How to make thoughtful decisions about health insurance, retirement savings, equity compensation, and the benefits that protect your family’s future.
Open enrollment season is here again. And while reviewing health insurance plans and retirement contributions may not be the most exciting thing on your calendar, it’s one of those annual decisions that can make a meaningful difference in your financial life.
For tech professionals, 2027 open enrollment isn’t just about choosing health insurance. It’s an opportunity to coordinate your retirement savings, equity compensation, tax planning, and family protection.
Your employee benefits may include opportunities to reduce taxes, build long-term wealth, protect your family’s income, and create greater flexibility in your life.
But more benefits don’t automatically mean better financial outcomes.
The goal isn’t to maximize every benefit simply because it’s available. It’s to understand which opportunities matter most for you, your family, and the life you’re building.
Your 2027 Employee Benefits Checklist
Before making your elections, consider these questions:
- Health insurance: Does your plan still fit your family’s anticipated healthcare needs?
- HSA and FSA: Are you taking advantage of tax-advantaged savings opportunities, including limited-purpose FSAs for dental and vision expenses?
- 401(k): Are you receiving the full employer match, and does your plan offer after-tax contributions?
- Disability insurance: Would your benefits cover your family’s spending needs? Can you elect after-tax premium treatment?
- Life insurance: Have you accounted for accelerated RSU vesting and any executive survivor benefits?
- Additional benefits: Are you overlooking educational assistance, legal coverage, wellness programs, or family benefits?
- Charitable matching: Could you make your planned charitable giving go further through employer matching or appreciated-stock donations?
You don’t need to make every possible change. But a thoughtful review can help ensure the benefits you’ve selected still support your financial plan.
1. Health Insurance: Compare Your 2027 Options Before Renewing
It’s easy to leave your health insurance unchanged from year to year. But the plan that made sense last year may not be the best fit for the year ahead.
Start by thinking about what 2027 might look like.
Are you expecting a baby? Planning surgery? Managing an ongoing medical condition? Or is your family generally healthy, with relatively few anticipated healthcare expenses?
These details can change which plan offers the best overall value.
Look beyond the monthly premium. Compare annual premiums, deductibles, copays, coinsurance, prescription costs, and out-of-pocket maximums.
A plan with higher premiums may be less expensive overall if you expect substantial medical care.
Also check whether your preferred doctors, specialists, hospitals, and medications remain covered. Provider networks and prescription formularies can change, even when the plan name stays the same.
HDHP vs. PPO: Which Health Insurance Plan Is Better?
One of the most common questions we hear is whether a high-deductible health plan (HDHP) or a traditional PPO makes more sense.
For someone with relatively predictable, limited healthcare needs, an HSA-eligible HDHP may offer meaningful long-term advantages.
For someone expecting significant medical expenses, a plan with higher premiums but lower costs when receiving care may be more attractive.
There isn’t one right answer.
We encourage comparing the total expected annual cost, including employer HSA contributions, rather than choosing based on the deductible alone.
Read more: HDHP or PPO: Which Health Insurance Plan Is Right for You?
2027 HSA Contribution Limits: Don’t Overlook the Tax Advantages
If you’re eligible to contribute to a Health Savings Account (HSA), don’t overlook it.
HSAs offer three potential federal tax advantages:
- Contributions can reduce taxable income.
- Invested funds can grow tax-free.
- Withdrawals for qualified medical expenses are tax-free.
These tax advantages apply at the federal level. State tax treatment may differ, including in California and New Jersey.
Unlike most Flexible Spending Accounts, unused HSA money can remain in your account year after year. It can also follow you when you change employers.
Coverage | Maximum contribution |
Self-only | $4,500 |
Family | $9,000 |
Additional catch-up, age 55+ | $1,000 |
These limits include employer contributions, and your personal maximum may be lower if you’re eligible for only part of the year.
For eligible households with enough cash flow to cover current medical expenses, investing some HSA assets for future healthcare needs may be worth considering.
Flexible Spending Accounts: Plan for Healthcare Expenses
If an HSA isn’t appropriate or available, a healthcare Flexible Spending Account (FSA) may help reduce taxes on eligible medical expenses.
