From VP of People to COO

A conversation with Jessica Zwaan, COO, Whereby

Jessica Zwaan and I both made the leap from people to COO so it was wonderful to talk with someone else who’s made this transition. We spoke about why People leaders can make great COOs, the multi-faceted role of COO, the risks execs have to take, what it was like bringing the Whereby team along after a pivot, and treating your culture like a subscription product. 

Your last name Zwann is fantastic. I’m a big fan of having a z in my name.

Yeah. It's an unusual letter to be able to have. So I think it's a privilege, I feel.

Me too. OK, on to the good stuff. Can you give us a quick background on you?

Yeah, absolutely. My name is Jessie or Jessica Zwaan, I'm the COO at a company called Whereby. Whereby is a video communications platform. We sell two different products. One is a competitor to Zoom or Microsoft Teams. It's a one-to-one or one-to-group video comms platform. Our primary product is video APIs. So if you're building a banking app, a yoga teaching app, or a recruiting platform, and you want to embed video conferencing inside that platform and not have to leave to go to a different tool or window, you can buy Whereby and you have this really beautiful video seamlessly integrated into your website or your app or whatever it is you're building. The product is wonderful, but the thing I'm really proud of Whereby is the culture of the company we've built.

Whereby is on a mission to make anywhere work. We've really embraced that in our team. We have a fully distributed team all over the world, and we have, I think, a very unique approach to remote working, a very unique approach to corporate culture. So I'm very, very proud of that. My history is in legal and people. I've been VP People at a couple of companies. I've worked in talent roles at large advertising agencies. I've worked in HR banks and mining companies since I graduated from university. So I have a long history in people operations, legal, and operations.

How did you become COO of Whereby?

I just wrote a blog about this over the weekend, so I'm feeling this is a very fresh topic for me. I'm ready, I'm primed, ready to go. I’m not one of those people who believe in manifestation. I don't think that the fairies are out there making things happen for you, but I am a very strong believer in making goals and making lists. If you name things, it will happen. For the last five or so years, I've really, really wanted to move into a COO position. I've been trying to move in that direction. I started at Whereby, as VP of People and legal looking after all of the legal operations and all of the people operations teams. Then I started looking after project management and kind of goal-setting those bits and pieces. I had always told the CEO Øyvind Reed that I wanted to move into the COO position and have a broader and more commercial role in the team. So this was something that was very much kind of being discussed from when I joined.

I was promoted into the COO role just under a year after being on the team. I think maybe about 10 months ago, we had a leadership shift. The COO that was in the position moved into revenue and sales. His background is in revenue and sales so that was a welcome move for him. I took over the only remaining piece of the puzzle that I hadn't yet, which was finance, and then customer support a couple of months later when there was another change in leadership in commercial.

If you had told younger me that one day you’re going to be a COO, I would've been like, "Nope." It was a surprise to me. I thought about leadership for myself and my own company, but leading another company was just literally not something I never really thought about. I love that you wanted the COO role. What drew you to the COO role?

I think one of the things that has always really appealed to me about the COO role is that it's extremely broad. You get an amazing bird's eye view of the entire company. In a lot of ways, that's what I really love about people operations as well. You really get under the skin of what's happening from wall to wall in a business. And I've always loved that ever since I first graduated uni and went straight into the working world. So for me, the COO position had the capacity to do that. One of the other things about it that I really liked was you moved very swiftly between these kinds of very metric-driven, repetitive and more analytical tasks into these high empathy, strategic conversations embracing a lot of people operations, you're moving from recruitment, for example, through to org design. You're moving from discussions around financial planning. And next thing you're talking about is how to build out a community strategy for customer support.

I love the breadth and depth of the COO role — of moving across the business from really structured work to really high empathy, communication-based projects.

I love that about the role too. It feeds all parts of your brain, not just the high empathy, but also strategic initiatives, and very detailed things to help the business move forward.

Absolutely. It feels like you get to be a little bit like clay in some ways as well. You never really get to stop learning and evolving and moving with the shape of it. It can be quite intense because you never really know what's going to happen or which shape you have to take on which day or which thing you have to become an expert in or a semi-expert in. But that's what makes it fun as well.

