Like A Girl

Pushing the conversation on gender equality.

Code Like A Girl

How to Climb the Startup Career Ladder Like a Boss?

“Duh…” Photo by Jordan Whitfield on Unsplash

I started my startup career in 2012 and my first job was being a support agent for Toggl — the startup that has made time tracking sexy again. Fast forward to December 2016 and I got the offer to become the CEO of Teamweek— the startup that will make resource planning hotter than ever. (Btw both companies are part of the same Toggl Group and share a HQ in Tallinn, Estonia).

So, how did I go from having zero startup experience and working on support emails to becoming the CEO of a (now) profitable company in 5 years? You could ask my mentor Alari Aho who witnessed my whole journey, or read what I have to say about it here:

Cultivate a variety of skills, don’t stay stuck in one field if your goal is to move to a management position

I read an article years ago that painted out career paths for high-earning professionals and CEOs (sorry, I’m unable to find the article). In short, it showed you will get promoted sooner if you cultivate your skills to become a valued professional on a specific field, but at one point you will be at the top of that ladder and it turns out it’s not that high.

If you really dream about a higher management position, you have to be interested in much more than what your current job is about. The promotions will take more time, but in the long run sky will be your limit. You should aim for continuous learning: read about team management styles and about project management methodologies, learn some basic coding, be interested in the startup ecosystem and some accounting knowledge won’t do you any harm either.

Just keep reading and learning!

Avoid making enemies and be smart with where you put your energy

“The bamboo that bends is stronger than the oak that resists” — Photo by Alex Keda on Unsplash

Just by being the ambitious girlboss you are, while climbing the corporate ladder and thriving in office politics, you will rub some people the wrong way — don’t feed that fire though! Here’s my advice:

Apply Jujutsu to office politics — “it’s the principle of using an attacker’s energy against them, rather than directly opposing it.”

When somebody is standing on your way to success, don’t spend your energy on fighting them. Either team up and help them to succeed or let them fail on their own — your choice.

Offer solutions, always

I hate when people give out criticism but don’t offer any solutions. Ugh…

Be the person who raises problems and offers solution A, solution B and solution C. Even when these problems aren’t directly connected to your current job but could be important for the whole company’s well being — definitely speak up and offer solutions.

This shows that you feel responsible for the whole company’s success and not only for your personal one.

Underpromise, overdeliver … and make it seem easy

Do more than is asked on your job and occasionally on someone else’s job too — just don’t show all the sweat that went into it (that sh*t is impressive). Your boss rarely wants you to overstep your boundaries and focus on other people’s jobs, when you should be doing yours, but sometimes it’s needed when you see something that only you can improve. And that also shows that you feel passionate about the company’s future.

Just remember, if you want to make it big, you have to constantly be the overachiever who makes it seem easy and not expect much recognition for it.

Make your boss rich

“If I could rename one country to “Money” it would probably be this one.” Photo by Roman Logov on Unsplash

This might be the most important thing here — money talks. Make sure your decisions and work will be directly connected to the company making profits and you will benefit from it down the line as well. When it comes to the next big promotion, your boss won’t care about the guy who went to the same college as them, or the girl with an impressive resume — if you have made your boss richer and they see it, you will be considered for that promotion 100%.

Say goodbye to your comfort zone

Do brave people ever feel fearful? Or is overcoming that fear what makes them brave? I think it’s the latter.

Most of the time I have no clue on how I should approach new situations, but I’ll push myself to face my fears. This has resulted in countless awkward meetings, variety of failures but also tremendous personal growth. (You really have no idea how many facepalm-worthy situations keep me up at nights.)

Fake it ’til you make it.

Dream big and always aim higher

Words have power.

Dream big and bravely announce your crazy-sounding goals. Somewhere inside, your inner self will start to subconsciously work towards these goals and years later you will be surprised to think back and see how it all came to life.

Don’t limit yourself with small goals, always aim higher than seems possible at that moment.

Learn to live with the imposter syndrome

It’s particularly common among high-achieving women. Even with all the success you have had, you still might feel from time to time that it was just luck and great timing.

I know about this phenomenon and have diagnosed it on myself (I also might be hypochondriac, it seems) but it still doesn’t make it go away. So I just live with it and take it as part of life and I think you should too.

Be patient and have grit

Climbing the corporate ladder hasn’t been a quick journey. There were plenty of times I saw my co-workers with same ambitions jump the ship and try to get ahead somewhere new. I would be lying if I told you I wasn’t questioning if I should make the same decision from time to time. But in hindsight I have learned —

grass really is greener where you water it.

You have to see yourself being powerful enough to make changes in current company. You have to stick out the bad and the good times and know that you are an important part of the company’s future success. This all takes time, so be patient.

Be transparent and vocal about your ambitions

If you want your boss’ job, be that badass bitch and say it. YOLO!

Also, have fun and don’t take yourself too seriously

Life is an adventure and we all choose our own path. You don’t have to conform to all the unspoken corporate business rules to succeed. Just dress as you like to dress, keep your sarcastic sense of humour, get excited about that free booze at conferences and just be your authentic self.

“Dress for the job you want, not for the one you have.” — FYI, I have been dressing for Mark Zuckerberg’s job for years now.

This is the most personal post I have ever published, I hope that someone out there will find it useful in some way. Cheers!

You can also follow me on Twitter and sign up for a free Teamweek account!