From Designer to Product Leader: A Career Chat With Jeni Oye
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We chat with Jeni Oye, Head of Product at Xero, about her career journey, which spans industrial design, entrepreneurship, and leadership in tech. From running her own jewellery brand to shaping tax products for the US and Canada, she’s got a wealth of experience and wisdom to share. Check out her story as she talks about her biggest career lessons, balancing work and family, and the challenges of product leadership.
What do you do for work today?
I work at Xero as a Head of Product, building tax products for our US and Canada markets.
What did you study?
I did my undergrad in Industrial Design at UTS, which is physical product design—cars, chairs, toasters, etc. I chose that field because it had form (art and design) and function (materials and manufacturing), which interested me.
I briefly dabbled in industrial design at Sunbeam before jumping on the internet bandwagon just as HTML and web design were emerging—yes, I’m showing my age!
I later did a Senior Executive MBA at Melbourne University to round out my business knowledge.
Can you briefly describe your career journey to date?
The first ten years of my career (1995-2005) were in web design. It was super fun because it was all so new — we were pioneering UX patterns, and usability was very challenging! Back then, the roles were labelled “information architect”, but it’s essentially what we call UX designer or digital designer now.
Then, I got married, started a family, and took the opportunity to do a startup from home. I ran Oye Modern, my online jewellery store, for five years, and it was one of the most challenging and rewarding parts of my life. To this day, I’m still super proud of what I achieved with Oye Modern.
It turns out I have a bit of entrepreneur in me, starting a few other businesses over the years:
- I started a web design studio called Meniscus about six months after I left University, but it only lasted six months because I ran out of money!
- I created a SaaS consulting firm GoBig, between jobs.
- I took over a startup that, within nine months, I shut down due to non-scalable tech and limited market opportunity.
Mid-career, I made a concerted effort to expand beyond design into business strategy. I did an MBA and got roles at consulting firms CEC and Accenture/Fjord. This is also when I started to move into leadership roles — I found myself selling and leading projects, and holding regional titles like Design & Innovation Director for Australia and New Zealand. But the best part was the work — we did impactful, cool projects in customer strategy, service design, and digital product design.
Then I found my passion for SaaS, and wanted to move into Product Management. It turns out I already had most of the skills; I just needed to convince someone else of that! I landed my first official “product” role as Head of Product at Fergus, which brought me to Xero, where I am today.
What's been your biggest moment of professional growth, and what did you learn?
Definitely my role at CEC - where I joined as a CX designer, and within a few years became a Director of the company. This role taught me a lot about myself, leadership, and about how to run a business.
It was tumultuous, energising, rewarding, and tough. We grew, we shrunk, we expanded services, we consolidated services. I had leadership coaching for the first time, where I had to accept my weaknesses, which was very confronting!
I attribute a lot of my professional growth to the founder of CEC, who provided space for me to lead and grow, but also pushed me well beyond my comfort zone.
You founded a jewellery brand. What lessons did you take from that to leading in corporate environments?
I was running Oye Modern while also having babies, which meant I had to learn how to prioritise and be efficient with my time, switch off and be present.
This was a huge lesson and a turning point in my career.
Before kids, I put everything into work. I would work late nights and weekends, and I enjoyed it. But there is nothing like having kids to put work into perspective. Without the forcing function, I would still be a workaholic and likely not as happy and fulfilled as I am now.
That meant that when I returned to working in the corporate world, I was able to meet or exceed my employers’ expectations while working 9 to 5 or less!
Who or what has been an unexpected influence on your career?
Looking back, you never know who is going to look after you when you least expect it! There were four times in my career when I had an old colleague hire me into a role that accelerated my career to new heights. Those were:
- A design leader at Sapient who approved my request to transfer to New York.
- An ex-boss who hired CEC for digital design work, which was CEC’s first digital work and enabled me to build the digital practice there.
- An ex-coworker who gave me my first official “product” role.
- A senior exec who hired me to be CEO of a startup in his portfolio.
Each of these was unexpected, but each created a turning point for me.
What are the main challenges you face as a product leader in tech, and how do you manage them?
Hmmm, so many! Here’s a few…
Don’t ignore or defer engineering decisions to your tech leadership. You need to know and understand just enough to ask good questions and ensure the technical solutions they are implementing are appropriate and scale for the future. I had to close down a startup because the underlying technical solutions were not fit for purpose.
You need data and insights to make good decisions, and sometimes I spend more time getting data than actually building a product! But you won’t build the right thing if you don’t have the right information. So, even if it takes time, get the data! Bonus tips:
- Don’t ignore the data because it doesn’t tell the story you want it to tell.
- Data doesn’t tell the whole story. You need information and insights from your data. Balance your quantitative data with qualitative research.
How has your design background shaped your leadership style and approach to problem-solving?
Interestingly, user research and testing have had the most influence:
- Conducting research forces you to be curious, ask open questions, and understand people’s motivations and context. When I applied this curiosity to my coworkers and clients, doors opened.
- Research forces you to test your assumptions. Not everyone is like you, and often, your assumptions are limited by your own experiences. Get evidence to support your hypothesis
- In design, you realise there is no perfect end state, everything evolves and there are always compromises. Design is never done. The product is never done. It just evolves.
I would add one other factor I learned from being a designer in tech, and that is that everything is about teamwork. Design is nothing without developers making it real and product managers ensuring it’s viable. And in any role, it’s always about teamwork because your business can’t survive without all the roles and disciplines it employs, and without that business, there is no job for you!
So respect and support all your co-workers; you need them.
What do you do outside work?
I’m a designer at heart, and I love to make things. For the last few years, I’ve been getting into Stained Glass. The only problem is we have run out of windows to do in our house, so now I’m hitting up all my friends and family for new projects!
I’m also into street art. We have a mural in our house by a local street artist Studio Dennis, and I have designed a 40m long mural to go down the side of our neighbour’s house, which we are about to embark on this summer!