There’s a stereotype that the COO is the successor to the CEO. Was that something you've ever thought about? Wanting COO as a way to CEO?

I was speaking at an event a couple of weeks ago about this. It was called, So You Want To Be A COO. There were a few different COOs giving their opinions about the role. It was the job of the people in the panel to be a little bit controversial and say things that kind of got the crowd going, got the other panelists going. Someone said, "You know what? I actually think COOs just want to be CEOs. That's what it is, you just want the big job." I can see how that is like an archetype of a COO. I think there's a whole Harvard Business Review article about the different archetypes, it's on there for sure. For me, honestly, the closer I have gotten to the CEO job, the more I have identified, I just don't think that's the path for me.

I had that conversation with my CEO. He asked this question openly, "Is CEO what you want to do next?" And I was like, "No, I don't think so." The idea of having to be that external-facing fundraiser, having to deal with the board, having to kind of cope with the kind of intensity and rejection of venture capitalist markets — from outside of the safety of due diligence, which is my kind of little lifeboat — that for me seems quite intense. I honestly just really prefer to be on the internal side of things I think, or at least for the time being… but never say never.

I'm the same. I ask because when I got into the COO role, people assumed I wanted to be CEO. I was like, "No, no, no." That’s not the job I want.

I think that the COO role is so fluid, which is why it makes me sad to see job ads out there for COO, which is pretty much exclusively management consulting and working at McKinsey and having an MBA. There are so many job ads like this. Is that even really what you need for this job? Do you need a management consulting person to come in? I don't know. It feels like there's a lack of understanding even inside founding teams and exec teams about what a COO is there to do. And then, you end up with these COOs that maybe don't do a job quite as well as they could. I mean, try to be very diplomatic there, but there are some COOs I've had in my past that I'm like, "I don't think your job is COO.

And if you think about management consulting and an MBA as a background, that's a very specific perspective around operational efficiency, which leaves out human beings, who populate the business we work in.

Yeah, absolutely. And more and more, one of the things that I strongly believe why people operations people make great COOs, is because ostensibly for the majority of a series A, a Series B startup, you are going to be looking after as a VP people or a CPO, 60 to 70%, maybe of the outlay of a company. And probably the biggest proportion of the G&A budget. You probably are the biggest spender in the company, or at least the person that's kind of responsible for the most money, unless maybe you've got a massive marketing team. So you've got these high empathy, very good communicators, who are battle-tested people leaders out there. They have good financial ops because they're managing these really complex P&Ls around people too. And they're being overlooked, because I think traditionally, people ops people, haven't been very good at kind of talking about the ROI of the work that they're working on but also maybe traditionally people's roles have been women-oriented and that doesn't really play very well against the move into a C-suite role, unfortunately.

I think folks in the people role who understand the business are often great at operating at an organizational level. They see the system, how the business organism operates, the culture — how one thing affects another thing — which is extremely important for a COO. They have to see the entire organizational entity.

Yeah, absolutely. Being able to understand metrics and how they interplay with each other is one thing, but being able to understand metrics and how they interplay with human behavior and dark patterns, that's another thing. It’s really valuable and that these are just skills that you pick up when you're kind of a battle-tested people leader, which I think a really good VP people should be able to make happen pretty easily.

I could talk about it forever because we have this thing in common and I don't meet a lot of us.

OK, I’ll move on. I understand you took the role while working in two companies. (laughs) I mean too two countries, not companies.

Yeah, two companies, that would've been a lot. I took the role of working in two countries. So Whereby is fully remote and hours agnostic, which is awesome. So you can work whatever time you want to work because you can work wherever you want to work. So time kind of becomes slightly meaningless to some degree. When I joined Whereby, it was kind of just a couple of months after the pandemic. I think it was maybe even during the first lockdown, which meant that no one was really exercising their freedom to work from anywhere, everyone was exercising their freedom from work from their home office. And then the year after I'd started, the Australian borders looked like they probably weren't going to open up for a really long time. Things started looking pretty dire with the travel inside and outside of Australia.

