How To Move From Corporate To A Startup Job

How To Move From Corporate To A Startup Job

From Dry Shampoo To Dry Cleaning

“Love what you do, put your heart into it and you will be rewarded.”

– Aaron Morse (Kiehl’s 2nd Generation, Family Founder)

If you are in your late twenties or thirties there is a good chance that you have been working in the corporate world for some time and you have an itch that you’ve been meaning to scratch.

You’ve built up a solid career, made great connections and are beginning to rise the corporate ladder, but something isn’t quite right. You may feel ‘stuck’, you may feel like you are not learning fast enough and that you need a new challenge. Perhaps your current company is a leader in its field, but you look around and see snappy young competitors eating away at your market share or you are exhausted by the politics and layers of bureaucracy standing in the way of getting meaningful work done.

On your daily commute, you read stories like this, you look at your current situation and wonder if the pace of change will ever be fast enough. You read stories like this, and you can feel a groundswell of opportunity and potential building up, just waiting to be unleashed.

The trouble is, you’re used to the good life. Great salary, perks, corporate gym membership, two holidays a year, company car. Maybe it’s not so bad after all? Maybe you can stick it out, climb the corporate ladder and figure out a way of working to live. Startups are hard, who wants to live to work, right?

I was in the same position as you. There is a wealth of information out there with tips on how to go from corporate to startup life but when faced with an incredible opportunity last year, I found there wasn’t a huge amount of information written by people who have actually gone through with it and lived to tell the tale. Our mission at ihateironing is to make our customers’ lives easier and if anyone finds themselves in a similar situation hopefully there are some nuggets in here that will help you with one of the biggest decisions of your life.

About Me

The startup world has always fascinated me. Having a background first in computer science followed by business and marketing, I was fascinated by the rapid rise (and even swifter demise) of companies like Napster in the early noughties. It is incredible that some of the biggest and most valuable companies in the world have only existed for less than twenty years and some of the most bankable blue chip companies like Polaroid and Compaq, have fallen by the wayside, due to what’s endearingly termed Digital Darwinism. 40% of the companies at the top of the Fortune 50 in 2000 were no longer there in 2010 and Cisco CEO John Chambers predicts that less than a third will make it through the next ten years. The legendary VC Marc Andreessen wrote back in 2011 that ‘Software is eating the world‘ and only the businesses that are able to adapt will succeed. Only last year, the CMO for the company I worked for previously flashed up a gigantic image of a dinosaur at one of our company updates and pointed out to the senior management that if the company didn’t adapt quickly, it would begin to flounder.

Against this backdrop, I began to challenge my thinking. While the company I worked for was a world leader in its field, I found that no matter what projects I was involved in, I couldn’t scratch the itch. I had a desire to move faster, to learn more and to expand my skills in ways which it didn’t seem possible to achieve in my day to day work. I came across a copy of Mihály Csíkszentmihályi’s book Flow, the psychology of optimal experience and had a lightbulb moment. Mihály wrote that

“The best moments in our lives are not the passive, receptive, relaxing times… The best moments usually occur if a person’s body or mind is stretched to its limits in a voluntary effort to accomplish something difficult and worthwhile.”

– Mihály Csikszentmihalyi

If you are going to be working for on average 50% of the waking hours of your life you should do something meaningful, difficult and worthwhile. This, to me, is the draw of the startup.

What to expect

1. You will wear many hats

My first few weeks in the business i was undertaking jobs I had never done before. In the corporate world you would be quick to say those three magic letters ‘NMJ’ – not my job. In the startup world ‘NMJ’ doesn’t exist. The operations manager will share doing the dishes with the CEO. The customer service team will write for the blog. You simply roll up your sleeves and get on with the task at hand and do it to the best of your ability which leads to the second big aha moment.

2. You will have more opportunities to learn

In the corporate world, continuous learning is constantly referenced. There are e-learning intranets, team building days out, big budgets for overnight management training courses and more. Many of these are incredibly worth while and well thought through by your HR / Learning team. You may find yourself in an organisation that is undergoing ‘Digital Transformation’ with measures put in place to raise the ‘Digital knowledge gap’ of the entire organisation.

