In my experience as both an operator and an investor, I’ve found that there are 5 common rules of thumb to land your dream startup job.
This isn’t a step-by-step guide to finding a startup job because you will find from talking to people that there is no standard path to get a startup job. However, these rules of thumb are a strategic framework that you can use to determine the tactics by which you can find your dream job.
1. The Best Jobs Aren’t Posted
In my entire career, I’ve never had a job that I got through a job posting. This is probably an extreme case, but my main point is that you should be thinking about what you would want in an ideal situation first, rather than be confined by what jobs are posted. In many cases, jobs are filled without any posting because many entrepreneurs tend to hire opportunistically. What would you do if you weren’t afraid?
In my experience, job descriptions are general guidelines to narrow the flood of applicants they get. Go above and beyond the job description to demonstrate your vision of what you can do for the company.
2. Quality, not Quantity
Pick 5 startups. Only 5. If you’re not passionate about the startup you’re talking to, it will be very obvious. Don’t be “that guy” who desperately wants to “work in startups” but has no passion for the people who run the startups you want to work for, or what the specific startup does. Do your homework.
Share the same vision and passion for the startup you want to work for. The onus is on you to show that you and the startup “coincidentally” have the same vision for the future. If you spread yourself too thin, you won’t be able to authentically achieve this.
3. Verify Your Authenticity
There are two ways to do this: externally and internally. External authenticity is how other people vouch for you. Internal authenticity is what you can do yourself to demonstrate your skills to your potential employer.
Examples of external authenticity are: getting a warm introduction from someone they trust; and building your “personal brand” by building thought leadership around a blog and Twitter interactions. For example, I got an interview at RRE Ventures because I had gotten to know Jim Robinson IV over Twitter.
Internal authenticity is about being the thought leader in a space that the startup is lacking in. This brings us to the fourth point:
4. Do the Job You Want and the Job Will Come to You
Once you’ve identified what your dream job is, don’t wait for that job to appear. Start doing that job and prove that you can do it, not only to your future employer, but also to yourself. Once you focus on just doing, you’ll find that opportunities will come to you.
This advice is applicable regardless of skill set.
If you are an engineer, hack on your favorite startup’s API, regardless of whether they host a hackathon.
If you’re a designer, do an unsolicited redesign of your favorite startup’s iPhone app UX. Be thoughtful about your thought process for the redesign.
5. People are Afraid of Micromanagement
One of the biggest fears of a startup CEO is that their new hire creates more work and micromanagement than they are supposed to solve. Everyone knows and expects that there will be some time needed to onboard and train a new employee, but because startups have such few employees, the marginal effect (both positive AND negative) of an employee is amplified. If you are 1 of only 7 employees in an early stage startup, everything you do has a strong effect on the startup’s trajectory. Contrast this with a big company, where, if a single employee slacks, the marginal effect on the momentum of that company is less easily noticed.
This point is related to the previous point. If you can demonstrate to your desired employer that you are not only capable of doing the job, but also that you are already doing the job that you are being hired for, they will feel much less anxiety because they have de-risked that aspect of potential micromanagement.
The act of hiring you should be a formality. You should make it obvious to a startup that, in order to achieve their vision, they need to hire you.