Cake Equity's Guide to Employee Stock Options

What is an employee stock option plan, how does it work, and how are they vested and exercised?
Employee stock options

Granting employee stock options can best be thought of as slicing up your company’s equity and sharing them with employees. There are many terminologies used, depending on where you are in the world: ESO, ESOP, ESOW, EMI schemes.

While there are differences in the way they're called, issued, or taxed, the concept and the intention is the same—to attract and retain top talent, incentivize growth, and foster team-focused culture.

A sliced cake representing ESOP abbreviation
The basics

What are employee stock options

Employee stock options is a way to give equity (or ownership) in your company to employees. A slice of the cake, if you will. 🍰

There are several ways employees can gain a slice of their company's stock option. For example, employees can buy the company's stock directly, obtain stock through a profit sharing plan or via worker cooperatives. But stock options are by far the most common, simple, and effective way to slice up the equity cake.

Issuing stock options to employees gives them the right (but not the obligation) to purchase company stock for a specific period of time at a predetermined price, known as "strike price".

Benefits of an employee stock option plan

Attracting talent. It’s no secret that cash can be tight for startups, which makes it hard to pay top dollar for talent. Using an ESOP, start-ups can offer tasty equity compensation to top-up slightly lower remuneration packages. The same applies for compensating startup advisors and developers at an early stage. Knock their socks off with your idea, pay them in equity compensation.

Retaining talent. It’s hard to attract top talent and even harder to keep it. Stock options are usually subject to vesting, which encourages sticking with a company until the stock options vest. That’s why it’s often called “sweat equity” – team members need to put in the blood, sweat and tears in order to eat their cake.

Opportunity for significant employee financial gain. By taking a slice of the equity cake, an employee can benefit from the increase in value of the stocks over the company lifetime. It offers hungry employees the chance to generate real wealth.

Salary top-ups. Tough times can often mean a company has to reduce staff salaries. To keep employee morale up (and the staff around), you can use equity compensation to ‘top-up’ paycuts with proportionate equity.

Incentivization. Potential ownership of a slice of the company means employees start thinking like business owners. It’s common to see a spike in collaboration, productivity, and innovation when employee stock options and other equity compensation are incentivizing the team. One cake, shared goals.

Tax benefits. In many countries, start-ups and their employees are eligible to receive substantial tax concessions when implementing employee stock options. For more information about the tax benefits in your specific country, please get in touch with our expert legal partners and enjoy special Cake fixed-fees.


Stock option terminologies

Before we dive in, here are some terminologies to help you better understand this guide.

  • ESO or ESOP means Employee Stock Options or Employee Stock Ownership Plan.
  • Exercise means the process of converting a vested option into an ordinary stock. An option can be exercised when the option has vested,and the exercise price is paid.
  • Exercise period means the period in which an employee can exercise stock options. Often, an employee won’t exercise stock options straight after vesting, and will wait to exercise them later on(for example, at an exit).
  • Exercise price means the amount to be paid by the employee to exercise the option. In many countries, an approved valuation is required to determine this price. This is often also referred to as a strike price.
  • Exit event means when the owners of a company “exit” the business by selling the business, for example by initial public offering (listing) or acquisition by a third party.grant date means the date the stock options are granted (or “issued”) to the employee or contractor under the offer.
  • Lapse means what happens to an option when specific vesting criteria is not met, and the option can be transferred back into the option pool for re-allocation.
  • Offer means an offer for stock options made to an employee or contractor, made via an esop offer letter.
  • Offer letter means the agreement setting out the number of stock options being allocated, the vesting conditions, and relevant exercise and stock options price. In some jurisdictions this is referred to as an award agreement or an stock option agreement.
  • Option means an option to purchase a stock.Until an option has vested and been purchased. It is not a stock. It is a legal right to purchase a stock at a later date, if certain conditions are met.
  • Option-holder means any employee or contractor who has been offered (and accepted such offer) stock options to purchase stocks under an esop.option price means the price the employee pays to be granted the stock options. In most jurisdictions, this is usually set at $0.
  • Start date means the date the vesting period starts ticking. This can be the start date of employment, or another date.
  • Strike price has the same meaning as exercise price.
  • Vesting means the process by which the option-holder earns full rights to their stock options, to allow them to be converted to stocks. This can happen by way of meeting certain time-based vesting conditions, or other performance-based milestones. Only vested stock options can be exercised to become stocks.
  • Vesting period means the time from the start date, to the date the last stock options will vest under the vesting conditions.

