Your Open Enrollment Checklist for Tech Employees

Open enrollment is your annual opportunity to review your workplace benefits and make sure they still fit your life and finances. This review can be especially important for tech employees since your compensation may include a salary, bonus, employee stock purchase plan (ESPP), stock options, restricted stock units (RSUs), and other equity awards, all of which can affect your taxes, cash flow, and benefits decisions.

Simply repeating last year’s elections may be the easiest option, but it may not be the best one. Changes to your family, your spouse’s benefits, your health needs, your income, or an upcoming equity vesting event can all change what makes sense.

Before you click “submit,” use this open enrollment checklist to review your options and make choices that support both your near-term needs and your broader financial plan.

#1: Review Your Benefits Package

Before you start working through your options, review your employer’s open enrollment materials and make a list of the decisions you need to make. Depending on your benefits package, those may include:

• Medical coverage, including plan type, deductible, copays, coinsurance, provider networks, prescription coverage, and out-of-pocket maximums.
• Dental and vision coverage.
• Health savings account (HSA) contributions, if you choose an HSA-eligible high-deductible health plan.
• Flexible spending account (FSA) contributions for health care and, if offered, dependent care.
• Life insurance, disability insurance, accident coverage, hospital indemnity insurance, and other voluntary benefits.
• Retirement plan contributions, investment elections, and beneficiary designations.
• Employee stock purchase plan (ESPP) enrollment or contribution changes, if your employer handles these elections during open enrollment.
• Beneficiary designations for retirement accounts, life insurance, HSAs, and equity-plan accounts.

#2: Confirm the Enrollment Deadline and Gather Materials

Open enrollment periods are often brief. In fact, the average open enrollment window for a U.S. company lasts just two to four weeks.

To avoid missing the deadline, be sure to add these dates to your calendar:

• The first and last day of open enrollment.
• The deadline for submitting your elections.
• The date your new coverage takes effect.
• Any separate deadlines for HSA, FSA, retirement plan, or ESPP changes.
• Any deadline for updating beneficiaries.

Keeping track of these details is especially important if you work for a company like Amazon, where open enrollment dates may vary by role and location. Keep an eye on your email and the AtoZ app for the enrollment window that applies to your specific facility or region.

You should also start gathering the information you’ll need to compare your options, including:

• Your current benefit elections and payroll deductions.
• Your employer’s new plan-year benefits guide.
• Medical plan summaries and provider directories.
• Prescription drug formularies, if relevant.
• Recent medical, dental, vision, and pharmacy expenses.
• Your spouse’s or partner’s benefit options, if you are comparing coverage.
• Your equity compensation dashboard, vesting schedule, and expected tax obligations.

Keeping everything in one place makes the review much easier.

#3: Compare Health Plans Using Total Annual Cost

You shouldn’t choose a health plan based on the monthly premium alone. Instead, consider your estimated total annual cost, including both premiums and what you may pay when you actually use care.

For each plan, estimate:

Annual Premium + Expected Out-of-Pocket Costs = Estimated Annual Health Care Cost

Then compare the features that can have the biggest impact on what you spend. For example:

• Payroll premiums: How much will come out of each paycheck for employee-only, employee-plus-spouse, employee-plus-child, or family coverage?
• Deductible: How much will you generally pay before the plan begins covering a larger share of your costs?
• Copays and coinsurance: Will you pay a fixed amount for certain services or a percentage of the cost after meeting the deductible?
• Out-of-pocket maximum: What is the most you could pay for covered in-network care during the year, excluding premiums?
• Network access: Are your preferred doctors, hospitals, therapists, and specialists in-network?
• Prescription coverage: Are your regular medications covered, and what copays, tiers, or deductibles apply?
• Out-of-network coverage: How much protection does the plan provide if you need care outside the network?
• Mental health benefits: What does the plan cover for therapy, psychiatry, virtual behavioral health services, and substance-use treatment?
• Fertility, maternity, and family-building benefits: If relevant, review coverage for fertility treatment, pregnancy care, adoption assistance, surrogacy support, and parental benefits.

It can also help to compare each plan under three scenarios: a low-use year, a typical year, and a high-use year. For the high-use scenario, assume your covered medical expenses are high enough to reach the plan’s out-of-pocket maximum.

This gives you a clearer picture of both the everyday cost of the plan and how much financial exposure you would have during an expensive medical year.

#4: Evaluate Whether an HSA-Eligible Plan Makes Sense

Many tech employers offer a high-deductible health plan paired with a health savings account (HSA).

HSAs offer valuable tax benefits: contributions may reduce taxable income, investment growth can be tax-advantaged, and qualified withdrawals for eligible medical expenses are generally tax-free. However, that doesn’t necessarily mean an HSA-eligible plan is the right choice.

Start with the health plan itself and make sure the deductible, coverage, and expected out-of-pocket costs fit your needs. An HSA-eligible plan may be worth considering if:

• You could comfortably cover the higher deductible from savings if necessary.
• Your medical expenses are relatively modest or predictable.
• Your employer contributes to the HSA.
• You want another tax-advantaged way to save for current or future health care expenses.
• You can afford to leave some HSA funds invested for the long term rather than spending them right away.

Take a closer look at the numbers if you expect frequent specialist visits, expensive prescriptions, ongoing therapy, planned procedures, pregnancy-related care, or other significant medical expenses. A high-deductible plan may still make sense, but the potential tax savings should be weighed against the additional out-of-pocket costs.