I found out my little sister was pregnant. It was a high priority for me to get home to see her, and also it had been three years by the time I got back. I had moved from London to Amsterdam when I started Whereby and then about six months later managed to get two flights for me and my husband to go back to Australia, to spend a couple of months there so that he could get his permanent residence visa sorted, and we could get married and also so I could see my sister have her baby. So there was this kind of crazy period of my life, where I moved to three countries within a year. So I was doing the COO role after I'd just moved into it from a 12-hour different timezone as the only person living an Antipodean life because no one else could get in or out of Australia or New Zealand. And yeah, it was a pretty hectic couple of months.

Was there anybody else in similar time zones or were they all in Europe and the States?

Not at the same time. There was someone in the Southern hemisphere, but Cape Town's time zone is very similar to Europe's. So yeah, I was the only person working in the Australian timezone. There was one other person in India who would kind of cross over me in the evening for a bit. So, I was working into two in the morning, I think most of the time, doing late-night meetings.

Oh yeah. Australia can be tough. When people in that part of the world are interested in working together I’m like, “Okay, let's have a conversation about time zones."

It's funny, at first I actually loved it, because I live on the Great Barrier Reef back home, and then I could wake up really in the morning and go for a swim on the beach. I could go out and enjoy the sun. It was so nice. Enjoy my family. And then, I would start work at three or four in the afternoon and finish up just after midnight every night. For the first couple of months, that was great. I was like, this is amazing. I want to do this all the time. But it gets harder as the months draw on. I was there for three months and a bit. And at the end, I was ready to get back into not being awake at midnight one or two in the morning, and seeing daylight.

I bet. How many people were there at Whereby when you joined?

About 40 people.

How big is Whereby now?

We're about 80 people now. At one point we were 120 and we've kind of gradually softly moved down to 80. Anyone listening now during the current markets probably completely understands how that, and why that has happened over the last six months.

I believe you all had to refine the product-market fit. Can you share more about that?

Yeah. So it has been, I think, just as turbulent professionally, as it has been kind of personally moving all over the planet and trying to get things going during a pandemic. So Whereby is obviously in video conferencing. Video conferencing is one area of the internet and the web that was hugely positively impacted by what is like a very, very devastating global event, which was Coronavirus. Whereby saw a ridiculous and completely unsustainable amount of growth within the first couple of months of COVID. We were expecting what we got in three months in three years. That's the kind of the scope of the impact that we had the first couple of months of the pandemic. The other thing is if you are a business leader, that's looking at cohort analysis or understanding customer profiles, there's nothing that would've prepared you for what happened when you started looking at the data that's coming into this.

We were a Series A kind almost like a seed-level company. All of a sudden we've got these million-dollar healthcare contracts and these massive customers and such a huge volume of B2C customers. We didn't know what these cohorts were going to do. We had absolutely no idea, but we had to start hiring to support the infrastructure we needed to have for these customers and to kind of meet this growth potential. So, 2020 was really about us trying to say, "Okay, we have to get the capital to deploy to make this happen." Thankfully, we managed to be a company that avoided some sky-high multi-billion dollar valuation amongst all of this. And for that, I thank my lucky stars. I think a lot of people at the time wished they would've got in and got this big amount of cash where they could, and now they're starting to regret it because they're seeing the golden handcuffs that have put a lot of businesses into in order to grow into these valuations. 

We launched Whereby embedded, our API embedded in your app within your product's business. That business just became extremely successful very, very quickly. We found that was probably going to be the best way for us to reach our mission of a world where anywhere worked, much faster than a B2C product. B2C product obviously, it's very popular, people do love it. There are a lot of power users out there at Whereby, but really what was missing in the market was a product that other companies that wanted to reach people via video and start being more remote-friendly and more hybrid, could use to make that happen. So that product became very, very successful very quickly. And we decided to shift all of our operational efforts to focusing on that. That doesn't mean we don't focus on meetings. Of course, our meetings rooms product we still use and still work on. Anything that we build into the embedded product naturally benefits meetings, because it's the same system.

So we pivoted our entire operational focus to focus on this newer product. Pivots are so hard. There's no other way to describe this. It's tough, that especially it was difficult. We moved from a B2C product, which people really understood, everybody in our team was a user ourselves. We dog fed our product, everybody loved it, we all really believed in this space, to this highly technical B2D kind of software product that if you can't read code, you can't even buy the product anymore. I think that was a huge shift for people who were already seeing like, "Well, we're being so successful in meeting's front, why would we change our approach? Why would we do this?" That was a whole journey for us.

