Startup Company Scaling

Scaling Up? The Challenges Every Start-Up Faces

August 30, 2023

In the ever-evolving landscape of startups and private companies, equity compensation has emerged as a cornerstone for attracting and retaining top-tier talent, and as your company grows, so too must your strategies for talent acquisition and retention. 

While traditional cash salaries still play an undeniable role, the potential for substantial financial gain through equity often becomes a primary motivator for educated employees, with restricted stock units and incentive stock options standing out among the myriad forms of equity compensation. This article delves into the complexities of these equity instruments, highlighting the challenges they present at different stages of a startup company’s life cycle and offering insights into navigating this intricate landscape. 

Understanding Equity Compensation

Before diving into RSUs and ISOs, grasping the broader concept of equity compensation is essential. At its core, equity compensation offers employees a stake in the company's future, aligning their interests with the company's growth and success. This alignment fosters a culture of ownership, where employees are incentivized to contribute their best efforts, knowing they stand to benefit from the company's success. 

RSUs: The Basics

Restricted stock units, commonly known as RSUs, symbolize a company's commitment to grant shares to an employee in the future, usually contingent upon specific conditions such as a vesting schedule. Unlike stock options, however, RSUs don't involve a purchase price. Once they vest, RSUs transform into actual company shares. 

Pros of RSUs:

Simplicity: RSUs demystify equity. There's no need for employees to grapple with exercise decisions or strike prices. 

Immediate Value: RSUs, upon vesting, inherently possess value. This contrasts with stock options, which can be underwater if the stock's current price dips below the strike price. 

Tax Structuring: RSUs offer flexibility in tax structuring, allowing for tax deferral until a liquidity event like an IPO or acquisition materializes. 

Cons of RSUs:

Liquidity Concerns: In the realm of private companies, liquidity is a luxury. Vested RSUs might not be readily convertible to cash, requiring employees to wait until a liquidity event. 

Tax Implications: RSUs bring along tax considerations. Their value, upon vesting, is deemed taxable income, potentially leading to a hefty tax obligation for employees. 

Learn More: NASPP | Restricted Stock Unit Essentials On Demand Course 

ISOs: A Closer Look

Incentive stock options, or ISOs, empower employees with the choice but not the obligation to purchase company shares at a pre-determined price, typically termed the strike price. If specific conditions are met, ISOs will also hold potential tax benefits.  

Pros of ISOs:

Tax Advantages: ISOs, when held for the required duration, can qualify for long-term capital gains tax rates, generally lower than standard income tax rates. 

Strategic Flexibility: ISOs offer employees the autonomy to decide when to exercise their award and obtain ownership of company shares. 

Potential Upside: A soaring company valuation can translate to substantial financial gains for employees, with the gain being the difference between the market value and strike price. 

Cons of ISOs: 

Underwater Risk: A declining FMV can render options worthless if the share price falls below the strike price. 

Cash Commitment: Exercising options will require a cash payment, which may strain some employees financially. 

AMT Pitfalls: A substantial exercise of ISOs can activate the Alternative Minimum Tax (AMT), ushering in potential unforeseen tax liabilities. 

Preferred Shares: An Overview

Beyond RSUs and ISOs, another equity instrument that often comes into play, especially in the context of investors, is preferred shares. Preferred shares, as the name suggests, come with certain preferences over common shares, which are typically held by founders and employees. 

Characteristics of Preferred Shares: 

Dividend Preference: Holders of preferred shares are usually entitled to receive dividends before any dividends are paid to holders of common shares. This ensures that they get a return on their investment before other shareholders. 

Liquidation Preference: In the event the company is sold or undergoes liquidation, preferred shareholders typically get their money back before common shareholders. Depending on the negotiated terms, this can be a multiple of their original investment. 

Conversion Rights: Preferred shares often come with the right to convert into common shares. If the value of common shares rises significantly, this allows investors to capitalize on the company's growth and potentially achieve a higher return on their investment. 

Relevance to Startups:


For startups, issuing preferred shares can be a way to attract investors, especially venture capitalists. These shares offer investors protection and ensure they get a return on their investment before other shareholders. However, for founders and employees, it's crucial to understand the implications of issuing preferred shares, as they can drastically impact the value and rights associated with common shares if not understood properly. 

RSUs vs. ISOs: Tailoring Equity to Your Company's Stage 

Early-Stage Startups: In their beginning stage, startups often operate with limited cash reserves but are flush with explosive potential. Here, stock options, especially ISOs, are the dominant form of equity compensation. They enable startups to dangle the carrot of future financial upside without immediate cash commitments. The inherent tax benefits of ISOs further sweeten the deal for early employees, who might be more amenable to embracing risk for a potentially massive reward. 

Later-Stage Private Companies: As startups blossom into mature entities, inching closer to significant milestones like an IPO or acquisition, the allure of RSUs intensifies. Escalating valuations can make the strike price of fresh ISOs less enticing. RSUs, with their direct ownership proposition and immediate value upon vesting, start to become more potent tools for employee motivation and retention. 

The Broader Picture: Equity Compensation in the Modern Era 

In today's hyper-competitive business environment, talent is the linchpin of success. Companies, especially those in the tech and startup sectors, are engaged in a relentless tug-of-war for top-tier talent. Against this backdrop, equity compensation has emerged as a secret weapon, enabling companies to woo and retain the best minds. 

However, equity compensation isn't a magic bullet. It's a nuanced instrument that requires detailed understanding. Companies must weigh the pros and cons of RSUs, ISOs, and other equity instruments, aligning them with their strategic objectives, financial health, and growth trajectory. 

For employees, the allure of equity is undeniable. The dream of being part of the next big startup, coupled with the potential for life-changing financial gains, is compelling. However, it's crucial for employees to be well-informed. Understanding the intricacies of RSUs, ISOs, and other equity instruments is essential to keeping a motivated and focused workforce. 

In Conclusion 

The world of equity compensation is intricate and filled with opportunities and challenges. The decision between RSUs and ISOs isn't black and white; it hinges on a multitude of factors, including the company's stage, financial health, and employee retention and motivation objectives. Both RSUs and ISOs offer unique advantages, and understanding their subtleties is a must for companies and employees alike. As the equity compensation landscape continues to evolve, staying informed and agile will be the keys to unlocking your company’s potential. 

  • Head shot of Jason Mann
    By Jason Mann

    Content Director