44 min read

Episode 16: Organizational design

The people ops pro who mastered legal, finance, and more on her way to COO.
Episode 16: Organizational design

Get ready for one of my favorite episodes of the pod yet!

This week's guest is a badass people ops pro turned lawyer.... with some finance and customer success expertise sprinkled on top, too! Suffice to say, there's a lot we can learn from her background.

And, if that wasn't enough, she's a rare COO who manages to keep the company's values at the center of every decision, while still prioritizing a really productive and profitable business. It can be a tight-rope to walk and she has lots of advice for doing it!

Whether you're an operations leader trying to balance mission and values with business needs, or a less-experienced operations pro thinking about the next steps in your career, this is a conversation you don't want to miss.

About Our Guest

Jessica Zwaan is an early-stage startup executive; currently COO at Whereby.

Jessica started her career in traditional HR roles at companies like Box and Goldman Sachs before stepping into People Ops leadership.

Since then, she's added a law degree and some serious skills in finance and customer success to her tool belt. All of which have helped her become what she often refers to as a "hands-on COO."

About this Episode

In this episode, we chat about:

  • Why Jessica refers to herself as a commercial or "hands-on COO"
  • How she uses product management practices to build a really unique and output-driven operations function at Whereby
  • Why she decided to go back to law school—and how she's up-skilled in other functions like finance, too
  • Practicing non-paternalism at work—and how this factors into offer letters and expense policies at Whereby
  • How the Whereby team works asynchronously across such varied time zones, and the very real trade-offs they make to do that

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Show Notes

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Mentioned in the Episode


Welcome to Opsy, a podcast for people doing opsy work in tech. I'm your host, Caro Griffin. Every month I dig into what Opsy work really is by talking to an operations pro who has something really cool to teach us—in a traditional part of ops like HR or finance, or a newer specialty like no-code ops or marketing ops. Thanks for listening!

Caro 0:28
Hello, everyone! Welcome to the latest episode of the Opsy Podcast.

I obviously have a very special guest because all of our guests are super exciting and special. And so, today, with us, we have Jessica Zwan, who is an early stage startup executive currently wearing the COO hat at Whereby.

She spent her career in HR and people operations, where she's developed a really unique perspective on how to run these teams. (Spoiler alert, it involves some strategies that you might typically associate more with a product team.) I'll let her tell you all about those and her awesome new book.

So, without further ado, let's get started. Jessie, thanks so much for joining me.

Jessica 1:05
Hey! So nice to be on the pod. I must say I love the podcast branding. It's so cute and so on brand for me. I'm obsessed. Is it the first time you've had someone shout out the Opsy brand?

Caro 1:19
During the podcast? Yes. Although, I do get compliments on it sometimes, which makes me happy as the former art school grad who has a little too much fun in Canva. [Laughs]

Jessica 1:25
Yeah. Girl, it's really cute. I love it.

Caro 1:29
It's funny that you say that because I actually had a note here that I was going to compliment you on your beautiful website, which is not so common for operations folks. So, a little plug there for anyone looking for some inspo. But it's just so cute! I love your branding—

Jessica 1:42
Thank you.

Caro 1:44
… Everything about it is just so cohesive and fun… One of the many reasons I wanted to talk to you today.

Jessica 1:19
Amazing. This is now what this whole podcast is going to be about. It's just us two talking about our own online brands and presence.

Caro 1:54

Exactly. We'll just toss compliments back and forth about how cool we are.

Well, to continue that trend… Tell me how cool you are. [Laughs] Give everyone a little overview of your career so far, so that people know where you're coming from and what you've been focused on.

Jessica 2:08

The introduction you gave was really nice. I don't like giving really long introductions to myself. But, yeah, I've primarily worked in people operations. I've got a background in people ops and legal. And I'm currently the CEO at Whereby.

Whereby is a fully remote video API business. In my role there, I look after everything from finance, people, legal, obviously, and then also customer success, customer support, business operations, and CSM as well. So, I'm kind of in a commercial operations-type role.

You mentioned that I wrote a book. [Laughs] Yes, I've written a book called Built for People, as well, that's come out fairly recently. And it is all about how to build your employee experience and your people operations team like you build a product function. It's really focused around the idea of making sure that you're building this kind of product that your employees are subscribing to and then really thinking about your operations team with output metrics and sprint planning and iterative feedback and yada yada yada. So, I really love talking about that.

Caro 3:12
Love it. We're definitely gonna talk all about that. I think that's something I… it’s one of the reasons I think I was drawn to you when I found you online because, as someone who kind of grew up professionally in this agile flow, I like very much still think in like sprints and planning and roadmaps and, I don't feel like that's as common as it should be in like operations team. So we're definitely gonna get into that.

But first, I want to kind of zone in on how you described yourself as a “commercial COO,” or as being in a commercial role. And I've also heard you describe yourself as a “hands-on COO”—on your very cute website, in fact. So, why don't you tell us a little bit about what that means to you, especially when you're leading so many functions?

Jessica 3:50

Yeah, I think when I say commercial, I don't mean like I am involved in sales, per se. But I would say that the way I think about it is more like, I don't spend a lot of time just only building internal stuff. I really like to spend a lot of time being very customer focused, very output focused.

I guess this idea of people versus a product thing is kind of helpful here, like the way that I think about the definitions of things…

I think there are like three products that every company has. You have your product you're selling your customers, which is like, you know, Harry's is subscription razors, Riverside FM is this beautiful platform we're using to record this podcast.

And then you have the financial instrument that you're selling to your investors, your shareholders. And that is a really important product because the higher quality your financial instrument, the better quality products you're able to create because you have better quality investors in the team. It's a very kind of virtuous cycle there.

And the final product is this employee experience, the company that you're building. And again, this is a very important product. [When you] build a higher quality employee experience, the more people want to work for you, the better fit they are to your USP, the better quality products you build, the better financial instrument, the same story goes on.

