If you want to move into an operations role, you have to be commercial, you have to know the business, and you have to be really, really good at outcomes and impact.

In this episode

In this insightful episode, we sit down with Jessica Zwaan, COO of Talentful, whose impressive career journey spans roles in HR and operations across leading tech and SaaS companies. Jessica shares her transition from HR to the COO role, discussing the significant learnings and challenges faced along the way. She delves into the importance of commercial acumen within HR, the necessity of being outcome-driven, and how curiosity can shape effective leadership.

In episode 9 of season 2, Jessica provides an in-depth look at how she structures meetings to ensure transparency and accountability, including her unique approach to the weekly business review meetings. She emphasizes the need for HR to adopt a more product-oriented mindset and shares practical examples from her experience at Whereby, where innovative solutions to operational challenges significantly improved organizational efficiency.

As a hands-on Chief Operating Officer with a background scaling technology, e-commerce, and SaaS businesses, Jessica brings a wealth of experience to her roles. She is a regular panelist and speaker at local and international events, sharing her insights on business operations, culture influence, and how she thinks about companies as commercial products.

This episode is packed with actionable advice on transforming HR functions, fostering a culture of curiosity, and building strong leadership teams.

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️ review and share the podcast with your colleagues.


Making the transition from HR to COO


Purposeful career moves


Challenges in HR roles


The impact of organizational structures on HR functions


The importance of open transparency and peer accountability in meetings


Building workforce autonomy and reducing parental culture


Incentivizing employees and practical solutions to business problems


Being “mostly right” as a leader

Resources mentioned in this episode:


Aydin Mirzaee (  03:20

Jessica, welcome to the show.

Jessica Zwaan  03:40

Thank you so much for having me.

Aydin Mirzaee (  03:57

Yeah, really excited to do this. So you’ve had a very interesting background at a variety of different companies, companies like Fox and whereby today your COO a Talentful for one thing I noticed in your background is that you started out you did a bunch of roles where you were head of people or people leader and today you’re shifting more to this role of a COO. And I’m curious how did that shift happen? And was a purposeful did you kind of accidentally or life happened and you moved in that direction, or just curious about like how that transition happened for you. I think it was like everything is a combination of fate and design. I didn’t study HR at all, I ended up in HR and then ended up really liking the work. But then the things that I liked about HR ended up being more kind of operations type work generally. So things like workforce planning, organizational design, compensation, and those things, obviously extremely close to the world of finance, structures, business operations. And then over time, I started becoming more and more interested in broadening the role, getting more involved in particularly in like the commercial side of things in the back office in building out not only just the structures that impacted HR, but also the structures that impacted legal for example, customer support, etc. And then I got offered the opportunity to make the switch into the COO role, which I was really excited about. And I took it so yeah, I think it’s a combination of fate. It happened. And then actually I started designing which the pots I really loved about the faith, serendipity. Very cool. And so how is this role different than what you were working on? Like? Do you feel that your focus is different? You just have more departments? Are you actually would you say that you’re going about things in a different way? Yeah, it’s a really good question. I think it is materially different in almost every

