You’ve Gotta Want a Startup

The other day, I was visiting the offices of a startup where I’ve done work for the last few years. The Director of Software was telling me of some of the challenges his company has faced in the last year, and it was not for the faint of heart. The product which they thought would be a huge hit turned out not to have the performance that customers needed, so they had to go back to the drawing board on the engineering; to conserve cash, they had to layoff most of the sales and support team they’d painstakingly built up to handle the anticipated bump in sales that never occurred; several of the bright, young developers they’d hired got tired of waiting for “the win” and left for what they perceived to be greener pastures at other companies; and then, to top it all off, the VP of Software Development that had been recruited less than a year ago abruptly resigned. Like I said, not for the faint of heart. But that’s all part of the ride that goes along with being in a startup.

When I interview candidates, one of the things I like to explore with them is what stages and sizes of companies do they feel most comfortable with, and want to work for? Sometimes I get an answer that, to be honest, kind of perplexes me: “Big or small, startup or established, it doesn’t matter.”

My experience, however, is that it does matter. Working in a startup isn’t like working in a more established company. There are way more unpredictable twists and turns, more challenges, and more demands placed on each member of the team, not merely in terms of workload (which in itself can be significant), but also in terms of the initiative required to anticipate and solve problems. In the words of one of my other clients, the VP of Engineering at a B-round VC funded company, “every day matters in a startup.” That’s so true.

If you want to get hired at a startup, having previous startup experience is great. But I’ve found that, maybe more important than the experience, is the attitude. Do you strongly desire to work at a startup, and for the right reasons? Have you thought through the pro’s and con’s, and are you prepared to make the tradeoffs and take the initiatives that will be required? Of course, many people who work at big, established companies have the “big company mindset”, but over the years, I’ve seen plenty of people who came right out of a huge company, went to a startup, and knocked the ball out of the park.

Joining a startup has many challenges, but offers many rewards that are difficult, if not impossible, to achieve in a larger, more established company. The education and experience you gain, even if the company is not ultimately successful, very often translates to higher compensation and better opportunities down the line at future jobs.

So, think carefully about whether a startup is right for you, or not. If you think not, there’s nothing wrong with that. Better to be honest with yourself. But if you get excited about the possibility of playing a key role in a small team that brings something new into the world, then, by all means, go for it!

What about the company I began this post talking about? Well, to borrow from Monty Python, “they’re not dead yet!” They have a number of loyal customers who, rather than abandoning them, worked with the company to provide detailed insights into why the first generation product wasn’t meeting their needs, and how to change it. The company undertook significant redesign work, and has been able to make dramatic performance improvements, which is leading to more sales. They’ve got a core team of committed, passionate people, which is making things happen in spite the of turnover. Like the customers, the investors believe in the company and are in it for the long haul, so they’re willing to invest more capital to see things through. And now they’re looking to bring a couple more great people into their team.

Maybe you’re one of them.