How to Get a Sales Job at a Startup

Maybe you’re sitting at a desk job feeling dead inside. Maybe you’re a fresh grad who doesn’t want to become a lawyerdoctor, and definitely not an academic. Maybe you watched Silicon Valley and think it’s hilarious (it is!) And you ask yourself: Is a job in sales at a startup for me?

HBO’s Silicon Valley

Inspired by Alen Mayer’s LinkedIn article on changing your perspective towards your approach to cold calling, I take a more “big picture” approach to getting a sales job at a startup by providing advice on how to change your mentality.

Why You Should Work at a Startup

Work get done – fast. Mark Zuckerberg recently changed Facebook’s mantra from, “Move Fast and Break Things” to “Move Fast With Stable Infra.” While this new slogan isn’t as catchy, it maintains the emphasis on speed. At an early stage startup, you can work directly on a product or service and witness it go from conception to execution within months. It can be incredibly exciting and rewarding, but it means you need to be highly adaptable and come up with solutions to problems that don’t always have a strict right or wrong answer.

Less hierarchy. Founders of startups tend to be more accessible: you only need to look at all the blog posts of startup CEOs and founders encouraging you to reach out to them directly. How often does a big company CEO do that? Even if they wanted to talk to you, in all likelihood they just don’t have the time. Recently, an employee of a big company told me how he was sharing the elevator with the CEO and was terrified to even make eye contact. Whereas at a small enough startup, you get to work with the CXOs directly every day. In fact, I’m writing this while sitting across from my CEO, COO, and CTO.

So you probably don’t need any more convincing, right? Keep reading!

How to Get a Sales Job at a Startup

Pick your flavor of Kool-aid. I won’t lie, startups have their disadvantages. It can be a terrifying, demanding experience. You might not have the best work-life balance, job security, benefits, or the highest salary. So why work at one? You need to genuinely believe in the product, or feel excited about the problem you’re solving, or love working with your brilliant colleagues, and preferably all of the above. In other words, you need to find your preferred flavor of Kool-aid.

Become startup literate. Every industry has its own language. In the startup world, you need to know and understand concepts like runway, disruption, pivot, angel investors, etc. Feeling clueless? Start by reading websites like Techcrunch and Pandodaily (Techvibes and Betakit for the Canadians), and books like Crossing the Chasm and The Lean Startup. Go to where the startup people are: Find relevant meetups (sites like Meetup and Evitebrite can be great) and start talking to people. Engage with people directly by commenting in LinkedIn groups, on industry blogs, on Quora, etc.

Always Be Customer-facing. Companies are constantly accused of not being customer-facing enough. Don’t fall into the same trap as a job seeker. Remember that a typical recruiter will spend, on average, 6 seconds scanning your resume. That means that, within the first 10 seconds, your resume needs to be able to answer, “Can this person do the job?” Now imagine you’re the prospective employer. Give yourself your 30-second elevator speech. Would you hire you? No? Then re-iterate until you would. Whether you contact prospective employers over email or through an in-person meeting, within the first 30 seconds, your pitch needs to be able to answer, “Why should I hire you?

Make them an offer they can’t refuse. In sales, you need to make it easy for the customer to say “yes.” It’s the same thing when it comes to getting a job. Make it easy for an employer to say “yes” by keeping this equation in mind:

Your value to the company > Your salary + Employer’s lost time and money in hiring, training, and managing you + Employer’s potential pain of having to fire you

When it comes to hiring, people tend to be risk-averse. If an employer can’t figure out how you can solve a problem or fill a gap, then there’s no point in hiring you. And don’t discount the pain of firing. It feels terrible and it’s a blow to the ego for someone to have to admit they made a mistake.

Every industry, company, and specific employer has a challenge they’re facing. Figure out what is it and work to become the person who can best solve it.

Looking for more job search tips? Read my post, 3 Crazy Job Search Tips — That Might Just Work! here.

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Ji-A Min

Ji-A Min

Head Data Scientist at Ideal
Ji-A Min is the Head Data Scientist at Ideal. With a Master’s in Industrial-Organizational Psychology, Ji-A promotes best practices and data-based recruitment. She writes about trends and research in talent acquisition, HR tech, and people analytics.
Ji-A Min

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