Jessica Zwaan  05:00

aspects. I feel like sometimes I get asked this question and then my answer to this is, it’s comes across as if I don’t have a lot of respect for HR, which is not the case, I want to say from the very top, if you’re listening to the rest of the things, I’m going to say no, that this comes from like the deepest place of respect for the function I kind of grew up in professionally. I think HR has a lot of systemic challenges that it faces, some of them self inflicted, and some of them not. There is this kind of general feeling that people operations teams, or HR teams aren’t very commercial, they don’t really know the business, they aren’t really driven by outcomes or impact. And rather, this like a lot of busy work or administration, that happens, I think that those things are absolutely necessary to break. If you want to move into an operations role, you have to be commercial, you have to know the business. And you have to be really, really good at outcomes and impact. And I think that’s the biggest change. But I don’t necessarily believe that things I was doing when I was in HR weren’t those things all the time, I think that the things I loved were, but the the kind of structure holds you back, if that makes sense. And I can kind of get into more details on that. But it’s complaints that you generally hear from the C-suite anyway, that people take them on very commercial, they don’t like the outputs. And those are the things I’ve really always tried to build against or make happen for myself or be involved in. And now I really feel like I get to do those things more. And it’s not that I didn’t have necessarily opportunities before. But I think the way that that function has been traditionally been set up, and definitely the roles that I was in and the companies I was in meant that I didn’t have that same ability to work in the way that I think is really effective now. Very cool. So some of it, you said is almost organizational. So I guess with the new role that you have, and now being in this role. So what are the parallels, like I would say like what are the things that are similar, and what’s very different. I want to kind of start from a cerebral place here. But I think it’s helpful is the way that how HR has come to be over time. And the development of that function is really interesting to me, it starts becoming something that has really impacted my work in like 1996 When the Olympic model was invented, and if you don’t know what the Olympic model, but it’s this idea of you have business partners, and you have centers of excellence or shared services built off the off that which is like payroll competition and l&d it all these siloed functions, right. And then you have business monitoring team that are kind of there to support leadership, and give insights to leadership about what’s going on within the team. I’m massively paraphrasing right now. But that’s kind of more or less the way that I grew up in HR. Right. It’s very kind of like, regimented and administer structure. Also, over time, work has massively changed, like my first job ever was scanning and printing letters of offer and mailing them to people’s homes to be countersigned and have that returned. And at the time, I was like, this is the best job ever, I love it. But the world of work has just changed so much since then, right? We have all these incredible tools, we have such a different way of approaching the kind of work we do the fabric of work. But I think that those institutional structures, they have still remained the prevalent way of doing business. And I think places like this, think about product management or product development. Agile has changed that not only just the way that you actually do the work, but also the structures in which that work is done. You have product squads now and Waterfall has gone and now people are working in this very iterative kind of real time, customer centric way, that change to our operational structure hasn’t really happened in HR. So I give you that whole context, because I think that was the part of the work that I think I was really frustrated, that wasn’t changing, I was seeing so many things changing, that I really enjoyed and saw the progress and saw the future of this ways of working. And now that I’m in the CLR role, it’s different because it is just a different job. I’m now getting to look at legal and finance in a whole bunch of other functions, which I really enjoyed it’s kind of cross functionality. But also I think the way that HR is set up means you don’t get the access to that cross functionality and that business insight that I now get, if that makes sense. Yeah, so this makes sense. So you saw the world around you changing and it almost felt like you wanted to make the same sorts of changes. But in order to do it, you needed a broader purview almost. Yeah, I think that’s true. I think also, there are a lot of things like I mentioned at the beginning that this kind of, there are some things which are hrs doing, and some things which have existed because of other perceptions, right? So these ideas about HR being commercial HR, not really the business. Some of those things come from, for example, leadership teams keeping the commercials from HR saying they don’t really need to know this information. That’s not really the kind of work they do. And some of it comes from a long history of HR leaders who don’t want to interact with the commercials. They’re not interested in really knowing much about what’s going on the p&l. And I don’t think that’s true for all of them. Of course, there are some brilliant CHR O’s that are very, very commercial. But I found that that was being at least kept from the ways that we were working deeper into


The old

Aydin Mirzaee (  10:00

would you say in your role as the COO at every company, it’s different. I’ve also heard that, you know, the COO role is very different, because it’s usually all the things that the CEO is not good at. And drawers are like really supposed to be complementary to each other in that way. How would you describe your role? Like, is that true? Is that does that anecdote hold in your situation? Or is it different? Do you focus on different types of things,

Jessica Zwaan  10:25

I still really do stick to this, I was actually talking to someone about this today. And I think a really good CEO is extremely complimentary, and like symbiotic to your CEO. My current CEO is really, really great at the external stuff, the vision, the what’s next for the company, the big strategy. And I really get a lot of joy in the detail of what’s happening day to day. So, you know, knowing everything about financial controllership and understanding, like how our modeling is being created, it needs to be kind of tailored to Hobbes to run a company and I don’t think any effective CEO can kind of do it all. I think that they probably shouldn’t do it all, even if they could. So I’ve definitely adopted the idea that you should be like in a symbiosis with your CEO, a CEO. That’s how I agree. Yeah,

Aydin Mirzaee (  11:14

that makes a lot of sense, and certainly jives with what we’ve talked about on the podcast with other CEOs. Do you agree?

Jessica Zwaan  11:20

What do you think? I’m interested to hear your perspective? Yeah,

Aydin Mirzaee (  11:23

I mean, that’s what I’ve heard as well, I think, well, you know, what are the I don’t know if you know, Cameron, Harold, he spent a lot of time being like, the CEO coach. And I think he was also coined as like the CEO whisperer. And so he has this whole Academy around, getting CEOs together and working with them and coaching with them. And he’s done this for 2030 years. He wrote the book on the topic. Yeah, it very much jives with that. And he’s been on our podcast, I think two times. Oh, okay. Great.

