Career guide: tactics to choose where to work
Best practices from Lenny Rachitsky, Claire Butler, Rex Woodbury, Amir Shevat, and more
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The next play career guide is our attempt to find you the best possible answers to your questions. We did that by asking some of the most talented people we know — people like Lenny Rachitsky, Claire Butler, Amir Shevat, Becky Sosnov and 30+ others — for their help in providing thoughtful responses.
Quick disclaimer before diving in: you should read the below as ideas and perhaps some suggestions but NOT prescriptive advice. There’s more than one way to live your life, and so our only advice is that you should think for yourself (if you want 🙂).
“I would like to join a startup but I am having trouble picking the company. There seem to be lots of interesting companies but I am not really sure what makes a startup likely to succeed versus not…what variables should I pay attention to?”
Choosing where to work is a multi-variable decision. You surely have several inputs: compensation, interest, impact, learning, balance, and others personal to you. Surely some of those inputs come into tension at times (i.e. you could join a company that promises more cash pay today but it’s in an industry you are not particularly interested in). And surely you’ll be forced to make choices with limited information.
The one thing you know for certain—and this is perhaps the only thing you can count on with complete confidence—is that every decision comes with tradeoffs. Choosing where to work is no exception. And so, when making these types of decisions, perhaps the single best thing you can do is ensure you’re thinking clearly and not being allured by misleading or even straight up false information (which happens a lot more than you may think!).
So in choosing where to work, the place perhaps to start…before looking elsewhere…is with yourself.
What do you want? What is important to you? And why is it important to you?
These sound obvious and simple but most people do not have solid answers to these questions.
Sitting with those questions, and perhaps all the adjacent ones, for more than one sitting (i.e. perhaps write down some answers, sleep on them, and then revisit them a few days later) can help you build a strong foundation.
Figure out what’s actually most important to you and really pressure test your responses. Be careful about being too religiously attached to any of your answers without clear logic behind them.
For instance, some people try to tell themselves they care a lot about a particular industry. They want to work, for example, in health tech or ed tech or ai. That may be true, but they also may care about other factors (like if the company is going to be successful or how much the role pays). Weighing those factors, seeing and making those tradeoffs — that’s where a lot of the work to be done is in terms of choosing where to work.
Another common example is company size. Some people get very attached to the idea of being on the founding team of a company. And so they race out of college to join a startup…and that startup…well it goes nowhere.
People say they want the "startup experience" and 100 is too large; trust me, a 100-person company (even a 500-person company) growing rapidly is still breaking at the seams and it feels like a startup. For people early in their career, I also recommend joining a company later than you think you should. Joining a generational company can set your career on a totally different trajectory. Joining as Employee 100 at Ramp or Notion or Airbnb will set you up much, much better than joining as "Head of ___" at a 20-person startup that doesn't go anywhere. - Rex Woodbury (Daybreak Ventures)
To put another way - it’s very good to have opinions and also very good to be open-minded, especially when it comes to something like your career where you directly get to experience the consequences of your decisions. “Strong beliefs, gently held.”
Once you have this core set of beliefs and hypotheses, then you can go out and collect external frameworks and best practices, and see how they mesh with your internal set of beliefs.
The opposite approach—simply doing what you read online ;)—may leave you floating in the wind. You may end up compromising what’s actually important to you and optimizing for things that do not really matter.
For example, a lot of people, especially younger people, tend to really care about signing a job that gives them an important-sounding title. They want to be a Director. Or a Head of. And so they choose companies based on the ones that will give them the most important-sounding titles.
Why? Well that’s perhaps a deeper question. Is it because they want a lot of responsibility and perhaps a title indicates that. Maybe. Or is it perhaps because they want to “set themselves up” for future roles and having a fancy-sounding title today will help them do that? Or perhaps, and calling out now that it may be some combination of the three, it’s because they want to “look good” in front of their friends and family.
Whatever the reason is, it’s doubtful to be a very great reason when compared to the cost of missing out on a great opportunity (simply because that great opportunity did not offer you a fancy sounding title in your offer letter).
Always optimize for the quality of the company vs. the title or the role. Once you get in the company, you can prove yourself and move to different functions. One of my friends joined Figma in a non-sexy, internal-facing role--she quickly proved herself and was moved to a quite important, company-critical role. Find any way you can to work at a generational company. — Rex Woodbury (Daybreak Ventures)
A lot of people tend to romanticize tech startups. They perhaps watch the Social Network and Shark Tank and think to themselves: “that should be me.” The cynic amongst us could roll their eyes at these mission-driven hustlers optimizing for impact and then pivoting their startup into some HR b2b SaaS solution. We are not cynics, though. We are pro-ambition, pro-experimentation, and pro-trying out new things. You never really know where things will go.
A piece of you, especially amongst the type A crowd, may want to try and turn the “company selection process” into a rigid formula. It may sound nice in theory, to have a fancy spreadsheet scoring different aspects, but this approach likely underestimates the role of chaos and the unpredictable nature of company-building. It’s so hard to predict precisely what will happen with your career. This is especially true in startup land. You’ll never know who you’re going to meet and where those opportunities will lead.
The second startup I joined, I wanted to deal with open source and work with the community on open source code. While the company was not a great success, that experience led me to a great job at Google. Now magically, I was able to move from Google to a rapidly growing startup called Slack very early, and when Slack went public, enjoyed that success. — Amir Shevat (Darkmode Ventures)
So if we’re saying it’s near-impossible or at least very very difficult to forecast precisely what’s going to happen to a company and to your career, what should you do?
Well, sometimes it’s just about taking the first step. Sometimes you just need some momentum.
If you have zero experience in tech sometimes you just need a place to start. When I was first looking for a job in tech I knew nothing about the industry. I had previously worked for retailer The Gap, where I realized I was not very good at or interested in fashion. I got an offer at a startup but I had no idea if it was going to succeed or not, but it had some reputable investors and the hiring manager seemed smart. I wanted to get my foot in the door so I just went for it. — Claire Butler (Senior Director Marketing, Figma)
Going for it can take many shapes. It often involves a combination of sending cold emails, doing new things, and making decisions under some degree of uncertainty. Going for it, whatever it ends up meaning to you, can be a way of minimizing your overall regret.
Another piece of minimizing regret is around collecting information, especially low-hanging information, so you can make an informed decision. Yes, it’s hard to predict the future. But also yes, there’s some information or signal you can collect today to help inform your decision making process. Inform is the key word here — no one piece of information will likely make your decision for you; you will always need to revisit your core personal priorities and weigh the tradeoffs. But bits of information can help you paint a clear picture.
One category of people who are in the business of gathering information are venture capitalists. VCs are “professional” startup investors—their job, not so dissimilar from your own when choosing where to work, is to underwrite startups (i.e. see if they are a good fit and likely to be successful). And they do this by collecting lots of information across often a wide portfolio of examples.
It always helps to build relationships with a few investors to learn their perspective on companies you're considering for a full time role - they will be able to give you a pulse on if they perceive the company to be doing well, and how they compare it to other startups in the market. — Lauryn Isford (Head of Product Growth, Notion)