Quick and Dirty Remote 101

So you wanna be a remote company? Sure. It’s better, but it’s also harder.

Jessica Zwaan
8 min readOct 14, 2023

I connect very easily with impatient people (I too am an impatient person). Sometimes I like to think of it as a blessing; as if the more impatient people I know the more ambitious we become as a collective. A murder of crows, a warren of rabbits, a ‘drive’ of impatients. As the volume and intensity around me as grown, I’ve noticed a trend in people wanting shorter and punchier advice on what to do to get where they want to go.

I don’t actually think that being impatient is virtuous, but I subscribe to the idea that sometimes some folks need a quick and dirty starting block to sprint from. There are people who want to gently pace through the halls of the mind, exploring their options — and those who want to just get stuck in and have a go, learning on the job. If you’re reading something called “Quick and Dirty Remote 101” you’re likely in camp two.

In my advisory capacity one of the primary questions I get asked is how to build a remote company that works. If it’s possible, if it’s practical, where to start, and how to do it now pls. It seems most CEO/Founders want something opinionated, simple to understand, practical. So here I am giving the ‘drive’ of impatients what it wants.

A couple of years ago I talked a lot more about remote culture and how to operationally build a workplace that truly worked cross-border. I haven’t really spoken about it much lately, I didn’t really know what I had to add to the incredible volume of noise out there. That said, I am in quite a few COO and CPO groups and it feels as though every second question is how to make remote or hybrid “work” so I thought I’d wrap up everything I’ve learned building Whereby over the last few years into a nice little starter pack.

At Whereby, we embraced a unique set of principles and practices that defined the way we operate. You may have already read about some of them. I’ll share what I have learned from the last few years of building Whereby including my successes and failures.

You can’t ignore it, but should you avoid it? (Maybe, actually)

The traditional ways we have learned to build businesses are being challenged. For some of the old guard out there, ‘Remote Work’ represents an omnipotent cryptid crushing down on their real estate investments, limiting their control over their employees hours, and undermining traditional power dynamics. I will leave Sam Altman and Steven Rattner out of my bedtime prayers tonight, but I’m sure they’ll be fine once reality settles.

Remote will kill us all!

As I’ve said in previous blogs, my book, and just generally when I ramble about on the internet opinioning my opinions; your company is building a product that people are buying when they come to work. Your employee experience is a subscription product. This means, your culture exists within a marketplace of culture, where, just like your consumer product, if you don’t innovate, you fade amongst the competition.

Look, remote work isn’t going anywhere. This means we have an obligation to consider if it’s right for who we want to be in the market. Put into my favourite little product analogy; if you were building a SaaS product at the dawn of cloud computing, and decided to dismiss anything that wasn’t on-premises… well if I were on your board I’d want to know your strategy.

For some of us, like Whereby, we’re building products that are quite literally designed in order to enable totally distributed, location-agonistic working. If you’re building that kind of product, with that kind of mission… and you aren’t embracing remote working as a strategic lever…well. Ok. Cool. Very cool.

If you’re building a consumer product with a physical presence, like delivery meals, photographing talent, delivery logistics, or a D2C element, well it probably makes little strategic sense to force a fully-remote strategy.

Believe me when I say this: you don’t need to include every single feature into your product. In fact, it’s quite sensible to not do that. Product teams know that building something which turns some customers off is a good thing, this ideally means they aren’t your ICP (Ideal Customer Profile). Your job in People Ops is to make sure you’re focussing on an ICP large enough to serve your goals, building what works for the talent that best matches your strategy, and not for everyone in the world, at risk of turning from Slack 2015 to Slack 2023: sometimes it’s better to just not try to be everything all at once.

So, and I really mean this when I say it, I need you to really consider if Remote is for your company. It might not be, and that may be a painful realisation. But, just like keeping your product on-premises, it can also be a wonderful opportunity within the right strategy.

Okay, with that said. You’ve carefully measured and weighed your strategy against the market, and you’re ready to go in: remote is for you. Let’s do it.


You’re going to have to throw out the traditional rulebook when it comes to policies and governance. Firstly, at Whereby, we kind of don’t really want to have any, so we’re non-parental. If you’re working remotely, a big hand won’t come out of the sky to show you the path forward, so we need to accept that we cannot be our team’s parents.

