Remote Work Interviews

Owl Labs (OL): Tell me about how you got to where you are in your career today.

Ryan Bonnici (RB): The short version for me is a combination of being in the right place at the right time, and working my ass off. The long version, since the age of 9 or 10, I knew I wanted to be a CMO when I grew up. I don't know why I wanted that or where that idea came from. And to add another goal to it, I wanted to become a CMO by the time I turned thirty. I've always set unrealistic high expectations for myself, and it's something I'm working on with my therapist, but that goal has guided me throughout my career.

I've always wanted to be a CMO because I've been obsessed with marketing from a young age. I used to love reading Adweek and reading commercial reviews from film festivals because my love of marketing started with a love of advertising. Then, I became more interested in marketing when I realized how difficult it was to measure the impact of advertising, and that working in marketing would allow me to touch advertising while still working on more metrics-driven work.

OL: You shared on LinkedIn your story of how talking to your seatmates on flights helped advance your career. How did you come to realize that?

RB: In high school, I worked hard to earn good grades, I got into university, and by the end of my first year, I was completely burnt out from working so hard. I decided to take a gap year, and I applied to be an international flight attendant. Did you know that?

OL: I didn't know that!

RB: It was a great fit for me at the time because I wanted to take a break from school and travel the world, but I wanted to meet interesting people and stay on top of the business and marketing world. My dad always tells me that when I was younger, I used to tell him how much I loved that he had a phone he could read emails on, and that I couldn't wait until I was old enough to have a phone and get emails of my own. This was when I was 8 or 9, if you can believe that. He would say to me, "Dude, you have no idea. Once you have a cell phone and can check emails anywhere, you will hate your phone." I think I get what he meant now.

So when I was a flight attendant, I would always try to chat with passengers on the plane, particularly in business class and first class (because in economy class, you're busy serving so many people, you don't have the time). I ended up chatting with incredibly interesting people, and on one flight, I met an executive at Microsoft who lead their marketing efforts in the APAC region. He told me Microsoft was taking on a cohort of recent graduates for a rotational program, so long story short, I applied for the program, went through multiple rounds of interviews, and was one of 10 candidates selected among almost 10,000 total applicants.

That was my first foray into marketing, and transparently, I was horrible at it back then. But I was figuring it out and I was learning, and I credit speaking with people I meet on planes with the start of my marketing career, and it taught me the value of networking. Now, I make sure to talk to seatmates in a way that's (hopefully) not annoying. I make sure not to bother people who are reading or watching Netflix because sometimes I don't want to talk, and I don't like that, either. But if we do strike up a conversation, I try to take a business card or peek at their ticket so I can learn their name and follow them on social media.

OL: LinkedIn and social media in general have made it much easier to network and make connections in a way that isn't strictly transactional.

RB: Absolutely. It's great to become internet friends and get context into someone's professional achievements and passions after networking with them.

OL: You got to travel for free, meet people and eventually used those connections to build your career. And now, you've achieved your goal of becoming a CMO by 30. Now that you're here, what are some of the big plays that your team is making this year?

RB: I've been at G2 for a year and a half now. When I first joined, the board had three big, hairy audacious goals (BHAGs) they wanted me to chase after. The first goal was to significantly grow our traffic. We have a software marketplace with customer reviews, and we work closely with vendors to sell them different subscriptions, content packages, and products, but none of that works if we don't have millions of buyers coming to our site every month to figure out which software to buy. Last year, we 3X'd our traffic, and this year, I'm hoping to 4X our traffic to keep expectations high.

The second goal was to build a well-oiled demand generation machine. We built a field marketing team and a marketing ops and automation team, and those teams are crushing it and helping drive a ton of revenue for the sales team.

The third goal was to build and grow our brand, and I didn't get around to doing that until almost a year into the role. We launched our new brand late last year, and it was my first career experience running a rebrand from start to finish. We shortened our name from G2 Crowd to G2, and we evolved the look and feel of our branding, the way we talk about our products to our customers, and our logo.