And what I mean when I say I'm a commercial CEO is, again, not that I'm a salesperson. I'm not a CCO, I'm not a VP Sales. I really like to think about the ops world—finance, legal people, etc.—with this very commercial lens of, like, you are building a valuable product that contributes back to this financial instrument.

It's not just a service function. It's not just an efficiency function. It actually has this inherent value. The better quality your business, the more effective they are, the more valuable your employee base is, the better quality investment you will get, the better product you'll build. This thing, I think, is a really commercial focus.

So that's what I mean when I say commercial COO.

And then the second question is [about being] hands on. And I think that's mainly just, I still kind of see myself as a bit of a builder. I don't spend a huge amount of time like in spreadsheets or anything like that anymore, unfortunately. I do love when my team lets me do things like that.

But I still am very much… I spend an hour a week in our customer support queues every week speaking to customers directly. I'm in every single one of our weekly business review calls with our entire business. I come to every single product sprint planning.

I'm very curious about what's going on inside the business and I really want to know. Even if I'm not necessarily the person on the ground building things, I think it's really valuable to actually be hands-on with the day-to-day.

Caro 6:30
Yeah, that makes sense. And I think it's a nice little overview of how you see that role. Because COOs, it’s a role that does range from company to company, and even kind of depending on the functions that are overseen.

Zooming in on that a little bit, tell us about the scope of your role and maybe we can dig in a little bit to it—it sounds like you have a long list of functions that you're kind of overseeing, everything from legal to finance and stuff. So, tell us a little bit more about that.

Jessica 6:54
I look after basically everything that comes up under that umbrella of like the company you are building rather than the product. The only exception I would say to that is probably support and success. I would say they're very customer focused. They're part of the product we're selling as a business.

You've rightly said, COO is a very nebulous role. And for some people, it's almost like a CFO. Some other folks, it's a very commercial, like sales type almost role. Some people really come from a [more] strategy background where it's not hands-on at all, it's very cerebral.

But yeah, I spend a lot of my time leading my team towards a big picture goal over a year or a six-month period. [I do that] through the implementation of really high quality output metrics on a quarterly basis, and then kind of guiding them along like a roadmap to deliver whatever they decide to implement in order to get that output metric that they've set.

And then I'm also kind of the point of escalation for anything significant from a legal perspective, or like a contentious exit of the people team, or a really difficult customer deal that we're trying to win over and they want me to get on the call with them. Those kinds of bits and pieces, too.

Caro 8:09
Makes sense. The escalation piece so often becomes unexpected, right? It's like, how do you plan for the unexpected… that you can't plan for. Thanks for breaking that down.

I’ve got to ask, do you have a favorite function? Do you have one that you gravitate more towards? One that you avoid when you can?

Jessica 8:30
There's an Arrested Development GIF of, “I love all of my children equally.” You know what I'm talking about, right?

Caro 8:37
[Laughing] I do, yes.

Jessica 8:39
Obviously, People Operations is like… I don't want to say it's my favorite, but it's definitely the one that I have spent the longest time working in. For me, the reason I love it is it's almost the most integrated. It touches literally every part of the company, right? Because you're literally like actually working with every single person that's doing every single type of role. And no other job, I think, in a company has that kind of scope.

You get to see problems and challenges in every single manager, like you get to see the successes and failures of the different goals people are reaching towards. You get to see the good and bad implementation of return on investment when it comes to both the team and the ways that they're spending their money, on either tools or something else.

And it's also the team that has usually actually the biggest responsibility, in my opinion, in terms of deployment of budget.Because you're essentially responsible for making 60% of a company, usually it's like a 60-40 split with headcount OpEx, right? You're basically the one that's responsible for making sure that you're optimizing that 60% that that your company is earning every month. Plus, benefits and office and off-sites and all of these other nice-to-haves, right?

So, you have this gigantic budget responsibility and this huge optimization opportunity, and it's cross-functional in literally every single team in the company. So, I really do love that aspect of the people team.

I like the finance function, as well, because there's something that's very calming about it. It can be captured on a spreadsheet. It can be captured on one dashboard or something... I don't know. There's something quite nice about being like, oh, “I have everything I need right here in this one big P&L I've created,” which just doesn't exist in any other team.

Caro 10:25
I also very much feel that calming aspect of finance. Even when I'm doing something in the finance function that I can't quite wrap my head around, or I'm confused by or whatever, there's something about like… this is black and white.

I almost think of it as like a different language where it's like you're learning a different language and there's a right or wrong answer. You're learning how to translate… What are these KPIs, what are these dollars and cents telling me about what's working or what's not working?

I feel like I really sense that problem solver in you that I so often find in COOs of like, “Yeah, I want my hands in all these departments and also all the other departments because I want to see what they're doing and what they're working on and what I can learn from them.”

Jessica 11:13
Yeah, completely. I think the finance thing is so funny because like, coming from a People and Legal background, I spent like 15 years of my life answering every question with like, “Well, it depends.” Like, “Well, it depends what we should do about this.” And, “Well, it depends whether we should pay this invoice,” and like, “Well, it depends.” But in finance, it's literally just like… Is it this? Yes or no? Like a number is a number. Money is money.

And I think there are some interesting things we could talk about finance. Like, you know, I don't think every dollar worth of revenue is like… not every dollar is the same in revenue, right? You can have good customers and bad customers and good deals and bad deals. But, for the most part, the things that you're dealing with in finance [are as ambiguous]. Very few of my answers in finance are, “Well, it depends.”

It's like, “How long is our runway?” Bam, this date, great.

Caro 12:00
Yeah. We can argue about how we calculate things, but at the end of the day, the data is the data, right? You can slice it a bunch of different ways, but it's our interpretation, it's translation. I love that.

My background has definitely been more like people ops and finance has come later. And I think, actually, I'd love to dig into that a little bit more. Something I often talk to ops leaders about, especially ones that have more of a people ops background is [about how they] like finance.

