One of the most common problems with any stock-based compensation plan is that both receiving and granting options do not fully understand the nuances. The founders need to first understand this well in order to structure offers with a significant stock component (or communicate the value and risk associated with options) to employees.

As a Founder, before you throw in options into the mix, you need to first educate the uninitiated candidates. Otherwise, you are wasting a precious resource that is in limited supply. Even after the education, some will continue to be sceptical, and some others will never understand the nuances sufficiently to make a rational trade-off. Those who have seen some form of stock-based compensation in an earlier role with a startup get it much better. The lessons learnt from past experience though, can vary from person to person. Some may have seen an exit and may have made good money. These are the ones who will understand and appreciate your stock pitch. Those who may have taken a pay cut to join a startup with the belief that this would be compensated many times over when they hit pay dirt with their options, but their options went up in smoke, are likely to be very sceptical about this asset class.

Therefore, if you take a one size fits all approach and grant an equal number of options to both these categories of individuals, you would be unnecessarily giving away a precious resource without getting anything in return. For those that are fixated on cash and are unwilling to budge, you needn’t offer them the same number of options as what you would offer someone who has a bigger risk appetite and comes at lower cash compensation. If you can judiciously discriminate in terms of the grant size based on the risk appetite of a prospective employee, your options pool will give you a much bigger bang for the buck.

Let’s first start with a Series A funded startup and from there go back (Seed/Angel) and forward (Series B/C).

The options pool post-Series A is typically 15% of the overall equity pool on a fully diluted basis. Typically, a Series A investor would ask the founder/s to make the provision. This has serious implications for the founder/s. Let’s assume that the pre-money value of the startup is $5 Million and the founder/s own/s 100%. The Series A investor would come in and agree to put in, say, $5 Million for a 50% stake with the proviso that after the investment, the founders would own 35%, and the balance 15% would comprise the options pool. Obviously, the investor is getting you, the founder/s, to create the options pool from your equity. So, be wise. If you do not need a 15% pool now, just go with, say, a 10% pool size. If you need to increase the pool size later on, you can jointly dilute with the investor and create the additional 5%.

What should be the quantum of the grant? The standard and well-tested practice is to consider anything between 1%-2% for a CXO, and between 0.25%-1% for a key hire one level below a CXO. A professional CEO may need 4%-8%. The bigger the valuation at the time of Series A, the lower the end of the range could be the size of the grant.

Now, you can go back to the Seed round. Based upon the extent of dilution expected after Series A, you need to work backwards. If you expect a 50% dilution, then the Seed round grants need to be double of what they are after Series A.

What should be the strike price? The best approach is to use the current market value. This is a clean design and ensures that those that come in at an early stage see a greater upside even if the grant size is the same as it is for someone who comes on Board later. So, the risk-takers that came in early have the dual advantage of a greater upside (on account of a lower strike price) as well as early vesting. Some startups tend to use the par value of a share as the strike price. This is not a common practice, though. The reason these startups have resorted to this approach is to assign and communicate the monetary value of the options at the time of grant. This makes it easy for someone who has no idea how to value options. Let us assume that a startup offers a salary of $125,000 plus stock options (with 4-year vesting) whose value is $300,000 at the time of grant. The value of $300,000 is arrived at by multiplying the number of options and the differential between the current market price and the par value. If the grant size is 30,000 options, the current market price is $11, and the par value is $1, then the current value of the options is 30000*(11-1), which is $300,000. Therefore, the equivalent cash compensation of this offer is $200,000 per annum (which is $125,000+25% of $300,000). The obvious error with this approach is that if the share price appreciates (and it is certainly expected to appreciate – and appreciate significantly), this calculation is totally flawed. If the share price quadruples in 4 years, then the terminal value of the options is actually $1,200,000, and the total compensation per annum is actually $425,000 and not $200,000. The other problem with the exercise price being at par is that irrespective of when a person comes on Board, the upside tends to be the same. This is a deviation from the fundamental design principle of an ESOP plan. The fundamental design principle is that everyone gets an upside depending upon the value creation that they have enabled during their tenure.

We’ll quickly introduce some terms – but we assume that most readers would have a sense of what these terms mean (at least the more common ones) and hence would just draw attention to some tricky pieces.

• Vesting – usual vesting period is four years. Some plans have a cliff of 12 months for the first vesting but have monthly or quarterly vesting thereon. Some other plans are simple and have an annual vesting. Vesting is not a tricky clause.

• Exercise – the very definition of an option means you have the option of exercising any time after vesting (and before expiry) by paying the strike price (along with any taxes) and acquiring the equivalent shares. Some startups may not allow employees to exercise their vested options because they do not want the hassle of dealing with a large number of shareholders or share sensitive information with them. A clause that does not permit an employee to own shares by exercising vested options is in my opinion, not a good thing.

