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Working for a Technology Startup

Consider the benefits and drawbacks of working in software development for a tech startup

"How stable is this place?" Prospective employees asked me that question during nearly every interview I conducted for my employer, a startup technology firm. I had to remind myself that I asked our CEO the same question when I first interviewed for a software development position with the company.

Related: The Business of Development: Guidance for Professional Software Developers

Before joining a startup, I had worked for two large firms: one with 40,000 employees and another with 10,000 employees. So when I received a phone call from a former business partner offering me the opportunity to work for a company of only eight employees, I was skeptical at first. Especially when I visited the office and learned that it was a 750-square-foot studio apartment. I had dabbled in my own small business on the side, but never as a sole source of income. How could I even consider leaving the safety of an established company? But leave I did, and after four years, I know that making the transition from large corporation to budding startup was one of the best decisions I've made.

Certainly, joining a technology startup is not the right career choice for everyone, though for some developers, working for one can be very rewarding. Over the course of this article, I will outline what startup life is about, what the team will expect from you, and how you should evaluate your choices when searching for one to join.

Should I Work for a Startup?

Particularly in their early stages, tech startups are notorious for crazy hours, impossible timelines, and chaotic, unstructured processes. Burnout is a looming risk for all employees, not only developers. This pace is typically offset, however, by flexible schedules, telecommuting, fun environments, equity, and other perks. Even so, the reality is that most startups do not operate on a nine-to-five schedule, and though they might not track hours, the team will expect you to do whatever it takes to build the business with urgency. Having to jump in at any time to help with a crisis, push through all-nighters, or perform tasks outside your job description is not uncommon.

Given the innate uncertainty and chaos that typify early startups, why would any sane developer work for one? For the thrill-seekers among us, this type of work-hard/play-hard environment is the ultimate dream.

As developers, we are a special breed. At our fingertips we have the power to turn thoughts into tools and tools into magnificent, powerful systems. This is our craft, and we thrive on using our skills to create meaningful, awesome software with as little interference as possible. Startups offer a unique setting that lets us leverage our abilities in creative and interesting ways and push ourselves to the extreme without many of the traditional boundaries found in a larger, more established company. In a startup, trial and error is the norm.

The technology industry is cutthroat and requires a company to keep its competitive edge through constant innovation—witness companies such as Facebook, Google, and Twitter, which rose from nothing to become massively successful and remain successful because of their ongoing innovation. In a startup, innovation is the responsibility of everyone in the organization. The principal role of developers at any shop is to engineer the products and solutions required by the business, but particularly within startups, developers are also empowered to look at the technology and determine how it can lead to new ideas. This is a big part of the appeal: Being part of a startup often gives a developer the opportunity to help shape the product offering and thereby the company model.

For those with strong career aspirations, startups also offer fluid growth opportunities because most roles are very loosely defined. Depending on the needs at the time, vertical and horizontal movement is often easier in a startup when compared to the rigid career tracks of a larger company. How career roles are actually implemented varies from one place to the next, as does the degree of flexibility within one's role, but generally you will find that your role is what you make of it.

What Kinds of Developers Do Startups Look For?

The easiest answer to this question is, "Obviously, they want folks who know technology like the back of their hands." This is entirely true, but a startup that is hiring effectively looks for much more in a candidate than just his or her technical expertise. There was a time when simply being able to write code that compiles was enough to get a job, but as technology has moved to the forefront of business, the emphasis has shifted toward hiring the right developer, and not just anyone off the street.

Although "good fit" is a subjective term, it is the most important aspect of recruiting. In my own hiring experiences, I've had to turn down many skilled developers because they were incompatible with the company, regardless of whether they aced the technical tests. What they were seeking in the position did not match the demands and pressures that I knew they would have to deal with as an employee.

The challenges facing a startup are numerous, so let's look at a few of them and how they relate to the search for talent.

The deadline is yesterday. Engineering a new product is a race against time. The company needs people who can build fast, even if it means not dotting I's and crossing T's. Developers who require drawn-out, highly structured release cycles, well-understood requirements, and lots of early design will probably not be chosen. As the product matures, however, a startup needs developers who can build the framework required to stabilize the system and take it to the next level. The best candidates can evolve with the company as it progresses through these phases.

