So you’ve decided you want to work for a startup. Awesome! But how do you get the job?

By Carly Chamberlain (Co-founder,

I’m the founder of the Brooklyn-based startup and we recently hired our first 2 employees. I was also one of the first employees at Airbnb and involved in the hiring of our first 25 employees.

Both of these experiences gave me amazing insight into what companies seek when making their first hires. I’ve concluded that the best early employees excel in three categories: enthusiasm, communication, and the ability to execute. Below I break down each of these three attributes and give you tips on how to demonstrate each of them during the interview process.


  • Talk about why you want to work for that company specifically, not just any startup
  • Match the tone of your cover letter and phone/in-person interview with the tone of the job description and website

When you’re applying to a company with fewer than 20 employees, the founders themselves will likely read your application.

Keep in mind founders have poured all their time, money, and energy into their company. The fact that they are in a place to hire employees is HUGE for them. They want to hire people who share the vision and passion for their company.

Don’t use vague statements like “I’m really excited” or “I think CaterCow seems great”. Explain why you think the company has a ton of potential that will show the founders how excited you are.

Our most recent hire did this beautifully and was kind enough to allow me to share part of her cover letter:

I think [easy simplistic ordering] is where your biggest growth potential lies. It’s the click of a button from a vendor you know you can trust and, even better, where you can switch things up for the target audience. Imagine an event planner who has a single fantastic resource-you!-to turn to, so whether they’re feeding a panel of thoracic surgeons or catering a vegan wedding, they know where to turn. In the best possible scenario, you could even have an app that was local to everyone’s phone or computer, so you’d entirely remove the impact on the person having to aggregate who wanted the chicken and who wanted the beef. Presto-less stress on your office manager, bride, or whomever is handling the order.”


  • Prepare specific examples of how you can help the company given their needs and your skills
  • Include zero grammatical errors in your cover letter/resume (I’m still surprised at how many your vs. you’re or it’s vs. its mistakes I come across)

Your ability to communicate clearly and effectively is a great indicator of your intelligence and every company wants to hire the smartest people they can find. Can you send in a cover letter with no grammatical errors? Can you explain something concisely without the reader/listener getting lost?

In phone interviews I always ask, “Given what you know about CaterCow, how would you help our company acquire new customers?”

Here’s a secret, there is no 100% correct answer. However, you need to be as specific as possible. Swap vague answers like, “Social Media” with “To start with I will assemble a list of the top 200 ad agencies in New York City. I will call 50 offices a day and ask to speak to the person in charge of catering…”


  • Start doing the job before you’re hired
  • Have examples from your past that demonstrate you are able to get your hands dirty and measure your success (ideally with numbers)

This is quite possibly the most important of the 3 and also the hardest to measure in the interview process.

Think of the hiring process from a founder’s perspective; we need to hire someone who will increase the value of our company. That won’t happen if we hire an “ideas guy”. It’ll happen if we hire someone who can get stuff done.

Our first hire, Sean, really wowed us when he started signing up caterers after just one phone interview (without us asking). He could have told us over and over again he was capable of acquiring caterers but showing us spoke volumes.

Remember, joining an early stage company is a two-way street. We have to think you’re the right person for our team but you also have to think we are the right company for you. Find the type of company where you are genuinely excited to do the things I listed above. Everything else will fall into place.

Are you an employee at a startup with other advice to share?

carly_chamberlain_headshotAbout the writer: Carly is the cofounder of Brooklyn-based startup, Before this, Carly and her cofounder were two of the first employees at Airbnb in San Francisco. At both companies, she has been responsible for a variety of roles including sales, marketing, customer support, community building and hiring.