How employee stock option plans work

The company creates an ‘Option pool,’ setting aside stock options that can be allocated to employees or contractors. Consider this one slice of cake, from which smaller nibbles are then allocated.

The standard option pool size is 10% but it can vary between 5% to 30%.

The option pool doesn’t need to be allocated immediately. In fact, it’s often better to leave unallocated stock options to use for later hires or to top-up remuneration packages.

To simplify how stock options work, there are 3 main things that needs to happen before stock option holders can eat their cake:

(1) Granting, (2) Vesting, and (3) Exercising

The employer grants stock options. If the employee complies with the rules, the stock options vest. Then they can exercise their options to purchase stocks. In this article we will deep dive on each part of this process.

At Cake, we’ve made it our business to research best-practice standards for employee stock option plans globally and in your country. We’ve done the hard work, so you can rest easy knowing our platform creates and delivers seamless employee equity program with tangible benefits. Learn more.
The Plan Rules

Stock option grant explained

An employee receives an agreement outlining the rules of his equity grant. Just like any legal document, signing this agreement binds an employee and employer to a set of terms.

In Cake's platform, a stock options holder typically receives an offer letter to start, and then a more detailed Plan Rules to be signed by both parties.

Why we need Plan Rules

The Plan Rules set out the rules and processes for option-holders and stockholders. The Plan Rules and the Offer Letter should be read and understood together. You can think of the Plan Rules like a stockholders agreement that applies to employee stock option recipients.

Plan Rules provide full transparency, helps avoid disputes and gives the company peace of mind that it’s protected in various scenarios.

Generally, the Plan Rules cover important issues such as:

  • The right of the company to buy stocks back from option-holders
  • The price at which the company can buy the stocks back from the option-holders
  • What happens if an exit event is likely to occur
  • Whether the option-holder can transfer his or her options or stocks, and the restriction periods on the transfers
  • The company’s right to take certain actions in the shoes of the option-holder, where the option-holder is not cooperating
  • The terms of any offer that are specific to each employee (such as the number of stock options allocated,

The Vesting Rules, and the Start Date will be set out in each Offer Letter.

The terms of any offer that are specific to each employee (such as the number of stock options allocated, the vesting rules, and the start date) will be set out in each Offer Letter.

The Cake platform prompts you to fill in these restrictions, and automatically populates the applicable restrictions into Offer Letters, to avoid any slip ups.

Cake has created Plan Rules using best-practice standards in the United States, or whatever country your employee is based. If you need to create Plan Rules, it’s important they comply with the laws and regulations of that specific country. Learn more.

Our expert start-up legal partners can assist with any amendments, advice on approvals required (like Board or Member approval) or the terms of your Offer Letters and Plan Rules.

The Vesting period

Vesting stock options

Under an employee stock option plan, the option-holder is not able to exercise until those stock options have vested. And until the options are exercised, the option-holder does not have any stockholder rights (like voting rights, for example). 

In other words, until stock options have vested, the option-holder can't gain full rights to their slice of the cake.

Vesting is a little bit like dangling a carrot. The purpose of vesting conditions is to tie some obligation of performance (or time) to the stock options.

This is why employee stock options are such a powerful tool for incentivizing your team to stay longer and work smarter towards the ultimate success of the company.

In an employee stock options plan, option vesting happens by way of:

  • Time-based vesting
  • Milestone vesting
  • or a combination of both

Time-based vesting

Time-based vesting can occur by way of a cliff, periodic vesting, or a combination of both.

Cliff vesting

Think of cliff vesting as the probation period for equity. It’s a period of time before any stock options vest. It’s usually set at one year, which gives the company time to see how the option-holder performs, before they receive any equity.

For example, if Tracey has a 12 month cliff, 25% of her stock options would vest 12 months after her start date.

Periodic vesting

These are options that vest gradually over a period of time (what we call as the "vesting period").

For example, if Tracey has a 4 year vesting period, after Tracey’s 12 month cliff, the remaining 75% of her options would vest quarterly, over 3 years. So, at the end of month 15, another 6.25% of her options would vest.

The vesting period will usually start from the employee’s start date. It can also be set retrospectively, so the employee is rewarded for any time spent in the business prior to the first grant date of options.

The start date can also be set to start at whatever other date the company likes. For example, a company can create a stock option plan where the start date for vesting is the same for all employees, regardless of when they started.

