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Should I start my career at a start-up?

By Joy Molan


Joy met with quarterlifer, Chris, to ask him about his experience working at a leading fashion tech start-up.

When Chris began job-hunting in his final year of uni, he never thought he would end up working at a leading fashion tech start-up. All he knew was that he loved fashion, but wasn’t a “Creative”, and that there was no way he was moving back to the suburbs after graduation. I met with him to discuss his experience of landing a job (and keeping a job) in the cut-throat climate of start-up-land, and what it’s like starting your career in a non-traditional business model. He shared with me the highs, the lows and the watch-outs most people don’t discover until it’s too late.


So Chris, did you always know you wanted to work at a start-up?


Hell-fucking-no. To be honest, I don’t think anyone knows what they want when they start thinking about careers. While I was at uni, I had interned at start-ups and I’d seen the limitations of small teams. So I didn’t think I wanted to work at one when I graduated. I always knew my real interest lay in fashion, but I’m not a creative person so I couldn’t see a way into it. For both these reasons, I decided to only apply to big, corporate grad schemes in my final year of uni. I got pretty far into the process, but I gradually realised that it wasn’t right for me. I would be in interviews with bosses talking dismissively to me about their own teams and at times I was treated like a number on a spreadsheet. This was all a huge red flag for me.


Eventually, I met with a recruiter who was able to help me find a job in fashion that wasn’t a design or creative role. Strangely enough, he had bumped into the founder of an exciting new fashion tech start-up at the gym. The founder, now my boss, was looking for new sales staff to join the company. Really I got my big break through a series of serendipitous events, which was amazing for me, but I’m sure is very frustrating for anyone reading this who is trying to get their foot in the door.


Has the reality of your job matched the expectations you had?


The salary came as a surprise, because recruiters will always upsell it to you. If you’re going for a sales role, you’re lured in by an OTE (“on target earnings”) figure. Recruiters do this to entice you, so you have to beware the difference between a base salary (usually around £24k) versus your OTE (maybe £30k), which includes predicted commission. Most people won’t hit that £7k gap – there’s about a one per cent chance you’ll make that. I wish I had asked my recruiter how many of their employees are making that OTE figure, because that would have prepared me for what my salary was really going to be like.


Does it take a certain type of person to work at a start-up?


Work ethic! For any kind of start-up, a good work ethic is so important. Most people who go into start-ups haven’t done vocational degrees, so you’ve got to take everything as a learning opportunity. You’re coming to the workplace after 16 years of schooling, with defined rules and pathways. Now you have to make your own way – and it’s weird. Don’t expect everything to come to you on the first day. Just be inquisitive, show that you care about what you’re doing and ask lots of questions.

What are the less attractive aspects of start-up life?


When I started, I was unsure of my job security, so I worked like a dog to gain recognition and accelerate. I think it’s an excuse to work you very hard for less money. You will be promised career progression that might not materialise or takes longer than you expect. I was told I had to wait for the business to change to discuss a promotion, which I found really depressing. I felt I’d been sold the promise of progression and it wasn’t happening for reasons outside my control.


In hindsight, I don’t regret working overtime because I achieved what I wanted to achieve. I made a good impression and discussions about promotions got easier. But I sacrificed my social life a lot and it impacted my relationship at the time. I guess I kind of regret it, kind of don’t…


What do good CVs look like in this sector?


So much gets chucked in the trash from the first line of applications, so you’ve got to make an impression with the cover letter. Your cover letter has to be about the company, not you. Your cover letter is for showing research about the company, thinking about the role itself and then lightly touching on your attributes. I saw one awful cover letter recently which was solely about how one guy “thrives”. Don’t be that guy.


How long do people usually work at a start-up for?


Commercial roles at start-ups are the most common kind of entry-level role and they are target-based. Lots of people struggle to hit those targets. Small companies can also be quick to hire people without proper vetting for sales jobs, because they need the people. This means that lots of people end up either being fired or leaving because they don’t feel supported. Retention is less than 50 per cent, and the 50 per cent that leave last roughly nine months to one year.


What’s a mistake you made or a barrier you faced, and what were you able to learn from it?


You’ve got to believe your own hype. I was too demure for the first few months and didn’t play up my own achievements. I didn’t want to fuck things up or not be able to deliver to a high standard I had set for myself. If you want respect you have to be aware of how other people view you. Otherwise, people will think you’re insecure or pity you. When I had to do cold calls at the beginning, 99 per cent would be shit. Then I’d have one good one and take that positive energy and channel it into the next thing. Value yourself, it will do wonders for your life.


What advice would you give someone who wants to get ahead at a start-up?


There’s only a certain amount that you can control. You can’t control everything about your life. Your first job is going to be stressful, and that’s fine. You shouldn’t feel guilty if you can’t do everything. Don’t panic or think it’s all on you.


Also, seek out opportunities to make an impression on the founder. There was an opportunity for me to present my vision to the company founder and he really liked it. Off the back of that meeting, he created a new role for me to help manage various projects and I was able to progress upwards faster.

Image by unknown Pinterest artist

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