Getting in the crosshairs of cross-border ESOPs


One of the biggest promises made during elections – US or India- is to make things easier for the common man to have his own business. One-window clearance, ease in obtaining credit and a simplified exit policy are all driving factors that have led to a colossal increase in the number of startups in both countries.

In the US, Delaware is considered the most business-friendly state and is a favorite among start-up owners when it comes to incorporation. Despite the pandemic, Delaware saw an 8.72% growth in the number of LLCs and a 13.97% growth in the number of corporations. Over two-thirds of Fortune 500 companies have their home base in this state! Google, Facebook, Apple, Coca-Cola, GE, and Alphabet are all incorporated in Delaware

Why Delaware?

Delaware is very attractive to investors because of its well-equipped courts that hear only corporate cases.It has a well-established legal system and corporate statutes which offer utmost legal security. It has a multitude of options when it comes to legal representation and legal education. This means that angel investors and venture capitalists would not bat an eyelid before considering an investment. In fact, some angel investors insist that the startup is incorporated in Delaware before they invest because of the straightforward rules.

Creating a Delaware holding company also allows one to do business anywhere in the world. When a non-US company incorporates in Delaware, the US continues to be the main place for receiving venture capital and other financings.

Setting up an ESOP for your Delaware startup

Startups cannot offer high-grade salaries right away. This is why they turn to ESOPs – a way to motivate and incentivize the employees to work harder since they now have ownership. They are also used to attract top talent and this is when ESOPs become the name of the game.

Here are some aspects to be considered before and during setting up an ESOP.

  • When to set up an ESOP? An ESOP should ideally be setup between the pre-seed and the early VC stage. At the pre-seed stage, ESOPs are not necessary but it is helpful to check how much equity is given to early recruits. After the first financing (seed), investors will usually need an ESOP but it can be closed without an ESOP. The first true VC round is when ESOPs will have to definitely be brought into the picture as new hires will seek greater equity. By the Late-VC stage, the ESOP should be standardized.
  • Size of options pool? Around 15% to 20% (some companies go up to 25%). The pool should be big enough to attract and keep the talent, but at the same time not significantly larger than foreseeable needs.
  • Drafting ESOP rules –setting out rules that apply to all options granted under the plan. These rules should include the process of granting options, how and when the employees can exercise these options, what happens if the employee leaves, and what happens in case of an exit event.
  • Approvals – Approvals will be required from the board and the shareholders.The approvals and resolutions that will be made should include details regarding ESOP rules, the number of options in the pool, and authorization to issue shares on an exercise of the options.
  • Granting the options –Each recipient should be sent a grant letter that includes the number of options granted and the exercise price, along with a copy of the ESOP rules. Once the offer is accepted by the recipient, an option certificate should be granted.

According to the Delaware Code, the terms upon which shares may be acquired upon the exercise of options should be stated in the certificate of incorporation, or in a resolution adopted by the board of directors providing for the creation and issue of such rights or options.

The board of directors may authorize 1 or more officers of the corporation to do 1 or both of the following:

  1. designate officers and employees of the corporation or of any of its subsidiaries to be recipients of such rights or options created by the corporation,
  2. determine the number of such rights or options to be received by such officers and employees; provided, however, that the resolution so authorizing such officer or officers shall specify the total number of rights or options such officer or officers may so award.

The board of directors may not authorize an officer to designate himself or herself as a recipient of any such rights or options.

Types of stock options: ISO and NSO

There are two types of stock options:

  1. Qualified Incentive stock options, or an ISO, are reserved for employees. It gives them an opportunity to buy the stock at a discounted price. ISOs are subject to capital gains tax if they are held until one year after exercise and two years after the grant date. The tax, however, is not due until the taxes are filed for that calendar year.
  2. Non-qualified stock options, or an NSO, may go to employees, company partners, vendors, or those that are not on the payroll. Unlike an ISO, an NSO is taxed regardless of whether the stock option is held or sold. The spread is counted as a part of the earned income and taxed at ordinary rates. The taxes are withheld at the time of exercise.