Milestone Vesting

Options will vest on the achievement of some defined milestone or performance hurdle. For example, the remaining 25% of Tracey’s options could vest on her ‘recording $200k in sales for the company during 2022’.

Generally, milestones are only appropriate when clear metrics can be defined. For example, a sales role where vesting is tied to result.

Most common vesting arrangements

The most common vesting conditions we see are: 25% of options vest after a 12 month cliff; the remaining 75% of options vest quarterly, over 36 months after the cliff date. You can have default vesting condition set up in your Cake account, or customise for each option-holder.

In Cake, vesting schedules are clearly set out in a visual format, for both the option-holder and the company to understand at a glance. When an employee is on leave for an extended period of time, Cake has a feature that lets you pause vesting too. Explore for free.

Keeping the team engaged

The Cake platform tracks vesting, and automatically provides updates as vesting events occur.

Cake also notifies the company and option-holders each time a vesting event occurs, so they are always reminded of the options they’re accumulating. A neat way to keep equity top of mind for teams.

Transparency on the Cake platform makes the options feel more tangible, and will avoid you needing to regularly provide updates to option-holders on their vesting status (admin can really take the fun out of sweet treats). Any startup founder can use some help in these areas, which is why the Cake app was conceived.  See for yourself, sign up today.

Vesting FAQs

What is an accelerated vesting?

The Plan Rules set out what happens to unvested options in the case of an exit event. Most Plan Rules contain an 'accelerated vesting’ provision, which provides that in an exit event, all unvested options will automatically vest. The logic here is to disincentivize employees delaying an exit event, to make sure their options have vested first.

What if options do not vest?

If the options do not vest (eg, because an employee does not stay for the entire vesting period), they lapse. This means they can no longer vest nor can be exercised by that option-holder. The lapsed options can be recycled back into the option pool and allocated to new employees, or top-up current employees. There is no need for a ‘buy-back’ for unvested options.

What if the employee leaves?

The Plan Rules may contain general ‘buy-back’ provisions, which give the company the right (but not the obligation) to buy company stock back from employees when they leave the company.

The Plan Rules may set out the price which the Company must pay to buy-back stocks when the employee leaves. The price will be based on the circumstances in which the employee leaves - i.e. whether they are a good leaver or a bad leaver.

The Plan Rules may also clarify what defines a good leaver or a bad leaver, and how the ‘Fair Market Value’ is determined.

What happens if the company is sold or listed?

The Plan Rules will specify what happens to the options if an exit event, like a takeover, occurs. Generally, the way the options are handled will be left to the board’s discretion.

Usually, the option-holder will be provided an opportunity to exercise their options, to become part of the sale or listing as a stockholder.

Alternatively, if the exit event is an acquisition, the acquirer will often choose to cancel the options instead and pay each option-holder the same amount as if they were stockholders. This avoids the option-holders needing to exercise their options, just to be bought out immediately after.

Will the options and stocks be diluted?

Just because an option-holder might be offered options equal to ‘3% ownership’ of the Company at the time the ESO offer is made, it does not mean they will always own 3%. Unless the ESO plan includes anti-dilution rights (which is very rare), the percentage ownership will be ‘diluted’ each time more stocks or options in the company are issued.

For example, if after making the offer, the company does a capital raise and offers new stocks for 20% ownership in the Company to an investor, the potential 3% ownership, has now become 2.4%, and so on. To simulate how your stocks will be impacted, try out our equity dilution calculator.

But this isn’t necessarily a bad thing. Investment generally means the company is on an upward trajectory. Would you rather own 1% of a $100m company or 5% of a $1m company?

The Plan Rules and the United States’s laws may affect the treatment of a sale or listing of a company. Cake’s global legal partners can assist you in understanding the relevant provisions in the United States.

Employee stock options, simplified

Employee stock option plans don't have to be complicated. It can be faster, simpler, and easier -- dare we say it, a piece of cake! 

Our end-to-end platform allows you to plan, create, approve and manage your employee stock options minus the complexity. On average, our solution takes 85% less time and costs 90% less money than the average DIY equivalent, and you can get set up in minutes.

Cake works closely with expert start-up lawyers and accountants around the world. If you want some extra advice, we can put you in touch with one of our partners.

Get started for free

The Exercise

Exercising stock options

Exercising stock options means you’re taking action to purchase shares of the company that has issued you equity, typically through a stock option grant.