And then, the inevitable happened, which is a great thing, which is the world started opening up again, and people had less need to be buying a video conferencing platform. Even if they loved Whereby, you just use it less, because you can go out and have face-to-face meetings. You can go back into the office and you can bump into your colleague at a coffee place where you can go to your doctor in person and have something checked out. People are still using Whereby, but the data started to emerge around retention, it started to emerge around how many of our customers were growing into the product, and how many the customers were utilizing the amount of product that they'd purchased. We started realizing that the cohort analysis that we had been doing was less optimistic than it was when we were in the pandemic of course. This is what a lot of SaaS leaders are seeing now.

So your pivot is complete. What does that look like? Is it more about sustainability and figuring out how to just continue to grow?

Yeah, exactly. And I think this is the story. I think a lot of startup execs are saying now it's about sustainable growth, it's about actually being able to look at those cohorts and retain them and sustainably grow the retention rather than see these crazy 100X, 50X multiples that we are being expected to continue to produce in the pandemic endemic, which yeah, just proving not possible anymore, but yeah, the pivot's done, the team has got through it. I think that there still will be, and always will be questions from some members of the team that have been there for the last couple of years. Was it the right decision? Should we have done that? And I think personally the answer is yes. I think it's easier and better for us to focus on both products via this lens. And it's more, I guess, straightforward for us to reach our mission. If we're enabling companies to enable better remote working and better remote facilitation of media and whatever else it is. So I do think it's the right decision, but I don't think a pivot is ever truly over if you still have members of the team that love the previous products.

People join a company, a lot of times, especially a startup because they love the mission, they love the product. How was that helping the team make the shift? What was hard about that?

A lot of people really struggled with it. I want to be empathetic to the team while also being empathetic to the leaders, and my peers during this change. Being a leader of a startup is a very lonely job at the best of times. And I don't think people that work in startups, and I am actually I'm glad they don't realize this. I'm happy that they're protected from this information, but I think people don't realize how often you are faced with trolley problems and how often the trolley problem is not just, oh, this $1 million idea or that $800,000 idea. And how often it's this bad decision we struggle with in a few months, or maybe the entire company gets destroyed.

Sometimes the choices are bad, worse, or terrible. The answers aren't easy and sometimes there isn’t a great decision or even a really good one.

Yeah. And sometimes the team that makes the decision agrees, it's the right decision, but they hate it. That happens. I think if there was a world in which Whereby could have been as successful as Zoom within the next six months, and we could have extended our runway massively and continued growing like we'd planned, and everybody loved us and we were on a billboard in Times Square, yeah, obviously, that's the path I would've picked. Yes, please give me that. That sounds amazing. But that was definitely not one of the options in the trolley problem we had. We had to pick between doing a painful product pivot because we had a lot of ambiguity around the data of our customer cohorts and what was going to happen for us in the next six to 12 months. And an extremely competitive marketplace.

We were up against Microsoft's Zoom and Google as a team of 120 people, which is just insane. If we didn’t make the pivot potentially the entire company went bust in a year. I don't think it would've ever gone bust, but there's definitely a reality in which we would've had to cut down to 20 people.

Like a slow death or slow decompression to something small.

Exactly. We would've gone back to being like a series A company after the pandemic. And maybe we would be back to 40 people or 30 people now, and that would've been the outcome. Before the pivot, Whereby had been the recipient of just a lot of great news, and the team hadn't been maybe appropriately educated on what might happen if that great news started to dry up. And it started to dry up. So we had to make really difficult decisions. And I think it was a shock for a lot of people. And one of the things I've kind of learned as I've moved through different exec roles is that no matter how hard you try, for some people, whatever you decide just will be a shock.

You mentioned the tension between folks working at a startup and then the leadership team, who's there to tend to the business and the organization. The tension between creating a great work environment and creating a sustainable business is tough. You also have more information available about what's going on and you have to make hard decisions.