Jessica Zwaan  11:51

I’m following a good legacy. Yeah, good

Aydin Mirzaee (  11:53

legacy. So yeah, definitely jives with all of that. But let’s talk about you’re going against the grain seeing the change happening around you and all the different functions and wanting more of that on the people teams, you’re bringing some of that change, I would love for you to maybe talk about some of the ways that in your function, you were able to change the role to be more modern. But the times,

Jessica Zwaan  12:16

I think it’s important to say here that I wanted that change. But I actually don’t think I was very good at it. This is actually one of the things that was most frustrating to me is I wanted to be more commercial and involved in more conversations and more broadly, conceptually aware of things. And I could actually see that this was something that was probably going to hold me back. But I knew that wasn’t a strength of mine. And I had to think like, what is it that’s caused this to not be a strength, which is why I say this, like this negative duality between HR and the business that comes from my own experience, right, like I saw myself being withheld from certain conversations. But I also saw myself pulling back from certain conversations, and particularly conversations about the numbers, and I put the numbers in air quotes for people listening. I still to this day, meet really talented people, leaders who when I ask questions, like, you know, what is your company’s EBIT? Or what is your like tech payback ratio for new customers? Or who is your biggest customer? And what is their MRR? And they don’t know the answers to those questions, because they feel like either they’re not given the answers to those questions and not visible to them, which I think is a real problem. Or they themselves are just, they’re kind of nervous or not confident to engage with those things. So I think for myself, what I ended up seeing was, this is going to hold me back more so than like, Oh, I’m frustrated, because everyone around me doesn’t get it. But I get it. Like I definitely don’t think that’s the world that I was in. I decided that I wanted to be like I had a really amazing VP of data when I was a VP people. And he was the kind of person who just, I mean, we’ve all worked with someone like this, like every meeting, anyone can ask him any question. And he just knew like he knew it. And like, you could ask him like, oh, you know, what do we think the retention cohorts gonna look like in blah, blah, blah? And he’s like, Yeah, I run the analysis is what I think and this is why it’s being driven by this. And then you’d ask like, oh, well, what about this other customer? Ah, that’s an exception. And this is what I know about them. He just could get into the details of the numbers and answer things really, in a super compelling way. And I just had a conversation with him, I was like, What do I need to do? Do I need to like learn SQL? Like, do I need to become a data person? What is this, and he gave me some really good tips about being really curious and not being afraid of numbers and getting, how important and compelling it is to be a person that really takes that kind of stuff seriously. And I think when I made that mental shift and said, like, well, first of all, I’m perfectly capable of it. And second of all, it’s actually almost existential to my growth. I think that’s when I really started to see a shift, I think is a very long winded answer to what you’re saying. But I think it was more about my own internal change than it was like, I don’t think it was a truly realized frustration in the entirety of the org. It was more like oh, this is holding me back. Oh, actually, Paul, This is also contributed by the way that HR is designed. It

Aydin Mirzaee (  15:04

reminds me of a bunch of similar situations that I’ve been in and also talked about on the podcast. So this idea of getting to the root of the numbers, we’re talking about it in terms of the people, leaders being more interested in that function. But it’s equally true for other functional leaders within the company as well, being interested in other parts of the business. And sometimes, like you said, maybe they’re withheld information. But other times, like there’s just not engaging, they’re not like leaning in to those sorts of areas. And so I think it’s broadly applicable to everybody that as you start to get more senior or if you would like to become more senior within an organization and be more impactful, it is helpful to know about all the other functions and not just your own, even though it may not be like immediately obvious why that information is going to be impactful for your day today. Totally.

Jessica Zwaan  15:56

I mean, companies are so likely to be hit by the elephant problem. I don’t know if you’ve heard about this, this idea that like if you see a tail, you presume the whole elephant but a lot like you have your piece you presume the rest is something else. I’ve definitely swayed back and forth over the course of my own journey between being kind of relentlessly curious in a way that’s been really helpful and relentlessly curious in a way that’s been really disruptive to people. And I think I have like there’s a balance, you have to try and strike that, right. But I think the on the whole, the drive to understand what makes this whole system work, what’s the truth here, and how these things interdependent and related, has only been beneficial to me and the companies I’ve been working at.