The rebrand was such a fun and eye-opening learning experience. I don't think I ever gave branding folks as much credit as they deserve, because there's so much that goes into it. Those were my three big goals last year, and we're still focused on them this year, too. This year, I'm focused on driving a few big, above-the-line and below-the-line campaigns to help solidify the new messaging and branding to reap even bigger numbers than last year.

This year is also more focused on the team. When I joined a year and a half ago, there were only five other marketers, and now we're a team of 50 marketers. I didn't expect hiring growth to be as significant as it was. What's great is we spent the same amount of money as we did in the years before, but I shifted resources away from expensive event sponsorships and reallocated it into headcount so we could build a strong team engine. It was fantastic to see us hit our goals and grow our team without increasing the cost of marketing to the business.

OL: That's crazy growth. Are you growing at that pace this year, too?

RB: Probably not. It was an awesome experience and now the team is in a great place to hit even bigger goals, so I don't think we'll need the same investments in headcount as we did last year. I didn't plan to grow the team as fast as we did last year, but we started seeing serious results from building a killer in-house team, and our board is incredibly supportive, so when they see the numbers going in the right direction, they double down on their investment in our vision.

OL: What does your team look like? Are you all co-located working together in Chicago? Or do some of you work across different offices or remotely?

RB: We're a hybrid team, with employees working in different offices and working remotely in other locations. Chicago is where our headquarters is located, and that's where the majority of our employees on the marketing team are based. We also have marketers in our San Francisco office, which is growing quickly. Our third office that recently opened through an acquisition is based in Bangalore, India, and we're growing our staff there. Then, we have remote employees based in Singapore, London, Kiev, and even some employees who work remotely in San Francisco because they prefer it to working in our office. Everyone's been adapting to the changes of a hybrid team, and some roles make it easier to work remotely than others, so it's a learning process.

OL: What are some of the biggest challenges that come with team members across different time zones, and what tools and frameworks are you using to solve those?

RB: The biggest challenge for us is creating an inclusive work environment for everyone, whether they work in an office or work from home. There are pros and cons to each working environment, which is why a lot of our employees who work out of an office also work from home a few days a week to do focused, heads-down work. Some of our other challenges include onboarding new hires, fostering inclusivity across different locations, and building relationships across different locations. One of my biggest challenges as the team leader is keeping energy levels and motivation high, even if I'm not working next to people every day.

Part of how we make progress on that is by flying everyone we hire out to HQ in Chicago for a week weeks so they get immerse themselves in G2 culture and get to know the team. We fly employees around to meet with their teammates in person as often as we can, and we pair remote team members up with an in-office buddy so they always have someone they can connect with if they need it. Given the industry we're in, we probably use more software than any company I've ever been a part of, which can have its advantages and disadvantages if you're not using it properly for communication and collaboration.

Because we're so distributed and because we use so many different tools, we set clear process around how we use our different team tools so people have flexibility but can still work within a framework we all understand for optimal productivity.

Having such a distributed team has made process around communication and documentation so important. When I first joined, we had a tendency to huddle together in person to brainstorm or share ideas, but we can't do that anymore. Even in Chicago, my team is split across three different physical locations. We have two offices in our current building, and another team sitting in an entirely different building because we're in the process of moving offices. Getting good at using technology to communicate and document decisions and ideas has been key for us. It's part of why I'm such a big fan of the Meeting Owl, because I love the way it lets me be in the room with the team when I need to be, no matter where I'm working.

Over-communicating is critical for remote and distributed teams. Part of building processes is about having a centralized place for sharing company updates. This place used to be Slack for us, and although it's amazing for quick, on-the-go communication, it's not as helpful for building a discussion board, and going back in time to see older messages and conversations you may have missed. It's hard to use Slack if you need to refer to a piece of information regularly.

