September 9, 2020 | Diversity & Access

A Start-up Might Be For You. Here’s How to Tell.

Michelle McHargue

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Michelle McHargue

A Start-up Might Be For You. Here’s How to Tell.

When COVID-19 struck, putting millions out of work and throwing us all into an existential crisis, the predictions for the impact on tech were grim, to say the least. But so far, the worst has – thankfully – not come to pass. Far from it, in fact.

The startup world is weathering the storm relatively well, between high demand for certain sectors like telehealth and e-commerce to start-ups raising $34.3B in the second quarter to IPOs coming back strong. Practically, that means some companies are taking advantage of this time and actively seeking to hire amazing talent ready to take the plunge.

Making the jump to start-up life can be a question mark for some even at the best of times. Right now, at this moment of relative volatility and economic uncertainty, it might be even harder to make the call. So how do you decide if you’re a good fit for start-up life and if start-ups are a good fit for you?  

Here’s what I tell folks who are considering this transition.

Know what start-ups are looking for

Small companies are taking big bets every single time they hire. They don’t have unlimited budgets or time; they need the best people possible for what they need at that exact moment as soon as possible. Most founders and hiring managers are looking for people who share some key qualities:

  • An ability to adapt and thrive when resources are tight (or nonexistent)
  • Independence; comfortable working without constant guidance or established processes
  • Willingness to learn
  • Flexibility because most employees are typically asked to take on projects that stretch them past the boundaries of their roles

If this sounds exciting to you, start-ups might be perfect for you.

Understand start-ups aren’t one-size-fits-all

Once you determine that you want to make the leap and join a startup, you really need to think about size and focus – and what you find appealing. When I joined Google, it had a 2,000-person workforce and was still very much a start-up. It’s a far cry from the image many of us have when we think of new companies: two to ten people, working on folding tables, in someone’s garage or basement. But start-ups exist in many sizes and stages. If you’re leery of the pre-seed bootstraps and shoestring budgets model, that doesn’t mean you should give up altogether. Set your sights on a Series B or C-funded company that might feel a little more established and solid. And note: one stage isn’t inherently “better” than the other. They’re just different.

Similarly, think through if you’re more excited about a B2C or B2B orientation, the industry itself, and the product. There’s no shortage of interesting companies; it’s really more about what’s interesting to you. 

If you come from a so-called Big Company, get ready to explain.

You’ve created a target list of start-ups you might want to join and now you need to prepare for the interview process. Start-up culture can sometimes be a little skeptical of the “Big Company” mindset. You see experience, discipline and pragmatism. They might see rigidity, bureaucracy and a lack of imagination. 

This isn’t true of all start-ups to be sure. But it wouldn’t hurt to spend some time thinking through your personal narrative – and emphasizing how you’d successfully manage the transition from a large established company to one that’s several times smaller. You might, for example, describe how you could build beneficial structures or frameworks for them as you’ve done in previous roles — and that you know how you’d do it solo or in a team of two or three. 

Alignment is essential 

It’s a bit of a cliche to say “You’re interviewing them as much as they’re interviewing you.” And yet, you are. It’s critical to do this well. If your values don’t align with theirs, if their culture doesn’t suit your vibe, the worst thing you can do is try to force-fit yourself into their mold. It’s very difficult to succeed given those kinds of parameters. Ask the hard questions. Don’t be afraid to inquire about what the growth mindset looks like within the company. If you’re a working parent, ask about being family-oriented; if you’re worried about it being a disqualifier, remember that any company that would ding you for having kids is probably not one you’d want to join. Whatever your values and priorities are, structure some questions to allow you to understand their perspective.

It doesn’t have to be “like for like”

Start-ups are the perfect place for trying on a new role; they’re a lot less prescriptive than large, established companies that often have very specific criteria that must be met to even be considered. Let’s say you want to jump into product management, you can be someone who was a sales exec or project manager in your prior professional life. You don’t need to have had a very technical role. Your start-up hiring managers just want to know how what you bring to the table will translate. Show them with specific examples – it’s not enough to say “I’m a great connector; I’m excellent at putting the pieces together to resolve problems and be strategic.” Show them. Make it clear how what you’re doing is complementary to what they’re looking for.

Whether at a big company or a small one, any new job or venture is a leap of faith. Even when you think you know it’ll be a certain way, you don’t. Not really. Don’t let the start-up path scare you. It’s fun, chaotic, and not always unicorns and rainbows – but it’s a huge adventure. And the exposure to such a diverse range of experiences – something you don’t often get at bigger companies – is incredibly valuable. 

Have you made the leap to a start-up? What’s surprised you?


Want to learn more? I recently spoke about this topic at the Liminal Conference. Rewatch the session here.

Work at companies inventing the future. Check out open roles at Costanoa’s portfolio companies: Careers