Aydin Mirzaee (  16:35

So one of the questions I want to ask you, and it’s really awesome to hear how maybe it’s almost like you did an identity shift, which you just focus on like, this is the future where I’m going and I’m going to be great at numbers. And I’m going to dig into all these things with curiosity. How did you make that shift? Was it literally just you decided and you became good at it? Or did you have to do some things to get up to speed? Did you have mentors or coaches or people in the company helped you? You just did a lot of work on your own? Yeah,

Jessica Zwaan  17:04

I wouldn’t give two S’s, this was I think, I kind of had my own journey. But that’s not what I’ve replicated for the companies I’m in now with helping other people go on the same journey. I kind of also hate saying journey all the time. So hashtag, I feel like I have an Instagram post or something. So sorry, if you’re listening to be like, Oh, another journey we’re all going on? For me, I think what I did was I had to kind of relinquish ego. I think there was a lot of relinquishing of not only ego, but I think that the kind of systems that HR is structured within mean that to let go of those systems, you have to almost completely deny that they’re effective. I don’t know if that’s super clear. But like the idea of like, okay, if we decide we want to build our HR team, more like a product team, which is what my book is about, we have to acknowledge and like really fully acknowledge, you can’t kind of half do it, that the way that we’re currently doing things is not working. And in order to do that, it’s kind of an eating your hat moment, right. So nobody wants to be a VP that’s already been going to executive meetings for the past six months, all of a sudden now saying, hey, what’s EBIT? What does it mean? Like, where does this number come from? So I had to kind of eat my hat on a few things and say, like, you know, what, actually don’t know if all these things are as effective as they could be. And I’m really interested in improving them, which ultimately, my CEO at the time, was really grateful to hear because he had his own concerns about things he was, he was kind of not keeping to himself, but definitely like kind of wrestling with. And then it was the process of really just asking a lot of questions, reading a lot of things I didn’t fully know how to apply yet, and then just kind of practice. But then I’ve been thinking more about, well, how do I kind of systemize that because I don’t think it’s helpful for everyone in my company to have their own moment where they’re like, oh, I need to be a numbers person, because someone said, so I thought about the idea of like, what really drove me to realize that I needed to do this was seeing appear in action and be like, Oh, that’s what it looks like. So what I’ve tried to do is build more commercial focused spaces and more numbers, focus spaces in my companies where there is a peer level of accountability. And one example of that, that I still learn from all the time, by the way, is our weekly business review meeting. So the web meeting, which is an Amazon thing, we’ve kind of adopted our version of it. And that is every week we get together and talk about the most important top line metrics as they apply to the company. Everybody in the leadership team and executive team that owns one of those metrics comes and we will talk about our numbers if they’re brought up. So if someone raises a question about something, we have to have a conversation about, like, why it’s going up, why it’s going down, what’s been the driver, but really crucially, the chair of that meeting changes every week. So I don’t chair it. Well, I do on my turn, but somebody new chairs that every week. And what that does is it builds like this kind of mechanized accountability structure. That means everybody even up and coming leaders have to take the opportunity to stand up and say, I don’t know the answers to all these things. I need to find them out. I need to push myself to get there. And I think that that’s been a really helpful All staying I’ve implemented to try and drive the way that I learned into something a bit more systemic.

Fellow  20:08

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Aydin Mirzaee (  21:09

What is the role of the chair during the meeting,

Jessica Zwaan  21:11

the chair has a couple of responsibilities, they have some like administrative things. So they have to make sure that the agenda is updated, they have to make sure that people have their data and they do a little bit of chasing, check in on like any action items making sure that people know they might have to present something. And then what they do is they effectively kind of drive the meeting. So we used to do five minutes silently reading the deck together. And now we do 15 minutes reading it in your own time in your calendar and then adding items into the agenda. And what you do is you put a call out which will be aligned. So to say one of the lines is line 47. MRR and my call out is interesting Mr. Ross seems to have gone down. But we added seven new customers this week in line 10. So what’s happening, what’s the kind of causal connection here, this either means that our new customers are lower than the churn we have. Or that one of these numbers could be wrong, or that we’ve had something else happen, whatever it may be. And then the person who owns those numbers or that number will then be called on by the chair and say Jess has made a call out this is what the call out says, Do you want to talk about this? And that person would then explain? Well, this is what’s happened is our theory. And the chair then decides, does that become an action item for next week? So let’s follow up on this trend? Or is that something that someone has to go away and think about and then present back in some capacity. And the chair has to be kind of engaged with those conversations, basically the whole way through deciding who speaks what the call out is giving clarity and then making the next steps for the next week. And we we say one of the rules is to without sounding too, like intense, it’s disengaged at your own peril. If you show up not having read the deck not having fully engaged as the chair, then the rest of your peers will be sitting in the room looking at you and wondering what happened.

