How to jump on a rocket ship

August 3, 2019 · 8 min read

So, you read my career management advice and you’ve decided you want to join a mid-stage, hypergrowth startup. Great. Now—how do you go about it?

I’m aiming this post at engineers, designers, PMs, and data scientists who are talented and ambitious but not necessarily “initiated” into the world of tech startups. The Silicon Valley job market is unlike most job markets. There is tremendous demand for great talent, and there is tremendous variation in outcomes of startups. There is less transparency in the market and far more hype compared to the economy at large. So my advice here is unlike most job-hunting advice, maybe even to the point of sounding a bit crazy to people in other fields or industries.

Finding opportunities

The best startup opportunities are not obvious; they’re not yet world-famous like Google, Facebook and Amazon. But they are well-known within startup circles. Here are some ways to find them:

Handling a flood of opportunities

If you have a good resume or you interview well, you will be inundated with opportunities. There will be more than you can handle. Here’s how to manage this and guide it to a good conclusion:

Deciding on an offer

OK. So you got a few offers. How do you decide?

Negotiating compensation

You have multiple offers in hand and you know which ones you are willing to accept. You even have a favorite. How do you manage the compensation issue?

Many people will tell you to negotiate. I am not an expert on salary negotiation, and I hate haggling. So here is what I suggest:

  1. Decide which of the offers you are truly most excited about, aside from compensation.
  2. Is that offer also the one with the highest comp? If so, count yourself lucky, and just take it.
  3. If not, tell them: “Thank you for this offer! I received multiple offers, and you are my top choice. However, I was offered $X by another company. Can you match that? If so, I will definitely accept. If not, I will still consider it, but I’m not sure what I will decide.”
  4. If they match your best offer, great! You got the best of both worlds. Go to step 2 and take it.
  5. If not, now you have to ask yourself: are you willing to take less money to work at your top choice? This is usually a good tradeoff (money for happiness), but it depends on the delta in both dimensions, and it’s a personal choice with no universal answers. Choose wisely.
  6. If you’re not willing to take the lower salary, then eliminate that company. Go to step 1 and repeat with the remaining offers.

What if you didn’t get multiple offers? Oops. Well, now you don’t have much choice (unless you want to extend your job search). In this case, I would look up whatever information you can find on salary ranges that are comparable based on role, location, and stage of company. The AngelList job board mentioned above is a good source, since those postings include compensation ranges. If your offer seems in line with the general market, again, just take it. If it is below market, mention these data points and suggest a number that you think would be in the proper range.

If you approach all this professionally and tactfully, the worst a good company will do is say no. (If a company rescinds your offer just because you politely tried to negotiate, it’s probably not a place you want to work.)

Understanding equity

I mentioned salary above, but any tech offer will also include an equity component. How to think about this part?

First, you should understand what you have been offered. If you don’t understand stock options or RSUs or whatever form your equity takes, ask questions or Google it until you feel you at least know what all the terms mean (such as “vesting” or “strike price”). There is plenty of information out there, and you shouldn’t be embarrassed to ask.

You should also understand what percentage of the company your shares represent, and you should know the last-round post-money valuation. Again, if a company won’t tell you these things, you probably don’t want to work there—but also, expect to receive this information under NDA and treat it as confidential. (You might also ask whether there are any nonstandard or “dirty” terms, such as greater than 1x liquidation preference; if you don’t understand these concepts well, though, you’ll have a hard time interpreting the answer. If you want to learn, read the term sheet series of blog posts by Brad Feld and Jason Mendelson, or if you want to go deep, read their book Venture Deals.)

If you are receiving stock options, you should know what expiration period they have after you leave the company: You want to see a long expiration period, like 5–10 years, not 90 days. (More context on this issue here.)

Of course, what you really want to know is unknown and unknowable: What will your shares be worth in an exit? Will there even be an exit? You can get super-analytical about this and build all the spreadsheets you want, but the reality is that the variance on outcomes is extremely high. You can dream about getting rich, and maybe you will, but you should be financially and emotionally prepared for your equity to be worth zero.

My take on equity at pre-IPO startups is that it’s less compensation and more of a promise: “If we succeed, you’ll get your share.” It’s not and can never be a guarantee of success. So just take it for what it is.

Happy hunting

Best of luck! And feel free to contact me for further advice in specific situations.

These days I do most of my writing at The Roots of Progress. If you liked this essay, check out my other work there.


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