Well, some people are scared about it and that's totally valid. But there's so many of us who are like, oh, I like finance, but how do I learn finance? How do I get up to speed on this? So often, I get asked, do you have resources or courses or books or something? And I've even asked some of my favorite finance people and they're like, eh not really?

I learned on the job. And, so, I'm always curious, how did you learn to do the finance function or at least oversee the finance function?

Jessica 12:50
I like the comment that it's scary because I think it is one of those things that feels scary, but it's actually like, again, I just don't think it's a very scary function.

Obviously there are multiple parts of finance, right? There's the statutory kind of accounting, statutory finance. That is like, again, it's very black and white. It's very learned. I don't think you need a COO to know statutory finance. You can hire somebody that is a statutory accountant or an external accountant and have them own that for you.

Then you've got the two halves of finance that I think are kind of most business. The accounting side internally that's not necessarily statutory. This is like building out your P&L, understanding what your runway is going to be, revenue recognition, your GAP [Generally Accepted Accounting Principles] standards in the countries that you're operating in, these kinds of things, right?

And that is, I think, what sometimes people think is the scary bit. But again, you don't need to be an accountant to be able to lead a team that's doing that work. Because, again, a large part of this is kind of like, there is one way or another way to do this. And maybe there are some strategic decisions that you can get involved in.

I've got a really excellent finance director who comes from a very tried and tested finance background. And she runs very well that part of the team. And I'll give her the strategic direction about what I'm expecting and timelines and communications and things like that.

But then there’s this third part of finance, which I really love.

Finance is a decision-initiating function in a lot of ways. It's this part of the business that's able to... If you think about FP&A or even getting involved in things like billing and the revenue operations side of things…. They're a function that can really help your teams make great decisions by informing them really excellently about forecasts that are coming up, or trends they've seen in the past, and help your team by helping them build out ROI calculations. That piece of work, I don't think you need to have a financial background to be really good at helping use numbers to tell a story or use numbers to inform a good decision.

That's actually the piece of finance that I spend the majority of my time thinking about. How can our finance team be the team that people feel like, without them, [they] would never have been able to make a great decision?

Caro 15:00

Yeah, totally. I mean, that makes sense and is really consistent with what I've done, in some way, shape, or form, and is consistent with what I hear when I talk to other people in similar roles.

I think maybe there is just that, part of what makes it scary is there, especially when you are self-taught or you feel like…

Actually, I would say this isn't even finance specific. I'll back up and say I think this is operations specific, because so many of us didn't study operations or HR in our undergrads. Everyone's like, “This is how I'm doing it. Are you doing it the same way?” There's this imposter syndrome sometimes that comes around.

I think with finance, because people are, like, well, I'm not “official.” And it's so to your point, right? That you can hire an accountant, you can hire external vendors. It is that strategic thinking [that’s important to bring to the table].

So, I hope that this is maybe some reassurance for anyone who's like, “Am I doing this right?” with finance? Because, you laid it out so nicely, the different ways that finance all rolls up and what finance really means, right? There's a couple of different types.

Jessica 15:55
Yeah, it's interesting. There are definitely moments where I think, if you've got really messy finance… not that your financials are messy, but that your record keeping or your forecast or whatever are really messy, that can be a really scary place to begin.

Like, I took over the finance function at Whereby and we had just grown so quickly during the pandemic that there was just a bit of chaos in how we were managing things. And it was no, like, discredit to anyone who was on the team before. It was literally just like, so much had happened in such a short period of time that we hadn’t had the chance to get budgets. We hadn’t had the chance to have a proper kind of cash model look ahead or a revenue model that connected back to a headcount plan. There were a lot of really big missing pieces.

And that is quite scary because that is then…. What skeletons are hiding in these closets that I have to go out and find? And then how am I going to deal with those problems? But ultimately, somebody has to. Somebody has to deal with them.

But a really strategic person that's good at making good business decisions with a skilled accountant? That's a great combo to be able to deal with it. Everyone should be more than capable, I think.

Caro 17:05
Yeah, totally. We're here to solve problems, right? Like, that's what we love. That's one of the reasons we're probably doing this job.

Well, I want to dive into another one of your functions. And that's legal. It's not often that I feel like I see lawyers and People Ops in the same person. I would love to hear what made you decide to go back to law school. Tell me more about that journey.

Jessica 17:29

Yeah, this is so funny. My first degree was in journalism and communication, but I actually did get into law school and I decided not to do it because everyone kept being like, “Oh my god, law school is so crazy, you're going to be overwhelmed.”

And I was like, you know, however young, I was like a baby and I was like, “Oh, I don't want to have no life and be studying for seven years. I'm not going to do it.” So, I actually pulled out before I even started. It was a non-starter for me.

And then, working in people operations, I was finding myself really frustrated with the fact that I felt like there were questions that I could easily answer, but I couldn't do it because I didn't have the knowledge in legal and how everything kind of pieces together and how to think about things.

I was doing a round of redundancies and we needed to have some legal support help us out with some things. And I just felt myself deeply frustrated like, why can't I self-serve this? Why can't I solve these problems myself? It was so overwhelming to figure out how to read the statutes and what the right process was.

It was just before the pandemic, actually, and I was working in a role where, again, I found myself feeling like I just didn't have the breadth and depth that I really wanted in my career. So I was like, maybe I'll just go back to school.

So, yeah, I went back to law school and I did my degree and I focused on the legal implications of remote work and cross-border was my last year focus of my dissertation, which is a nice little crossover between contract law, employment law, and a few other bits and pieces.

I just really loved it. I love studying, so it was a vibe.

Caro 19:08
A vibe, yeah, for sure. [Laughs]

I feel like that dissertation topic and these intersections of employment law and remote work and all of that is a super interesting topic. One that I'm definitely interested in, and I'm guessing it's of particular interest to a lot of our listeners. We have a pretty large community in London, so the UK component, but also just more broadly, I think, post-pandemic, this is something a lot of companies are still navigating and trying to figure out.