Aydin Mirzaee (  22:49

Yeah, I love that. And thank you for explaining how it works. It’s very interesting, this idea of changing the role of the chair in that way. So just as I’m infinitely curious about this idea of the way to run these different meetings. So how long is the meeting? And what if there are no call outs? What if everything just looks normal? You all and super early? Like come in leave after five minutes?

Jessica Zwaan  23:10

Yeah. So the 15 minutes is held everyone’s calendars. It’s just private time. And then we have 45 minutes synchronous? And yeah, sometimes we have a meeting where everyone comes in and does their call outs, sometimes. So this is a one important thing to say here is the Chair will generally have to decide should there be call outs, like they would have also gone through that dock and said interesting. I haven’t noticed any call outs here. So then the kind of prompt would be well did your the chair like what did you? Did you have something that you wanted to call out? You didn’t put in? Or as soon as the Chair will say like Yeah, look, it looks like a fairly standard week, little bit of a summary. I’m going to post a summary in the chat all about this. But let’s catch up next week. That’s it. But I think zero call outs is extremely rare. The lowest I’ve seen is like one or two. And sometimes they’re negative or concern. And actually sometimes they’re positive like congrats, this numbers going really well. There’s been an upwards trend for the past six weeks shout out to the person. But

Aydin Mirzaee (  24:02

this is different than your executive meeting. Right? So you have something separate with all the execs. And are these like two different time slots are they like back to back or how’s that for it handled

Jessica Zwaan  24:14

how exactly to happens on a different day. And our exec meeting is much more about like longer form systemic challenges, strategic opportunities that are happening or that maybe wanted to discuss. Whereas the web is like, the way that I describe it is the web AR is there to tell you, if you cross the street, whether you’re going to be a hit by a car in a day or hit by a car in an hour, it’s there to tell you whether or not the cars already hitting you could hit you or will hit you. And your exact meeting is much more about like how are we going to prevent the car from hitting us what’s coming up in the future that we should have better safety features should we institute a zebra crossing? So that’s kind of like how the town planning analogy works.

Aydin Mirzaee (  24:52

Yeah, I love that. You’re gonna get hit by the car with an hour or in a day or or week or a month. So yeah, that’s super are helpful. And just going back to this, though, I guess part of it was the learning was if you participate in a meeting like that, that in itself could be super instructive. So how would you get other team members? Because Can anyone come to the weekly Business Review? Or will they have their own equivalent versions? If someone is not part of the executive team? How do you build a company where the people who want to have the ability or the systems in place so that they can keep learning more about the business?

Jessica Zwaan  25:28

It’s a really good question. And I’ve seen it happen two way. So whereby it was open to the entire company, it was not just the exact team that attended, by the way, it was anyone that owned a metric. So it might be the head of marketing, and the VP marketing could also be there, right? It could be finance, my finance director, and I would also attend, so it was anyone that kind of owned or should talk to those metrics, which comes to that. But everyone in the entire company was invited, if they’d like to attend, they were welcome to pop it in and listen, and then we always recorded it. And we always share the recording with the entire company. So everyone in the company could see the kind of content of those conversations, I think that’s really interesting. And I actually think that it really worked very, very well for whereby we’re extremely transparent company. So that really works for us. At talent level, we have an open to our executive team, our SMT to a senior management team. So VP directors is going to heads that come along to and a couple of other people that are in really important metrics. So for example, in the resourcing team, and we do not record it, we do not share it with the entire company. But what we do do is a lot of the teams, particularly our delivery teams, were a professional services company, they have their own kind of baby WBS. So like the second tier level of metrics down, I would say that those meetings are probably a little less like high pressure, maybe they’re not quite as structured, but they definitely thought they have servers. So deck templates, same agenda template, etc. But of course, you haven’t got the entire exec team. And they’re also asking questions, which takes a little bit of the pressure off. Yeah, it’s

