It starts back in 2015 — well, technically before then, but Skyscanner onwards was where my career really started to get interesting. I had just given up my role as a Senior UX Designer at Skyscanner to come work at a Barcelona startup of 12 people to lead design.
Fast forward to today and that startup I joined which had less than one year of runway is now worth $2.7B. I'd like to claim four-years-worth of hard work contributing towards that achievement.
From 12 to 750, now what?
With TravelPerk outgrowing its position as a startup, I began working with another Barcelona-based company looking to revolutionize the hospitality management sector — Amenitiz.
Working with three co-founders, I designed the first version of the product, supported with branding and marketing and worked with the team through their critical go-to-market stage.
Staying on for a couple of years as a product and design advisor gave me a great opportunity to see things evolve while continuing to play a part in supporting the companies growth. Amenitiz has since secured it's series A round and now employs more than 300 people globally.
Alongside advising Amenitiz, I took on the challenge of becoming an Executive, joining Boatim as their Chief Product Officer. Despite the fancy title, I was very much in the weeds each day working closely with our team of around 15. Along with our CMO, I helped set a vision, deliver our go-to-market strategy and did it all whilst still pushing pixels and managing our small product and engineering team. Talk about context switching — this was next-level, even for me.
Climbing the ladder
After a number of years building products from scratch I pursued an opportunity to work at a larger organization. With the tech org alone being almost 300 people, I joined the team to become highly focused on craft as a Lead Designer. I wanted to move away from management and see what life was like outside of the chaos of startups and the time-suck of people management.
My IC stint was short-loved and after only a few months I was promoted to Head of Design and later to Director of Product Design where I had the pleasure of leading an amazing team.
However, moving further and further away from the craft and focusing more on team culture, organizational structure and — let's be honest — managing all the politics that come with working in larger orgs, there was a large void forming in my professional life which I desperately wanted to fill. I learned a lot there as a manager and a leader but it's not what I set out to achieve working there.
That Goldilocks moment
After almost 3 years working as a Lead, Head of Design, and finally Director, I slid down a few rungs of the ladder to go work at Sona as a Senior Designer in a 50-person startup where I could focus on craft again.
It was a great experience working with a new tech stack in a new industry, however, that team quickly doubled within the year and after only 2 years the product was already pretty well established — to the point that the need to support legacy parts of the codebase were a real drain on product acceleration and innovation.
I had found myself in a startup, working day-in, day-out designing, speaking with customers and doing what I thought I wanted, but just like Goldilocks' porridge it just didn't feel right. On paper, I had found what I was looking for but there were some aspects that I was still seeking — but what were they?
Be clear with yourself
After countless conversations with my partner and some personal reflection, it was clear that what I was seeking was something even earlier stage. When I looked back at TravelPerk, Amenitiz, and Boatim I was working with teams who were under or had just broken double-figure head count.
In those experiences, I was thinking about sales, marketing, customer support, engineering, product, and of course design. As a designer, your job is to solve problems and create value for people both externally — your customers — but also internally. Design can play a pivotal role in supporting and growing out other functions and I felt that was a big piece that I was missing at Sona.
For example, when TravelPerk was launching new products for customers or looking for ways to optimize the customer support experience for our customers and our agents, I was able to play a very active role in leading and supporting those initiatives.
Perhaps those conversations with my partner and some self-reflection sent out a little something into the universe as it wasn't long until I received a message that would set the stage for my next career move.
Here we go again
So, here we are today, three months into my new role as founding designer at Pensero. How did I get here? Luck and good timing you could say.
Not actively looking for a role, I was approached by a former colleague, grabbed a coffee and had a few calls with his co-founder. Within a week or two, the very thing that I was looking for had just appeared right in front of me.
I arrived as the 7th person on the team, and of course, the only designer. I’m deeply involved in the product, committing to the codebase weekly, joining sales calls, supporting marketing efforts, and exploring our product-market fit. I have arrived.
After some time away from writing, I would really like to use this new chapter to catalogue my journey as a founding designer, now against a very different, AI-filled backdrop that has disrupted many industries and roles in the past year or so.
If you are reading this and would like to learn more about working in startups or would like me to focus future articles on specific topics, feel free to reach out and connect on LinkedIn.
Until then, have a great week!