Stock FAQs

when should i ask for stock options

by Jacklyn Gaylord Published 3 years ago Updated 2 years ago
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When negotiating stock options, ask if the company has a standard scale. That scale typically means that those on the executive level (CEOs, CFOs, COOs, CIOs, the VPs) will be given a much greater amount of stock options than a person coming into the company at a middle management role.

Tips to consider when asking for stock options
If the company seems like it's growing at a steady pace, then you may consider taking out a higher number of shares. Though, if the company seems like it's not growing, or if it even appears to be shrinking in size or financial value, you may pass on stock options.
Apr 26, 2021

Full Answer

What should I consider when asking for stock options?

Here are a few tips to consider when asking for stock options: When asking for stock options, it's important to consider the future of the company. If the company seems like it's growing at a steady pace, then you may consider taking out a higher number of shares.

When should you buy puts on stocks?

As another example, if you are an aggressive investor who likes long shots and is convinced that the markets are headed for a big decline within six months, you may decide to buy puts on major stock indices. 6. Establish Parameters

Are stock options a good idea for start-ups?

But in the world of start-ups, enough people got very wealthy from stock options that they remain a great tool for attracting early-stage talent. There are a variety of reasons employers want to offer stock options. Discounted company stock can increase a loyal employee’s compensation without hurting profits.

What is a stock option and how does it work?

A stock option gives an employee the ability to buy shares of company stock at a certain price, within a certain period of time. The price is known as the grant price or strike price, and it’s typically based on a discounted version of the price of the stock at the time of hire.

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When should I buy my options?

High Certainty Of Growth. Startups are usually loss making. But if there is a high certainty of growth with a proven business model that will allow the company to eventually make a profit, then it's probably a good idea to buy your options. You should know better than most how well your company is doing.

When should you start exercising stock options?

Generally speaking, if your startup does well, it's better to exercise your options as they vest. We'll go into the two main reasons why - tax treatment and cash flow – but the quick-and-dirty answer is that if you trust your startup to grow, you're better off exercising your stock options as soon as you can.

Can I ask for stock options in a job offer?

Always negotiate your base salary before you discuss other types of benefits, like stock options. That's because companies typically have a framework for stock options that they offer to employees at certain levels in the company. When negotiating stock options, ask if the company has a standard scale.

Should I take stock options or higher salary?

The better strategy with stock options Stock options are an excellent benefit — if there is no cost to the employee in the form of reduced salary or benefits. In that situation, the employee will win if the stock price rises above the exercise price once the options are vested.

How much stock options should I ask?

Stock Price If the company is planning new financing in the near future, ask what the expected price per share will be--and then discount it a bit, because it hasn't happened yet. If you're pretty certain that it's going to happen soon, discount it 10 percent. If it seems less certain, maybe use 20 percent.

Do I pay taxes when I exercise options?

You have taxable income or deductible loss when you sell the stock you bought by exercising the option. You generally treat this amount as a capital gain or loss. However, if you don't meet special holding period requirements, you'll have to treat income from the sale as ordinary income.

How do I ask my boss for stock options?

How to ask for stock options in a job offerEvaluate what the discount is. ... Find out about the most recent appraisal. ... Determine the type of stock options offered. ... Negotiate salary. ... Learn the company's guidelines for stock options. ... Request your employer to write a contract.

Are employee stock options worth it?

How much your stock options are worth hinges on how much you bought them for at the discounted rate, and how much you sold them for. If a company is growing and the stocks are rising in value, then your stock options will be worth more than you paid for them.

Why do employers offer stock options?

Stock options are a popular way for companies to build a strong relationship with employees and to motivate them to work hard in the interests of the company. Stock options are also a way to encourage employees to stay and not be tempted to leave and work for a competitor.

Can stock options make you rich?

Since an option contract represents 100 shares of the underlying stock, you can profit from controlling a lot more shares of your favorite growth stock than you would if you were to purchase individual shares with the same amount of cash. When your chosen stock flies to the moon, sell your options for a massive profit.

Can company stock options make you rich?

Employee stock options are contracts which give you the right to buy a set number of shares of the company's stock at a specific price over a finite period of time. “If they substantially grow in value, they're an awesome way to create wealth,” says FlexJobs CFO David Hehman.