• What is the strike price? How does it impact a grantee? The strike price is what the grantee needs to pay to convert the stock option to a share. Normally, the strike price is the current market price, but usually, it is at a slight discount to the current market price. Periodic adjustments are made, but the reality is that there is a lag. So, if the strike price is $3 and the market price at the time of grant is $4, then the value upon grant is already $1. If the stock price goes up on an average by, say, 50% per annum, then at the end of 4 years, the share price is 1.5^4*4, which is nearly $20. Since the strike price is $3, the value is $17.

• Will a grantee get diluted in the subsequent funding rounds? Yes, of course, she would. That is the reality. Assume you own a 2% stake in a company that is currently valued at $50 Million. Your value is $1 Million. Assume the company raises $25 Million at this valuation (pre-money value of $50 Million). The post-money valuation of this startup is $75 Million. However, your value is still $1 Million. But you own a 1.33% stake now. Notice that your wealth hasn’t disappeared or shrunk. You just happen to own a smaller stake in a bigger company!

• What is pre-money and post-money, and what are the implications for me? It doesn’t impact you as an employee a great deal. So, don’t bother. You would have figured out from the above example that the post-money value of a startup equals the sum of the pre-money value of the startup and the quantum of funds fundraised.

• What happens when you quit? This is the trickiest part. Most startups expect you to exercise all your vested options within 30-90 days of separation. This can be financially very onerous, especially if the current market price is much higher than the strike price. Since most employees cannot cough up the required cash to exercise the options or do not want to be saddled with a risky and illiquid asset, they have no choice but to hang on (if the upside looks attractive) or leave the options on the table and walk (if the value is not attractive enough). Exercising vested options is financially draining because you not only need to pay up the exercise price, but also pay the tax on the difference between the current market price and the exercise price, upfront. Startups use this exit barrier to hold on to employees even after options vest without necessarily having to throw in additional hooks by way of fresh grants. Some startups are generous and allow you to exercise vested options anytime before expiry even after separation. This gives a grantee a lot more leeway and flexibility. The obvious question is why would a startup want to do this knowing full well that they are losing a retention hook that comes free of cost? In our opinion, those that allow this flexibility do it because they believe it is the fair thing to do.

• What happens if the startup gets acquired before your options vest? Look for a clause on “change in control”. Most startups allow for an acceleration of vesting when there is a change in control (in layman’s language, it means an “acquisition”). Some startups allow 100% vesting upon a change in control, and some others may offer a 25% acceleration. The latter is much more common. The 100% acceleration is truly very rare because it can deter a potential acquirer by acting as a mild poison pill. A 25% acceleration just means that if the startup gets acquired within 28 months of your coming on Board, then even though only 50% of your options would have vested under a simple four-year vesting plan, the acceleration clause ensures that an additional 25% automatically vests (taking it to 75%). We know of a high profile startup that did not have this clause. It got acquired in less than 12 months of a good number of senior hires coming on board. When the implications of the fine print became evident, all hell broke loose! What was surprising, though, was that senior-level hires had come on board without reading the fine print. We have been discovering that this is common practice!

• In the event of a change in control, what happens to my unvested options? That depends upon the terms of agreement between the two parties to the merger/acquisition. The unvested options may just be forfeited, or, they may be converted into equivalent options of the acquiring company; or a percentage of them may be deemed to be vested and paid off.

Restricted stock is another instrument (commonly referred to as RSU). Unlike an option, an RSU is a share with some restrictions (usually on when you can sell). Hence there is no strike price. If you are granted an RSU with a 12 month vesting, it just means that you will own a share at the end of 12 months. Unlike an option, an RSU can never go underwater because there is no exercise (or strike) price. Therefore, an RSU will always have some value. Most startups prefer stock options in their compensation plans and avoid RSUs. On the other hand, listed companies prefer RSUs. The logic is almost entirely tax-related. In the case of an RSU, the tax needs to be paid upon vesting (because you actually own a share), and paying a huge amount of tax for acquiring an illiquid asset does not appeal to anyone. However, if the company is listed, the tax can be paid by selling a portion of the vested lot of RSUs.

The tax treatment varies from country to country, but in every country the tax treatment for RSUs is different from the tax treatment for options.

Liquidity options before an exit are very limited and rare. In those rare situations, three things can happen:

• The company can buy out your options at the current market price (or at a slight discount). Whether to sell and realize some upside or wait it out for better returns until an exit, is a choice the employee needs to make.

• A new investor can also buy out some options along with some founder shares (called secondaries).

• If there is a lot of restlessness because of a lack of visibility to a liquidity event in the foreseeable future, then an existing investor may also choose to provide key employees with some liquidity and keep them motivated to stay on.