One of the responsibilities you have in exec teams is that we’re being paid by the board and by our investors to make big bets. Somebody in the company has to be making big bets and big decisions. Those big bets and big decisions come with risk. Those risks can be really devastating if it doesn't turn out. People can lose their roles. You may have to shut down an entire product arm. The team can work on something for six months and that thing gets just scrapped.

 If you don't trust somebody on your team to be making those big bets, then your company won't grow. If you trust somebody to make those big bets, you have to acknowledge that the person that you entrust with those decisions is going to get it wrong sometimes, that's the nature of risk. 

If a company generally doesn't believe that I'm the person that they want up the front, making those decisions, and they think that they would prefer to do it, or someone else would be maybe a better decision, I will be the first person to say, I don't want to work for a company that doesn't have the faith for me to make those decisions and make those big bets. I'm grateful to say, I think at the moment our exec team still has that. But I think that really is the core of the job description is being the person that facilitates really difficult, large decisions to see greater profitability of the company.

And it's not just about lining investors' pockets, but so that people can continue to be at this workplace. So we can continue to have a workplace that provides a good environment for people.

Yeah, absolutely. If you are someone out there in the world asking for your company for opportunities to grow, and then also expecting that your exec's job is to protect the company as it currently exists, that’s a hypocritical statement. If you have opportunities to grow, there are risks. And if you have a just protected workplace where everything remains as it is, then you are working for a cooperative, which is amazing. And maybe that's actually what you prefer to do. I would encourage people to explore that opportunity, but extremely fast-paced career growth and a low-risk work environment are not two things that tend to go hand-in-hand.

You articulated so well something startup employees sometimes can struggle with. I think people like startups, or they don't. I love scaling startups. I love the chaos, when we're outgrowing resources, we don't have enough, or we don't know where to put them. I find that so much fun.

Oh my gosh, you sound like me. That's so funny. I always start like, "Oh my God, I can't wait until we have a budget. I can't until we wait until we have this, I can't wait until that," and then I get it. And I'm like, "Oh, I just wish that things were broken again. So I have something to fix."

It's fun. I enjoy the challenge of where do we take the risks? How do we make this sustainable? I'm less interested in the very early, can we build something? I’m interested in building the org around something so that it can become something in the world.

Yeah. Yeah. Me too. That's definitely the fun spot.

I think we're a specific kind of person. Some people enjoy the startup part of the mature business. I would never be an executive at a more mature business. That's just not for me at all, though maybe a startup. Have you worked at a bunch of startups before this or more scaling?

I would say the majority of my experience is series A to series B. We know we already have a product for working through product-market fit and then kind of scaling headcount. I do have some experience in seed-level, pre-product market-fit startups. I have some experience in much larger companies. I worked at McCann Worldgroup as group head of talent for our whole advertising infrastructure in the UK. So I have got a kind of more varied range of experience. What I think probably my archetype is, is really around places where change is required and maybe the business has lacked a little bit of TLC. So one of the things I really loved about McCann when I worked there, was when I had an interview with the CEO, he said that they were starting to see people leave the team and get other offers. And also, started to see people that really from an interview process get competing offers from companies that they just had never seen as competitors before.

So they'd always traditionally seen Grey and Saatchi and all of that as their competitors. And all of a sudden people were leaving for Facebook and Deliveroo and Google, and they were like, "What does that even mean for us? What are they offering?" We had the opportunity to build out and understand how do we compete against this very new marketplace of companies and how do we build something internally that can kind of be a machine that helps you continually adjust this for the market? That's kind of my fun. When there's the product of the culture or the product of the business needs a little bit of TLC and someone gets to come in and say like, "Okay, let's look at it and spruce it up."

Well, I can also see that in a scaling startup, because in my experience, most startups don't hire very experienced People people. They tend to under-hire in the people area. When it comes to scaling the business, they’re under-invested. They have organizational debt.

Yeah. I think the kind of perception of what a people person is, has changed quite significantly through the pandemic. I think a lot of businesses realize that “Oh, this is a very commercial role that we really need to have a little bit more focus around who we have in these positions.” One of the things I have always quite loudly hated in the HR world is when the people team is the one that's responsible for organizing team drinks and that's what culture is. The people person's the one that organizes the pin the tail on the donkey game on the Friday in the office. And I'm like, this is the person that you have in charge of 60% of your investment every month. You've got them doing pin the tail on the donkey on a Friday afternoon. This is not what this job is.