These programmes are laudable and I have no doubt that they will add value to every organisation that undertakes them. One of the major challenges I’ve found in my personal career is that, you can go to three fantastic seminars or training sessions a year however the real learning is conducted on the job.

If your firm employs agencies or specialists to advise on the strategy, create the video and produce professional reports on your SEM strategy, how will you ever learn anything more than a conceptual understanding of what is taking place at a very high level.

Reading the excellent book Rise, by Patty Azzarello, the argument goes that the higher up in your career you progress, the less the technical skills matter. I would agree with this for the most part in today’s economy, however I’m not sure it is sage advice for the future.

The UK government predicts that the number of people in self employment / the freelancer economy is going to increase exponentially in the coming years. It would appear that the people who are going to be able to add value to the companies of the future, from a marketing perspective are people who familiar with the high level concepts and can articulate a clear vision but they have been in the weeds and know how the nuts and bolts of a campaign work. Forbes has charted the rise of the Technical Marketer or the “new mad men“, eConsultancy calls it “pi- people“.

Pi-shaped people are “marketers with a broad base of knowledge in all areas, but capabilities in both ‘left brains’ and ‘right brain’ disciplines. They are both analytical and data-driven, yet understand brands, storytelling, and experiential marketing.”

Ashley Friedlein, eConsultancy

3. You will get results faster

It can be frustrating to have to wait to sign up a new vendor, or wait 6 months for the legal team to approve a new technology before you can even get started. In the mean time the competition is surging ahead and you have to work even harder to catch up. There is nothing more gratifying to work in an environment where barriers are minimised, the path is clear of excessive red tape, and you have the flexibility to test your hypothesis quickly. One of the first things you will relish in the startup environment is the short cycle of having an idea, getting it approved to test, tracking the results and if successful rolling out a change that can have a huge impact on your business.

4. Your success (and failures) will be more visible

With the increased speed of implementing new ideas and campaigns, inevitably you will find that some ideas will work very well and others may even have a negative effect. In a corporate structure, the business is well insulated against making decisions that can negatively affect revenue. There are agencies, consultancies, legal teams and countless review meetings before a project or idea is signed off. The benefits are obvious, the aversion to risk is high and it is likely to have less chance of failure. There are however, downsides to this approach. Your more agile competitors and hungry disruptive startups are speeding ahead while you’re on your fifth review meeting. If the project ends up not being a success, the failure is rarely discussed and really dissected to see how the whole organisation can learn. Best practice databases are setup to share the wins but it is rare to find a ‘Misses’ folder where others in the company can view a case study of what didn’t work and how to avoid making the same mistake in future.

The antithesis of this behaviour is found at some of the best ‘unicorn’ tech companies, ‘startups’ valued at over $1BN. Google’s motto is to ‘Fail Fast, Learn Faster‘. Facebook’s motto until very recently was to ‘move fast and break things‘.

When you make a mistake at a startup, it will be visible for all to see. You will likely find that as long as it’s not a regular occurrence your team will be more tolerant and will take an interest in finding out why it didn’t work and how to improve for the next campaign.

5. Your work environment may change for the better

This is an area where corporates are catching up. For a long time it was received wisdom at startups that allowing people to be themselves at work and not have to conform to stuffy dress codes or work in the same location every day was conducive to happier employees. Traditional firms such as PWC are starting to realise that in order to continue to attract great talent, they need to relax the rules a little. As competition for talent hots up, startups are upping the ante even further. Facebook recently announced their new paternity leave programme allowing father’s to take up to 4 months off, fully paid. Netflix allow employees to take unlimited vacation days. In addition to the perks of being able to work from home, startup are offering core hours, flexitime, ability to bring pets to work and much more.

