Should I stay or should I go now?
June 21, 2011 11:16 AM   Subscribe

I'm bored working for a monolithic company and am considering taking a job at a 10-person startup. What should I ask my prospective employer before making the decision? Details within!

I work for a large media company. It's a 'good job' in the sense that I'm comfortable and paid well for the business and my age (26). I have a very good relationship with my boss, and I've gotten raises and a promotion in the ~2 years I've been here. I have every reason to believe that if I stay here, I'll be able to keep doing well in the company.

The problem is that I'm bored. Part of this is just the nature of being at a company of this size: we're accountable ultimately to shareholders, and most of the important decisions had been made before I started here. Part of it, I'm aware, is just my nature and where I'm at in life (I often want to try the new thing, even if the current thing is more than satisfactory).

Recently, a former co-worker, who left year ago to work for a small tech startup, reached out to offer me a job there. His company is, in the next few months, going to launch a new effort that I believe has some legs, and I would be a key part of that (sorry to be vague but I don't want to out myself or either company in question). It is, in short, a gamble: there are many others trying to do what they are, and while I know ex-coworker to be a good guy and whip-smart, I'm not certain why THIS company will succeed where many others have not. Also: they have enough money to stay solvent for a while, so at the very least I could count on them being able to employ me for a year or two.

I really love the idea of working at a place where I'd have so much more freedom and space to create, as opposed to now, where I often feel like a cog in a machine (and a machine I don't even really love or believe in, at that!) When we last talked, ex-co-worker said that he likes working there because he has so much leeway and freedom to learn new skills. Everyone is able (and required, I'd think) to contribute in all sorts of ways -- it's scrappy, and if there's no one on staff who knows how to do X, then someone simply has to learn it. I like that kind of environment very much.

The pay at the new place would probably be similar to my current salary; I'd also have equity in the company (I don't at my current job). I'm going to meet with him again soon to ask some more questions about the gig.

So: what do I ask? What other advice do you have for how to think about this decision? What are the benefits and drawbacks of working for a company with a dozen employees? What's your experience with working at a small tech company? If it fails -- as I know most do -- did you regret your decision to work there, or was there valuable experience to be gained?

Many thanks for your insights on all this.
posted by anonymous to Technology (10 answers total) 7 users marked this as a favorite
Ask how much they work. It's very unlikely to be 9-to-5, and weekends may be involved. It's not necessarily going to grueling death marches all the time, but at startups at this stage, everyone is usually expected to pitch in to fill in the gaps, even if it's work that's tangential to your actual job description.

Make sure you're OK with this lifestyle before you get into it.

Without knowing exactly what you do, it's hard to suggest questions that will ensure that you actually have the creative freedom that you expect, but you do want to check on that, too.
posted by ignignokt at 11:24 AM on June 21, 2011

If it fails... move on, you've earned another badge. Badges are good.

What should you ask your self about your current job?
posted by run"monty at 11:32 AM on June 21, 2011

Do they have actual revenue? How long can they last before they run out of money? How are they funded? Do they have millions in VC behind them, or are two guys mortgaging their houses to do this? Make sure you really understand the money situation and are comfortable with their funding and plan to get to a cash-flow positive state. You don't want to find out that they had just enough to launch the product, but no funding for marketing and sales to get it out there and get it sold. I've been there, done that. It's not fun.
posted by COD at 11:45 AM on June 21, 2011

Are you in the U.S.? Do you depend on your employer for health and medical benefits? Does the new company offer similar benefits? Many start-ups don't due to their size. You'll want to understand how much independent insurance or benefits will cost you when considering the new job offer.

That said, I work for a smaller company after leaving mega-corps and I *love* the freedom it's given me. Worth all the uncertainty and demanding work. Despite no benefits (I'm covered by my spouse), it would be really tough to go back.
posted by ninjakins at 11:46 AM on June 21, 2011

I like to ask: "Are you profitable?" If not: "When do you expect to become profitable?"

If the answer to the second question is more than one year, those are often rosy projections too far in the future to be meaningful.

You need to know if there will be a paycheck for you down the line.
posted by Atrahasis at 11:49 AM on June 21, 2011

You didn't indicate how many years you've had under your belt for your current employer, but if it's less than 2 years it isn't that great, but if it is something like 3 or 4 years then you are in good shape. (It is a good thing to start a career in a certain domain with a 'large monolith' to understand both how things are done, as well as pick up a lot of good practices along the way.)

As one who jumped ship to a VC-backed startup, you need to look at this from a critical 'is this a viable business' perspective. (For the record the startup I joined is still in business and still making a go of it, but after many changes in management and direction, which I knew was going to happen given that year I was with them.) By 'viable business', you understand the cost of their good or service they offer, you understand the value proposition in the marketplace for that good or service, you understand the barriers to entry to your competitors, you understand the substitutes for your good or service that could cause your shiny new employer to not look so good aways down the road.

I'd go for a raise in pay - something on the order of 10-15% more, to compensate you for the risk you are taking. Ignore any 'value' of equity at this point, yet you should ask sensitive questions that may not get an answer in the interview(s) but shows that you care about how large (relatively-speaking) your stake in the organization is. Startup companies, if they are run well from the start, understand that they need to attract top people and pay a premium due to the fact that they want top people, in addition to the downside risk of not being a sustainable business.

It sounds like you will enjoy the flexibility and challenge of a small organization. Be prepared to work very independently, think about all the non-visible support structures you have in your big monolithic corporation, and imagine that in the new gig the HR department is one person who also might be taking care of all legal matters simultaneously.

One question for the interviewer(s) would be for them to describe the company culture, that can lead down to a very useful discussion.
posted by scooterdog at 11:54 AM on June 21, 2011 [1 favorite]

Are you single? Startups take a lot of your time. This can be a ton of fun if you work well with your co-workers. You can often drink at work, party hard, and work hard. The company often pays for all these perks. There's often stressful situations. Can you handle that?

Also ask yourself this: If the startup fails, what are my options? Can you get another job easily enough? Will it be hard on you if you're unemployed awhile?
posted by hylaride at 12:13 PM on June 21, 2011 [1 favorite]

As COD mentions, the amount of cash and the burn rate of that cash in the company would be very important to me were I in your situation. It's ultimately where they get the funds to keep you in beer and ramen. Equity is pie-in-the-sky at this juncture, and I would happily sacrifice a percentage of equity offered for a higher salary.
posted by jasondbarr at 12:21 PM on June 21, 2011

Guy Kawasaki wrote a blog post titled "Nine Questions to Ask a Startup" here:

They're sort of dull questions, but he's an experienced VC, and I imagine at least some of these would be helpful!
posted by thelatermonths at 1:12 PM on June 21, 2011 [1 favorite]

Make sure you like the people. Seriously.

Oh, and the less fancy the founder's office, the better. Someone who really wants their company to succeed is not spending cash on fancy office chairs.
posted by maryr at 5:54 PM on June 21, 2011

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