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Startup Careers Series - #5

Do you really need “startup experience” to get into a startup?

We see the roles, we read the requirements, and somewhere in the process, we start to feel like there’s a barrier we can’t cross: “startup experience preferred”, “fast-paced environment”, “ability to operate with ambiguity”. We start to think, "I don’t have that. So maybe I’m not what they’re looking for".

But here’s the question: is it really about experience, or something else?

Because many people working in startups today didn’t start there, they transitioned from other environments, often without a clear “startup background”. So the real issue is not whether we've worked in a startup before, it’s whether we can operate like someone who has.

What are startups actually trying to de-risk?

When startups ask for “startup experience”, they are not looking for a label, they are trying to reduce uncertainty. They want to know, "Can this person handle ambiguity? Can they take initiative without constant direction? Can they adapt when things change?". These are not tied to a specific industry; they are tied to how we work. The challenge is that we often present our experience in a way that emphasises structure, process, and stability, while startups are trying to assess flexibility, ownership, and problem-solving in uncertain conditions. So there is often a mismatch, not of capability, but of signal.

How do you position yourself without that label?

This is the shift: you don’t need to prove that you’ve worked in a startup, you need to demonstrate that you can operate in one.

Recognising this is important, but the responsibility still sits with you. If you present your experience in a way that doesn’t reflect how you think and operate, the signal will remain unclear. That starts with how you position your work. Instead of describing what you were responsible for, focus on how you handled complexity, how you navigated uncertainty, and how you made decisions without complete information. Show where you’ve taken ownership beyond your role, where you’ve adapted to change, and where you’ve solved problems without clear instructions. You also need to connect your experience to their context; make it clear how what you’ve done translates to the challenges they are facing now.

Because in startups, hiring is not about where you come from; it’s about how quickly you can become relevant. The people who break in are not the ones with the perfect background; they are the ones who make it easy for others to see how they would operate in the role.