How do you ask for equity in a job offer?

How to negotiate equity in 9 stepsResearch the company. ... Review the company's financial potential. ... Research similar companies. ... Read the offer carefully. ... Evaluate the terms of the offer. ... Address your needs and the company's needs. ... Speak with the employer during negotiations. ... Keep your negotiations focused.More items...

What is authorized option?

Authorized options include those which have not yet been granted. In order to calculate your potential future dilution, estimate the number of additional options that will be authorized and added to the option pool. The size of a startup’s option pool will vary, depending on its maturation.

What does it mean when an option pool is significantly below this range?

If an option pool is significantly below this range, it may be an indication of either; (i) a company that is stingy with its options, or (ii) significant future dilution may occur, once the option pool is increased to accommodate future option grants.

How big is a startup option pool?

However, the pool’s size, as a percentage of a company’s Total Capitalization, is generally between 15% and 20% at a company’s maturity.

How long do shares vest?

In most cases, your shares will vest over a four-year period, with a one-year cliff. Under such an arrangement, if you leave your company within the first twelve months, for any reason, you will not vest any shares. Once you have completed your first anniversary of employment, vesting usually occurs on a monthly basis.

Can a company increase its option pool?

It is very common for companies to increase their option pool over time and a well-run company will manage a capital budget as a means of estimating its future option grants. As such, it is very reasonable to ask for an estimate of additional options to be authorized before the company’s exit.

How long do you have to exercise options after leaving a company?

Typically you’ll get 90 days or 3 months to make the decision after leaving.

How many options are in an RSU?

A rule of thumb is that an RSU is worth about 3 or 4 stock options (in the tech industry).*. If the company is offering you an equal number of RSUs and options, RSUs are probably the right choice. If the ratio is less favorable to RSUs, then you’ll have to think through these other pros and cons to make your decision.

What is an RSU option?

Because an RSU is basically just a stock option with a $0 strike price, and a stock option is always going to have a strike price higher than $0. (Though, in early stage startups, sometimes not that much higher!) The lower the strike price, the less you have to pay to own the same one share of company stock, the better.

Do RSUs gain more than options?

Both RSUs and options benefit equally from the stock price increasing, it’s just that usually companies offer many times more options than RSUs, so you’d enjoy those stock price gains across more shares of stock.

What is stock option?

Basically, a stock options give employees the right to buy a pre-specified amount of shares in the company over a certain timescale at a pre-determined price, which is generally lower than the price offered to investors. You’re sitting down to a salary negation, and you’re offered a stock option plan. Don’t sweat it – just ask the right questions: ...

How long do you have to leave a contract before the cliff vesting?

Also ask about cliff vesting – often if you leave before the “cliff” your contract specifies (let’s say the cliff is one year, and you leave after six months ), then you don’t get to exercise any of the stock options. 9 Things to Never Say in a Salary Negotiation. 3.

Can you extend vesting if you are laid off?

In some cases, the company you currently work for may allow you to accelerate your vesting schedule if the company is acquired. They may also offer extended vesting if you are laid off during the acquisition. Be clear about what would happen in this scenario so that you’re not stuck later down the line.

Why do companies offer stock options?

There are a variety of reasons employers want to offer stock options. Discounted company stock can increase a loyal employee’s compensation without hurting profits. Vesting programs can help build longer-term loyalty among employees. The sense of shared ownership can foster a strong corporate culture.

What is stock option?

A stock option gives an employee the ability to buy shares of company stock at a certain price, within a certain period of time. The price is known as the grant price or strike price, and it’s typically based on a discounted version of the price of the stock at the time of hire. Purchasing the stock shares at the grant price is known as exercising ...

What is it called when you buy stock at the grant price?

Purchasing the stock shares at the grant price is known as exercising your options. Employees who exercise their options and sell their shares when the company’s stock is trading significantly higher than the grant price have the potential to make a lot of money. For example, say you have the option to buy 5000 shares at $10 and sell ...

What happens if the stock price is lower than the grant price?

If the stock price is trading lower than the grant price, the options are said to be underwater. Exercising options is useless if the employee can buy shares of the company stock for less on the open market.

Why do employees have stock options?

