Designer to CEO – The Path Less Travelled

So in about 1984, my dad came home with our first home pc.

Wasn't really a pc, it was something called a Spectra Video, SV 3 2 8.

This was in the days of the Commodore 64 and the Atari, they were the big ones.

And the Spectra video, you, it was like a keyboard.

You plugged it into your television, and you could play awesome games that were, streamed or they were coded onto.

Like an audio cassette, so you put that into a little player, and you played it, and it came through to the Spectra Video, and you could play games.

And I think the most awesome thing about the Spectra Video was that it was shit, and Commodore and Atari had the market totally sewn up.

And so there were very few games, and there were very few good games for it.

But what it did have, they had a partnership arrangement with Microsoft in the early days that gave them an early license of BASIC, the programming language.

And to me as a six year old boy, once I'd exhausted the games, there was this programming language that I could go and start making my own games with, which was quite an amazing thing.

And also because of the tape device for getting, for actually getting the games onto the machine, you could go into the games that were, that, that were sold with it, and you could look at the source code.

So you could really dig into, how people were building games.

And for me, this was a big thing.

And I think that it was, kind of one of those critical intersecting experiences where I was always going to be a designer.

This was the path that was preordained for me.

But it was this combination of design plus software, which was just a magical turning point.

And I think without that Spectra video, there was no way that would have happened.

And so this intersecting experiences as we go by, but this for me was one of those key intersecting experiences.

So I wanted to tell a few more stories, because I think that to me that's a great way of, it's a shame Matt's gone, but to me, I'm one of the bards, that's for me one of the great ways of, helping people to understand information.

We're gonna go through a few more stories.

That was the first one.

Let's do a few more.

In 2011, I joined Atlassian.

Atlassian was a fairly small company there.

I was the fourth designer in the company.

Our customers still called it Jira.

Altasian, we were very early and not super well known.

But we were growing really fast.

In the time that I was there, we grew from, I was the fourth designer, I was the designer on Jira, and by the time I left, there were 30 designers on Jira all working for me.

And we had a massive team of designers.

The company itself was massive.

We IPO'd a month later, which meant I missed all the great parties, but, it was, an amazingly growing company.

And I think the reason for that incredible success of Atlassian, was design was heavily entrenched at the board level.

And I'm not just talking, Juergen Spangel, who was our head of design, who was a critical part of the success of the company, but it was the fact that Mike and Scott cared deeply about design.

Design was a critical, part of how we thought about ourselves as a company, and entirely supported by the founders of the company.

And I think without that support, without their absolute encouragement, we would not have been able to do things like building one of the early big design systems, the Atlassian design system, and a lot of other systems of scale.

Systems of scale being such an important part of why Atlassian actually works.

A lot of people don't understand that it's those systems of scales that allows, in my time 1500 people team and now been, I don't know, 10, 000 people working at Atlassian.

15, 000 people working in Atlassian.

Those systems of scale are a big part of why the company works, workshops and things like the playbook to enable people to work together, to collaborate, to understand how to collaborate together, to understand what the rules of engagement are for collaboration.

Storyboarding is such a big, part of it.

We, at one point we took the whole of JIRA, every screen that we could find in there, because nobody knew how to do it.

Big or deep it was, admin goes on for about 500 pages.

We took every screen that we could figure out and we mapped them all on the wall of the company.

We had them literally down one whole wall of one floor, round the corner and round into the meeting rooms, just to try and understand what JIRA looked like, what the surface of the scope of this thing was.

And that was one of those systems of scale, because once you can see it, you can start to understand it.

Systems of scale are the things that we build to allow us to have a base to start from.

So we don't have to always start from square one.

We can start by building on our own shoulders and get bigger and bigger.

Having design principles are a critical part of it.

When you have design principles, you have rules that you can, again, start from that help you to not have to make the decisions all the time.

That helps you to give, to have those fundamental underlyings of what a decision is going to look like.

Partnerships.

Is the most insane system of scale that Atlassian has.

A lot of people think of, Atlassian tools as old fashioned and a bit kludgy and a bit shitty, and partners are there to, help implement them.

That's actually a power play by Atlassian.