I have so many questions, but I don't even know what to ask about. [Laughs] I guess… How has that informed how you, like, run Whereby? In terms of how you classify people, or manage benefits, or I don't know, is there anything that sticks out there?

Jessica 19:50

Yeah, I mean, things have already changed so much from when I did that dissertation a couple of years ago. Obviously, like, the pandemic has just really, like, thrown spanners into the works. And so many countries have responded back much quicker than I think people predicted at the time.

Whereby is fully distributed. We have three entities. We have the US, which is where I am, the UK, which is where our CEO is, and then Norway, which is where our executive chair and our partial owners are.

So, Norway is our HQ, we were founded in Norway. But we have people everywhere. We have people in about 15 different countries, from like India to Chile.

We kind of use a bit of a mosaic of hiring coverage. We have basically a Notion page we send out to you when you get offered to work for Whereby that gives you options about which contract you'd like to sign. And, obviously, the three entities are an option. You can go and live in one of these entities, if you have the right to work.

So, if somebody is based in the UK, generally, they'll just do the UK contract, but if someone's maybe based in France, but is British, and they're like, “I actually kind of want to spend nine months of the year in the UK and a bit of time in France, back and forth or something,” then they may actually get some advice and go for the UK contract.

There are obviously some legal considerations there, which we include. You have to spend 181 days inside the country for a lot of tax jurisdictions, and there are a few other bits and pieces. But then we offer two options for distributed workers, [a contract agreement and an employment agreement].

For example, there's a member of our team that also did some university lecturing and other kinds of side work, outside of their work with us. And, for them, going down the consultancy route made a lot of sense because they were like, well, I have multiple income streams, and I actually consider myself to be like, almost self-employed in the way that I work. So great! They did that. And we just made sure that we set up everything so that we were compliant in terms of taxation, that they were very clearly a self-employed person, they had their own entity set up, etc.

The other option is we have an Employer of Record relationship, where we can employ people through an Employer of Record in multiple countries, which some people opt for just for security, and also they don't have the means or the reasons to set up their own self-employment.

Caro 22:00

Interesting! I don't know that I've ever come across a company that gives employees the choice. I feel like normally it's like, “we're in the US and you're in the US, so we'll employ you as an employee in the US.” And, if you're outside the US, you're going through Deel, or Remote.com, or another Employer Record. So, that's definitely an interesting approach.

Have you always done it that way? Or was this like a post-pandemic or post-law school decision?

Jessica 22:25
Whereby was fully remote before I joined and we were fully remote before the pandemic. We've always been a distributed work workplace, and that's because our product is all about enabling work from anywhere, enabling people to connect.

One of the things that I do pretty much with every company when I first start working with them, especially if I'm kind of building a function, is that I run a very badly named—maybe we can come up with a better name—workshop called Organizational Design Principles. Very dry, doesn't sound good, this is the Goldman Sachs in me coming out. [Laughs]

Organizational Design Principles are basically like the principles of which you agree as a leadership team about how you wanted to build your org. Do we want to be highly hierarchical or very flat? Do we want to have T-shaped team members or very specialized team members? Would we like to have a dominant junior workforce or would we like to prefer to hire very senior people?

These decisions help you make cohesive choices. One of the things I've really seen companies struggle with when they kind of get into this like scale mode is like, for example, the CMO really wants to do a bunch of juniors and have an internship program. Maybe they really love the idea of the team being highly hierarchical, like lots of headcount, lots of people. And then your VP Product is like, I want to have very senior people, very lean teams.

All of a sudden, when the intersections start touching each other, it just falls apart because you've got really senior people trying to interact with really junior people or really specialized people interacting with really T-shaped people who want to behave like generalists.

Coming up with a general set of principles around how you want to build your org at large I think is really beneficial.

When I started at WebEye, we did that exercise and one of the things that really came out of it was we need to have a very strong culture of non-parentalism, or non-paternalism or maternalism, which means that basically, if we are fully remote, which we are, we believe then the best way to be fully remote is to be completely hours agnostic because you can't be fully distributed and then be kind of forcing people to work certain hours, it starts becoming quite brittle.

We said, okay, so if we're hours agnostic and people can work whatever hours they want, the next question is going to be like, how do they self-manage?

Well, we can't hire really junior people because that will be quite difficult for us. We need to hire people that are fairly senior and also thrive in a very non-parental environment that are able to make their own decisions and raise their hand when something goes wrong.

That became one of our kind of dominant org principles, which is that we have this non-parental, highly autonomous culture.

Some people hate that, absolutely hate it. And we had some people that worked in our team that didn't like it, and we’ve had some people that got through the interview process that didn't like it. But at Whereby, that is one of the principles by which people thrive.

Now, the reason I'm giving this big, long-winded story is because the idea about giving people the choice about which type of contract they would like to sign, I think, is a very good example of staying true to that. We are giving you all of the information you need to make a decision. We are not going to parent you in this choice.

If you want to just be in the UK and be employed through a UK employment contract, then obviously that's the choice that you will make, that's no problem. But if this is something that you're genuinely interested in reading the different templates of contracts available to you and really making an informed decision here, you have all the tools available to do that. We aren't going to tell you what the best choice is for you. So, yes, that's kind of the reason why we've done that.

Caro 25:49
Yeah, I love that you went through that explanation. I was dropping mental bookmarks to come back. There's so many things I want to dive into there.

Maybe the first is, because you were talking about the title being dry, it just so happens that yesterday, I was giving a talk for a cohort and they had assigned me that exact same title. [Laughs] And I was like, this is dry. We're going to call it Growing with Intention. And I was like, that's like slightly more like, I don't know… something. But I had sat there and was like, what else can I call this? And I couldn't come up with a sexy name either.

Although mine was literally more about building a hiring roadmap. And yours, I think goes even further back to the beginning, which I love, and I'm already plotting, like, how do I get to attend this workshop? How do we get you to give us this workshop?