Generally you’ll find the atmosphere, more relaxed and less stuffy, you’ll dress smartly but there’s no pressure to wear a suit. You’ll work with incredibly passionate people who are dedicated to the same goal as you but look out for each other. In my experience, the people I’ve had the pleasure of working with are incredibly special to me, after just a short time they feel like family. They’ll tell you when you’re working too hard, make copious amounts of tea for each other and the days fly by as we make the time to catch up and find out what’s important in their lives. Despite this they are incredibly professional and dedicated to making the business sing and I count my blessings every day I get to work with such a smart and talented bunch.

6. You’ll learn to do more with less

This is perhaps one of the biggest learning curves of all, but the most rewarding. No longer will you have access to a huge budget and the best consultants to hone and refine your strategy. If you’re lucky, your budget may be a tenth of what you’re used to working with. You will learn how to hustle, how to be frugal, how to do more with less. You’ll learn that while you may not have budget to pay a videographer, you can just as easily learn the software yourself. You may lament the loss of an in house designer but you might find a way of updating the visual style of the blog yourself. You may miss out on an expensive, training session on Facebook marketing, but find a million resources online to learn yourself, along with some great tools to get you better results.

What to weigh up

Before you take the plunge and turn your back on corporate life, there are a couple of caveats and areas where you need to examine carefully. It’s certainly not a decision to be taken lightly.

1. Your lifestyle will change dramatically

You may be thinking of buying your first house. You may be used to beautiful, expensive holidays in the Caribbean every year, and / or multiple city breaks, the best dining your local city has to offer, the pleasure of upgrading to the latest iPhone the month it comes out or getting into the gold circle for your favourite live act.

Unless you secure a role in a startup with deep pockets it is unlikely that they will be able to pay you the same salary you received in your corporate job.

If a startup is matching your corporate salary, it’s likely to be later stage, with significantly less risk but on the flip side very little potential to own a share of the business.

Before you take the plunge, think carefully about what you will be giving up. If you have dependents in your life, like a partner or child it would be irresponsible to jump in without considering their near term and medium term needs. You will have to invest time in crunching the numbers, seeing what you can live without and potentially even moving further out of the city to balance the books each month.

2. Risk Appetite

How comfortable are you with uncertain outcomes? Do you get sweaty palms when planning a holiday and you’ve not got every last eventuality planned out meticulously in your spreadsheet? Does the thought of being jobless for over a month scare the pants off you?

Startups are by definition risky business. 90% of startups will fail with the vast majority of them failing in the first 3 years. If you are lucky, you will find a startup with a great management team, incredible market and resources and capital to make a success of the opportunity in front of you. Not everyone will be lucky and you need to be comfortable with the fact that it could all end abruptly and you’ll need to pick yourself back up, dust yourself off, pause for a moment at the incredible skills you’ve picked up and get back out there. The chances are that it’s a calculated risk as what you will learn in a short time at a startup will be incredibly useful should you ever need to change course. I’m convinced that the smart employers of the future will view time in a startup, even if not a unicorn, as a huge positive.

3. Business Plan & Compensation

While it is unlikely that the startup will be able to afford to pay you the market rate, it is important to do your due diligence on the business. You are investing time and money (in the form of lower compensation) in this new endeavour, the very least you can do is ask the right questions and treat it as an institutional investor would do. While it is impossible to predict future performance you should be able to build up a general picture of the size of the opportunity, the team, the market and ask the right questions to ensure you are making the best decision for you and your family. Don’t be shy about asking what the burn rate is, the amount of runway until new funding, who the investors are and the share structure if this is part of your compensation.


If you have an itch that needs scratching, don’t wait to find out what could have been. Get started today investigating if the opportunity is a good fit for you. Anyone I know that has worked for a startup has acknowledged that the opportunity doesn’t come around too often and when it does you should grab it with both hands – or at least grab it with one and give it serious consideration.

It is an honour and privilege to do the job I do. You know you are working at your dream job when you can’t wait to get into the office or pull the laptop open at home to solve the latest challenge. It’s fun. It can be all consuming if you let it. It can be mentally tough and some days will grind you down, but most importantly, you feel in charge of your own destiny and significantly more likely to make that ‘ding’ in the world.


  1. Escape the City:
  2. Work In Startups:
  3. Video on Flow, the secret to happiness:


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