If you can get those partners to actually invest their time and energy and fall in love with the product, and take them with them as they grow, that's actually one of the reasons Atlassian was so successful as a company.

It's because actually the tools are a little bit hard to set up.

And so those systems of scale really empowered us as a company and made us a very powerful company.

We're also really great, and this is something that I think came from Mike and Scott and from Juergen, really great at creating space.

Allowing people to have the space they need in order to be able to go and create the things they needed to create.

Because, Design, as everybody in this room I'm sure knows, design is a slow act, it's not a fast act like building software, design is an incredibly slow thing, it takes time, it takes patience, it takes space, literally, you need space to spread out, like we had the map of Jira up on the wall, you need space in order for people to be able to respond to things, to be able to understand how things work.

Designers, a lot of the act is to absorb all the information, to, to ferment that information inside of your mind, and come up with solutions that are based a lot on gut and instinct.

This is how creativity happens, and storytelling, another big, part of that.

You need that space to tell stories.

To each other.

This is how you share things up and down the chain, is by telling stories, helping people to understand what it is that you're doing.

You need ferment, right?

You need to be able to have everybody soaking in ideas.

And without that space you haven't, without that space, you haven't got a great team.

I love this quotes by an artist, American artist named Robert Henry.

The object isn't to make art.

It is to be in that wonderful state which makes art inevitable.

And I think that's what creating space is all about, and it's such an important thing.

And such an important place to be.

I'm at Atlassian, and, I'm working in a software company.

I think one of the reasons I joined the software company was because of those early days falling in love with code, that's actually what led me to start my own startups earlier in my career, and then you know, come to Atlassian working on software as a design leader.

And one of the things I realized that, was that our infrastructure was a mess.

We had a massive team just dealing with identity.

We ran a project to change, some billing plans in Jira, and it took us a year and a half to do it.

Infrastructure was just this total shit show, and I realized I'd been struck by this, I don't know, a decade earlier when I started my own startups, and I'd eventually given up on those startups, assuming somebody would solve infrastructure.

I come to Atlassian and I'm seeing hundreds of people in the business just dealing with infrastructure.

And I thought, what the fuck is going on here?

And this was another one of those intersecting experiences, and we'll see later how that plays out.

But it was really important to identify that, to notice that, to observe it, and to try to understand what it actually meant from a, business perspective.

And then I left Atlassian, and it was dark days as a designer.

I joined a company called Campaign Monitor, and it was a company in flux.

It had been started by two amazing founders who I was hired to come and work for as the head of design.

And they had recently, just before I started, taken on outside investment and stepped away from it.

And it was a company that was going from being one of the most amazing product led companies, at that point they were basically neck and neck with MailChimp, although MailChimp had just introduced Freemium plan and had soared off, into the distance.

And Campaign Monitor was trying to figure out what it was.

Took out outside investment, the founders wanted to take a break, they took a step back.

And you have this change in guard and change in approach to the company.

It went from being one of the most amazing product led companies to being a company that was led by mergers and acquisitions, right?

It became a company that was led by finance, which, as a head of design, is a really shitty place and not somewhere you particularly want to be.

And at the beginning, I really felt like there is no seat at this table.

Our CEO is a CFO.

This is a very different world for me.

I don't have Mike and Scott and Juergen advocating for design.

I'm trying to advocate for design in a company that isn't driven by product development.

It isn't driven by building great products for people.

And it took me a long while to build that understanding, that this was not an intentional thing, but this was just how they thought about things, and this was a different mode of business.

And it took me the longest time to realize that this was the biggest opportunity that I've had so far as a designer, was to learn the language of business.

And it's really years later that I understand that if you want to be the most powerful designer you can possibly be, This is what you've got to do.

You've got to learn the language of business.

Because business does not give a shit about design thinking.

Business gives a shit about business outcomes.

And if so, if you can align design needs and design outcomes to business outcomes, you become the most powerful force in the room.

I think as designers we tend to underappreciate the impact that we have.

We have a tendency to, because our art is a slow one, we tend to not keep up with the conversations in the room quite, in the same way as, chief revenue officers and, people with business backgrounds.