We're using a few different tools now to accomplish this. We use Atlassian's Confluence and Guru for a couple of different purposes. We use Atlassian for internal blogging, and we use Guru for sharing content people need to refer to again and again. We find Atlassian works really well as a feed of the most popular content each week, but from a search perspective, Guru's a bit more accessible in Chrome. We use a lot of different tools, which is part of our DNA as a company so we can learn about the different leaders in the software space, and we get to test a lot of software for free before deciding what to use for our own team.

OL: To your point about building and maintaining culture when you have a distributed team, that's something that we hear a lot when we talk to leaders who are building remote companies or starting to enable remote work. What advice would you give to leaders who are concerned about how remote work would impact company culture?

RB: There are a few components to addressing this challenge, but the biggest hurdle is simply trying something new as an entire company you haven't done before. For leaders that have been in the game for a longer period of time that have seen the workplace start to shift to a completely different model than what was the norm 10 or 20 years ago requires a huge mental shift. Old-school management models didn't involve a lot of trusting employees, and leaders needed to see employees in the office, or they weren't getting the work done, and it can be hard to trust people enough to let them work remotely if that's something you're not familiar with.

Five or six years ago, when I started managing people that weren't based in my own office for the first time, it felt unusual, and I had to learn how to overcome physical distance to still build trust and rapport on my team. The thing I love about remote work and managing remote workers is that it forces you to set up expectations around OKRs -- what are an employee's objectives, and what are the key results that they need to deliver on? Remote work forces you to set up a 100-day plan and put the infrastructure in place before that person starts, because they're not sitting across from you and it's not as easy for them to maybe get in touch with you regularly. (While it's easy to do that with technology, new employees don't want to be constantly chatting or video conferencing with their boss every time they have a question.

Remote work forces managers to set clear expectations for employees so they understand their expectations and what success looks like in their role. There are pros and cons to this, but remote managers I speak with have described how their relationships with their employees become very task-focused and outcome-focused. Because you aren't sitting with that person, you can't see them putting in the hard work, so you rely on their results for coaching and performance reviews. If they're a content person, you're looking at traffic. If you're a demand gen person, you're looking at lead revenue.

Leaders need to start experiencing remote team management and company leadership because, frankly, it's the way industries are turning. Employees are starting to set the rules around work-life balance. I wrote an article for CNBC recently about how I block two hours a week on my calendar for therapy. I didn't ask anyone for permission to do that, I simply set a personal boundary for myself during "traditional" work hours. That's something that I need to do for my own mental health, and I'm a better person at work and outside of work because of it.

My work supports me, and I'm lucky for that, but I shouldn't need them to support me -- that should just be a no-brainer. As more and more people feel comfortable bringing their whole selves to work, employees are starting to set the rules for what they expect from their employer. Now, we hire people who let us know as early as the interview process of how and where they work best. We want people to be able to optimize for results, and that includes where they work.

Furthermore, the war on talent is getting more and more fierce. If you're only hiring in the locations where you have offices, you're going to end up overpaying for only a tiny fraction of the global hiring market. If you want the best people and you want the best results for your company, I don't think there's any other option than to open up your team to remote work.

OL: I appreciated the article that you wrote about blocking time for therapy on your work calendar, and I've read similar articles about working parents blocking time on their calendars for pumping, or leaving at a specific time to pick up their kids from childcare. How can leaders encourage employees to bring their full selves to work in similar ways?

RB: In these instances, it doesn't matter what leaders say they believe in if they're not walking the walk and leading by example, especially when it comes to something outside of the norm. It shouldn't be outside of the norm, but it still is to see people leave the office at 4:30 to pick up their kids, or block time out on their calendar for mental health or pumping or whatever they need to do. Leaders need to do it themselves to set a positive example and encourage employees to build a work schedule around their lives, and not the other way around.

