So You Want To Work For A Startup…

I’ve chatted with a bunch of designers recently who told me they’re really interested in getting gigs working for startups. Several asked me if I have any advice, so I figured I’d write a quick post about things I’ve learned over the course of my last 9 years in the startup industry.

I’d say that the key to making a successful jump into a startup is first defining exactly what it is that you value in a workplace.

It dawned on me early in my career that I don’t love working for startups in general — I love working for MY startups because they fit my lifestyle and personality.

There are a series of questions you need to ask yourself to know if a particular startup is right for you:

1. What is the startup’s view on work life balance?

I’m a mom, and it’s important for me to be able to work remotely, either on occasion or full time. Days when my kiddo is running a fever and can’t go to school, she can lay on the couch next to my desk sleeping while I work. I don’t lose any productivity by taking a sick day, and my team still meets our deadlines. We utilize a set of fabulous communication tools that let us communicate as clearly (or even more clearly to be honest) as we would in a traditional office. I’m fortunate to work for a fully distributed company now that is very family centric.

Other startups require extremely long hours in the office and 100% dedication to the job to the point that there basically isn’t room for anything else in your life. Tons of people love and feed off of that intensity, but it’s not for me.

Often times people join a startup expecting scenario A, but wind up in scenario B, and feel like they’re drowning. Make sure the work/life balance is a good fit for your lifestyle and personality before you sign on the dotted line.

2. Do they have a benefits package that suits your needs?

Some startups invest tons of money in benefits packages to attract talent, others advertise hefty starting salaries with little to no benefits, and still others have no benefits and low salaries, but they offer stock options. The list of scenarios goes on, but what it really comes down to is: Do they or do they not offer what you need? (Then you get the rare few like InVision that offer all of the things because they’re the best.) 😄

3. Is the company working on something you’re passionate about?

This is extremely important. When you join a startup, you need to be excited about what you’re working on, because things can get crazy. If you’re not committed to the product, you’ll never make it through the rapid growth stage.

When you jump into a startup environment, you are kind of jumping into a casino situation. You are betting your salary that the company is going to take off and soar. Just as it goes with gambling though, there is a chance that the company is going to flop, and with startups, more often than not this is the case. (I’ve been super fortunate to land in two extremely successful startups back to back; it’s definitely not the norm.)

You need to take a hard look at the company, their values, their long term plans and how passionate their senior leadership and employees are about making magic happen. Then evaluate whether or not you’re passionate enough about the company and the product to take the gamble.

4. Does the company have room for career advancement?

One of the coolest things for me about working for the startups I’ve worked for has been the opportunity for cross-departmental career advancement. At my last startup, we had entry-level folks who came into the company in one department, only to discover they had serious passion for another area of the company. They didn’t need to quit to find an opportunity to advance their careers in a totally different direction — the company did a ton of hiring and promoting from within.

When you join some startups in the early stages, you end up wearing tons of hats. Be prepared to do all kinds of things that “aren’t in your job description.” The neat thing about those environments is once the company starts to grow, oftentimes (but not very time) you can work with senior staff to carve your own niche, and focus on the portions of the job you enjoyed most.

There are other startups that take a “once you’re in a position you’re stuck there” approach and hire externally for the most part. Think about your career goals, and look into the ability to move within the organization you’re considering to make sure it’s a good fit.

5. Do these people seem like folks you’d enjoy spending time with/feel inspired by/trust with your career and could turn into a work family?

Some people are going to read this and think it’s lame, but in all seriousness, when you’re working at a startup you spend a huge amount of time with a small group of people. While differing opinions are great, because they often lead to killer innovation, the ability to get along as a group after sharing those differing opinions is huge.

You need folks who are on the same page, are borderline obsessed with making your company succeed, and who are willing to do whatever needs to be done in order to make that dream happen. Being able to collaborate doesn’t mean being similar, or all thinking the same way (your life would be horribly boring, as would your products, if your whole team was made up of clones of you), it means being able to communicate productively in a fast-paced, intense environment. Make sure the startup team you’re interviewing with feels like a good fit for you before you dive in.

If you’re aligned on all of these points and decide to go for it, get ready for an incredibly exciting roller coaster ride that may lead to dreams becoming reality. Or the ride may fly off the track and crash and burn. But that’s the fun in working for a startup, right? The excitement is in the gamble.

A List Apart (ISSN: 1534–0295) explores the design, development, and meaning of web content, with a special focus on web standards and best practices.