Aydin Mirzaee (  26:52

super interesting to see how all that stuff rolls into each other. I guess the thing that I want to just keep the discussion going on is this idea of how you transformed the people function, or at least like the things that you wanted to do. I think the insight that you mentioned was, say product teams, it’s no longer waterfall engineering, there’s new ways that people can build products, whether it’s Scrum or other methodologies, or agile, what were some of the things that you learned from that process, and that you encourage in your people teams today? Wow,

Jessica Zwaan  27:25

this was so much now that I encourage I almost basically rip off the entire of product management into People Ops. But I think the thing that really started my thinking around this was when I was in London, I was really inspired by the amount of community work and community sharing that was going on in engineering and design as well. But a lot of engineering where people would get together and like, also open source was a really interesting thing for me, people were really open sourcing information. And I started thinking like, well, what could people ops do in the same vein, we should, you know, I think like meetups and things were happening. But it was maybe more instructional or kind of inspirational and less real open source kind of sharing and the hacking and solving problems together. And I think that that started to change in kind of 2016 time. And then I started thinking like, well, what other things can we take? This is really working. And then I started being naturally because I was really at the same time trying to push myself to be more numbers orientated, started learning and being really focused on output metrics. And how could I build a team that was more focused on deliverables and changing something that really mattered to the company. And then piece by a gradual piece, I ended up setting up my team in 2018 2019, in squad formations and specifically focused on specific output metrics as their goals and delivering pieces of work to try and affect those output metrics are basically just ripping off like squad methodology and product management. I started working with a founder who saw me solve problems in that way and said, like, you should write a blog about this, because I think people would be really interested in what you are doing. And then I did that. And then people seem to really liked the blog. And then I was reached out to by my publisher, and I ended up writing a book on it. So that’s the journey that I went off.

Aydin Mirzaee (  29:10

I mean, that’s amazing. So you actually just based on the blog post, you had people reach out to you to write the book. Yes.

Jessica Zwaan  29:15

But that happens all the time. I hear lots of people talk about this. Actually, I think it’s a surprise to some but yeah, there’s a lot of people that write blogs on medium or substack. That publisher gets in touch and says like, we’d love you to extend on this or you know, do you think you could write more on this topic?

Aydin Mirzaee (  29:28

Can we talk about like real life scenario and example, or a story of like how this works in practice, or like how you solve a problem in this new Spotlight format, just to like, really tell the story of what this looks like, versus what it would look like without this new format?