Jessica 26:33
Oh, it's so much fun.

I do this great exercise in the workshop, which I actually just encourage everybody to do generally. The entire leadership team comes, so like 5-6 people, and I give an X-Y grid with a bunch of different things, like how much leverage do you want people to have versus how skilled do you want them to be? Do you want people to be almost like an investment banker, where they're responsible for like huge portions of your portfolio, or do you want to be more like Amazon, where people have very little leverage, and they’re in a very defined role. If someone on Amazon changes one little thing, Amazon is not going to be affected, right? Because their roles are very, very low leverage.

Or, another axis is around skill. Like, is it like Google DeepMind, where everyone has a PhD? Or is it like, again, like an Amazon Warehouse, where you can come in and learn the skills to do it in a day or two?

I asked everyone in the workshop to plot their company where they are today, and where they want to be in five years time. Like, where's the aspiration that you want us to be? Not the team, the whole company. All the leaders put themselves in this little grid where they want to be and then I say, great, now I'm going to listen to you for the next 20 minutes while you all agree on two locations.

And then I have to just listen to them argue about where they want these two post-it notes to be, which is hilarious because often the engineering leader is like, we want everyone to have PhDs. And then the person in marketing is like, we don't mind, we can train them on the job. And then all of a sudden these two people have to argue it out.

It's hilarious.

Caro 28:
I immediately had the vision of that GIF or, it's not even a GIF, it’s like a meme, but there’s a house burning in the background and this little girl in the foreground who's smirking. [Both laugh]

The scenario that you outline with the marketing person, the engineering person—it’s exactly how I would imagine it to go.

Do you find that they really do find common ground as a company or that, generally, there are some caveats of, like, yeah, but engineering is going to be more here and marketing is going to be more here.

Jessica 28:47
They find common ground. I do say to them, if you really believe your company is an exceptional situation, and you have this, like, second organizational design structure that exists within your true organizational design… Fine, you can pull out the other team.

But, just remember, there's only so many things that your company could be an exception on before you start becoming like an overly complicated business, right?

Caro 29:14
That's a great way of putting it and a lot nicer than how I've sometimes put it. [Laughs] I'm usually like, you're not a snowflake. You're not special. I know you think you're special, but you're not special. [Laughs again] So, I'm going to save that for my back pocket. It's a much more tactful way of saying it: You can only be an exception in so many ways.

Jessica 29:29
Exactly! You can only be an exception in so many ways.

But, yeah, I think generally people find common ground and they reach this point where the conversations can get quite detailed about where people would like teams to be and why.

I think the exercise is also really beneficial for me. It’s obviously about figuring out the true center, but what it's really about is encouraging the leaders to have a really general and open conversation about their actual ideal org. And really hear each other's challenges about it.

It's not about putting the post-it note on there. I don't actually care if they never finish it. What I want them to do is to have an actually engaged conversation about, well, no, it doesn't make sense if we hire 25 interns next year because my team doesn't have this same structure.

Getting them to understand the way that the other is thinking about things and realize that they have to compromise on even this.

Caro 30:21
Yeah, absolutely. I think that's a great takeaway for everyone listening, to have these conversations sooner rather than later.

I also really want to dig into what I think of as async culture, but you called it hours agnostic, which I love. So often, I feel like I talk to operation leaders who are experiencing problems and they're like, how do I solve this problem?

And I'm like, this is a symptom of a larger problem around async communication, or like running a team and not being clear about it. It's like not being able to plot on the x to y axis of how hours agnostic you are and like how much overlap you need.

It’s such a messy pile of problems and people circle it and aren't quite sure how to approach it. And, so, I would love to hear more about how, at Whereby, you foster that and facilitate it, especially as like the operations team who is so often responsible for the policies and procedures and stuff.

Jessica 31:16
Going into this idea of non-parentalism again, we crafted this doc, which I think is public... If you look up our open handbook, you'll find it. And this doc talks very openly about the fact that every decision we've made at Whereby is a trade-off between something good and something bad.

We've picked hours-agnosticism, which is, we think the right thing to do, given the fact that we're fully distributed and we're building this product and it connects back to the mission. This is the reason we're doing it.

The great thing about hours agnosticism is that, if it's 2pm and you want to go skiing because a great snowfall just fell, then be my guest. Go out and do it. Cancel the rest of your afternoon focus time and go make it happen. Bad side about hours agnosticism, someone in Australia wants to have a 1:1 with you at 7am, you're going to have to get up and have a 1:1. You can't have the good without the bad, and that's something we've been very open with our team about.

If someone comes to me and says, I'm really frustrated because a person put a meeting in my calendar at 8 p.m., my response back would be like, well, what would you do if you were going for a mortgage or something and your bank put a meeting in at 8 p.m.? Be a grown-up. Respond back and make a plan that works for both parties because you need to get your mortgage and you need to have this meeting.

I can only help you facilitate that conversation that you get to an outcome you're happy with, but what I'm not going to do is tell you that we're going to lock your working hours down in a specific way. That's your responsibility to figure out how that works.

And again, some people in our team love that. And some people in our team who have had in the past worked for us when this kind of new way of working came in, really struggled with that, because they found that they were like, having to now take responsibility of a thing that they didn't necessarily want to take responsibility for at work, which was their time, in a new way.

That's kind of like the main thing, from a policy decision.

And then I would say the other thing, as well, is that our teams are spread geographically quite far so I think I have a lot more responsibility to be very careful and thoughtful about how I plan stuff into the team's calendars, but also what's coming up for them around that structure.

I’ll give you an example. We have quarterly planning every quarter, same as every team probably in the world. [Laughs] We have a retrospective and we have a goal planning session and they are always in the calendar a full three months before so people know when they are and we always have a clear agenda about when you are expected to be there, when it's optional to be there, etc. And one of the things that I also need to completely avoid as a leader is like coming up with a structure in that meeting.

