As a financial planner, evaluating job offers for high earners has evolved into an art form that goes beyond calculating the base salary.

While the appeal of perks like free lunches, gym memberships, and in-office catering options is undeniable, these surface-level attractions are often used to distract from an otherwise lackluster package; they’re the cherries on top, not the whole sundae.

Dig deeper, and you'll find that a job offer’s real value lies in its potential for long-term satisfaction and growth. This includes both flashy benefits and more substantial elements like equity compensation, retirement plans, and health insurance. 

Equity compensation, for example, is particularly significant in tech and high-growth industries and can make the difference between someone with a very comfortable financial lifestyle today and someone building multigenerational wealth. 

This guide explores everything you should consider beyond a job offer's salary component, helping you see the bigger picture and make informed decisions that align with your financial goals and career aspirations. 

Equity Compensation

Equity compensation has become a significant part of many compensation packages, particularly in tech and high-growth industries. 

Typical forms of equity compensation include stock options, Restricted Stock Units (RSUs), and Employee Stock Purchase Plans (ESPPs).

Stock options give you the right to buy company stock at a fixed price in the future. Consider the vesting schedule, strike price, and potential for appreciation.

It also helps to cozy up with the tax implications of various types of equity compensation. 

Incentive Stock Options (ISOs) are exclusive to employees and have potential tax benefits. If you hold the shares for at least two years from the grant date and one year from the exercise date, gains can be taxed at the lower capital gains rate rather than as ordinary income. 

This favorable treatment, however, comes with the risk of the Alternative Minimum Tax (AMT) in certain scenarios.

ISOs are often used by publicly traded companies and private companies planning to go public to retain top talent, particularly among executive-level employees. 

Notable examples include large tech companies like Google and Amazon.

Non-Qualified Stock Options (NSOs) can be granted to employees, directors, contractors, and others. Unlike ISOs, NSOs do not qualify for special tax treatments. When exercised, the difference between the exercise price and the stock's market price is considered ordinary income and is taxed accordingly.

These are common in startups and private companies that want to include a broader range of stakeholders in equity compensation plans.

Restricted Stock Units (RSUs) are company shares given to employees as part of their compensation package, which vest over a specified period. 

In the case of companies like Stripe, RSUs may include "double-trigger" provisions, requiring both a vesting period and a liquidity event, like an IPO, before they can be fully realized.

Once vested, RSUs are considered income and are taxed at ordinary rates. The advantage here is that RSUs often provide more value certainty than options, as they don’t require an upfront payment to purchase shares.

Employee Stock Purchase Plans (ESPPs) allow employees to purchase company stock at a discount, often 10-15%. These plans can be a great way to invest in your company, but knowing the tax treatment is crucial. 

Suppose you meet both holding period requirements (holding the stock for two years after the start of the offering period and one year after the purchase). In that case, the difference between the stock's fair market value at purchase and the discounted price you paid (known as the "discount") is taxed as ordinary income. 

Any additional gain above the fair market value at the time of purchase is taxed at the lower capital gains rate, which is generally more favorable than ordinary income tax rates.

Companies like Apple, Microsoft, and Tesla offer ESPPs, encouraging long-term employee investment​.

Bonuses and Incentives

Bonuses are a popular means of sweetening the deal for both parties and, typically, safeguarding an employer from non-performing hires. 

The type of bonus and trigger criteria generally vary per industry and role.

For example, finance careers, such as investment bankers, hedge fund managers, and private equity analysts, frequently offer substantial bonuses tied to individual performance, investment success, and firm profitability.

Software development roles, data scientists, and cybersecurity analysts frequently include bonus structures linked to project completions, product launches, and meeting performance metrics.

Sales roles, on the other hand, often receive bonuses for meeting sales targets or sometimes as a percentage (or specified amount) of each sale. 

Regardless of the role and niche, the best annual performance bonuses are typically tied to clear performance objectives that are within your reach and your locus of control. 

Companies may offer very high-performance bonuses and a slightly lower base salary to incentivize production-heavy roles like sales.

Have a clear picture of what you’re getting into when considering any role with performance bonuses. If possible, review the company’s history of bonus payouts to understand the likelihood and consistency of receiving these bonuses​ and what’s considered a reasonable individual performance target. 

On the other hand, signing bonuses are one-time payments given to new employees when they join a company. These are common for roles with in-demand specialized skill sets and can compensate for benefits the new hire might lose when leaving their previous employer​ or considering an alternative offer elsewhere. 

Retention bonuses are often offered to key employees during transition periods, such as mergers, acquisitions, or going public. These bonuses are typically tied to the employee remaining with the company for a specified period​. 

Retirement Plans Package

When evaluating a compensation package’s retirement plan beyond the basic availability of a 401(k), a few key considerations must be made.

