Finding your dream job at a startup

by Aaron O’Hearn, CEO/Co-Founder of Startup Institute 

Dream Sequence

Finding your dream job at a startup. That’s easy. It should go something like this:

You meet someone out at an event or party somewhere, and if they’re in the startup community chances are  they’re probably cool and pretty inspiring. They talk about changing the world and you decide they’re the one. So you email them to grab coffee, follow up by meeting some members of the team and presto - you’ve got yourself your dream job. Boutique beverage on your desk and sporting a brand new Mac setup that even Apple employees envy. Ah, you’re working for a startup.

Pinch yourself. Yep, it’s time to wake up.

What’s it really like

While working for a startup can certainly feel like being part of a big, extended family; its not always easy to get there. There are also many [low] lows in that roller coaster you’ll be riding on that truly make you appreciate the high points. The good news is that as a team, you’re all in it together; which is part of what makes this kind of job so special.

To try and capture what being a part of this family is like, I asked a few folks to describe to me, in one word, how they’d summarize their work experience at a startup thus far:

Supportive, intellectually honest, transparent, together, contribution, happy, real, impactful, satisfying, exciting.

Becoming a part of this family is part art, and part science.

Be a line, not a dot

I’m going to parallel the process of ‘finding your way in to a dream job' to the fundraising process Mark Suster talks about in his post on why investors invest in lines and not dots. I’m a believer that when you’re pursuing a startup to work for [Yes. When YOU are PURSUING], you have to be making progress and getting that team more excited about you over time.

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If you substitute Entrepreneur for You, and the Investor for a CEO - you have the scenario where you are pursuing a job and proving a track record before that CEO decides to hire you. Depending on the stage of the company, it may be someone else making the hiring decision, but the same logic applies.

You want to be building excitement each time you interact with someone at that startup. Prove you have skills they’re looking for and the self awareness to apply them.

Your personal Venn diagram

Defining your dream job takes more reflection and self awareness, things I’ll touch on in future posts. For now - consider the good ol’ ven diagram a simple, guiding compass of your ability to land an amazing job at a startup.


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Proving yourself as a progressive and positive sloping line gives you a chance to really highlight your skills, but also express your passion in a productive way. While companies hire for skill, the great ones also care deeply about your passions and where you’re going in life. Each dot you create on that line gives you a unique opportunity to reflect if you’re still in the overlap of your personal ven diagram.