So You Want a Job at a Startup?

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• July 14, 2011
• By Adam Zuckerman and Géraldine Le Roux
• 11 Comments

Startup life can be sexy – flexible schedules, casual work environments, tree houses, a brilliant crew of co-workers, the promise of riches… But the perks often cloud the underlying truth of working at a startup: it ain’t easy.  Long hours, sprawling responsibilities, and a high risk of failure are just a few of the hurdles that you can be sure to encounter.

Yet when it comes down to it, jumping ship to a startup could be one of the most rewarding moves you’ll ever make. Small teams can accomplish big things.  If you find the right one, you may end up building a product that touches the lives of millions.

Is startup life right for you? Perhaps. If it is, here are a few tips to help you find (and land) your dream startup gig:

1. Identify your risk tolerance

Saying that you want to work at a startup is about as generic a statement as “I enjoy hamburgers.”  Startups run a wide gamut of products, cultures and stages of business. Some startups are bootstrapped out of the founder’s basement while others have loads of cash in their coffers from multiple rounds of funding.

Ask yourself what you need in terms of culture, salary, location, health insurance, savings and responsibility.  Do you want a company that is just getting started, or one that has successfully raised capital or is generating revenue? Getting in at the ground level of course has risks, but the reward can be much higher.

2. Figure out your skill set

Understand what you bring to the table. Importantly, be honest with yourself. In the beginning, most startups have a few founders and employees who split responsibilities.  Effectively, early start-up employees are true modern day renaissance people as one person may well run product development, marketing, sales and recruiting.

As the startup grows and reaches a critical mass (normally just about 25 employees), the need for renaissance employees starts to wane.  Instead, positions, roles and responsibilities become more streamlined.

If you’re a programmer, life may be easier for you as it’s straightforward to clearly convey your skill set (and odds are — you’ll always be in demand regardless of the size of the startup).  On the other hand, if you’re a “business” or “ideas” person, you may find the need to stretch your skill set outside of your comfort zone when applying for a position at a relatively young start-up or narrow your diverse abilities to a specialty when applying for a position at a larger startup.

3. Identify your targets

Once you understand your risk tolerance and have a clear sense of what you bring to the table, come up with a short list of startups that interest you. You need to live and breathe your product at a startup, so make sure you narrow down your search to the companies that really make you tick.

Next, take a look at each start-up’s people and culture. Find out who works there, check them out on Twitter, read the company blog, ask around to get a sense for the company’s reputation. As important as it is to love the company’s product and mission, you absolutely have to love the people too. We’ve all heard that your happiness at a job is hugely dependent on the quality of the people you work with. This is particularly true at a startup — you’ll be spending a lot of time with your colleagues, and this time may very well be spent awkwardly cramped in a studio apartment.

4. Customize your outreach

When you’ve identified the few startups you’d love to work for, start thinking of how you can stand out. Ensure that you customize your outreach for each start-up.  Demonstrate that you’re an avid user of their product, or come up with a creative way to contact them.  Far too often, startups receive generic introductory emails that quickly get pushed to the circular filing bin.

Above all else, show that you understand and are passionate about what the startup is seeking to accomplish. Do yourself a favor and do your homework before you send an introductory email. The little things in your communication make a huge difference. foursquare makes a point to write out their name in lowercase in all of their branding, their blog, etc. An email where you mention how much you love “Four Square” is sure to get you immediate VIP entry to the “no” pile. Whoever is hiring at the startup does not have much to judge you on, so be diligent and show that you care.

5. Follow up!

Employees at startups are short on time and may ignore your first email or attempt to get in touch. Most of the time, it’s not because they’re not interested. They’re just swamped and forgot about it. Don’t hesitate to reach back out again. Do so in a way that’s genuine and again, make it very customized to the person you’re looking to talk to. After the 2nd time and no word back, you may want to back off and find an alternate way to get in touch (i.e. seek an intro from someone who knows people there).

If you’ve already chatted with someone at a startup, make sure to touch base with them periodically (once a month). Startups may not be in an immediate position to hire when they meet you, but once they do have the budget to hire, they’ll want to do so quickly. Stay in touch to stay top of mind.

Good luck on your job search!

Adam Zuckerman is an entrepreneurial attorney and MBA with a passion for bringing people together in the D.C. entrepreneurship community. Connect with him on Twitter.

Géraldine Le Roux is the marketing manager at HelloWallet. Connect with her on Twitter.

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