I cannot enter that meeting and say, like, these are our output metrics, here's some ideas about how we might want to do it this quarter. I have to already have a really clear understanding of like, okay, so this quarter, we're going to have this meeting at this time, does that work for everyone? And this is our plan.

I have to spend a lot more time being very intentional about how we're going to work together. I can't come up with that on the fly because it starts really like throwing a wrench into the team's world when they're having to figure out what to do together, at the same time as being informed how they're going to do it, and which time it's going to be, and whose calendar they need to work with. It starts becoming very complicated and stressful for them.

I think that's one of the things I find leaders fail with when they try to work remotely. They don't really see it as this whole operating system change. They see it as like, well, I can just do the exact same things I do now, which is rock up to a meeting and tell everyone, let's brainstorm how many meetings we're going to have next month. And everyone's like, “Well, we're also doing this at the same time as planning our projects, and at the same time as we've all been waking up at five in the morning to make this happen. What the hell?”

Anyway, it's a bit of a rambly answer, but hopefully that's helpful.

Caro 35:00
No, yeah, very helpful. Thinking of it as an operating system is a really crucial distinction.

This is like so much of the pushback that we see now with this whole return to office push. Part of that conversation is like, this wasn't remote work. This was working from home during a pandemic. And what is remote work versus like, what is working from home? Because in my mind, they're two different things, right?

If you and your team are all in the same city, working the same hours, it's very different then a team like Whereby with people in all kinds of countries, who really has to think about, what do we use meetings for? Because meetings aren't just their 1:1s, they’re team brainstorming, they’re planning, they're stopping by someone's desk and asking a quick question. You can't use it for all of those things. You have to get aligned on like, what do we use meetings for? And then, like you said, there’s the responsibility of the leader to do that prep.

Jessica 35:51
Exactly. When remote working became more prevalent, I think it gave this permission for people to start questioning the fabric of decisions that we've made, which is a good thing. I think questioning and changing things is a really good thing. But, what this has started leading to, has been a really valuable shift between the worker and the employer, with questioning what is the problem we're solving by doing X? What is the problem we're solving by bringing everyone into an office? What is the problem we're solving by doing...

Employees started saying, well, we don't need to do good work in the office. Like, if the problem that you're solving is having everyone together because that's where we're most productive, then the answer to that problem is actually, it's false. The hypothesis isn't proven true. So, your workforce really started expecting your leadership team and your operations team, to come up with policies and ways of working and, solutions for them, products for them, features for them, if we're talking product management talk, that actually solved a legitimate problem. And I think that that expectation is, first of all, a brilliant thing because it means that it's a higher bar for your people and operations team. They can't just do something because they want to or because it's easier because it's a solution everyone else is doing.

I also think it encourages a much more valuable contribution from a people operations and an operations team. You have to be doing stuff that actually solves problems, not just stuff you think solves problems or that is a nice solution.

That is now cracking open questions around like, “Okay, so you're saying that we can only be remote three days a week. Well then, why is it Wednesday?”

Sometimes it's just literally like, we want to do a day because we're a client-facing business, and we want to have clients on site, and Wednesday's the best day for our clients, and that's the answer to the problem. And for most people, actually, a cognizant answer to a genuine problem will actually make people be like, okay, that's fine. I get it. No problem.

It's when you start being like, “it's just because we need a day and Wednesday's the day,” that people will start being like, well, kind of F you.

Caro 37:56
Yeah. I think it's natural to like buck against that, right? Especially if it inconveniences them, like traffic is worse on Wednesdays, or they have to drop their kids off at school on Wednesdays, or whatever the case may be.

This used to come up a lot for me with transparency, because that's a big value of mine as a leader, and I want to work and build companies that are radically transparent.

I think it just allows us to all make better decisions when people are looped in, when they know the financials, when they have that information. When I get push back on it, what it really comes down to, I think, is can you trust people to be rational human beings? And to hear a reasoning and say, ok, got it.

So often, when you really boil it down, that's what the pushback was, and I was just like, yeah, I'm gonna tell them why I picked these two health insurance plans because even though we had a town hall to discuss health insurance plans, because X, Y, and Z. And, if they don't agree with me, that's fine. Most of the time, they understand that I listened to them and I'm giving the reasoning as why we picked the plans, and then they're adults, they can move on.

Some things, we can agree to disagree on and just like, move on. But, so often, it's an avoidance of tough conversations and a lack of trust in people. Like, have the tough conversation and trust people to be adults.

Jessica 39:23
You’re trusting these people with your entire code base and speaking directly to your customers and access to your Twitter logins…

Caro 39:32
And your Stripe account and your money…

Jessica 39:33
Exactly! Here's a great example of something that I think is really funny in the same kind of trust space, right? Which is connected to paternalism and good decision making and all these things.

Again, fully remote, we're a company that really is giving people a lot of autonomy. A lot of the time, people aren't logged on at the same time as their manager. You're pretty much independently working for like three or four hours a day and you need to get something done. So, I said, I want everyone in the whole company to have a credit card that they can use to make purchases as they need to. There's a cap—it's like 500 pounds a month; for managers, 2000 pounds or dollars a month. But it’s there to use.

If you're writing a blog and you need a stock image, buy the stock image. If you need to get some lunch for your team because you're a manager, grab it. I don't care.

Basically, there's no expense under £500 or £2000 that's so bad that we can't retrospectively have a conversation with someone and say, hey, the third delivery in a row probably wasn't appropriate, let's just rein it in, shall we?

So, we implemented that and we actually give people access to those cards the week before they start working for us. And we say, you start working for us in a week, you've got this credit card, you've obviously signed a contract with us, and you can use this to purchase your laptop, purchase stuff you need for your home office. We've given you a doc about how we suggest you use it and, you know, ask us if you've got any questions.

For so many people, that's such a massive positive for them when they join. They're like, wow, I can't believe you're trusting us. We haven't even started on the team yet, and you're already giving me full access to everything that I need.