That said, (first failure!) when I first started I learned pretty quickly that people need some element of guidance for their own sanity, and case studies are incredibly appreciated as a way to understand what’s expected. For that reason, we have some guidance (which I know, I know, is kind of policy in another word) and one “official policy”.

In addition, and perhaps most controversially, we are “hours agnostic,” which means we encourage our employees to work in ways that suit them best, breaking free from the obligations of time zones and rigid schedules. This flexibility extends to communication patterns and planning around availability. If your team is global, then timezones are arbitrary.

I’ll write a blog on hours agnostic one of these days.

Async Communication is King 👑

In your new world, asynchronous communication reigns supreme. We’ve shifted the focus away from endless meetings and long email threads. Instead, you need to begin to record critical meetings, post them, and summarize them on Slack (yes I still use it although I dunked on it). This approach ensures that information is accessible to all, promoting efficiency, autonomy, and inclusivity.

Want to know more about Async work? Read Here (this Remote one is like, really good). Here. Here.

Transparency as the Norm

Transparency is an annoying word because it kind of ✨means anything✨. At Whereby, we build everything “in the open,” from sensitive metrics in WBR meetings to traditionally guarded topics like compensation. Our cultural thinking and “ways of working” are not only shared internally but are also discoverable externally. I feel a bit strange about adding this one into a ‘remote advice’ because I think it’s just good advice point blank, but anyway here we are. If you’re expecting people to work alone in their home or a co-working space, or a van or wherever, you need to give them information to independently solve problems.

Want to know more about Transparency? Check out This. This is also interesting. Open Org are sick.

No Fixed Offices

Even in regions with a higher concentration of employees, like London, we’ve resisted the allure of fixed offices and I think you probably should too. Our goal has been to avoid creating in/out groups and maintain a level playing field for all team members. (Failure two) That said, we did, once, have some fixed offices in Norway and Oslo. More unofficial than official, but quite quickly it became clear to us that resources and principles were pinching in strange ways. Teams weren’t working asynchronously by default, and losing sight of their global peers in feedback and collaboration. We closed all offices in 2021 and redistributed every cent to our Working Environment Stipend.

Me cancelling our leases.

Invest in what our team needs

Collaboration tools are the backbone of our operation. We’ve invested in tools like Loom, Miro, Notion, and Whereby of course 🎉. These tools not only facilitate real-time collaboration for our team, but also make asynchronous work a delight. Further, we have a $3k home office stipend. This money can be spent on coffee, co-working, and equipment. We do this because we acknowledge that Remote work is not a cost-cutting exercise, it is a strategic lever. We have a team who have consistently communicated that they have what they need to do their best work, wherever they are.

Performance management matters (even more)

Despite your startup status, when you shift to Remote you must maintain a robust performance management structure. This means being laser-focused on outputs and outcomes, ensuring that our team is accountable and driven to succeed. I’ve written a lot about performance and reward, and now Peerful is in the world I care even more. Whereby was, for me, the kindling of the crucial nature of performance on remote work. If you’re building a location-agnostic, hours-agnostic, non-parental workplace, and then measuring people with biased methodologies — you’re really missing the point.

Cross-Border Employment Made Easy 🌐

We’ve removed the pain of administrating cross-border employment by adopting flexible structural approaches. In short: we adopt whatever is globally expected, or the minimum statutory threshold, and try to offer that accross the board. We partner with Remote as an EOR, we employ policies that bring all of our team to the same level playing field: unlimited holiday to meet and exceed statutory requirements, transparent salaries, multiple contract formats, and consistent benefits, we empower employees to choose how they work best in a way that doesn’t force us to operate multiple different ways of solving problems.

If I had one piece of advice for leaders

Lose your ego. Or else, remote work removes it for you. You have to see yourself as a peer and not a celestial body on which work pivots. Your physical location and presence is not your identity anymore, you yourself as a leader will be judged on outcomes and behaviours, rather than charisma. It’s a hard curve for weak leaders, I’ll give you that.

Me and my cat, looking professional

👉 Buy my book on Amazon! 👈
I talk plenty more about this way of working, and how to use product management methodologies day-to-day, I’ve been told it’s a good read, but I’m never quite sure.

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Jessica Zwaan

G’day. 🐨 I am a person and I like to think I am good enough to do it professionally. So that’s what I do.