During the pandemic, I was getting invited to speak to lots of conferences and events where they were like, "Do you do drinks online after work on a Friday afternoon?" I was like, "No, that's not my job. I have never thought about doing that." It's not important. There are people out there whose jobs are doing social committees and things like that. But that's not what people ops are there to do.

If you’re hiring a people ops person into your startup and giving them the job of organizing team snacks, then yeah, your company's going to be underfunded in people operations and have organizational debt, but everyone's going to have really great snacks. It's just a math problem. People problems plus snacks do not equal fewer people problems. It just equals more snacks. 

I'm nodding along because I have the same opinion. Organizing a happy hour is like the last thing I want to do. I'm not interested at all. I've never been a generalist. I've kind of bopped around I think in part because I think I saw a lot of that thought, that doesn't make sense to me, because I've always thought about the business. I love pinball but pinball machines, that's not going to change our business.

Yeah, exactly. I think we're on the same page.

You're only the second people person I’ve had on. The other person was Maria Campbell, who is now the COO of Griffin. I’m so excited she’s moving into that role.

Friend of the pod, friend of the pod.

Yes, a dear friend and the first person interviewed for the series.

Oh, oh my gosh. She's an angel.

She’s great. I met her while I was researching products to help new leaders. We've been thick of thieves, ever since. I love having you both to get this perspective out in the world. I hope founders read this and think, “We need to bring in somebody with people, and organizational skills to the business sooner than we think.”

Yeah. I completely agree.

Your culture and the company that you build is a subscription product. Just the same as a product you build for your customers. Every single month your employees are deciding whether or not they want to keep subscribing. That decision is based on the policies you have, the compensation they receive, the way that they're working together, the products they're building, and their manager. They might hand in their notice at any point. That's them canceling their subscription. 

You have a group of people in operations. They are the product managers of this product that you're building. And if you, as a founder, or CEO, aren't treating that like a product and are just treating it like a bunch of processes that you whack together every month and report on, then you are going to be missing out compared to companies that do.

I think there are a lot of companies that do treat it like this, that maybe don't explicitly say this, but that's the places where you've got the most successful cultures in the world. Think about the Netflix culture deck. Everything that they launch, it's like the Netflix way of working is their whole own product stream. And it's really good. What they do is really good. It's very effective. So, you speak to a lot of founders who are like, "Oh, I want to be like Netflix." And you're like, "Okay, great. Well, let's start thinking about this commercially, let's start doing X, Y, doing Z." And you start investing here and they're like, "Oh no, Ugh. I don't want to do all that. I just want to... Can't you just write a blog about it?" Like, "No."

Is this how you got investment for your product? You wrote a blog and then went out and like, "Hey, who wants to come give us a bunch of money?" And actually, maybe if you're on the blockchain, that actually is what you did. So like yeah, wow to you.

I've read a bit about the founding of Netflix and how they really live that culture deck. That culture is no joke. That document is not a PR document. They really live that. That takes a lot of effort to get there, takes a tremendous amount of effort. Not just let's sit in a room and talk philosophically.

What do you think, what's been hardest about moving from the people to the COO role or about being a COO under the conditions you've been in?

Look, I'm not going to lie. The first six months were really rough. I always say to my team that the first six months or first couple of months after you get promoted are always going to feel terrible, because you've just gone from feeling safe and successful and you know what you're doing, everyone's praising you and oh my gosh, you're nailing it. Then, all of a sudden, within two weeks, you are like, there's less oversight, there are higher expectations. You've got all these new tasks to do. Whereby does what a lot of companies do and say, you need to be meeting 75% of the expectations of the new role before you can get promoted. I think people have this perception of well, companies make you do that so that they don't have any risk, and so that they can get more money out of you or something along those lines. And maybe for some companies that is true, don't get me wrong, I think there's a lot of bad actors out there.

But for the majority of companies, and definitely for Whereby, the reason we do that is because if you got promoted into a job where you had not been demonstrating those things, you were going to be feeling so much pain. That first year of your job is going to be terrible. And you will churn or struggle to find the joy, because you will just feel like, "This sucks. Everyone is demanding, expectations are high, and the feedback is tough…. Give me a good day!”

