How to Navigate Options in your Employment Contract

April 7, 2014 — 2 Comments

Over the past few years, I have helped many of my friends understand options in their employment contracts.  Most candidates have a general misunderstanding and discomfort when it comes to options, so I’ll give a brief overview to try and shed some light on the issue.

First, options are not equity.  If you receive options, you won’t actually own any of the company yet.  You are being given an opportunity to buy shares at a later date for a fixed (and predetermined) price per share.  You will make money by buying at the predetermined price and selling during an exit event at a new, higher price.  Without an exit event (sale, merger, or IPO), you won’t be able to sell your illiquid shares and your purchase will represent an investment in the company’s future.

Options vest (become exercisable) over time based on your vesting schedule.  If you leave the company at any point, you will typically have ~90 days to exercise your vested options or you will forfeit them. If you are leaving the company because it isn’t doing well, it’s unlikely that you will want to invest cash in exchange for shares.

On the flip side, if a company gets bought for a valuation that is 10x larger than it was on your grant date, you can immediately convert your vested options into shares and sell them for a 900% profit (assuming no dilution, which is highly unrealistic).

Almost every company will insist on a 1-year cliff so that none of your options vest until you’ve been with the company for a full year.  But what happens if the company gets bought after 10 months of your being employed there?  If you don’t have an acceleration clause (and most contracts do not come with one), you get nothing.

Things you should look for in your contract

  1. A grant date – Important for many reasons including determining when your vesting schedule / 1-year cliff begin and for tax purposes.
  2. A strike price – At what price you can buy shares of the company.  Options are exercised and converted to shares by paying the company the strike price per share.
  3. Total # of options granted – With this you can determine what your cash outflow will be if all your options vest and you buy shares at the strike price.  Keep in mind that the company will probably issue additional shares to you each year or with each promotion.
  4. Total # of shares currently outstanding or % of the company your options represent – How much of the company will you own (prior to dilution) once all of your shares vest?  If they give you the total shares outstanding, you can just divide your # of shares by the # of shares outstanding.
  5. Dilution – This is where the company issues additional shares, which they will do for multiple reasons.  You should assume that your % ownership will be 1/2 of what it is now by in an exit event.  They probably won’t give you dilution protection, but it doesn’t hurt to ask!
  6. Vesting schedule – Typically 4 years.  Vesting is the rate at which your options become exercisable.  Before any of your options vest, you can’t convert them into ownership and there is typically a 1-year cliff on vesting.
  7. A 1-year cliff – Will likely be in every contract and prevents the employee from having any options vest in their first year.  If you have a 4-year vesting schedule, 25% of your options will vest on your 1-year anniversary.  Be wary of any cliffs that have a longer duration, especially if you don’t have an acceleration clause.
  8. An acceleration clause – Single trigger if the company is acquired and double trigger if acquired and you get fired.  At a minimum, 25% of your options should vest in a single trigger and another ~25% in a double trigger situation.  Many contracts won’t include anything about acceleration, so make sure to bring this up.  This is particularly important if the company is doing well and has already raised significant ($2m+) capital, as they are more likely to be an acquisition target in the near-term.

Have you come across anything that I’m missing?  Please let me know in the comments or shoot me an email.  I’m happy to dive deeper into any of these topics or speak with you 1-on-1 if that would be helpful.

2 responses to How to Navigate Options in your Employment Contract


    Hey, nice article! I have some anecdotal evidence on the acceleration clause. One offer I received initially did not include acceleration. I discussed this with them, and the company pushed back for a couple reasons.
    1.) It’s not as important for engineers, because often if a company is acquired, it is FOR the engineers. Thus the acquirer (let’s say… Google) wants to ensure the engineers stay for at least a year. This means if there are acceleration clauses, Google will dictate that they be taken out as a requirement of the deal.
    2.) Acceleration clauses are generally reserved for business guys (who might actually get fired during an exit), or very senior people (including engineers) who can throw their weight around. For anyone else, it can just be a nuisance, or worse, a deterrent for an acquirer.

    Also… regarding cliff dates. This same company actually offered 6-month cliff, because they thought you still know one way or the other if it’s a good fit by 6 months, and thus it speeds up that forcing function for both parties without significantly decreasing information.


      Blake, thank you for the comment. This is a great anecdote and it is true that engineers are probably better protected than other positions. In addition, the company offered a 6-month cliff so you are less exposed.

      Companies like Google are used to seeing acceleration clauses, so it’s hard to imaging this being a deterrent. Employees will still be incentivized to stay for at least a year as they will be issued a new stock option plan by the acquirer that will include a 1-year cliff.

      In an acquisition that involves cash, employees be given the option of cashing out their vested options. An acceleration clause will result in your having vested shares so you can participate in the buyout.

      Your unvested shares will roll into the new stock option plan, so you won’t actually lose anything if you don’t have acceleration. However, if the acquiring company does fire you and it’s before your cliff you won’t get anything and will lose your options.

      Everything in a contract is negotiable, so if your company is pushing back on acceleration, reducing the cliff to 6 months (as this company did) is a pretty good tradeoff. You could also push for higher salary to offset this risk. Sometimes presenting these options upfront and letting the employer chose is a good way of maximizing your results. I’ll write a post on negotiating employment contracts in a couple weeks.

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