And a big skill for designers to learn that's behoven of you, if you want to be a great designer, you have to hone this skill.

And it's the one skill that none of us designers want to hone in any way.

We hate this skill.

And Atlassian was really good at allowing us to ride that line.

And Atlassian, basically nobody besides GMs had any discussion about, costs of anything, right?

So we didn't have to care.

I was a head of design.

At a team of 30 people, I did not know how much my people get, got, paid or what the total bill for my people was.

It was irrelevant.

And we were allowed that abstraction because it allowed us to think about things in the right way.

We got to think about not how much does this feature cost us to build, but how can we make the biggest impact for our customers?

And that is what makes a great product.

Campaign Monitor, suddenly a totally different thing, but starting to learn that language of business is such an important skill.

And starting to add to my intersecting experiences map, we've got design, we've got building software, we've got this learning about infrastructure, and then we start to layer on some business.

And so I'm starting to build a more rounded version of myself.

And then I joined Shopify, which is, again, one of the great companies with one of the great CEOs.

Again, Toby, a person who creates space for design.

Actually, quite unwittingly, I'd say some of the greatest designers of our generation are Toby, Mike, and Scott.

They're people who don't have any of the formal training or even understanding that they are designers.

But who do all of the right things to behave as designers.

I'll give you a great example.

Toby, was testing out our support experience.

So he phones into a support agent, and the first thing he does is get put on hold.

And he's sitting there on hold and it's the same shitty elevator music that we're all so used to.

And the first thing he does the next day is, he says, get rid of that fucking elevator music.

Put some good music on that people want to listen to.

If you're going to be stuck on hold, and there's nothing we can do to alleviate that.

At that time, we had 1, 500 support people in a company of 6, 000 people.

We cared about support.

We did everything we could to get people, off hold and onto speaking to a human being.

But sometimes you're going to get stuck on hold.

Kill the crappy hold music, right?

And that, to me, is just a representation of how much Toby and Shopify cares.

About the experience of the company.

About the experience of the product.

This is down to the product level, service design, everything else design, right?

This is you think about the whole company.

This is what killing, to me, killing the whole music means, is think about every single interaction somebody could have with your product, your company, the people that work for you, and optimize that experience so that it is a great one that people can fall in love with.

Kill the whole music.

The next thing that Shopify does, and especially in my role here, I was leading a team of 70 designers, researchers, and content writers.

My view was no longer to think about, how do we think about this micro interaction in shipping, but rather, what are we doing in three years time?

Because it's the three years time that we're building towards.

Everything that we're doing right now in shipping and order fulfillment and order management, all of these things, ladder up to a much, much bigger product, that we're building in three years time, not in a few months.

And I think as a, as you, as everybody grows in their careers as designers, as you move on that path from being an individual contributor to a leader, and hopefully to one day being a CEO, the job is to go as long as possible in the thinking.

The further out you can look, the more valuable you're going to be, the more powerful you're going to be, and the more ability you'll have to look longitudinally at problems.

Going long is such an important skill, but bringing purpose to things, right?

I think that if you look at Atlassian's mission, or at least when I was there, was to, unleash, there you go, unleash the potential of all teams, right?

Shopify, make commerce better for everyone.

These are great, purposes.

I think Shopify is such an interesting one.

It's only really about a month ago that Shopify changed its, website to say make commerce better for everyone.

And that's because it took them 20 years of existing to earn the right to say that on their home page.

Up until now, they've had to say things that are much more tangible and tactical, go and build a business, and it's only really our having earned that right to say that.

They've had that purpose for the longest possible time, and they've only really been able to start using that as a way to talk about themselves, in a recent few years.

You have to earn that right to have that big, grand purpose.

But I think if we don't have that big, grand purpose, we're only doing small things.

Kinde was started, this is, my company, Kind was started with a view to reinvent the way that software companies get started, with a purpose of creating a world with more founders.

That was the biggest thing that we thought we could possibly do.

The biggest impact that we could make in the world.

And I think if you're not going at things with purpose, then you're going to end up having a very short and limited view of the world.

At Shopify, I was sitting down with, one of my team one day and she was really struggling with, I don't know if I have purpose in this thing.

