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Advice / Job Search / Finding a Job

How to Convince a Startup to Take a Chance on You if You're Coming From the Corporate World

After deciding you’re ready to call it quits on corporate life (farewell stability!), you managed to get an interview with a startup you’ve been dying to get in front of. You’re pumped. But you’re kind of freaking out, too. The job description says they want someone who knows how to use a bunch of tools and software that you’ve never used before. Not to mention, there are some skills and experience listed that are “preferred” that you don’t have either. At your current job, you’re a specialist—it appears here the company’s looking for someone who can do the work of an entire department.

Should you be worried?

Well, I’m a startup founder who has hired lots of employees over the last few years. And I can tell you point blank that the answer is “No.” I’ve hired people with no product management experience (twice, in fact!) to be product managers. I’ve tapped people with no customer service experience to work directly with our most important customers. And I’ve let someone with no previous marketing experience head up our marketing programs.

You might think this sounds nuts, but I’m not alone. Lots of other founders hire for attitude rather than aptitude, too. Because, in the startup world, most hiring managers prioritizing bringing on candidates who can make things happen.

So, how can you can make that clear in your interview—without being misleading? There are two key ways you can show them you’re the kind of candidate who will walk through walls to deliver results, whether or not you check all the boxes in the job description.

1. Talk Your Way Into A “Try And Buy”

If I interview someone who seems to have the right attitude and at least some of the skills I’m looking for, I’ll have them start working with us on a part-time, paid trial basis. That trial lets me figure out if those skill gaps on their resume are going to be a problem or not. And before you’re like, “I’m not quitting my full-time job with benefits so you can give me a test run,” I’ll tell that I gladly work around full-time positions and am open to being flexible with timing. Yes, it’s a lot of work, on top of your work, but think of it as a trial run for yourself, too. Hate doing this for 15 hours a week? Imagine doing it for 40, or 50.

Some startups love to do “Try and Buys.” But others don’t propose them proactively because it’s not the way they’re set up. If you’re talking to one of the latter, listen to your interviewers closely and then ask questions to find out what challenges they’re facing. You can start with with questions like: Where do you see the most drop off in your sales process?" or "Are there certain acquisition channels you'd like to test out in the near term?"

As you listen to the answers, ask yourself: Where could I come in and make an immediate impact? Figure that out and then pitch them on your own “Try and Buy” that’ll solve the problem.

And note, it’s OK to take time to think about this. Don’t feel the need to blurt out a half-baked idea as the interview’s wrapping up. Instead, take a deep breath, go home, think about what you learned, and put together a real presentation. It’ll not only be more impressive, but also give the hiring manager a fair chance to think it through as well.

Skeptical about this really working? I would be too. So, here’s a lightly edited one we put together with a prospective hire:

She did it, she killed it, and now she’s onboard with us full-time.

2. Do the Job Before You Have the Job (Or Even the Interview)

Remember that startup hiring managers just want results—whether it’s helping them design an awesome product, make more sales, or generate more marketing leads — within a reasonable amount of time and without a lot of supervision. You can show off your ability to deliver results through a pre-interview project.

For example, let’s say you’re meeting with the company for a product manager role. Before going in for that interview think about what could you do to show that you can get the result the hiring manager wants (a great looking, functional, addictive product) without having the technical skills (e.g., HTML, CSS, Photoshop) they’re asking for?

Well, you could make a list of 20 things you’d change about the product and why. You could ask 10 of your friends to use the product and create a summary of their feedback. And with all of that data you could mock up five new product screens in a free tool like this or even in PowerPoint. (Heck, you could hire someone to do a mockup for you for less than it would cost you to buy a fancy coffee. By going this route you got the job done and showed off how resourceful you are in the process.)

This tactic isn’t just limited to product roles. You can put these projects together for marketing gigs, sales jobs, operations—it’s all fair game if you’re willing to brainstorm things that would help the startup’s business and show off your hustle.

Need more examples? Here are a few that candidates did when interviewing (or before interviewing!) with top companies like Evernote and Dropbox.

Put Yourself in My Founder Head to See Why This Works

Through your successful “Try And Buy” period or a pre-interview project you proved to me that you could make a big impact. Even though you didn’t have every single buzzword or acronym listed in the job description.

Now, why would I keep interviewing people when you’ve shown me you’re the solution to my problems? You see, I wouldn’t. I’d be taking down that job posting and giving you an offer letter in a hot startup minute.

Photo of interview courtesy of Hero Images/Getty Images.