It’s Not All Unicorns and Rainbows: A Guide for Evaluating Whether You’re a Startup Hire

Anne Weiler, co-founder and CEO of WellPepper, shares valuable questions to determine whether you are the right fit for a startup, or should look elsewhere.

Image for post
Image for post

So you want to work at a startup? It looks like a lot of fun, right? All those free lunches, dogs roaming around the office and yoga breaks? Startups are a ton of fun, if you’re the right person to be at a startup. If you’ve never worked at a startup, it’s hard to know. Especially if your previous experience was all at big companies. Here are a few tips that can help would-be startup hires and startup hiring teams.

The reason that startups emphasize all the fun and flexibility is that it’s hard, hard work. Startup work days are never 9–5. Those meditation rooms can double as nap rooms after all-nighters. If something breaks, if a customer is upset, it may be all hands on deck to fix it. Startups offer flexible work environments, but also expect flexibility from their teams.

If you’re looking for work at a startup, you’ll find that they all share similar characteristics:

  • Fast pace: the first mover advantage is real
  • No instructions: you’re often inventing the way you do things the first time you do them, because it is the first time they have been done.
  • Each team member can have a huge impact. (This can be good or bad.)

We see a lot of candidates for our open positions, and some of them seem to like the idea of a startup more than the experience of working for an actual startup. How do we know? In our interviews we test for skills that are crucial for startup success. Want to find out if you have what it takes? How many of the following can you say an enthusiastic yes to?

  • You can create something out of nothing. There are no manuals or guidelines, and you’re expected to create, whether that’s in marketing, sales, or product development.
  • You are a problem solver. Startups are often resource-constrained, whether that is time, money, or people. You may be disrupting an industry or competing with entrenched players. You’ll need to think creatively, work with tight deadlines, and see problems as opportunities.
  • You thrive on ambiguity. There are no right answers. One of the reasons A/B testing is so popular in startups, is that you don’t know the answer. If you’re building a new market, there is no roadmap.
  • You have a high tolerance for risk. Startups are risky. The statistics prove it out.
  • You are very clear about your skills, your ability to get things done, and you believe in yourself. People will tell you you’re a hero when you fix a big problem, but they won’t give you a pep talk while you’re thinking through it. Instructions are usually what to do, but not how to do something.
  • You are willing to wear many hats. I’ve had interviewees brag about “working outside their title” to show they are flexible. Titles don’t matter inside a startup: you’d better be thinking about the best for the company at all times, not whether your title permits you do do something. If something needs to be done you do it.
  • I asked our MBA intern Nick about this and he thought it was one of the most crucial elements of startup success and similar to running into a bear in the woods. “You have to look bigger than you are, and if each person is able to step outside their role and deliver what’s needed you can do that. Just as you have to look bigger than you are when you see a bear.” (Nick is going places here in the Pacific Northwest.)
  • You are wildly optimistic. You believe in the founders, you believe in the product, you believe in the mission, and you believe in yourself. Note that is “wildly” optimistic, not “blindly” optimistic. You have to be able to see the challenges.

If you mostly answered no, then you may be attracted to the idea but not the reality of startups. Maybe stay where you are and see whether you can work on a riskier new project and also spearhead some changes in the environment to emulate startup culture: free lunches, dogs, and yoga.

If you can say yes to most of these and are interested in working at a startup, begin interviewing and see if you can find a good fit where your “nos” can become “yesses”. Maybe a later stage startup: one that has raised significant capital and has customers is a good fit for you.

If you can say yes to all of these, and you’re not already working at a startup, you may want to re-evaluate your career choices. If you’re already looking, know that as an early hire in a startup you’ll face some incredible challenges but also have the opportunity to shape the culture and contribute to the success of the business.

Anne Weiler is CEO and co-founder of Wellpepper, a clinically-validated and award-winning platform for digital patient treatment plans. She co-founded Wellpepper in late 2012 with Mike Van Snellenberg to address issues in communication and continuity of care after a personal experience when her mother was released from 6 months in the hospital with no instructions and a month for a follow up visit. Anne’s expertise spans concept to go-to-market for technology startups and established businesses. Prior to Wellpepper, Anne was Director of Product Management at Microsoft Corporation. She joined Microsoft in 2001 with the acquisition of Canadian web content management company Ncompass Labs.

Springboard Enterprises

Written by

A network of influencers, investors & innovators dedicated to building high-growth women-led companies transforming technology & life science.

Been There Run That

Where influencers, investors, and innovators meet to build great women-led businesses. Our 777 women-led companies have raised $10.3 Billion, including 20 IPOs.

Springboard Enterprises

Written by

A network of influencers, investors & innovators dedicated to building high-growth women-led companies transforming technology & life science.

Been There Run That

Where influencers, investors, and innovators meet to build great women-led businesses. Our 777 women-led companies have raised $10.3 Billion, including 20 IPOs.

Medium is an open platform where 170 million readers come to find insightful and dynamic thinking. Here, expert and undiscovered voices alike dive into the heart of any topic and bring new ideas to the surface. Learn more

Follow the writers, publications, and topics that matter to you, and you’ll see them on your homepage and in your inbox. Explore

If you have a story to tell, knowledge to share, or a perspective to offer — welcome home. It’s easy and free to post your thinking on any topic. Write on Medium

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store