But we have never… this is not true, we've had one instance of abuse over the three years we've implemented this policy. One instance of abuse, and it was a very unfortunate situation with somebody who was very aggrieved and made a silly decision that they apologized for post-fact, right?

That is less than the amount of abuse that I have had on previous expense policies that required top-down approval.

Caro 41:25
Totally. And it goes, I think, back to that whole thing of, everything the people ops team does needs to be solving a problem. And I think, in the same way, all of your policies need to be solving a problem. And you have to ask yourself, is this a real problem or is this an assumed problem?

This is something I try to do a lot, where I'm like, is this a boogeyman? [Am I doing it this way] because we've always done it this way? “People are gonna abuse the credit card.” And it's like, are they? Because at the end of the day, do they want this small charge under 500 pounds more than their job?

Jessica 41:55

Caro 41:56
I always ask myself, what's the worst outcome? That we lost 500 pounds and had to have an awkward conversation? Versus how many times did someone waste time because they're waiting for permission? How much time did I have to spend giving people temporary credit cards, setting them up and figuring out permissions issues?

I feel the same way about logins—just give them the damn login. When it becomes a problem, we'll reign it in.

Jessica 42:26

Caro 42:26
Within reason, obviously, but like, you know, there's a lot of things… I don't care if you have access to our Canva account, you know…

Jessica 42:35
Right, go nuts. I've literally had people leaders, when I tell them about this policy, this approach we've got with our credit cards, right? And this is just one small example of, again, we've given full access to our data as long as it's not personal information, and like a bunch of other stuff, right?

I've given this example to people and they've literally been like, “Oh my gosh, I could never do that.” And I will tell them, look, our experiment of this, and other companies I've worked with who have rendered a similar thing, has proven time and time again, this is a very effective way to manage the team. And it's very effective and efficient for them to solve problems.

They would still be like, “No, I still couldn't, I still couldn't do it.” What if, what if, what if? And it's like, imagine if your team found out? If I found out that somebody thought of me that way, that worked with me and my company, I would be absolutely mortified. If they're like, “Yeah, she's great and we trust her with our payroll, but if we gave her a credit card, you never know, she might just spend it on Amazon delivery. Like what?!”

Caro 43:37
Yeah, it's like you're gonna see the expense. That's the thing. You should be hiring people that you trust who are going to do good work, who aren't going to abuse a credit card. If the way you have to find out that they're not trustworthy is that they spend 500 pounds? Okay, cool. We dodged a bigger bullet, you know?

I feel like all of this is actually a really great segue to your book. [Laughs] I'm making a couple leaps here, but I feel like it’s running teams with this problem-focused mindset of identifying a problem and working backwards from that and making sure that you're solving a problem, right? When you're not just prioritizing things for the sake of prioritizing them, or because other companies are doing them, I feel like it ties in. I would love to hear from you about this.

You talk about running ops teams like a product team. You've written a whole book on a related subject. What does that mean to you? Tell us about that. Then we're going to talk about the book specifically.

Jessica 42:34
Yeah, the book. Oh my gosh.

This whole thing came out of that three products dichotomy thing I was mentioning before. I wrote this blog post, maybe three or four years ago, something like that. It was about the idea of running a people operations team like a product function—analgizing your employee experience to a subscription product that people subscribe to every month. And then when they resign, they are kind of churning off your product, and talking about how, really, you have a responsibility to stand out in the marketplace of culture. You're making decisions that are trade offs to attract or detract your ICP [Ideal Customer Profile]. And what is unique about your business?

So often, I was seeing companies just go out and be like, “We're great because we have beanbags, and we have a snack wall, and you can come work for us.” This is just not an interesting proposition to a lot of people. But also, I really saw it get very heightened during the pandemic where operations leaders would send out a survey to their entire company being like, “Do you think we should work from work remotely?” And the company would respond back with, “Here's what we think.” Like, how many days do you think we should work remotely? Which days? Like asking the company this question in a big survey. And I was like… What massive company-spanning, operating-system-level decision would you put out to a random anonymous survey?

It's an insane proposition to me, but I think it was just such a perfect reflection of the fact that a lot of businesses are operating their actual company as this homogenous soup of vague solutions that they've pasted together or generalized preferences from a group of people and never really had to think about like, what do we want to be? And is it okay if we turn off certain people? Because that, ultimately, is what's going to end up happening when your team really loves working where you're at and being very, very crystal clear about it. But also, you being able to make actually informed and opinionated decisions around things like how you operate expenses or how you operate your hiring process, whatever.

That is basically the kind of logic I took into this blog post I wrote, and then I ended up writing this whole big book about, how to build your people and your operations teams with this mindset, how to think about things with user experience in mind and doing user research, and actually thinking from first principles when solving problems instead of solutions-oriented thinking.

So like, oh, I want to implement new benefits. Well, great, these are the benefits I had in my old company, I'll just bring them in here. No.

Now, it's like, what is the problem we're trying to solve? Who is your USP? What are they interested in? Do research with them. Ask them questions. Figure out the tactics. What's the strategy? What are you trying to get? Is this what's best for your mission as a company? Then implement the solution.

It means that you end up having these much more commercial and output-orientated people and operations teams who are actually there to deliver value to people and not just there for compliance and to run internal programs and be busy.

Caro 47:38
Who would you say is the audience for the book? When you were writing it, who did you think was going to get the most out of it, or who needs to read this, I guess?

Jessica 47:45
I've written it with three audiences in mind. Founders, people that want to build a company and like have ideas about how they'd like to do it. Chief operating people, people responsible for the actual company operations, and then obviously people-people as well.

And actually more and more, I've had VCs interested in reading it because they're really interested in kind of influencing their teams to think this way and influence their founders.

So, it really is written from that perspective with a big focus on people teams. But it’s really for kind of all leadership in the operations world.

It's funny, though. I’ve found that the founders and COOs really like the book, and they really like what's in it. A lot of people do, too, so I don't want to discredit them, but they really naturally understand it. They get it. A lot of founders are already very product-oriented people. Maybe they're actually builders themselves. They come from an engineering background or a product background.