For employees with equity compensation, an HSA can also play a useful role in your broader tax strategy. A financial advisor who understands stock-based compensation can help you evaluate the tradeoffs and decide how HSA contributions fit alongside your other tax, cashflow, and savings priorities.

#5: Estimate Your FSA Contributions

A flexible spending account (FSA) lets you set aside pre-tax dollars for eligible expenses, but it comes with an important limitation: depending on your employer’s plan, you may forfeit unused funds at the end of the year. Some plans allow a limited carryover or grace period, while others follow a stricter use-it-or-lose-it rule.

Before choosing your contribution amount, estimate what you are likely to spend on. This might include:

• Deductibles, copays, coinsurance, prescriptions, dental care, glasses, contacts, and other eligible health expenses.
• Child care, preschool, day camp, or adult dependent care if you have access to a dependent care FSA.
• Planned procedures, orthodontics, therapy, or vision expenses.

If you previously had access to an FSA, use last year’s spending as a starting point, then adjust for anything you already know will change. If your plan has a use-it-or-lose-it structure, it’s usually better to make a realistic estimate than to maximize your contribution and risk forfeiting money you don’t spend.

You’ll also want to check if contributing to a general-purpose health care FSA can make you ineligible to contribute to an HSA. Some employers instead offer a limited-purpose FSA that can be used for eligible dental and vision expenses while preserving HSA eligibility.

#6: Review Disability and Life Insurance Before Increasing Coverage

Disability insurance can be one of the most important benefits for a working household. Before open enrollment, review both your short-term and long-term disability coverage and ask:

• What percentage of your salary would the benefit replace?
• Is there a monthly benefit cap?
• Does the policy cover bonuses, commissions, or other variable compensation?
• Would the benefits be taxable if you receive them?
• How long is the waiting period before long-term disability benefits begin?
• Does the policy provide partial benefits if you can work only in a reduced capacity?

For tech employees, pay particular attention to what the policy excludes. Many employer disability plans replace only a portion of base salary and may not account for RSUs, stock options, ESPP gains, bonuses, or other forms of variable compensation. If a meaningful share of your total compensation comes from equity or bonuses, your actual income replacement may be lower than you expect.

Review your life insurance at the same time. Employer-provided coverage can be a useful starting point, but it may not be enough if others depend on your income or you share significant financial obligations. Compare your workplace coverage with any individual policies you already have, and check whether the employer coverage is portable if you leave your job.

#7: Review ESPP Elections Alongside Equity and Cash Flow

An employee stock purchase plan (ESPP) can be a valuable benefit, especially if your plan offers a discount or lookback provision. However, increasing your contribution rate also means directing more of each paycheck toward company stock, so it’s important to consider the impact on both your cash flow and overall investment exposure.

Before changing your ESPP election, review:

• How much will be withheld from each paycheck during the offering period?
• Will those deductions make it harder to fund emergency savings, pay down debt, contribute to retirement accounts, or cover upcoming expenses?
• How much company stock do you already own through RSUs, stock options, or previous ESPP purchases?
• Could trading windows, blackout periods, or company policies affect when you can sell?

An ESPP discount can make participation attractive, but it doesn’t remove the risks of holding employer stock. If your salary, unvested equity, and investments are already closely tied to the same company, consider consulting with an advisor who’s familiar with your broader financial situation before increasing your ESPP contributions.

#8: Update Beneficiaries and Account Details

Open enrollment is also a good time to review the beneficiary designations tied to your workplace benefits. In many cases, these designations take precedence over instructions in a will, so make sure they still reflect your wishes.

Review beneficiaries for:

• 401(k)s and other workplace retirement accounts.
• Health savings accounts (HSAs).
• Employer-provided life insurance.
• Supplemental life insurance.
• Deferred compensation plans, if applicable.
• Equity plan accounts, where beneficiary designations are available.

While you’re there, confirm that your address, emergency contacts, and dependent information are current. Pay particular attention after a major life event, such as marriage, divorce, the birth or adoption of a child, or the death of a loved one.

#9: Coordinate Benefits with Your Spouse or Partner

If you and your spouse or partner both have access to employer-sponsored benefits, compare the two plans before making your elections. Putting everyone on the same plan may be convenient, but it’s not always the most cost-effective or comprehensive option.

Compare:

• Premiums for employee-only, employee-plus-spouse, and family coverage.
• Provider networks and whether your family’s doctors and specialists participate.
• Deductibles and out-of-pocket maximums.
• Employer HSA contributions.
• Prescription drug coverage.
• Fertility, maternity, pediatric, therapy, and specialist benefits.
• Any surcharge for covering a spouse who has access to their own employer-sponsored plan.
• Dependent care benefits and how household contribution limits apply.

This comparison can be especially important when one partner receives a significant portion of compensation through equity. RSU vesting, stock option exercises, and ESPP sales can create uneven income and tax obligations throughout the year. In that situation, a plan with more predictable medical costs may be worth considering even if the paycheck deduction is higher.

#10: Partner with Simplicity Wealth Management for a Comprehensive Benefits Review

For tech employees, open enrollment is an opportunity to consider how your workplace benefits fit alongside your equity compensation and broader financial plan. As your income and stock-based compensation grow, the choices you make may have a greater impact on your cash flow, tax strategy, upcoming vesting events, and long-term financial goals.

Simplicity Wealth Management has nearly two decades of experience helping busy tech professionals make sense of equity compensation and the financial decisions that come with it. We can help you weigh your options, understand the tradeoffs, and choose benefits that support the life you’re building. Book a complimentary Simplicity Session to get started.