A common 401(k) match percentage formula is 50% of employee contributions up to 6% salary. This means that if an employee contributes 6% of their salary to the 401(k), the employer contributes an additional 3%, effectively offering a 50% return on the employee's contributions up to that limit.

Say you have a $250,000 salary and contribute 6% ($15,000) to your 401(k). Your employer would add $7,500, making a total contribution of $22,500 for the year.

The IRS specifies that employees can contribute up to $23,000 in 2024 and up to $69,000 in combined employee and employer contributions. 

However, reaching the maximum of $69,000 typically involves more than just standard matching, as it often requires additional employer contributions, especially if the employer match is modest.

However, some 401(k) plans allow for after-tax contributions, which are critical for a Mega Backdoor Roth, a nifty strategy for legally contributing larger amounts to retirement accounts over the standard limits. Through a Mega Backdoor, a high earner with an aggressive retirement account strategy could easily contribute beyond their standard contribution and employer match up to the 2024 limit of $69,000. 

You should also understand how long it takes to fully own the employer's matching contributions. Some companies have a cliff vesting schedule (e.g., fully vested after three years), while others use a graded schedule (e.g., 20% vested after each year). 

A shorter vesting period is advantageous if you anticipate changing jobs sooner rather than later.

Review the variety and quality of investment options available within the plan. Look for a diverse range of low-cost index and target-date funds, which can simplify decision-making and reduce fees over time; you don’t need unnecessary high fees eroding your retirement savings. 

If the plan includes company stock options, be cautious about over-concentration in a single stock. 

Diversification is key to mitigating risk, so be sure your retirement plan offers a variety of investment options to avoid excessive risk tied to the company's performance; it’s generally advisable not to hold more than 10-15% of your portfolio in your employer's stock for this purpose.

Lastly, evaluate whether a Roth 401(k) option is available. This option allows for after-tax contributions with tax-free withdrawals in retirement. This can be a very useful tool for tax diversification. 

The Benefits Package: Health, Vision, Dental, Life, and Disability Insurance 

Good health insurance is the standard for high-paying gigs; employers want you to be focused on the job, not worried and distracted by sorting through health insurance plans independently. Due to the company's scale, employers can also negotiate better rates. 

Still, there are a few considerations to make. 

Balance your premiums, or the monthly amount you pay for your health insurance, with other costs like deductibles and out-of-pocket maximums. Lower premiums often mean higher deductibles, leading to more out-of-pocket expenses if you need frequent medical care​. 

The deductible is the amount you must pay out-of-pocket before the insurance starts covering costs. Lower deductibles are beneficial if you anticipate needing regular medical services. The out-of-pocket maximum is the most you will have to pay in a year; after reaching this amount, the insurance covers 100% of additional costs​. 

Companies pay about 70% to 80% of the premium costs, with employees covering the remaining 20% to 30%. The employer's contribution might be lower for family coverage, often covering around 50% to 70% of the total premium cost. 

Comprehensive plans that include medical, dental, and vision insurance are also common. Check if your preferred doctors and hospitals are within the plan’s network. Depending on the plan type, out-of-network care can be significantly more expensive or not covered. 

Some employers offer Health Savings Accounts (HSAs), which provide a triple tax advantage of tax-deductible contributions, tax-free earnings, and tax-free withdrawals. 

Additionally, life and disability insurance helps keep you and your family covered in the case of your death or disability. 

Making Cents of Financial Factors Beyond Salary

The “one company man or woman” is the exception these days; it’s inevitable that you’ll encounter various job offers throughout your career.

Before evaluating job offers in detail, consider the personal and professional development perks that come with the territory. 

Many companies, particularly in the tech and startup arenas, tout their lavish perks— gourmet cafeterias, yoga classes, on-site haircuts, etc.–. While these perks can make the workplace feel like a playground for adults, they do not always indicate a company's long-term investment in its employees.

Always be mindful of your personal financial trajectory. Keep your career aligned with your current lifestyle needs (and, let’s be honest, wants) and retirement demands. 

See the forest for the trees and look beyond the job offer in front of you. Consider the company's stability and growth prospects as your foundation. Is the company a fleeting star or a steady contender? If the equity in your comp package looks great on paper, will it look great at its next possible liquidity event? 

This is exceptionally important for startups– is it a rocket ship, or would it be a high-flying gig for a few months before you need to find a new job? 

Financials aside, the true measure of a job offer lies in its potential for professional growth and long-term satisfaction. 

Whether through continuing education programs or clear career advancement paths, the best opportunities are those that invest in your future as much as you invest in theirs. 

After all, job satisfaction isn't just about today’s paycheck or tomorrow’s benefits; it's about building a sustainable, rewarding career that aligns with your personal and professional goals. 

So, while the perks and bonuses can make the job offer sparkle, make sure the core package provides a solid, enduring glow that pays you what you’re worth (salary and bonuses), gives you skin in the game (equity packages), protects your future (retirement packages), and protects your present (health and other insurances)