Startup-Curious? Advice for Going to a Start-Up

BigCo leaders should be clear about the impact they've driven and be ready to forget a lot about their corporate success

I met some “startup curious” leaders at Twin Cities Startup Week last week. These are early and mid-career folks who have good track records at companies you’ve probably heard of, but they’re looking for jobs at startups. Some were in a career transition, some were happy in their current role, but looking ahead, planning their next move. All wanted something different with their next job.

Its easy to see why a role at a startup might seem enticing. It’s potentially a blank slate, a chance to do important work better or in a more meaningful way. We’ve all probably been there: When you’re deep in powerpoint for your VP’s boss’s boss, you start wondering how cool it might be to join something smaller where you can just turn around and talk to the person who actually gets the shit done. Who doesn’t want to drive a speedboat around a slow, boring battleship?

It’s also easy to understand the personal motivations of a leader seeking a reboot in a startup. They’ve built so much knowledge, they learned all the hard lessons. They want to teach, guide, and empower emerging talent. All of that is great, of course. But that’s not the real work in a startup.

Startup teams are in a dead sprint and may not care about you’re magnamity and good intentions. They just need execution and impact.

If you know a “startup curious” leader at a Big Co or if you’re considering it yourself, this article from the talent team at Madrona is a good reality check.

Key takeaways:

• Startup leaders are skeptical - They are doubtful you’re able to move at their pace or have the relevant skills they need to thrive/survive.

• Understand What Growth Stage To Target - Do the hard work to understand what size and stage of company will be best for you and your experience. Earliest stage startups (pre-seed, pre-revenue) have very different needs than orgs that are scaling (series B, growth equity).

• Get clear on your actual impact - A lot of BigCo leaders talk about the impact their teams make vs. what they’ve actually done themselves. In a startup, you’re going to be hands-on more than you imagine. Think through the impact you’ve made, and be able to translate what was your actual role in making it happen.

But startup leaders will also be doing a vibe check when they talk with potential employees or partners. They’ll be worried you’ll bring your BigCo culture baggage.

Based on my own experience having worked with entrepreneurs and advising hundreds of growth and product leaders, the most important thing to bring to the table (along with your skills and experience) is a palpable sense of energy, curiosity and ambition. The desire to get shit done. To define and then solve hard problems, fast. To learn and apply new tools, ideas and methods, fast. You will have to communicate that you’re going to be additive to the culture and momentum.

To find a good match, you’ll have to lead the startup leader/entrepreneur through the process of understanding how you can really help them (vs potentially slowing them down). And, that will mean you’ll have to have your own “pitch” straight.

Its tough to transition from BigCo to startup, but potentially a game changer for you, your career and the startup you join. The way you pitch yourself will be the first sign that you are ready to make the transition.

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