For employees, stock options can result in tremendous wealth, particularly if you join the company at an early or growing stage.

Is stock option good?

All else being equal, stock options are generally a great perk. While they offer the potential to amass great wealth, however, there’s also the potential for frustrating disappointment. If you accept a job with stock options, it is helpful to ask the human resources representative if there is any guidance or advice to help sort out stock options ...

Do stock options expire?

Stock options have expiration dates and will be worthless if held too long. But deciding when to exercise before the options expire can be difficult as well. One camp says hold out as long as you can, waiting for the pinnacle price. On the other hand, you may risk waiting too long and miss the peak, or else exercise too early and miss more growth.

What is a participating preferred stock?

Participating preferred – Participating preferred comes with a set of terms that increase the amount of money preferred holders will get for each share in a liquidation event. Participating preferred stock places a dividend on preferred stock, which trumps common stock when a startup exits.

Can common stock make you rich?

Common stock can make you rich if your company goes public or gets bought at a price per share that is significantly above the strike price of your options. But most employees don't realize that common-stock holders only get paid from the pot of money left over after the preferred stockholders have taken their cut.

How to pick a specific option?

The six steps follow a logical thought process that makes it easier to pick a specific option for trading. Let's breakdown what each of these steps involves. 1. Option Objective. The starting point when making any investment is your investment objective, and options trading is no different.

What are options used for?

Establish Parameters. Options can be used to implement a wide array of trading strategies, ranging from simple buy and sells to complex spreads with names like butterflies and condors. In addition, options are available on a vast range of stocks, currencies, commodities, exchange-traded funds, and futures contracts.

What happens if a stock is above $33.01?

If the stock is above $33.01 at expiration, it is in-the-money, has value, and will be subject to auto-exercise. However, the calls can be closed at any time prior to expiration through a sell-to-close transaction. Note that the strike price of $33 is 8% higher than the stock’s current price.

How to find the right option?

Finding the right option to fit your trading strategy is therefore essential to maximize success in the market. There are six basic steps to evaluate and identify the right option, beginning with an investment objective and culminating with a trade. Define your objective, evaluate the risk/reward, consider volatility, anticipate events, ...

What is the first step in trading?

Your first step is to formulate what the objective of the trade is, because it forms the foundation for the subsequent steps. 2. Risk/Reward . The next step is to determine your risk-reward payoff, which should be dependent on your risk tolerance or appetite for risk.

How long before an option expires?

This is the number of years before the option expires. It's often 10 years. For the purpose of this valuation, I would just use the vesting period--four years in most cases, but you should confirm with the company.

What percentage to use after Series B?

After Series B, use 80 percent. For later rounds when a company is doing well, 60 percent. You might need to interpolate depending on the risk and the stage. Just keep in mind that the volatility is a proxy for risk, which is correlated with upside.

What is the best underlying instrument for option traders in terms of bid-ask spreads?

Slippage can add up, so it’s best to focus on high liquidity stocks and options with tight bid-ask spreads. SPY is the best underlying instrument for option traders in terms of bid-ask spreads. Less liquid stocks can have wide spreads which can result in significant slippage.

Why is it important to check the bid-ask spread?

Why Is It Important. When looking at a particular instrument for trading, it is important to check the bid-ask spread. Wide spreads can increase the costs of trading in that instrument via something referred to as “slippage”. Slippage just means not getting filled at a good price.

What is the difference between a bid and ask price?

For any financial instrument, be it a stock or an option, there is a bid price and an ask price. The bid price is the best (highest) price someone is willing to buy the instrument for. The ask price is the best (lowest) price someone is willing to sell the instrument for. Makes sense if you think about it.

When will bid ask spreads widen?

Bid-ask spreads will widen when volatility picks up and the market starts moving quickly. From mid-February 2020 to late March 2020 volatility experienced a huge spike amid the coronavirus pandemic. The VIX index jumped from around 14 to 85 in the space of a few weeks.

Do at the money and out of the money put have a tight spread?

It’s a similar story with the puts where the at-the-money and out-of-the-money puts have a tight spread, but the in-the-money spreads start to blow out. One point worth noting here is that the very far out-of-the-money options will naturally have a tighter spread.

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