How to exercise options

Does an option-holder have to pay to exercise their options?

Usually, an option-holder must pay the exercise price to exercise any options. The Offer Letter will set out the exercise price.

The need to pay an exercise price can confuse recipients. For example, if an option-holder received $25k worth of options as a top-up on their remuneration package, it would not make sense for them to have to pay $25k cash to exercise those options once they’ve vested.

However, it is rare that an option-holder would ever need to do this. Either:

  • the exercise price would be calculated by a valuation method which yields a nominal price per option (i.e., $0.01 per option), or
  • the Option-holder can hold off exercising the options until there is immediate value in doing so (i.e. at an exit event).

If the exercise price is high and the option- holder wants to hold off on exercising the options, they could keep the options as ‘vested options,’ and not exercise them until:

  • an exit event is occurring, and they can be part of the sale or listing as a stockholder, or
  • they will leave the company and the company elects to buy the options back at the increased value. Owning a smaller part of a bigger Cake can be very sweet indeed

Can an option-holder sell the options or stocks?

The Plan Rules will set out all the rules relating to selling Options and stocks. The Plan Rules will often provide an exception to the rule for a disposal to an affiliate, for example, a direct family member, or a family trust.

Big decisions

Why stock options

Why would I do an ESOP instead of issuing shares directly?

ESOPs are the most popular method of granting employee ownership for start-up companies.

Less admin

They require much less admin. Imagine employees are issued stocks up-front, which are then subject to vesting. If the employee does not satisfy the vesting requirements, the company is able to buy those stocks back at a nominal value ($1).

However, if, for example, a company issues stocks directly to 15 employees, and only 5 of those employees satisfy all of the vesting requirements, the company would be required to conduct stock buy-backs for each of the 10 employees where the vesting criteria was not met.

This can be a time consuming process, as it will require members resolutions, buy-back agreements, and updates to your country’s regulator (if any).

Comparatively, ESOPs are less of a headache. If option-holders don’t meet the vesting requirements, the stock options will simply lapse, and can then be recycled into the option pool to be used for further offers. Simple.

No upfront payment

Under an ESOP, the option-holder is not required to pay anything up-front to accept the offer.

Under a direct issue, fair market value must be paid for the stocks on acceptance of the offer. This can sometimes cause confusion and delays, and ultimately might make the offer feel less like a slice of cake and more like a plate of vegetables.

With employee stock options, the option-holder only pays when it exercises the option, and it is often a nominal value.

Exercising FAQs

How many options should I allocate to my team members?

No two companies are the same, so it is important to specifically consider your own staff, and your plans for the next few years.

Above all, every company should keep team incentivization top-of-mind.

  • Size of the pool. A good starting point when thinking about option allocations, is to consider the total sizeof the option pool. For example, if the company has an allowance for a 10% option pool, and it wants to offer options to at least 20 team members over the next couple of years, it clearly needs to take this into account in making the allocations.
  • Valuation of options. It can be useful to work out the value of options by considering how much they’d be worth if they were offered as stocks as part of the most recent capital raising round. This is especially useful where the options are being offered as a remuneration package top-up, as the company can clearly communicate how they decided how many options would be offered, based on the most recent valuation of the company.
  • Role v Time. While option allocations will sometimes vary between roles, it’s more common for them to be based on time spent in the company. For example, the early employees will have higher allocations, and the later employee allocations will be smaller, despite them being in similar roles. Although this isn’t to say late joiners can’t get higher allocations – it all comes down to the specific values of the team member and company goals.
  • Common percentages. It’s quite rare for an employee or contractor to receive more than 1% fully diluted ownership in a company, except where that team ember is a senior hire, or the options are in substitution fora significant salary package. Please keep in mind that where the recipient is an employee, they must be paid at least the minimum salary under the employment laws relevant to your jurisdiction and this salary cannot be substituted with Options in most jurisdictions.

How do I value my company for an ESOP?

Often, a company will initially be valued internally to determine how much equity they want to give to each participant, and then the company will apply the ESOP specific valuation to set the exercise price in compliance with any tax rules.

The United States may have specific valuation requirements for setting the exercise price for an ESOP. It is important that you ensure you use the correct method of valuation to access any available tax concessions. Cake has expert legal and valuation partners in the US who specialise in providing ESOP valuations. Just reach out if you’d like to be connected with them!
The Regulatory stuff

How are stock options taxed

In the US, stock options are either incentive stock options (ISO) or non qualified stock options (NSO).

