December 7, 2023
Disclaimer: I'm a first time Co-CEO of an enterprise saas company, willing to be vulnerable. I'm also a mother of two young children. This blog is an expression of my personal views and learnings. If it's helpful great. If not, no offence taken.
My personal goal this year was to level up my integrity. I’ve come to learn that my brain is programmable. There are things about it that are great. If I isolate them I can double down and expand on those things. Like adding a new feature to a product. There are also things about it that are not so great. I think of them as thinking errors - like bugs in code.
Coming from a background as a software engineer I love that analogy. Because if you can identify and replicate a bug then it’s quite likely that you can write some code to fix it. I’ve been doing it for years now. One of my best bug fixes ever was to stop over-thinking. The more bugs I've fixed the more capacity I've had to add features.
I buy into the notion that our personalities and our intellect are not fixed. I’m captivated by the idea that I can continuously refine and improve how I think. So, I invest effort into improving the interior of my mind. This has not only benefited me but everyone around me.
As a CEO I recognise that I have an even greater responsibility to keep doing work on myself. Why? Because a good version of me can support and catapult the people I work with, and the organisation I work for. A bad version can create discord and chaos.
Who you are is defined by how you show up in the shadows. It's easy to appear awesome on forums like LinkedIn, where you can curate your content. It's easy to appear awesome on a public forum like a conference panel. Or a company wide talk. Or a TV show. Events where you've had a lot of time to prepare and the conditions are ideal.
But who you really are is defined by how you show up in the shadows. When there isn’t an audience. When there’s nobody to impress. Particularly when things get really hard.
In these moments, you need to decide who you're going to show up as. Are you going to show up with integrity, be reactive, or shy away from the difficult thing that’s sitting in front of you?
According to the dictionary integrity means a few things:
In 2022 I felt like things were happening to me. My reactions were coming from a place of either fear or personal desire. This was letting down my integrity. Towards the end of the year I was in a pretty bad place.
I could see things playing out in a suboptimal way. I wasn’t showing up as the best version of myself. To be fair I was really tired. We all were. I knew heading into 2023 that if I continued on that path it wouldn’t be good for me or the great people around me.
Deep down I realised it was self-doubt that was preventing me from stepping up my integrity.
So, the first thing I did in 2023 was lean into a situation that wasn’t going well. I got honest with myself about the role that I was playing. And I thought long and hard about how I could show up differently.
You see, supporting people you agree with is easy. Supporting people you agree with and also get along with is even easier. The real challenge with integrity is supporting people even if you don't agree with them or get along. Because that's when your own fears and desires start to interfere.
So a first step towards my goal was simple:
Sound simple? Don't underestimate how prevalent avoidance is. Even at the most senior levels. Even in large organisations. It doesn't matter who you are - avoiding things is just easier.
The first time I did this in a really deliberate way I got a positive reaction. All the conditions were present. I didn't agree, I didn't feel at that moment we got along. But still I followed the three simple steps above. The very next day I got unsolicited positive feedback. So, I kept doing it.
Not only did it help other people, but it also helped me. I became more efficient. Both mentally and emotionally. The change must’ve been pretty evident. A few months into the practice, one of my Co-CEOs took me out for lunch. He voiced how impressed and curious he was about the shift. That was great validation, so I doubled down.
I began to trust myself more, and other people started trusting me more. After about six months my mental feature enhancement stabilised. Enough that it became a default setting, without much pre-processing required.
This freed up more capacity in my brain to focus on improving other areas.
In the meantime 2023 unfolded as yet another challenging year to run a business. Not just for us at Joyous but for most everybody. The macro economic environment has been nothing short of a horror show. The capital markets turned to shit. Inflation - a shocker. Most other tech shops around us did layoffs during covid, some more than once.
For a bit more context, Joyous is an enterprise saas company. This year our enterprise prospects got a lot more conservative with spending. Most of them have also done layoffs.
But we remained optimistic.
As the year progressed we were not meeting the growth targets we'd set during the previous year's booming market. So, we did a tonne of work on go-to-market strategies and experiments. We believed it was enough to shift things in the right direction.
There's that optimism again.
But it wasn't enough to counter the slow down in sales cycles.
We also raised capital right before the recession late in 2021. And we have always been conservative with spending and employee growth. This gave us the luxury of a long runway, one that few others had. It felt like we had all the time in the world to turn it around or wait it out.
This combined with our optimism created the foundation for Fantasy Land.
By Q3, I could no longer ignore that things were not shifting as quickly as we needed them to. But, we still had plenty of runway. So, it felt counter intuitive to react. I was still living my best life in Fantasy Land.
And then came a few more signs. An offhand comment from a board member. A graph on revenue that shook me. Something shifted inside me.
I can remember sitting in my bedroom one Friday night in September thinking: Shit. We are gonna have to do some hard things. And I'll need to lead the way.
It's not that I was feeling desperate, it was that I felt compelled to do the right thing.
And so started my journey from Fantasy Land to Reality.
I leaned on my integrity. I decided to navigate this really hard, really difficult thing with confidence. I knew what we needed to do. Like most companies had in the previous 18 months, we needed to restructure. I communicated it with care, transparency and held space for everyone around me.
Until then I have never been part of a restructure, let alone lead one. So, this was new ground for me. Actually, a lot of what I do is new ground for me. But still I leaned in. I worked with the team around me to figure out the path forward. I was inclusive, generous, and kind. We did the hard thing, had to say goodbye to some incredible humans, and now here we are. The remaining team.
Walking amongst the ever growing tech population well and truly grounded in reality.
I have taken away a few key learnings that will help us stay permanently grounded in reality. Maybe they'll help you too.
I am confident that if we can keep practising these learnings we will succeed. We will also be able to resist the urge to return to Fantasy Land, and remain grounded in Reality. We are a small group of thoughtful people who I wholeheartedly believe can and will change the world.
As my Co-CEO Mike Carden points out, alongside our challenges we’ve also had many great successes in 2023. So, in recognition of those:
No company is without its challenges, but few companies are vulnerable enough to admit it.
So...what's my challenge for 2025? Finding peace.
Ruby is a comedian-turned engineer, previously leading product at two global tech companies, she has been CEO at Joyous for 4 years. Her passion for making a positive impact on people’s lives is perfectly matched with the mission of Joyous to make life better for people at work.
She enjoys working across all parts of the organization and is passionate about product direction and data science.
She is the co-author of Joyfully, a book about shared leadership, modern organizational structures, and a new way of working. Her second book Pathways, is a guide to help woman and other under-represented people get a job in technology in six months or less.
She was the Winner of the Product Category for Women Leading Tech Australia 2022 and a finalist in the Inspiring Individual Category of the HiTech awards in 2023.
