10 Steps To Finding a Job at a Boston Startup

It’s no secret some of the best job opportunities in the Boston area are in technology startups. Last year venture capitalists invested almost $5 billion in local companies, making the tech sector one of the fastest growing segments of our local economy. In addition to the professional freedom and challenges that comes with joining a startup, the re-opened IPO market and a steady flow of M&A hold out the possibility of financial success should you pick a winner.

But choosing the right startup can be challenging for professionals already in the community, and even more so for those looking to get in. Here are 10 steps to get you on your way to your next job.

#1: Define Requirements

The first step of any job search is to define what you are looking for. Your requirements will often be driven by what you seek (e.g. strong team, increased responsibility, more professional freedom, potential financial success), as well as what you learned from personal experience to avoid (e.g. poor management, lack of transparency, long commute). Writing out your requirements before you start the process makes it easier to target the right companies and choose from the best among them.

Before starting your search, take some time to update your LinkedIn and Angellist profiles, which increasingly have replaced resumes. At a minimum you should make sure your profile is complete with regards to your experience and education, but I’ll confess to being sucker for a good profile summary. Startup hiring managers will commonly also look to your Stackoverflow and GitHub profiles if they want to know more about you.

#3: Identify Target Companies

There are thousands of startups in the Boston area, but probably at most a few dozen that are right for you. The key for a successful job search is to find as many of the potential target companies as possible. I recommend maintaining a spreadsheet of your target companies, with fields for capturing important criteria (e.g. industry, investors, amount of funding, location). Angellist and the BostonStartupsGuide will provide great starting points for identifying potential target companies, and you can use news sources such as BetaBoston, Xconomy and Boston Business Journal to continue to add to your list. As a general rule, I wouldn't rule out a company based on your inability to find an open job opportunity on their site. Many startups will make opportunities when they meet the right person.

#4: Do the Gut Check

Before you expend energy trying to find the right startup, make sure it's really what you want to do. Having spent almost my entire career in startups, I know there really is no other place for me to be. But for many people, the downsides (e.g. fast pace, long hours, risk, ambiguity) can outweigh the benefits (e.g. accelerated learning, freedom, financial opportunity). There are also people who just cannot work in a startup, where their inability to deal with ambiguity and/or lack of execution skills will result in them being bounced back to the job market. The only right decision here is to do your own gut check. If you are at all ambiguous about your desire to work at a startup, there is a pretty good chance you really should be looking elsewhere.

#5: Go Direct

There is really nothing wrong with using a good Boston recruiter to represent you in your search, provided it is driven by your target list and not the jobs the recruiter has available. But the real issue is that there really aren’t many good Boston recruiters. In fact, many local recruiters are downright bad. So if you don’t know the handful of recruiters who have made positive reputations in the startup community (hint: send me an email if you don’t know them), your best bet is to go direct. While it may take longer, the results will almost certainly be better.

#6: Network

At the start of a search, your goal should be to learn more about as many interesting people and companies as possible. The best way to do this is to informally grab coffee to network and learn more. I know this can sound daunting, especially for introverted geeks like myself, but in general you can almost always get someone at a company to meet if your purpose is sincere. Send a direct email with the reason you want to talk (e.g. want to learn more about the company, network with an entrepreneur, learn more about the industry). Set a personal goal for the number of new people / companies you want to meet per week as a means to drive you to maintain regular level of networking.

#7: Take Your Time

A good job search should take months, not weeks. Relax and enjoy the process. You will be meeting lots of interesting people and companies. A successful search will be like Neo in the last scene of the Matrix, where the fabric of the Boston tech scene will begin to reveal itself to you. ;)

#8: Expect Transparency

Once you engage with a company, you should expect to get all the necessary information from them to ensure you are making the right decision. The further you get into the process, the more transparency you should expect, since both you and the startup are about to make a substantial commitment toward each other. Define a list of questions and work with the hiring manager to ensure you get them all answered. No person in the company should be off limits to you in your search to get as much information as possible about a company (I’ve even had candidates insist on getting a demo from the VP of sales).

#9: Stay on Top of Tech News

Stay plugged into what is happening in Boston startups through news sources (e.g. BetaBoston, Xconomy and Boston Business Journal) and blogs of investors, entrepreneurs and tech personalities from the local area. The more you know, the more likely you will be to find the right company.

#10: Do Your Due Diligence

One of the better known VCs once said to me: “You tech guys always get caught up in the technology and forget that big businesses are almost always built by successful entrepreneurs and investors who have built big businesses.” His point: successful startups will surround themselves with quality employees, customers, partners, investors and board members. When you think you have found the right company, don’t just let them check references on you - you should be checking references on them.

If you get stuck or need advice, feel free to reach out to me directly at joe.kinsella at gmail.com.