and I was ready for a break.

And so at that time I applied for a role with Quantas, which is Australia’s largest airline and got accepted into their international division. And so I then took a year off from uni. I basically paused my degree and was a international flight attendant. Which was kind of bizarre, but it was exactly what I needed because I wanted some time off, and I wanted to just like explore, see the world and save some money. So I was able to visit and travel to some amazing countries and cities and I saved up enough money to buy my first investment property. So it was a really awesome year. And then after that year I realized pretty quickly that OK, I really want to continue with college and university and getting that degree so I could work. And so I then started doing full time university and part-time flying. So it was kind of an odd job to have while at college. But I would basically do my classes from Tuesday to Thursday and then Thursday afternoon, I’d fly out to LA or to South America or to Hong Kong and spend a few days there and then fly back and then I’d land maybe on a Monday morning or Tuesday morning and I would just go straight to uni and do more classes.

So it was kind of bizarre, but it was a lot of fun and it gave me a really unique outlook on uni life and was a lot of fun. I saved more money than I could’ve imagined. Not that it was a great necessarily paying job. But I was living at home at the time and so it was just saving a little mine.

From there I met an executive on board one of my flights in first class that worked at Microsoft who told me that Microsoft was hiring. I then reached out to Microsoft and went through that whole process. I thing about 2000 people had interviewed and they grouped it down to I think bout six or eight people that actually got jobs. Microsoft don’t typically take in university grads or people still in college. They typically will hire at like the 10 years of experience point. So it’s kind of rare for them to do that, in Australia anyways.

So, I started working at Microsoft-

Max Altschuler:

So what was that conversation like? How did you meet that executive on your flight and how did you connect with them in a way where it got you to that next meeting so to speak?

Ryan Bonnici:

Yeah, good question. It was a really long chat I guess. And I am just really passionate about business, I’m really passionate about marketing and so when I had a tech marketing exec on my flight, it was a perfect storm for just my curiosity. I think of anyone that’s in their job, when someone younger than you comes to you and is showing a clear degree of interest and asking you lots of questions, it’s impossible not to want to help them and answer their questions. I basically just remember having a really in-depth conversation with [inaudible 00:09:00] they work for Microsoft. I spoke with the Telegraph in the UK actually last month, for about 30 minutes and they did a really in-depth piece around how I recommend meeting and making business opportunities on board planes. Which goes into a whole lot more detail than probably we want right now. But yeah, it was a great chance encounter.

Max Altschuler:

So you meet this person, before we get into your time at Microsoft and the rest of the story, any really good like a go to cocktail party stories from your time as a flight attendant?

Ryan Bonnici:

No, not really. It was an amazing job. Flight attendants are a lot of fun. So we would go out on the town in new cities around the world which was a lot of fun. But when we were in cities it was more so hanging with flight attendants and pilots and then when you’re on board the plane, you would be spending more time with customers.

Ryan Bonnici: And I think it actually taught me quite a lot about customer service, to be honest. Which now as a CMO, obviously customer service is such a big part of marketing and leveraging your existing customers to close more customers and retain customers as [inaudible 00:10:21]. It was really interesting and fascinating to me actually because if you think of a big airline, right, the majority of the people that are engaging with customers, flight attendants and airport staff, they’re typically the most junior people at the business. So Quantas school had a really amazing and really structured program that I want to say was like a 10 week training program that taught us everything about etiquette with regard to economy versus business class versus first class, how to refer to wines, how to know what paired with what, how to deal with all sorts of situations as well as how to evacuate an aircraft. A lot of amazing training there which I still think about today because when you were such a big company as an airline is, you need to ensure that every single touch point that a customer may have, with airlines a lot of that is with people, is aligned to the vision of the business and typically the CMO or the CEO is setting that. So, something I think about it today. Something that I haven’t really ever had to deal with being in B2B marketing as much. That’s less of the case

Max Altschuler:

So you had some really interesting lessons learned. I always think about that like depending on what role you’re going into versus your job that you had maybe in high school or college. What can you learn, should you work in the restaurant industry if you’re waiting tables if you’re going to be in sales so you can get customer interaction? Or should you be a flight attendant if you’re going to work in marketing or customer support? So it’s really interesting that you got some things out of that that you’ve used over the rest of your career as you’ve become a tech executive and it’s kind of interesting to see that kind of transformation and evolution happen. Where you’re still kind of reaching into the bag of tricks from previous careers that are completely different.

So you get into Microsoft and you’re one of the few that doesn’t have a 10 year or anything like, so what does that training program, what does that job look like? First job out of college?