The audience I've actually had the most trouble with hilariously has actually been people directors, who just don't really want to get it, maybe. And maybe that's a mean thing to say, but the preference is like, I really like my Centers of Excellence/HR/Shared Service/Payroll team model, and I don't want to change that…

Caro 48:58
“I want to solve the problems that I find fun, whether they're verified problems or not.”

Jessica 49:01

Caro 49:02
For better or for worse, some of those people are really good at their jobs when you think about the job in that particular narrow lane. And, also, sometimes these are the people that are… I'm just gonna say it, they're the ones who give HR the reputation that we have sometimes.

Jessica 49:25
Yeah, the workplace police.

Caro 49:28
Yeah. And so I guess like, I wouldn't have predicted that but, now that you say it… I'm like, oh, yeah, that totally makes sense. I've met plenty of people who would really buck at that idea.

It's like how customer support or community management, all these things that sometimes can be a little sales adjacent at a commercial, for-profit business… There are always people who really buck against that, like, “I don't want to sell. I just want to do this little thing.” It’s the same thing of like, “I just want to take care of my people. I don't want to think about it as part of a business or product.”

Jessica 49:59
Completely. In the book, there’s a whole chapter dedicated to me being like, your whole job can't just be doing 1:1s with people and advising them on their challenges they're having. The HRBP [HR Business Partner], kind of people-partnering role is really important. And I say that there's like two halves to everybody in people's operations job.

One half is what I call human operations, which is like advisory work, coaching, mentoring, running through difficult situations, being there for people during tough times, etc. Yes, 100%, your job still contains that. But that is there, really, to service the qualitative data that you need to build great products to solve their problems and to further the business.

And that other half of the job is what you need to be getting measured on constantly, because that's the output of being really great at listening to people and getting advice and standing beyond the pulse of the team.

I think a lot of people push back on this model because they really love doing the advisory and discussing and coaching and everything else. And when, all of a sudden, we say that you also have a responsibility to actually build things and not in a silo and not just copy and paste other policies and not just make a pretty progression framework that nobody reads… You actually have to build something that's fit for purpose here. It starts, I think, making people a little uncomfortable because then they have to change their entire world, I think.

Caro 51:20
Yeah, and they have to be held accountable to whether it works or not, right? Which can be scary if that's, you know, new to you.

I just want to be like, yes, yes, preach. Something I want to repeat once more for everyone in the back is like… the 1:1s and that people stuff you do has to be the qualitative piece to everything else you're doing. I think that that's such a great way of thinking about it and something that's so often missed.

Well, now you've written a book. It’s been out in the world for a couple months so I'm sure I can't be the first person who's like, yeah, you did this huge thing. When are you going to do another one? [Both laugh] Are you like, no, I'm good, one was good?

Jessica 52:00
I mean, never say never, right? I don't want to be like, “I'm never writing a book.” And then, in like five years time, someone's like, “Remember that podcast you did at Opsy where you said you're never writing a book?”

I don't think I will. I definitely don't have any other ideas. So there's nothing to write about, but…

Caro 52:21
I don't know. I think there are like seven things in this episode that I'm like, Jess, please write a whole book about that because I would read it. I'll make you a list for your next book.

Jessica 52:30
Yeah, I’d love that. Thanks. [Laughs]

Caro 52:33
How long did it take you to write the book on that note, out of curiosity?

Jessica 52:37
Beginning to end, it took me like—in pure writing time—almost two years.

Caro 52:40
Plus, like the 10 years of your career that gave you the expertise to be able to write it.

Jessica 52:46
… And then like, I think there was probably like six more months on either side of the book proposal, discussion, contract stuff, and then like closing out, marketing, cover design, that kind of stuff.

It was a long process and I stupidly went into it, literally, with this thought in my head like, “Oh, it's like writing 10 blogs.”

No, girl, it is not like writing 10 blogs. What were you thinking? Oh my God, I'm so stupid. [Both laugh]

Caro 53:07
Oh man, yeah, so for anyone listening who's thinking about writing a book—girl, it's not like 10 blogs.

Jessica 53:14
No, it is not 10 blogs. It is like writing one gigantic blog that takes two years to write. Like, that's exactly what it's like. It's writing a book.

Caro 53:20
[Laughs] That's how long it takes me to write one blog post. I overanalyze and rewrite, you know, it's like... I treat every blog post like it's a dissertation. And then I'm like, this is too long, no one will want to read it. And it's like, “Yeah, bitch, because you spent two years writing it.”

Jessica 53:35
I will literally write a blog post on a whim. I will not write anything for months and then all of a sudden I'll be like, I want to write a blog post about X. And then I'll just on a whim at 10 p.m. spend two hours and just write this blog post and post it out in the world and then completely forget about it.

Then six months later someone will be like, hey, I read this manic blog post you wrote about progression frameworks, and I actually hate them. And I'm like, huh, yeah, I probably shouldn't do that. But anyway, it's life.

Caro 54:00
I'm envious. I love that you do that. And, also, I don't think I would describe any of your blog posts as manic and I have read, I think, almost all of them. So, kudos to you and your 2am brain. May we all be as smart and articulate as 2am Jessie.

And, on that note, I should let you go.

Thanks so much for coming. I feel like I could stay here and pick your brain all day. So, thank you for letting us all peek into that great brain and all the great stuff that you're working on.

Jessica 54:29
Thanks, love it.

Caro 54:30
This was super fun and interesting. And everyone, follow Jessie online. I'm gonna put all the links in the show notes and make sure to buy her awesome book. Mine is on order and will be waiting for you when I get home.

Jessica 54:40
Amazing, well, I hope you like it. I would love the feedback as well. If anyone has anything, let me know what they think about it.

It was lovely chatting to you. I had such a fun time. We should definitely do it again another time and otherwise I'll speak to you soon.

Caro 54:50
Thanks again.

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