5 Offer Letter and Stock Option Secrets CEOs Don't Want You To Know

leadership sales consulting for startups sales leadership startups women in leadership Nov 16, 2023

Navigating the intricacies of stock options is akin to deciphering a complex code, especially when you're at the negotiating table with an offer at hand from a startup. As a Sales Leader, understanding the nuances of stock options can significantly impact your financial gains and overall job satisfaction. Here are five crucial secrets that many CEOs might not openly share but are instrumental in shaping a favorable offer:

1. Fully Diluted Outstanding Shares Matter

The number of shares in your offer may not be as critical as the percentage of the company you own. Fully Diluted Outstanding Shares represent the total common shares available for trading. Knowing this percentage provides clarity on your stake in the company and is vital for evaluating the true value of the stock options offered.

2. Early Exercise Clause: A Tax-Saving Strategy

An often overlooked aspect is the presence of an early exercise clause in the stock option grant. This clause allows you to exercise all your options, even the unvested ones, potentially saving a substantial amount in taxes, particularly if you file an 83b election. If you have the financial means and a low strike price, this can be a strategic move.

3. Pre-Negotiate Severance: Safeguard Your Future

This one isn't about stock options but should be a non-negotiable part of your job offer. Sales leadership roles at startups can have an average tenure of around 18 months. Considering the volatile nature of these positions, it's wise to pre-negotiate your severance. Having a clear agreement in place can act as a financial safety net in case your journey with the company takes an unexpected turn.

4. Negotiate Change in Control: Protect Your Investments

Understanding the implications of a change in control is crucial. If the company undergoes an acquisition while you're still in the vesting period, your unvested stock options could be at risk. Risk of being worth NOTHING. Negotiating to have all unvested options vest upon a change in ownership control safeguards your financial interests. Also research a concept known as "Double Trigger." You're likely to be offered this which would be fine too as a fall back negotiating position. 

5. Qualification for QSBS: Tax Efficiency for Startup Success

In the context of early-stage tech startups, the qualification for Qualified Small Business Stock (QSBS) can be a tax game-changer during a liquidity event. This qualification offers favorable treatment for capital gains if specific requirements are met by both the investor and the company. Understanding and ensuring QSBS qualification can lead to substantial tax savings.

Empowering Sales Leaders for Financial Success

These secrets are not just financial jargon; they are the keys to unlocking a Sales Leader's full potential for financial success in the early stage startup world. Acknowledging these aspects can not only impact your current negotiations but can also pave the way for a more secure financial future.

Empower Yourself: Ask the Right Questions

To empower Sales Leaders further, I've compiled a comprehensive list of questions crucial for evaluating a leadership position. These 16 Smart Questions can guide you in making informed decisions about your next Sales Leadership role. Download them here.

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