Joining a Startup: What to Know Before You Leap

To stay at an established company or embark onto startup wilderness? This a question that loves to torture MBA students and seasoned business professionals alike.

The decision to transition to a startup will likely be one of the toughest in your career. I know that firsthand. Many years ago, I found myself wrestling with whether I should stay on the fast track at a consulting company or take a chance and join a startup. A mentor saw my excitement for the startup’s vision and encouraged me to take the leap. That leap changed my career for the better, empowering me to subsequently build, and invest in, many other startups.

As an Entrepreneur in Residence at Harvard Business School, I spent time with MBA students who are interested in joining startups. I’m frequently asked: How should I go about joining a startup? What are key decisions to consider? Which role should I target?

I went to the best source of advice: MBA-holding executives who joined startups early-on and helped lead their companies to scale. For those of you aspiring to transition to a startup, here is what you should consider before making your move.

Evaluate Three Dimensions

A thorough deep dive into a startup will help you understand if it’s in a position to succeed. To determine a startup’s funding status, dig into Crunchbase or Pitchbook to uncover how much funding the company has raised and who their investors are. For insights into company culture, don’t forget to look at Glassdoor and LinkedIn.

Katie Burke, Chief People Officer at HubSpot, recommends thinking about a startup’s growth potential on three dimensions: whether the company’s industry is likely to grow, whether the company is well-positioned to take advantage of that growth, and whether you can grow personally and professionally.

Burke says asking the right questions is key. “Make sure you ask how decisions are made, how the company cares for employees when things are hard, and about how the organization prioritizes culture and values.” Get specific, she advises. “Most people ask vague questions on that front ‘do people like it here? do you value culture?’ and the real value is in the specifics ‘can you give me an example of when something wasn’t working and how you fixed it?’”. Drill into all three dimensions to know if the startup you’re considering has a culture that you will thrive in.

Get in Early, Make a Mark

When I left consulting to join a startup, I tried to keep an open mind and took on anything and everything that came my way. This led to rapid increases in responsibility, and that gave me a real voice in where the company was headed.

As a first-year HBS student, Yi Chen seized the opportunity to join a startup called Toast, working directly with its founders. Toast was working on an idea to transform technology for small and medium-sized restaurants, just like the one Chen’s parents had. Chen recognized the chance to apply his personal experience and passion to the company as Toast’s fifth employee.

“I got the chance to see that they valued my opinion, strategic vision, and listened to my experiences growing up in a family restaurant,” said Chen, who today is Vice President and General Manager of Consumer Products at Toast.

If you join early on, your insights and actions become the critical ideas that shape what a company becomes. Leaders rely on you for your productivity, problem solving, and ability to scale. It’s a golden opportunity to leave your mark.

Forget the Job Description

I work with MBA students who are fiercely goal oriented and attracted to well-defined roles. When it comes to joining an early-stage startup, its not always possible to map to a specific job description. If you are willing to consider a flexible role, you can focus on what really matters: learning a ton.

“You’ll never learn more than when you build a business,” said Colin Raney, Chief Marketing Officer of the online pharmacy PillPack which was acquired by Amazon last year. “From working through technical issues, designing processes, figuring out operations and people management, you will have a chance to gain knowledge across the entire business. You’ll learn five times more at a startup than you would at a bigger company,” Raney says. “There’s just so much more personal development that comes from building something from scratch.”

When you move from a large company to a startup, you may give up the comfort of a well-defined job description but in exchange you’ll be rewarded with learning and experience that exceeds any one title.

You Just Jump

I’ve seen talented professionals rule out startups because they feel too risky. Startups can be a wild ride, but they can also lead to a deeply fulfilling career. Anna Marie Wagner, a Senior Vice President at the synthetic biology company Ginkgo Bioworks, spent a decade on a steady career path before redefining her relationship with risk. “Once I started reflecting, I realized I was more scared of waking up in 20 years and regretting not having thrown myself at a problem I was passionate about than I was of joining a company that went belly up,” she said. When she entertained the idea of joining Ginkgo, her mentors urged her to give risk a chance. “Now that I’ve tasted the thrill and the responsibilities that come with being a leader in a startup, I’m not sure I could ever go back,” she said.

For those who are prepared for hard work and aren’t afraid of uncertainty, there are few things as exhilarating as joining a startup. Before you make your move, do your research, and be honest with your expectations. When you come across the right team, don’t waste the opportunity. In the words of Sheryl Sandberg: “If you’re offered a seat on a rocket ship, don’t ask what seat. Just get on.”

Jennifer Lum is a Managing Partner at Biospring Partners and an Entrepreneur in Residence at Harvard Business School. Twitter: @lum