Joining product at an early stage startup? Here is how I went about it
About a year ago, I went from building product at a large public company (Dropbox), to a post Series-A startup. I often get private questions about why I made that transition, how I made my decision, and what it has been like.
There are good reasons to join a startup. It’s exciting. The increased ownership. You’ll learn a lot. The financial windfall if the startup does well.
Yet, startups are risky. A large number of them fail. Startup experiences vary. How do you ensure that the one you’re joining is right for you?
Today, I want to share how I made my decision and went about my job search process.
1. Decide what you want and write it down
As with any large decision, it always helps to write down what you want. What matters most to you and why. Post-Dropbox, it was clear to me that I wanted to try out early-stage product. At a company just around the Series A mark.
Before even starting out my job search, I wrote a short document with a list of principles that mattered to me for my next role. It included all sorts of things I wanted to look for. I split it into various sections: company / problem space, product, team, compensation, even how I expected to be feeling!
Here is a template for what I wrote down when I was doing this. It might seem silly to do this. These principles will be your decision guiding north-star later.
2. Source opportunities from the best people/places
Just applying to a random startup felt too risky/unknown to me. On the other side of the table, I always had the best candidates for my teams through referrals. So, I decided to source from people that I knew.
I made a list of the amazing people that I knew and respected. Do the same for yourself. Some were VCs, and others were entrepreneurs/operators. I reached out to them, even if it had been a while in some cases. I told each of them what I was trying to do and in some cases even shared my “what I’m looking for” doc.
Surprisingly, every single one of them was responsive. They introduced me to potential opportunities that I wouldn’t have ever heard of. I am grateful to have had their support. My moral of the story: don’t hesitate to ask.
3. The interview process is a two-way street
A startup interview process is substantially different from that at a large company. My interviews tended to be more focused on fit, culture, and sharing stories (vs. solving classic PM interview questions). Also, unlike large companies, I almost always interviewed with individuals I’d be directly working with.
The interview process is a great way to know your potential future teammates, and to get a pulse on the culture. Can you see yourself working with this group of people? You’ll get to know the company, product, and the team better. (Pro-tip: make sure to ask for the demo of their product when you’re interviewing)
The biggest thing to consider here though is that it’s not just the company interviewing you. You’re interviewing them too. Do your research. Prepare to ask lots of questions. You’ll learn a lot from the answers you get.
4. 10x the diligence of a VC
Following my interviews, I still felt that I had to learn more before making my decision. One of my mentors told me the following about joining startups:
When it comes to joining a startup, think like a VC. VCs do a lot of diligence for the startup they invest in. Though, they have ~10 companies that they’re invested in at the same time. As an employee, you are investing your career in one. Do 10x the diligence.
Find out all the ways in which you can find out more about the company and the team. Here were some of the things that I did, that you can do too:
- Talk to the founding team/CEO
- Meet investors and board members
- Look at term sheets and the cap table
- Talk to potential customers and see if the product resonates
- Get references on the leadership
- Talk to those who have left the company
- Ask to sit in on a sales call
- Do a small short-term project
- Watch for the key metrics and compare with benchmarks
- Read your the entire employment contract and talk to a lawyer if needed
If you already know someone at the startup whom you trust and can rely on, then some of these might not be necessary. Indeed, part of me felt that I was going overboard. In the end though, I felt that I had a lot of answers to make my decision even as I went went through this diligence process.
5. Go back to your principles
Once you have all the answers you need, the decision making process is hopefully simple. One opportunity stands out to you by the end of it. You’re excited by it and you feel confident about jumping in.
Sometimes though, it’s easy to get swayed and you might not be sure what you really value(this happened to me). This is where the principles you wrote down earlier come in. You can see what you prioritized all the way at the beginning, when didn’t have the paradox of choice.
Lessons for me
This whole process wasn’t without its set of lessons for me. Being naturally numbers oriented, I felt that at times I was being overtly logical in this decision making process. My biggest learning through this process is to equally balance the thinking part and the feeling part. It’s as much a decision of the heart as it’s of the mind. Passion for the product, a weird feeling about being excited to be a part of a team — these things all matter.
The second lesson is to trust yourself. The future is inherently uncertain and that’s part of the fun in joining a startup. No matter how things go, you will learn, grow and come out for the better.
How have you thought of this? Let me know!