Burnout. As mentioned previously, you should not expect casual eight-hour days. You will be putting in hours—a lot of them. This is why self-commitment is vital. As clichéd as it sounds, the type of work you choose to do should not feel like a job but instead be an extension of your own personal software development lifestyle. Those who thrive on the ebbs and flows of aggressive engineering will do very well. Finding enjoyment in what you are building is the key to avoiding fast burnout; thus startups look for people who share this philosophy.

Innovation and quality. Extremely rapid software development often comes at the expense of quality, and for the experienced entrepreneur, this is an understood reality. Cornering the market first and adapting to customer demand is usually better than producing a hardened, well-built application that won't sell at all. A successful CEO once said, "If you have not rewritten your application after the first year, then you probably did something wrong." As a softer skill for developers, this means appreciating the time versus quality predicament and knowing how to create the best output within the smallest window of time. Well-qualified candidates know when to write throw-away code and when to build something more robust.

How Do I Find the Right Startup?

Just as startups are not looking to hire everyone who walks in the door, neither should you go to work for the first startup that you find. Because you are committing yourself to working your tail off, you should be sure that the company you choose will give you the enrichment you need to keep going. You will also want to be sure that the company's business model is something that you believe in and fully understand. If you cannot rally behind the company's goals, you will be looking toward the exit when times get tough.

Take time to read about the company's founders, board of directors, and investors. How committed are they to the company, and how successful have they been elsewhere? The answers to these questions will tell you a lot about their motives: Are the company's principals in it for a long haul, or do they want to build and sell to the first good offer? Either of these outcomes is fine, but it should align with your interests as well. If possible, meet with the founders and let them tell you their story. A startup is usually at a recruiting disadvantage without the name recognition that long-established companies have. The startup leadership knows that they need to sell you on the benefits of working for their company.

Try to avoid startups that do not test you rigorously. I have had candidates join our firm and tell me that they chose us over other companies based on our interview process alone. Talented developers want to be challenged each day, and that means the opportunities within the company should push you beyond your comfort zone. Whether you'll be learning from more experienced and knowledgeable colleagues or mentoring a team yourself, the key is to not jump into a situation where you will stagnate.

Come to your interview armed with lots of questions, and do not hold back. You can find a plethora of tips and suggestions about things to ask just by doing a basic Internet search. Here are a few questions that I have found evoke particularly interesting responses.

What brings you to work every day? I recommend that you ask this during each round of the interview. If the people you talk to cannot express why they enjoy being with the company, that is not a good sign. You should look for teams that have a lot of energy and dedication to the mission at hand.

What keeps you up at night? Depending on how honest your interviewers are (or how much they are willing to tell), this question reveals a lot about where the company needs help. That is not a bad thing! No startup has it all figured out, and there is a reason they are seeking your help. As long as the response involves solvable problems, you will learn about opportunities for you to make an impact.

What was it about prior developers that did not work out? I have been asked this question only once in an interview, and I was taken aback when it happened. The question forced me to look at our staffing in two ways: It caused me to think about why we parted ways with those we lost and why the longtime employees remained. From the answer to this question, you will gain insight into what it takes to survive as a developer within the company and what the firm will expect from you in both the short term and long term.

If the company closed up shop tomorrow, would you regret working here? There is no right or wrong answer to this question. The reality is that most startups fail, despite the tremendous amount of work that the employees performed while the doors were open. The answer, however, will tell you what frame of mind folks will be in during rough patches. Even successful startups go through dark periods, and you want to get an idea of how committed to the job and company its employees are, even during the most stressful times.

Reaping the Rewards

The startup phase will last for only so long before the company morphs into a small, medium, or maybe even large business. During this time, the structure, process, and notably the company culture will go through dramatic changes. Because many companies offer stock options with a vesting period of a few years, adaptability is a crucial trait that can help you through these transitions, so that you can reap the rewards of your commitment to the company.

As with any job search, you should take into account your stage in life and what your goals are before deciding whether a startup is right for you. At the outset, working for the startup will undoubtedly require a significant portion of your time, but doing so can be a highly rewarding experience, both financially and professionally.

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