The Ins and Outs of Joining Your First Startup Team

By Adam Salomone

I talk with many aspiring entrepreneurs about joining early-stage startups, whether in the food space or in the larger innovation arena. Oftentimes, these job-seekers approach the hiring opportunity in the same way they might a more traditional role with a larger company. Given the risk inherent in joining a startup, where the future is far from certain, it's perilous to forgo a more in-depth examination of a startup's prospects before jumping on-board. Whether because a job seeker is enamored with the mission or vision for a particular startup, or because an in-depth analysis can seem too direct or prying, it can be common to ignore these common indicators of startup health. But, if you find yourself in this position, you owe it to yourself and the company you are considering joining to tackle these thorny issues upfront.

Below is an inexhaustive list of questions and issues to explore with the team. Individual situations may require different kinds of questions, but these are meant to cover three main areas:

  • The current financial health of the company, as well as the forward-looking business plan.
  • The vision for the company and the 3-5 year plan to get there.
  • The overall culture at the company, and the founder(s)' expectation for how team members work together.

While it may feel uncomfortable to be so upfront in delving into the below, beware joining a team where the founder either cannot or will not articulate answers to these questions. 

  • How much money have you raised to date? What's the current runway for the company and when will you have to raise your next round of funding? If you've raised money already, who are your investors?
  • Is there a board of advisors or a formal board that oversees our operations?
  • What are the plans for the next round of funding? What is the anticipated timing and size? Are you in conversations with any investors about the next round of funding?
  • What is the status of the company's product? Has it launched yet? If so, how many customers do you have? If not, when will it launch? Can you walk through a demo of the product (even if it's in beta)?
  • What is the business model? Can you share detailed financial projections for the business?
  • What companies are your primary competition? How are they different? How are you better? 
  • Where will the company be in 3 years? 5 years? In terms of size, funding, revenue and overall impact in the market.
  • How are you envisioning the responsibilities for this position? How does it relate to the rest of the team?
  • How many employees are on the team currently? How does everyone work together? What are your hiring plans for the next 12 months? How will you find those people?

You'll notice that many of these questions are similar to what a potential investor might ask. While it's a subtle distinction, there is an opportunity cost and an investment that you make in joining a startup where the future is uncertain. So, you have to think of yourself as an investor in the company and ask the appropriate questions to evaluate the opportunity. You should get a sense right off the bat of whether a founder has a good handle on his/her business. If you come away without a clear sense of the vision, don't be afraid to follow-up and ensure you have a strong level of understanding of where the business is headed.