The interesting thing that happened when I started sharing my therapy hours on my calendar was more people on the team opened up to me about struggles they're dealing with or their own mental health journeys. Greater transparency into your team's personal lives and stories helps you build trust and stronger relationships -- and it helps you work together to do better work, as a secondary benefit.

As an example, about three months ago, I wasn't in a good mental health space, and I thought I was fine to come into work, but within an hour of getting to work, I started having an anxiety attack and realized I couldn't attend my meetings or see people. I was a hot mess. So I canceled all of my meetings for the day and told everyone, "Hey, I'm taking a mental health day." I didn't think much of it, but because my social anxiety was so high, but I felt vulnerable saying that to so many of my coworkers.

I was glad I took the day because I needed it, and then when I was back in the office, I was happy to hear employees telling me that me doing that had helped them feel more comfortable knowing they had that option if they ever get to that place. As a leader, it feels good to offer people that kind of inclusivity by leading by example. Mental health, like any kind of health, falls into diversity and inclusion, and we need to get better at talking about mental health in the same way we talk about physical health. Everyone's very proud to talk about their physical health when they discuss their workout routine or their diet, but people don't talk about what they're doing to help their brain in the same way, which is arguably the most important component of health.

Part of what drove this change was I recently joined the board of a nonprofit organization called Bring Change to Mind. It was founded by Glenn Close, who was inspired by mental health challenges in her family, and she's the chair of the board. There's an amazing board of executives who are all dedicated to reducing the stigma around mental health. One-third of people have mental health disorders that are diagnosable and, of those people, two-thirds won't seek help, and a big reason is due to that stigma. Everything is so treatable today, and my experiences in therapy have made me passionate about reducing stigma.

OL: Thanks so much for sharing that. I appreciate your commitment to your employees' and your own wellness journeys. The conversation around remote work usually centers around more affordable office space or lower salaries than if your employees were based in New York or San Francisco. But remote work can help move the needle on diversity and inclusion, too. It opens your team up to different markets, different working and learning styles, and different personal backgrounds. It's a conversation worth having, because even if it's important for a business' bottom line, it's the right thing to do, too.

RB: Absolutely. If you're the leader of a company, your people are your bottom line, so you need to invest in them to achieve the results you need. Remote work is a win-win in that way, because it helps your employees, and they like it, too.

OL: You made a good point about candidates setting the tone for the types of workplaces and benefits they've come to expect from a job offer. I read a survey that said flexibility is more important to candidates than salary, which I was shocked by.

RB: I believe it. I've seen so many of my own friends that worked in investment banking move into other fields where they earn a whole lot less, but they have more free time and more happiness, which makes that money and flexibility more valuable. In an ideal world, you'd get both, but if you have to choose one over the other, it makes sense that more people are choosing flexibility so that they're at least happy, because money doesn't buy happiness. I went down that path and tried to make that work, and it didn't make me happy.

OL: What are some of the leadership learnings or trends you've adopted in your career?

RB: I'm a big fan of conscious leadership, and I'm still a student of conscious leadership. As a leadership team at G2, we do an off-site every quarter for two days where we gather together and invite an amazing leadership coach who will run a conscious leadership off-site. They're pretty freaking intense. Most people on our leadership team have, at some point, myself included, cried in front of the whole group. That only happens when you really trust everyone that you're with and when everyone's being conscious and open and vulnerable together.

Conscious leadership is something I'm still learning about, but it's very practical in terms of how it applies to how you do work, and whether you're working above-the-line or below-the-line. "Above-the-line" refers to doing things at work with your team with positive intent, and "below-the-line" refers to doing something with negative intent. It's about looking at what's driving what you do and how you communicate, and it's been an eye-opening experience for me. I've also been doing a lot of therapy, which is helpful for my work life as well, but conscious leadership has been a big mental model that's influenced me as a leader.

I think all executives should have a therapist. I'm biased because my wife's a clinical psychologist, so a lot of our friends are psychologists as well, and it's very normal in my friend group to see a therapist because all of our partners are therapists. Everyone I know who's done intense therapy has become a better person for it, and I've certainly have seen myself become a better leader as a result.