Ryan Bonnici:

It was pretty comprehensive, and Microsoft obviously they’re an amazing company and I think it was a great place for me to start and I learned and connected and was able to just grow from meeting so many smart people. I think what I learnt really quickly though personally for me was just that I love to be a part of a really nimble business. And once you get to the size and scale that Microsoft was at, it’s really difficult. And I’m not sure where they’re at today. A lot of my colleagues, I’d say probably about like 80 percent of the people that started with me then are still there today. So still love it, still obviously amazing place to work. But for me I’ve just realized quickly that I wanted to be working in a place where I could have more impact and more autonomy to do things that maybe were a little bit different but that were higher return potential.

So I moved from Microsoft then to Exact Target, they kind of poached me, I guess you could say. Microsoft at the time was Exact Target’s biggest customer. Exact Target obviously being one of the world’s largest email marketing companies, which was acquired by Salesforce a few years back. But at the time, Microsoft was their biggest customer, had a database full of millions of customers in contact around the world, so they used Exact Target. And I was a power user at Microsoft of that platform, so there weren’t many people that were super experienced with Exact Target in Australia. So Exact Target kind of tapped me on the shoulder, and it was perfect timing because they were still around, I wanna say like the 1500 mark, maybe a thousand [inaudible 00:14:18] mark, and I was going to be the first marketing hire in Australia and in Asia Pacific. So, you know, to me it was like the perfect opportunity given that I’d be able to really build out a strategy, learn and fail and make mistakes, learn a lot along the way.

I was with Exact Target for a few years before they were acquired by Salesforce. And what was really fun, I guess through that whole process, you know, Exact Target and Salesforce both go after pretty similar customers, larger enterprises is their area of focus mainly. And I felt like I really learnt that enterprise B2B marketing playbook, which leverages [CXO 00:15:00] dinners and events to build relationships between sales and prospects. It’s a very event heavy playbook I’d say as well, where you’re pulling in customers and having them get on stage and speak about how they use your product or service to do what it is that they do, and you use that obviously to nurture and build new relationships and new sales opportunities. It was a really fun playbook and I did that for let’s say five or six years between those two companies, and learnt a heap.

But then I also learned really quickly that for me, A, I wanted to eventually start my own business so I wanted to have for B2B SMB experience. And the main difference between the two, like between SMB and enterprise B2B marketing is typically that enterprise B2B marketing has bigger budgets. If it’s less scalable, it’s more one to one, which works really well for Exact Target or Salesforce, and you can afford to spend millions on big events and millions on DPR agencies and PR campaigns. But I always knew that I eventually wanted to run my own business and wouldn’t have millions of dollars to throw an event at PR. So, you know, for me it was really important to then flesh out that SMB marketing skill set.

And around that time HubSpot were launching in Asia Pacific. And so again, it was, you know, good timing. And I was chatting with them for about a year before I moved, with their CMO at the time, and got really excited about the company and the skill set that I would learn there. It was funny because I was chatting to our [inaudible 00:16:36] recently, who I still think of as a good friend. And saying how when I joined HubSpot from Salesforce, I thought I was a bit of a hot shot. I thought that was a great marketer, I probably would have rated myself eight out of 10. And then I learned really quickly that there was just so much to SMB marketing and scalable marketing that I didn’t know anything about. So really learned a lot at HubSpot over the last three years that I was there. It was amazing experience to be honest, and I feel super lucky to have been with them through so much growth. Now they’re public and when they launched on the New York Stock Exchange, I think the ticket was around $20, $30 a share and now they’re around a $120, evaluated around, $4 billion. So I’m just like so bullish on where they’re going and really believe in the team and the product.

Max Altschuler:

Would you consider going to HubSpot your MBA in marketing?

Ryan Bonnici:

Great question. You know, it’s funny. There’s certain companies that are known for certain things right now. Like if you’re a salesperson, the best company to kind of work for, I think, that will teach you really repeatable sales smart sales, consultative sales, but then also the aggressive sales and everything in between, is Salesforce. And if you’re a marketer, really the company to work for if you want to become a great marketer, I’d say is HubSpot.

I wouldn’t necessarily say it was so much of like an MBA of sorts, but I definitely learned a lot about how to build a scalable business and learn from some of the smartest people that I’d ever worked with. Many of whom had done their MBAs, mostly at MIT or Harvard. So yeah, I have just so much respect for that team. Some really great friends still there obviously.