I don't know What I'm doing here anymore.

Why am I at this company?

She'd been there for I think 15 years already and she was starting to feel really disenfranchised and I sat down with her and I said, you do realize the impact that you're having.

What Shopify does in the world is, allows people who have zero opportunity, zero, skills necessarily, zero training, zero education.

It gives them the opportunity to take a product and to sell it on the internet and potentially become a billionaire.

And those people, each one of them, if they can grow, if they can succeed, they're gonna hire a whole bunch of people, right?

And so you become this, Shopify and the retailers who work on it become this massive job creation framework.

That's the most amazing purpose you can possibly have.

And so for us as designers, it's about understanding what the purpose of the companies we work for are.

And relating to those purposes.

And if you can't relate to that purpose, then maybe thinking about what it is that you're doing there and whether you actually want to be there.

Because if you're building without purpose, it's a pretty hard life.

And design, software, business, and infrastructure, and then at Shopify starting to layer on this commerce piece.

Understanding how people sell things on the internet.

And so my intersecting experiences map is starting to feel quite interesting.

I'm starting to see these things that are happening that feel like they're all intertwined.

And really that marries down to the fact that infrastructure, which is really composed of things like commerce, it's composed of how you bring software together, how you bring business into software, and commerce and, software infrastructure, starts to me to look like a universal problem.

I start to understand that every single company, because Shopify also had a team of a hundred or two hundred people figuring out identity, a whole nother stream figuring out identity how subscriptions to people were being done.

If you wanted to change a subscription plan, it was a massive, thing.

And so I start to see this problem that infrastructure is a universal problem, that every SaaS company has it.

And I realized that I wanted to go and do something about that.

I was leaving Shopify, I had an opportunity to go and do something different.

And I realized that like the problem of of how you sell things on the internet, which Amazon and Shopify had solved.

Or the problem of how you communicate on the internet.

Facebook, Slack had solved this problem.

There was this infrastructure problem with infrastructure software that every engineer in this place will tell you about is a massive, problem was hitting every single one of them.

It was one of the last universal problems that existed in tech.

And so I decided to go and solve that.

And this is the thing you hit, right?

Designers don't start companies.

We all know that.

There's one freaking designer on the whole Fortune 500, on the whole Fortune 500, that's Brian Chesky from Airbnb, right?

There's no others.

Designers don't start companies.

We all live with this mentality.

People, if they're rising through the ranks, they rise out of product, they rise out of engineering, they rise out of sales, they never rise out of design, and I think this is fucked up.

I think this is actually such a huge mistake, and I think the world is missing out on such a great opportunity, because what if they did?

Design at the center of a company is a totally opposite view of companies that you're used to seeing, right?

That traditional business leaders, the CFO that I had at Campaign Monitor, that's what you typically think of as a business leader.

Designers build things that people love, and that doesn't just mean products that people love, that means companies that people love.

That means all of those designed experiences that Toby and Mike and Scott embed in the company.

Killing the hold music, making experiences that people can fall in love with.

This is what designers bring, but for some reason we bring it at this limited function where we're just thinking about nuanced experiences.

We're not thinking about how do you bring the whole company along to be a designed experience.

So what if designers did that?

The role here, this is the role of the CEO.

It's three functions, right?

Culture and storytelling.

Who better in the world is there to talk about storytelling than designers?

This is what designers do for a living.

They def, culture is a designed experience.

You design a culture.

It has to be an intentional thing.

When we started Kinde, we started by defining the values first.

Before we basically had any product, any company, any team, we had a set of values that defined who we wanted our team to be, because we very intentionally set out to create that thing.

The second role of the CEO is people in hiring.

If you want to create a great team, you go and deliberately construct that.

You find people who resonate with you.

And you need to understand, what you want to create, you need to design the company and bring those people together.

And a lot of my role today is designing the people and interactions that we are as a company.

And the third role of the CEO is promoting and getting new things, right?

This is defining what the product is going to be.

And so as you migrate from your early in your career as a designer, migrating through design leadership and to hopefully see your role, a lot of your, change in what you do is, that longitudinal view.