To change course, I was speaking to someone about Radical Candor, which I'm a big proponent of, when they had a lot of criticisms and reasons not to employ it.

There are a lot of new leadership styles or approaches, but I think a conscious leader would look at it as they're all small tools, and that, if you're being conscious, you're going to be radically candid with an employee if you're present with them in that moment. I still love what Kim Scott shares in Radical Candor, but it might be phasing out.

OL: I'm a fan of Radical Candor myself, but I've found that feedback can still be challenging to hear in the workplace if it isn't counterbalanced by assuming positive intent -- on both sides of the conversation.

RB: I totally relate to that point, because I'm such a big proponent of feedback, but it can still be hard receiving. No matter how much practice and training you've had, it's so easy to get defensive and start making excuses for yourself when someone talks to you about ways you can improve. One thing I've been working on myself and with my team this year is talking about how, when someone gives you feedback, if you respond with anything other than "thank you," you're almost guaranteed to put your foot in your mouth. In the moment after receiving corrective feedback, there's no other in-the-moment feedback than, "Thank you."

It doesn't matter how conscious or humble you are -- if you respond by going into the excuse mode, you'll devalue the other person's feedback, make it look like you can't accept feedback, and makes it less likely that person will share their thoughts with you again. Instead, if you give yourself 24 hours to cool off and reflect, you'll be able to fully process what the person was sharing with you and start implementing it. I find that a lot of people's first impulse after receiving impact is to justify why they did what they did. We all experience impostor syndrome from time to time and don't like to feel as though we don't know what we're doing, so it's a natural impulse reaction -- which is why it's so important to pause before responding to feedback.

One thing that's important to remember if the person giving you feedback is your manager or teammate is, 99% of the time, they understand the context of your work properly. When they're giving you feedback, they know if it was a last-minute project you had to rush to complete, or if your budget was constrained, or another context that can impact results. The quicker you can own their feedback, process it, and put it into action, the better your relationship and your work will be. They don't want you to push back or give excuses, and they don't want to tiptoe around you if you react poorly to the feedback they're only giving to help you improve. Feedback is so key in the working world, I wish we learned how to receive it better as children and teens and young adults in school and university.

OL: When you're growing up, your parents always tell you that making an effort is what counts, but in the professional world, effort isn't the only aspect of being successful. It's also about planning, execution, and the results you can achieve. It can be a tough lesson to learn after your first 22 years of life when you start learning other measures of success in the working world.

RB: The things our family and friends say to us growing up helps shape us. I'm so conscious of the unconscious gender bias we all have -- myself included. I noticed sometimes when I was talking to my friends' children, if I was talking to a young boy, I'd tell him how strong or tough he looked, but if I was referring to a young girl, I'd call her adorable or pretty. It's so hard not to make value judgments based on appearance -- especially when we're conditioned into specific gender roles and descriptors from the time we're literally infants. I don't do this with kids anymore, but you even see it happening between men and women as adults, too. How often do we comment on brides' remarkability or commitment at straight weddings the way we do with grooms? Unconscious bias can shape the way we give and receive feedback to everyone, including in the workplace, which I'm focusing on un-learning. Things like stress and performance and burnout can become emotional for people in the workplace, and I want my team to feel comfortable bringing that part of themselves to work, too.

OL: That's fantastic to hear. It's so important to train ourselves to un-learn the process of assigning value judgments to things like emotions, relationships status, or health that we've been taught from a young age. I've personally been trying to change my language around food because I realized I'm a person who verbalizes when I'm being "good" or "bad" with my diet. It's bad for my relationship with food, and it's bad for the people around me who hear me saying I'm "bad" for eating a slice of pizza. I'm trying to be more cognizant of not assigning positive or negative terms to different foods because, even if it's not all technically "good" for you, a balanced diet is absolutely "good" for you.