Jessica Zwaan  29:44

Yes, I actually talked about Wednesday, so it’s like fresh on top of my mind. One of the issues that we had at whereby when I first joined all of our team at that time, almost all of them were based in Norway and Scandinavia. And if you have ever worked in Scandinavian businesses before it’s getting even culture, it’s very standard to take basically a whole month off in summer. And that’s how that culture runs. Now, that’s difficult to run a SASS company where you’ve got the vast majority of your team off of one course of a month, I’m sure you can understand customers still need conversations and contracts willing to be created and etc, etc, etc. So it was a problem for us for resourcing perspective, that we wanted to keep our Scandinavian Roots was very important for us. So we started thinking like, how can we do a couple of things, organizationally, we were growing anyway. So there was a big focus on let’s make sure that we’re kind of further distributing our workforce across various time zones. But from a very specific HR problem, it was how do we encourage people to give better runway and clarity on like, when they’re going to be booking holiday, it’s like a really small example. But it’s something that I think a lot of teams are familiar with, like a lot of people have struggled with this like resourcing challenges before. So I think a kind of standard HR team with like a VP, people, maybe a people pot or two people admin could say, we’re going to implement a policy that says, you have to give us at least two weeks notice or your holiday will get canned, you’re not allowed to take it, you’ll get a slap on the wrist, you’re gonna be in trouble if you try, which is just not a very nice customer experience in this kind of analogy, that you’re a customer of the employee experience. And then usually what they would do with that team is they would tell their people partner and their admin, draft up the policy, make it into a PDF, send it out to everyone, and then start making sure people do it like disciplinary people who don’t take give us the requisite notice, etc. And usually, you’ll pull recruiters off doing something else completely unconnected to the reality that you’re, you’re in. I really didn’t like that approach. And I think within the people ops as a product methodology, the kind of way I think about it is that your company is building three deeply interconnected products, you’ve got your consumer facing product, which is time management tools, or video conferencing, or professional services or raises, if you’re Harry’s razors, whatever that is, we’re all very familiar with that. You have your fiscal product, which is what your VCs are buying, or shareholders or private equity, or you if your bootstraps, you’re getting some kind of dividends from that potentially as a customer. And then you have this employee experience product. And those three things are very, very important. Your employees experience product is a subscription product. And if one of them fails, they all fail. So if your employees or decide to stop subscribing, or you start getting a lower quality of return on investment from those employee customers, then you’re going to create worse products, your physical product will suffer, etc. It’s like a kind of collective relationship. So thinking from that mindset, I was like, how could we build something that really encouraged our subscribers to continue subscribing and get higher value higher return on investment here? So I had a very clear problem is we were missing out on this potential revenue over the course of summer, because we had too much absence and too much unknown absence. So I said to my team, I need you to go and find ways to solve this problem. So they went away, did some user research and came up with three hypotheses that they wanted to try and challenge with building something. The first one was, people didn’t really like using our HR system, it was people forgot the link, and they couldn’t figure out how to log in. They were messaging their manager and saying, Hey, how do I book holiday again, and the manager will say, When do you want on holiday and kind of have like an Off the record conversation about it, it never got recorded anywhere. The second hypothesis is that in the time, we most needed people to book holiday, which was January and February, ahead of time, people just weren’t thinking about it, because they just got off Christmas. So like, you’re not in that headspace. And then the final one was that there just was no incentive for people to book holiday, there was only a disincentive if we introduced some new kind of like prohibitive rule. People weren’t encouraged to do it. So how do you encourage people other than to say, Please, please, please, and then went away and put three souls in place. One was we put a new HR system that connected with Slack, and we got a little slack bot, you know, help people see when available holiday was coming up. And they could just do it directly in Slack. So it didn’t have to message the manager anymore. That is forward slash holiday sorted. The second thing is that started the year update we’d send out we also put a note in there have been like, hey, some great deals on holidays over summer, like don’t forget, just like a nice little encouraging nudge, like, don’t forget about this. This is the time where you get really good deals that couldn’t be better for your budget, if you want to book holiday, now’s the time. And the final thing was we started encouraging people by saying if you book holiday six months in advance, and you take it, we will give you a voucher for $250. For an extra night, stay wherever you want. Oh, wow. And all of a sudden, people started booking holiday was six months in advance, because we were focused on solving the problems and seeing some kind of outcome rather than just band aiding it with policy.

Aydin Mirzaee (  34:29

Yeah, that’s awesome. I love the approach. Thank you for walking us through it. Because just like any sort of business or product problem, you came up with your hypotheses, you validated you did probably user interviews in this process. And then some of them were like quick wins, like, you know, implement the slack bot and then other ones were larger, incentivizing things, and that’s amazing. And so did you try anything that didn’t work? Or did all three of these things they were just the right ones and they happen to do the trick. Yeah, I

Jessica Zwaan  35:00

think on a holiday one, I think that was a couple of other things. So the middle one with the kind of newsletter encouraging people in January, we only really found that helpful in I think the first year, I think after that the problem had kind of been mostly resolved by the two operational things we did. And the fact that we extended out kind of working parameters hours by adding people in from other cultures and other kind of ways of taking holidays. So we found that that middle one, like kind of served its purpose as a one time deal, we didn’t have to keep investing time and energy into doing that again. So we stopped doing it after the first year, what do you think was the right decision? Like I don’t, I didn’t love my team doing busy work for the sake of doing busy work.

Aydin Mirzaee (  35:40

Yeah, that makes sense. And finding things that aren’t as effective is part of the process. So thank you for sharing that. I guess this is all in line with this idea of and you wrote a Medium post about this on the topic of autonomy in the workplace, just talking about how we’re all grown ups here. And not everything needs to be through a policy, but you can actually establish guard rails and incentives. And there are other ways to get people to incentivize them to take certain courses of decisions.

Jessica Zwaan  36:09

Yeah, totally. This bloke got a little bit of heat, some people didn’t like the content of it, which I think is fair. I don’t think everything I posted, what didn’t they like? I think, again, going back to the first thing, I think, not everybody, there was a couple of LinkedIn messages. I got someone’s having a WhatsApp message. I think there’s this perception that because I had criticized hrs role in building like what I call parental cultures, that are saying HR is exclusively responsible for building a parental culture. And I don’t think that’s true, if that’s the impression that came across, that really wasn’t my intention. But I think that people teams are ultimately responsible for the efficacy of this like 60% of your p&l, that is headcount. So I think diverging blame and saying like, was actually its management culture. It’s actually like the leadership team. That is probably true. But also like there’s an element of like, reclaim your power here, you are probably the biggest budget holder in terms of efficacy and your company, like your marketing team probably has 10% of the budget that they’re managing, you have to make sure 60% is a good investment that is huge. So in my opinion, I think this idea of like, building a non parental culture is the idea of relieving everybody from a world in which they are hand held by management and HR. And instead, you set up systems like the WB, er, where people are experiencing through like mechanized leadership, and being given very clear information that’s going through a process of user research, rather than feeling like there’s like a big parental hand guiding them on that career journey, which I think can come across to a lot of people as being like very hands off cold, and maybe not so caring. But that’s really not my intention.