As seen above, the main difference between the two types of stock options is at the taxation level.

The Alternative Minimum Tax (AMT) comes into the picture for an ISO for wealthier taxpayers or when the spread is large. This might cause one to pay more in taxes than he would otherwise. A proper ISO exercise and hold strategy must be devised with the help of professionals to avoid an AMT trap. By choosing an appropriate time to sell the stock, one can avoid the AMT adjustment or simply opt for long-term capital gains tax.

In a nutshell, if the ISO is held and sold in the same calendar year then the ISO gains are taxed as regular income and do not require an AMT adjustment. If it is sold within 12 months but over two different calendar years, then the ISO is taxed as regular income but requires AMT adjustment. The same happens when the shares are sold at least one year after exercise but less than two years after the grant date. If the shares are sold at least one year after exercise and two years after the grant date, then the ISO gains are taxed as long-term capital gains and require adjustment to AMT. Since this is a complicated process, it is suggested that the help of a CFO consultancy service be taken here to avoid paying more than necessary in taxes.

For an NSO, the minimum NSO exercise withholding requirement is 22% for up to $1 million in spread value and 37% if over $1 million. NSO taxes for employees need to be withheld by the employers, but for contractors, they can be given a Form 1099 which implies that they can handle their own payments.

409A valuation

A startup needs valuation to grant ESOP on a tax-free basis.

For a public company, the value is determined by the market. For a private company, it is done by a third-party independent appraiser. These valuations need to be done annually, or if the company has an event such as a fresh round of financing.

It establishes the base price of a company’s common stock i.e. it is the price at which the company’s employees can exercise their stock options.

A 409A valuation is also needed if it is a US company with subsidiaries in India, an Indian company with subsidiaries in the US, or it is an Indian company with employees who are citizens of the US.

A foreign company can issue stock options to employees and directors of their Indian offices (Foreign options). Similarly, an Indian company can offer ESOPs (Indian options) to employees and directors of its holding company or subsidiaries in the US.

The penalties for not complying with 409A when issuing such stock options are severe for the company and for the employees too. Employees will be needed to pay a penalty of 20% and a premium interest tax of 1% above the federal underpayment penalty rate on failed compensation from the vesting date forward. Additional penalties may apply if the income was understated.

Cross border ESOP for Indian subsidiaries

Foreign companies can issue stock options under their ESOP schemes to employees or directors in their Indian subsidiaries as “Foreign Options”. It can be done provided that

  • The Foreign Options are offered globally on the same basis.
  • The Indian subsidiary files an annual return with details like the exercise of aforesaid Foreign Options by its employees.
  • The amount payable on the sale of shares held pursuant to the exercise of Foreign Options by Indian employees is repatriated to India within 90 days.

For Vanilla stock options offered by a Delaware holding company to its Indian employees, according to FEMA, there are no restrictions or monetary limits on the amount that an option holder can remit towards the exercise of Foreign Options provided the foreign holding is not less than 51%.

Foreign Options can also be issued on a cashless basis such that there is no money outflow from India. This Cashless mechanism should be setup clearly in the ESOP plans to avoid breach of contract and foreign exchange laws.

Complexities with cross-border ESOP

A significant part of the issues relating to cross-border ESOPs is related to administrative and compliance issues.

The entire global income of a tax resident of India is taxable in India, irrespective of source. The first trigger of taxation is when the ESOP is exercised and it would be taxed at the hands of the Indian employee as perquisite. At the time of sale, the gains will be considered capital gains and be taxed in India. The only positive side to this is that since India has a DTAA with the US, there will be no double taxation.

The foreign shares that are allotted to an employee are considered as holding foreign assets and need to be disclosed in IT returns by the Indian employee. ITR 2 or ITR 3 needs to be filed and disclosure of shares needs to be made in Schedule FA. This is made more complex due to the difference in filing time of ITRs between India and the US.

To know more about how to register your company in the USA from India, click here.