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Starting Your Career: Startup or Big Corporate?

Choosing where to start your career can be a daunting task—if you’re lucky enough to be in a position to choose. Many college graduates are sent into the world with a lack of marketable skills and experience, meaning they’re often forced to work anywhere that agrees to take them.

As unfortunate as that reality sounds, it’s still wise to look for companies that suit your skills and values, and are best positioned to help you achieve your career goals. Admittedly, this is not something I was aware of in my early twenties.

Shocking right? A naive 21-year old that thinks he’ll magically land his dream job on the first try. I spent the first six months of my career applying for design jobs, only be rejected for—you guessed it—a lack of experience.

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Before this, I had never considered working for a startup. Honestly, I didn’t really think it’d be something that’d interest me. The perception I had of startups was struggling companies in a rundown, thrown-together office with a lack of perks and job security. I couldn’t have been more wrong.

Throughout the past few years, I’ve had the opportunity to work in and with a mix of young exciting startups and much larger, more established organisations. I’d like to share my thoughts on what these two very different types of environments can offer those starting out in their careers, exploring the pros and cons of both.

The Start-Up

My first experience in a startup came from desperation more than an informed decision.

After what felt like hundreds of rejection letters, I knew I needed to change my approach. At the time, I had gone back to college to study for a postgraduate certificate in mobile application development. The college had a careers advisor with whom I shared my frustrations about the current job market with. She advised me to consider a smaller startup, as they would be likely shorter in funds and therefore be more open to hiring less experienced people that demanded lower salaries.

So I did, and it paid off.

After cold emailing three or four startups in my city, I got a reply from the CTO at a company called Soundwave. He informed me that they weren’t actually looking to hire a designer but thought I should pop in for a chat nonetheless. Two days later, I met with the founders for a quick chat around what I was looking to get from Soundwave and how I saw myself contributing.

Within a day I had a phone call to say they were happy to take me on as a paid intern working in a product design role.

Over the next few months, I settled into my role and tried to learn as much as I could from our senior designer. It went well—really well. I loved everything about it.

The fast, often scrappy nature of a startup means that things are ever changing. There’s no set schedule, no corporate bullsh*t. No agendas. Everyone shared a common goal and everything we did was focused on working towards that goal. I wore many hats and got to work closely with people that possessed vastly different skillsets to my own. I learned so much from these people. More than they’ll ever know.

It was an experience that kick-started my career and shaped how I think about what I do, and how I can be of value to the company I work for, now or in the future. That internship turned into a full-time role that I held up until the company was bought by Spotify.

Looking back, a startup was the perfect environment for someone in my position looking to build a generalist skillset. Because startups are usually shorter on staff, there’s an expectation that employees will wear many hats, often taking on responsibilities outside of their job description. This isn’t for everyone, but I enjoyed it. It pushes you to leave your comfort zone and learn new things.

Of course, one downside to this is there can sometimes be a lack of rigid structure or senior leadership in your particular department, meaning you could lack a sense of direction that you may receive at a larger organization. My takeaway was that, although starting my career at a startup was great, I would need some time to work under designers more experienced than me, maybe even joining a large design team so that I could learn from experienced people in my field.

In addition to everything I learned at my first job at a startup, one more really important thing I learned is that you should approach job seeking with a human touch—particularly when applying to startups.

My role at Soundwave wasn’t advertised online. The company wasn’t even looking for a designer. But through one cold email outlining my experience, ambition, and excitement about the company, I landed a job I really loved.

Relying solely on the job board alone is a bad strategy. Only applying to the roles advertised and going by the book means you’re just another number, another CV to review. There’s no personality behind your application. It’s hard to stand out. Harsh as though it may seem, these companies have sometimes hundreds of candidates to review, so, unfortunately, it’s true.

The Big Corporate

When my time at Soundwave had come to an end following the Spotify acquisition and I was looking for a new role, I knew my next step was an important decision.

As much as I had enjoyed startup life I felt the opportunity to work with a large design team and more importantly, learn from more experienced people in my field, would be the correct next step.

In July 2015 I joined MTT, a product agency with an already established design team operating in the travel industry. At the time, I had interviewed with three companies, receiving two offers, one of which was from MTT. My decision this time wasn’t actually based on the company itself, but on whom I’d be working with.

They had a head of user experience with a couple of decades experience in the design industry, something very hard to come by these days. It was clear that I’d be working alongside people with plenty of industry experience, and working in a team with strong leadership.

Upon joining, the differences compared to Soundwave were very clear. Everyone had a specific role within the company. There were entire departments for roles I had previously seen shared between people and even taken on myself! There would be no more role changing, at least nowhere near as much.

On the day I joined the company we were acquired by Travelport, a real behemoth of the travel industry with offices on every continent, and thousands of employees around the world. Working with larger product teams, I learned how to work effectively with developers, product managers, project managers, tech leads etc. With so many competing agendas, you’d be surprised at how quickly you need to develop a backbone and stand up for your work. If you think something isn’t right, say it.

Things may not always go your way, but in a team of 10+ people, things need to move fast, corners are sometimes cut, budgets and timelines change, so often its a case of the squeaky wheel gets the oil. Developing the confidence to defend your work and its importance in the overall scheme of things is essential.

Of course, doing it in a respectful and constructive way is also important. No one likes a jerk, so having some empathy for others in your team goes a long way.

I don’t want to make it sound like working for a larger organisation was a non-stop war of competing egos. It wasn’t. This is just the reality sometimes in larger companies. It has its disadvantages, but there were advantages too.

In my time there, I worked in a design team led just about as well as it could be. Everyone had a structured career development path, with progression through various levels clearly defined. The skills you needed to develop to advance to mid and senior roles, right through to management, were extremely clear, and because of the size of the company, there was plenty of room for progression.

There was also a real sense of job security. The company was an established player in its market, boasted more than a dozen long-term customers and were profitable year after year, so there were no worries that it would all come to a sudden end. Depending on what type of person you are, this may be a quality you look for in a company.

Personally, the people, product, and culture are the most important things I look for. I’ve always found it easier to get a feel for these when looking at startups as the teams are generally smaller and the interview process more personal.


Needless to say, nothing written above can be used as a sweeping statement. Every company has unique DNA and comes with its own culture.

The most important thing is this culture is made by the people there, and I’ve learned when choosing where to work that this is one of the most important thing to look at.

At time of writing, I’ve been at MyWallSt for the last six months. Very similar to Soundwave in size and structure, the one big difference for me is my skillset. Taking some time to work with and learn from people at a larger organisation means I can bring what I’ve learned into my current role at MyWallSt.

Design is an ever evolving field, especially in tech. Its role in organisations has become more important over the last several years, so much so that you’d be hard pushed to find a Fortune 500 company not investing in it in some capacity.

Startups too are at an immediate disadvantage if they fail to think about design from an early stage. As a designer at a growing startup, it’s my role and responsibility to ensure the design is being used in the most effective way possible, contributing to the growth and success of the company. Being able to call on the vastly different experiences I’ve had at both Soundwave & MTT has been invaluable and has taught me to work more effectively with engineering, customer experience, and content teams to ensure every touchpoint of our users’ experience is constantly improving at MyWallSt.