New leaders fear they're failing. They wonder, "Am I doing it right?"

They’re too scared to ask, because now they're in this new role and, "What should I say? I don't want to admit that I'm suffering here." It's not a nice time. Being promoted is really, really hard. And I don't think enough people just talk about it. Everyone's like, "Yeah, like I'm promoted, that's awesome." And no one ever says like, "Oh, I got promoted. It was the hardest six months of my professional career." Moving into the COO job, there was a lot of stuff I was already doing. I already had full ownership over pretty much the majority of business operations, all of the people in talent, legal, project, and kind of program management and goal-setting. The only new thing I really took on is finance. And I was already doing all of the budgets and headcount forecasting.

So it wasn't like I took on a huge amount of stuff in the first couple of months. And it was still brutal. Just that the step up in my own expectations, the knowledge of how much I wanted it, the amount of stuff I needed to start learning, the things that people were coming to me for, maybe even that wasn't quite my job, but I hadn't identified yet what clay I was meant to be molding into. We talk about how it is molding into clay. I really, really struggled at first, and it was during that time when I was in Australia anyway, and I was kind of going through a difficult time personally. There's a lot of stuff happening with my family. So I think one of the things I would say is if you're forging this kind of path for yourself, then be aware and everyone be easy on yourself, be kind to yourself.

Yes, of course, those things, be kind to yourself and have people around you that can support you, but don't be surprised when you find it harder than you hoped you would, because you probably will. And if you aren't, maybe that's a good thing or maybe you haven't been able to take on as much as you could, and there's more opportunity for growth there for you, but try to be sustainable about that.

That's such good advice. Transitioning to a new role is always hard. When someone gets promoted, I'm like, "Okay, are you ready?" Who's helping you transition into this role? It's why I do what I do. Moving to a more senior leadership role or a really big role like COO is a huge shift. It's really about the transition because many times those huge leaps, they’re different jobs. VP of people is a different job than COO.

Yeah. Completely. I mean, basically any job once you get into that senior place, I think it's moving into levels in your more junior career. I'm extremely positive and I'm very forthcoming with promotions in a more junior level, I think, than I am with more senior roles, because the roles very dramatically change between directors and heads of, and directors and VPs. Looking after one function and two, and there's no way to really prepare yourself for that other than just doing it. So yeah, I think the more senior you get, whatever you move into next is just a completely different kettle of fish you have to kind of get to grips with as you do it.

What advice would give to someone who wanted to make a transition like this?

I think one of the things that I constantly kind of go back to, is this idea that it's really important to be opinionated and not just opinionated without basis. Be successfully opinionated maybe is a better way to describe it. It's like, there's a very big difference between having lots of opinions that are based on nothing and you aren't successful in doing the things you're meant to do somewhere else.

But if you've got a good hold on the team you're working on, your functional group is working well, you're head of people and things are working well, you have a good understanding of the projects you're working on, things are successful, you're reaching your metrics, you seem to be doing your job to a high degree, it's a really good place and opportunity for you to just be opinionated about other things in the business.

At various times in my career, I was probably more cautious about being opinionated than I should have been. I think, especially in the people operations role, I had this nagging feeling, like, "Oh, I'm not part of the commercials. I'm not part of the product. So I shouldn't be getting involved in discussions around that. I don't want to step on anyone's toes." I wish I could go back to myself five years ago and say, once you have your ducks in a row and your team, be radically opinionated about what other people are doing.

This doesn't mean getting into the detail of the weeds of their operational day-to-day. But if they present a strategic plan and it isn't aligned with not just the culture and the progression of your company, but if it's not aligned with the way that you see the company progressing in five years, you are a leader, as much as anyone else. Have an opinion on what they're doing, and understand it. And if you're sitting there watching your finance team's presentation, you don't understand it, so you can't have an opinion, figure out how to understand it. Go and read something, ask someone, sit with someone and say, "I don't get it. Can you read me through it again? I want to have an opinion." I just wish I could find even a 20-year-old baby Jess who just graduated and say, "Be okay to have opinions about other people's things." I think that would've really helped me more than I thought it would've hurt me, which is what I was scared of at the time.

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