It's not just designing those small individual things, but promoting and killing new things at a bigger and bigger level.

And so the role of the CEO and the role of the designer in a lot of ways is fundamentally the same thing.

People want products that people can fall in love with.

At the end of the day, this is why Apple is so successful.

This is why Airbnb is so successful.

Shopify, Atlassian.

These are companies that are incredibly successful because they built products and they built experiences that people could fall in love with.

And so today, I'm the CEO of Kinde.

We started in 2021, unlike Darth Vader, and Kinde is the culmination of all of these pieces.

I brought together my love for software and my love for design.

I brought together my understanding of how business works and how infrastructure works and how commerce works into this one place where all of these problems that I'd seen could hopefully be solved and that is what we're trying to do.

We create a ton of space, we allow time within the team and this is the benefit of having me as the CEO.

It's such a weird thing to have a software, a traditional B2B SaaS company headed up by a CEO.

A lot of people ask me, what the fuck, how, what were you headed up by a designer?

People are like, why have you, why is that the setup?

And because actually I believe that the model of traditional SaaS B2B businesses is totally fucked up.

I think that having engineers and product managers up in the role of CEO in those companies means that you end up with typical B2B SaaS companies.

And I think that the big transformation, the big impact that we can have is to create companies that allow space for the team to be creative, for the team to story tell, to create that environment of creative ferment.

And that's not something in many companies, but when you do see it, it often results in truly great companies.

Airbnb, Shopify, Apple.

These are great companies because of those systems, because of those, that space creation.

We could bring in systems of scale, if, we started with having our values, as I said, we started by having product principles that helped us to formulate how we would build great products.

We have planning sessions that are design driven, and then we do all the same things that you would do as a designer in your, normal teams.

Design system building, workshops, storyboarding, briefs.

Design systems was one of the first things we introduced, because it had been so successful at Atlassian.

We realized the value that design systems brings.

And the value that design systems bring, by the way, is yes, they help to accelerate engineering, but they also mean that designers don't have to think about nuanced design.

Designers can think about the impact they're trying to have the problems they're trying to solve.

This is why we believe in design systems as designers, not because they help engineering teams, although they do that too.

We had, we do storyboarding, we do, we have design principles.

We have a partner program and we think about how do we get those partners to help scale us as a business.

Having that language of business, if you remember, that was the darkest time for me.

But I think one of the most powerful things as a CEO, a lot of my role is looking at spreadsheets, looking at how we're performing as a business.

And I believe it's that marriage of business outcomes and design outcomes that has made us a great company that is growing really fast.

We think about customer first, revenue second.

This is really important.

It's something that I learned at Atlassian, and I think it's such a design minded way of thinking about things.

If you put the customer first, and you think about what their problems are, and you think about revenue second, the revenue will come.

If you think about revenue first, you're going to be in trouble, and so we always think about how can we help our customers to be as successful as possible, and that is going to translate into revenue in the long run.

And we kill the hold music.

We do everything that we can to create a great service experience, product experience, and everything else experience.

This is what our customers need.

People want great products.

We think really long.

We think years into the future about what it is that we're going to go build and how we want this company to be.

And we do everything with purpose.

To create a world with more founders, to me, is the biggest calling of my life.

To help more and more people to have the opportunity to go and start startups and go and reinvent that the way the world works is the biggest thing that I can do in the universe today.

And I hope that I can help hundreds or thousands of founders to find their calling and to go and do something bigger.

We start with purpose as a company, it's so important.

And so this is my call to you.

This next story is really your story.

If you're looking at what you're doing right now and you're asking yourself, Is what I'm doing big enough?

Am I having the impact?

As designers, a lot of our role is to think bigger, is to have the biggest impact possible.

And if you're looking at your job and you're thinking, is what I'm doing big enough?

And if you're looking at your role and you're thinking, am I building somebody else's dream?

If you're doing that for too long, Then you're not having the impact that you want to have in the world.

And this is my challenge to you.

You are called to service as designers to step up and to start making those moves towards growing into the future CEOs of the world, because I think that the world needs more companies that are headed up by designers.

Go and give people wonderful tools and they'll make wonderful things.

Thank you.