Then from HubSpot I was kind of ready to then take what I learned over the last 10 or so years and pull it together and lead marketing for G2 Crowd. Some people think that eing in a CMO role from late twenties is kind of a bit crazy. But I think what’s really interesting, and one of the hacks that I’d say for anyone trying to hack their career is, I reckon what you really ultimately want to do is try and be a big fish in a small pond. And I was really lucky to live in Australia at the time. Typically the way tech companies grow, and I’m sure you’ve seen this yourself, once they’re scaling, when they’re having success in the US, they typically then the European office. When they start to nail that European playbook, then they’ll typically always launch an Australian office. And that’s mainly because right, like London or Dublin both speak English, business is done pretty similarly to the US. And then once they’ve done that then Australia goes next. And so if you can position yourself as the person that’s growing companies and is really skilled at launching companies in a certain region, I think that sets you up for success.

It’s weird, a lot of people have been asking me in the last few months, how I’ve been finding being a new CMO, and it’s bizarre in that it actually doesn’t feel really any different because I always kind of was doing the same thing. I was building end to end marketing strategy in Asia Pacific and I was hiring the teams out from being the first employee and I was building out the whole strategy. I was really fortunate at HubSpot and Salesforce and Exact Target to work for marketing leaders that were very autonomous and they gave me kind of the resources I needed. And then I could leverage what the US or the European teams were doing, but then also had the flexibility to do what was right for our region. So yeah, while I never had a CMO title, I think being a head of marketing in a region for the last three jobs that I’d done actually really nicely set me up for this.

There’s still some differences in nuances, right, like now I work directly with our CEO and our president and I spent a lot of time connecting with our board members to ensure that the direction we’re going is the direction that they feel best about, and sometimes pushing back on them or our CEO or our president. And so some of those elements are a little bit more different. I don’t think there was maybe as much, scrutiny isn’t the right word, but maybe there wasn’t as many people double clicking in on what I was doing with my last team, just because we were out of sight, out of mind, being on the other side of the world. So that’s been something that I’ve gotten used to pretty quickly here. But yeah, I’m loving it.

Max Altschuler:

That’s a good segue, I wanted to ask you more about the differences between corporate and start-ups. Because you’ve worked for Salesforce and Microsoft who are some of the bigger companies in the world. And then you also worked for a private companies that were close to IPOing like HubSpot and Exact Target and then now G2 Crowd, which is probably on the path IPO, but I’d say isn’t anywhere near where HubSpot and Exact Target were, at least in vicinity to the IPO. So what are some of the differences, similarities and some of your key learnings?

Ryan Bonnici:

I guess if you think of my career path, I’ve kind of gone from big to medium to small and it’s kind of like scaled down, I think, as I’ve gotten more experience and I’ve been willing to step up more and more. And so I think I wouldn’t want to have been, to be honest though, a new marketer at a startup. Like I wouldn’t recommend going straight into a really fresh small company only just because I think that typically a start up what drives that is the product or the service being good or a good fit for the customer base. And so I think what happens is that the companies tend to grow really organically out of the back of that. And naturally obviously do sales and marketing too, which helps. But I think that like sometimes it can be, like if you haven’t had that experience at a bigger company, you’re kind of then just doing whatever the CEO or sales thinks is best, which sometimes is, sometimes isn’t, but it doesn’t really teach you to learn and to test and to be data driven.

I think what I’ve done and what I’d recommend other people do, is try and grow and join a mid size company or a bigger company, whereby you’re working under someone that you really admire and is incredibly smart and good at what they do. Because I think that’s really the most important thing. It’s like the learnings that you will get and the autonomy that you’re getting from being able to try different things and new things. You know, that’s what I loved about my time at HubSpot. I was one of, gosh, I think by the time I left there was 200 marketers, so a huge marketing team, like 10 percent of the business was marketing. And for some people that might be too much specialization and not enough, like ability to do multiple lots of different things. It was nice because everyone at HubSpot, because of that specialization was able to become a real expert in their field. And we would talk a lot about that at HubSpot, and I still talk a lot about it today with my team, about the importance of becoming a t-shaped marketer.

People have different views on that, but I think ultimately it’s good to be a generalist and to understand all the key areas of marketing, being digital and automation and email and events and in-person. But I think if you can then, once you have that generalized understanding, go a little deeper into one area in particular. I think that’s then what helps you start to really build your brand and make a niche for yourself and become known as that girl or that guy. And that’s what I think I’ve done and you know, try to teach others to do.

Max Altschuler:

So would you suggest that, going into your career if you know that you want to be a CRO, a CMO, somebody who comes into an organization, maybe doesn’t start the company but works high up and takes them through the early stages through IPO or acquisition within a bigger company. Would you say that that’s the best way to go? Obviously your experiences led you that way, but would you have done everything different? Because you went from big medium small.

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