Under incentive stock options:

  • Grant: There is no tax paid at the time of the grant. Take note that only employees can be granted stock options. Contractors or advisors cannot be granted options.
  • Exercise: No ordinary income tax is incurred at the time of exercise. Instead, the difference between the exercise price and the fair market value of the stock at the time of exercise, also known as the spread, is not immediately taxed. However, it may trigger alternative minimum tax (AMT) implications, which could require the employee to pay additional taxes.
  • Holding Period: To be eligible for potentially favorable tax treatment upon the sale of ISO shares, the employee must hold the stock for a specific period. This holding period begins on the day of exercise and ends on the day of the stock sale. The minimum holding period is typically one year from the exercise date and two years from the grant date. Meeting these requirements may allow the employee to qualify for long-term capital gains treatment.
  • Sale: If the employee meets the holding period requirements, any profit from the sale of ISO shares is taxed as a long-term capital gain. The capital gain is calculated as the difference between the sale price and the fair market value of the stock at the time of exercise. Long-term capital gains tax rates are typically lower than ordinary income tax rates.

Under non-qualified stock options:

  • Grant: There is also no tax paid at the time of the grant. Unlike ISOs, NSOs can be granted to both employees and non-employees, like contractors or advisors.
  • Exercise: When an employee exercises their NSOs, the difference between the exercise price (the price at which the employee can purchase the stock) and the fair market value of the stock at the time of exercise is treated as ordinary income. This amount is subject to federal, state, and local income taxes, as well as Social Security and Medicare taxes (also known as payroll taxes).
  • Holding Period: After exercising the NSOs, the employee becomes a shareholder and may choose to hold the stock for a period of time. During this time, any appreciation or depreciation in the stock's value is treated as a capital gain or loss when the employee eventually sells the stock.
  • Sale: When the employee sells the stock, any difference between the sale price and the fair market value of the stock at the time of exercise is considered a capital gain or loss. This capital gain or loss is subject to capital gains tax rates, which can vary depending on the holding period. If the stock is held for more than one year, it is considered a long-term capital gain and may be taxed at lower rates than short-term capital gains.

It's important to note that tax laws can vary between jurisdictions, and individual circumstances can impact the tax treatment of employee stock options. It's recommended to consult with a tax professional or financial advisor for specific guidance based on your situation.

In the USA, the regulatory requirements will vary from state to state. As always, our expert legal and accounting partners are ready to help you work out which rules apply to your stock option plan.

Cake can help

Simplifying employee stock options

On average, our solution takes 85% less time and costs 90% less money than the average DIY equivalent.

Our ESOP feature allows you to plan, approve, implement, issue and manage your ESOP in minutes. Our recipe? The perfect blend of automation and professional advice from expert partners.

Grow your company, reward your team, eliminate the hassle.

Issuing stock options to anywhere in the world

Download these localized Employee Stock Option Guides in PDF format:

🇺🇸 United States Stock Option Guide

🇦🇺 Australia Stock Option Guide

🇮🇳 India Stock Option Guide

🇮🇱 Israel Stock Option Guide

🇳🇿 New Zealand Stock Option Guide

🇵🇭 Philippines Stock Option Guide

🇸🇬 Singapore Stock Option Guide

🇰🇷 South Korea Stock Option Guide

🇬🇧 United Kingdom Stock Option Guide

This article is designed and intended to provide general information in summary form on general topics. The material may not apply to all jurisdictions. The contents do not constitute legal, financial or tax advice. The contents is not intended to be a substitute for such advice and should not be relied upon as such. If you would like to chat with a lawyer, please get in touch and we can introduce you to one of our very friendly legal partners.

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Cake superhero
Charlie Ross
Chief Operating Officer

Charlie Ross is a founding member and the Chief Operating Officer of Cake Equity. In this role, Charlie takes the lead in ensuring everyone at Cake is happy, healthy, and hungry for more growth!

Before stepping into the COO role, Charlie served as Cake's Legal Counsel, supporting the company through many complex legal matters, drafting legal contracts, and providing legal support to startups across various industries. As Cake transitioned from a boutique law firm to a full-pledged SaaS platform, Charlie played a pivotal role in productionizing our equity offerings, raising capital, and bringing Cake to where it is today. Under his leadership, Cake has been able to focus on product-led growth and help more startups as the company expands into new markets.

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