Aydin Mirzaee (  37:48

Yeah, no, that makes sense. And thanks for explaining that. It’s very interesting, as you put it as the 60% of the budget, it makes sense, like it is the most valuable resource that any company has, and thinking about it that way. Certainly, really helpful. Just this has been an awesome conversation. We’ve talked about a number of different topics talking about, you know, the the role of the CEO, what that looks like, lessons from being in the people leadership function, the things that you learn from other functions and building those into the people function, how to become more analytically oriented for everyone in the company and learning these high level metrics that drive the business. Lots of great conversation there. We always like to end on a few rapid fire questions. I’d love to ask you a few of those. The first one to start with is, is there any sort of leadership advice that you think is very underrated that more people should listen to?

Jessica Zwaan  38:41

My previous CEO, Andy Tyra used to say this to me all the time. And I kind of used to write it off a little sorry, and if you’re listening, but I think it’s very true. This idea of like be mostly writes, you’re not going to be old ways, right? But as long as you are more frequently correct than not, that is probably the best you can do especially in like a rapid scaling circumstance, you have to make decisions very quickly, often unlimited information. As long as you are more right than wrong. You’re on the good path. Love

Aydin Mirzaee (  39:10

it. And is there a favorite resource that you have something that’s really helped you in your journey, whether it’s a book or podcast, or just any sort of resource, it’s like really helped you in your leadership journey that you’d like to call out?

Jessica Zwaan  39:22

I’ve been calling out this is so specific, it’s maybe not less on like the whole of my leadership time, but I’ve really really loved it the last couple of years and that is reading medium articles from practitioners or sub stacks for practitioners listening to podcast for practitioners that aren’t in your space. So I read Ben stencils blog, who is a data CTO, breaded choose blog and product management, the black box a PM, which I really love podcasts like this, if you’re not necessarily a kind of organizational manager, but rather an executive that’s a bit more focused on like the technical like a CTO or something. These kind of things like it’s so beneficial. Listen to experts. from other fields to learn what you can learn from them, and just generally, so you can have more meaningful conversations.

Aydin Mirzaee (  40:06

Yeah, that’s a great one. I often find that even for if you’re in one type of business, talking to people from other types of businesses that aren’t in the exact same vertical or niche that you are, is also very helpful for just like creativity and understanding, like things that you can borrow. So love that. And thank you for mentioning all the different ones that you read, suggested that this has been really awesome. Thank you so much for all the advice and all the learnings that you’ve shared. For all the managers and leaders constantly looking to get better at their craft? Are there any final parting words of wisdom that you would leave them with?

Jessica Zwaan  40:41

Goodness me? I think this idea of curiosity and ego need to be detached in some way. I think it’s okay to be extremely humble in your curiosity. And I think the best leaders I’ve ever worked with, are deeply interested in like getting on the ground of customer support and asking like, Oh, why do you put that workflow in? Or like, Why did how do you use this template, and getting to know the details of the company, it’s not only really good for your ability to understand how the company works, but it’s also really, really good for building rapport with people that actually, I think some of the best ideas, the best strategy shifts that I’ve ever bumped into myself, or even just seeing within my leadership team external to me have come from a place you least expect and if you let your own ego get in the way of your curiosity, you may have missed the big picture. That’s great advice,

Aydin Mirzaee (  41:37

and a great place to end it. Jessica, thanks so much for doing this.

Jessica Zwaan  41:41

Thank you so much for having me. I really appreciated the chat and a really thoughtful questions.

Aydin Mirzaee (  41:45

And that’s it for today. Thank you so much for tuning into this episode of the Supermanagers podcast. You can find the show notes and transcript at If you liked the content, be sure to rate review and subscribe so you can get notified when we post the next episode. And please tell your friends and fellow managers about it. It’d be awesome if you can help us spread the word about the show. See you next time.

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