RB: I could be more mindful of that too. We all could. Sometimes, I'll bring a ton of chocolates over to my desk at work, and if people ask why I'm eating so much candy, I'll justify it by saying that I'm tired, or I'm in a bad mood, or I'm having a bad day -- implying that I otherwise shouldn't be eating that chocolate. That might be my feeling at that moment, but it's wrong to voice it to people around me. You can eat a bunch of chocolate while still being perfectly healthy, and we shouldn't be judging certain foods or entire meals as "good" or "bad."

OL: It's about taking away the culture of punishment and rewards based on food or exercise. That's a huge part of self-esteem, body image, and self-worth, and the same can be said for emotions in the workplace, or mental health, or anything like that.

For a final thought, because this conversation is making me hungry, when you think about the direction that remote work is taking, what do you think the future of work is going to look like 10 years from now?

RB: I don't think anyone can deny the direction work is taking -- technology is allowing us to always be "on" and available to work. Because of the technological advancements and reliability and affordability of high-speed WiFi, the line has been blurred between work-life integration, and we can work from anywhere, whether we're in the office or on vacation with our families. The current state of work is testing our willpower and discipline and boundaries, and they will only continue to be more tested as technology and the workplace advance.

This morning, for example, I slept for three hours from like 10 p.m. last night to 1 a.m., and I've been wide-awake and working since then because I picked up my phone and started digging into my inbox. As more companies and individuals start embracing remote work, the availability of technology and different time zones will start putting remote workers in a position of needing to reinforce their schedules and boundaries. Part of the beauty of remote work is being able to work on a schedule that works best for you, but if you're online and working at all hours, you'll start burning out quickly.

We'll need to build clear rules around how technology can be used to help us maintain those boundaries for work-life balance. Slack allows you to like mute notifications between certain times, but your coworkers still have the option to send you a notification anyways, so you need to be disciplined with your notification settings to make the technology work for you. I changed my phone settings so I only receive Slack and email notifications if I check the mobile apps, so my ability to be disturbed during my personal time is completely within my control.

All of these new technologies mean we're going to have to learn new ways of coping with digital and notification overload so we can be productive when we're working while still being able to relax and recharge during our personal time. This might mean we do more digital detoxes or build different barriers and boundaries so our coworkers can't disturb us as easily. There will be a different solution for everybody. There's no time as exciting as right now because it's so much easier today to build a business today than it ever was. If you're building software or you're launching a product, there are so many ways you can do that quickly and affordably. The adoption of remote work helps facilitate the rapid building and growth of businesses, but it can also come with these challenges we've talked about. There's a lot of opportunity, but there are challenges that come with it, which I'm excited to keep trying to figure out on my own while learning how others do it, too.

Key Takeaways

1. Building a strong distributed team culture starts with new employee onboarding.

With team members working in a variety of different offices and locations around the world, Ryan explains that G2’s new hire onboarding process involves flying remote employees to the company’s headquarters for several weeks for training and in-person team collaboration, as well as pairing them up with an in-office buddy so they always have a point of contact.

2. Executives should lead by example in order to demonstrate and implement new behaviors and processes within an organization.

Ryan’s focus on bringing his whole self to work helped other team members to be more open about stress and burnout, work-life balance, and self-care. He recommends other leaders publish personal priorities on their work calendars, such as mental and physical health care and family commitments, to help encourage their employees to take the time they need to prioritize their professional and personal commitments.

3. Employees and managers should take time to process and think about critical feedback before responding.

Hearing critical feedback about your work is never easy. To make the conversation more productive and helpful, Ryan suggests the recipients of feedback start by saying “thank you” to the person giving them feedback, taking 24 hours to let it sink in, and then rescheduling time to talk about how you’ll implement it. This pause will keep the working relationship positive and prevent defensiveness from keeping people from hearing the suggestions and guidance.

To learn more, read our interview with Hacker Paradise CEO Spencer Jentzsch next.