FSAs generally have use-it-or-lose-it rules, although some employer plans offer a limited carryover or grace period.
Before electing a contribution, review what you realistically expect to spend and whether your employer offers either provision.
Limited-Purpose FSAs: Especially Helpful for Braces and Dental Work
If you’re contributing to an HSA, you may also have access to a Limited-Purpose Flexible Spending Account (LPFSA).
Unlike a traditional healthcare FSA, a limited-purpose FSA generally covers eligible dental and vision expenses while allowing you to continue contributing to your HSA.
This can be especially helpful if you have children who may need braces or other orthodontic work in 2027.
Orthodontic treatment can cost thousands of dollars, and using pretax dollars to cover eligible expenses can create meaningful savings.
Limited-purpose FSAs can also help pay for dental procedures, eyeglasses, contact lenses, and other qualifying expenses.
A few things to consider:
- Plan ahead for larger expenses. If your child is starting braces in 2027, review the orthodontist’s payment schedule and your FSA’s reimbursement rules before choosing your contribution.
- Check your employer’s rules. Limited-purpose FSAs generally have use-it-or-lose-it provisions, although some plans allow a limited carryover or grace period.
- Coordinate with your HSA. Using an LPFSA for eligible dental and vision costs may allow you to preserve more of your HSA balance for future healthcare expenses.
For families anticipating significant dental or vision expenses, this is one of those smaller benefits decisions that can make a meaningful difference.
Dependent Care FSAs: Another Benefit for Families
If you have young children or other qualifying dependents, look into a Dependent Care FSA.
This is separate from a healthcare FSA and may help you pay eligible childcare or dependent care expenses with pretax dollars.
Review how this benefit interacts with the dependent care tax credit, particularly if both spouses work or you have substantial childcare expenses.
2. 2027 401(k) Benefits: Employer Matching, Roth Contributions, and Mega Backdoor Roth Strategies
Your workplace retirement plan may be one of the most powerful wealth-building tools available to you.
But for many tech professionals, the opportunity goes well beyond the standard 401(k) contribution.
Start With the Employer Match
If your employer offers matching contributions, understand exactly how the match works.
Some employers match each paycheck. Others make annual contributions or provide a year-end true-up.
That distinction matters if you’re considering maximizing your 401(k) early in the year.
You don’t want to accidentally miss part of the employer match because of how your contributions were timed.
Traditional vs. Roth 401(k): Which Makes Sense?
Traditional 401(k) contributions generally reduce your taxable income today, while qualified Roth distributions can be tax-free in retirement.
Which option is better depends on your current marginal tax rate, expected future tax situation, and broader financial plan.
For someone receiving substantial RSU income, bonuses, or other equity compensation, traditional contributions may be especially valuable during high-income years.
For someone earlier in their career or temporarily in a lower tax bracket, Roth contributions may be more appealing.
The right choice isn’t necessarily the same every year.
After-Tax 401(k) Contributions and the Mega Backdoor Roth
Many large technology employers offer something that can be particularly valuable for high earners: voluntary after-tax 401(k) contributions.
These are different from Roth 401(k) contributions.
Depending on the plan, they may allow you to contribute beyond the standard employee elective deferral limit, up to the applicable overall annual contribution limit.
If the plan also allows Roth conversions or rollovers, this can create an opportunity commonly called the mega backdoor Roth strategy.
For someone already maximizing their regular 401(k), this may provide additional tax-advantaged retirement savings capacity.
But the details matter.
Employer contributions count toward the overall limit. Plan provisions determine whether after-tax contributions and Roth conversions are available. And the timing of conversions can affect taxes on any associated earnings.
Learn more: Is a Mega Backdoor Roth Strategy Worth It?
Review Your Investment Allocation
Open enrollment is also a useful reminder to revisit how your retirement savings are invested.
Has your stock allocation increased after a strong market year? Are you approaching financial independence? Does your retirement portfolio complement (or duplicate) the exposure you already have through company stock?
You don’t need to make dramatic changes every year.
But your investments should still support your long-term plan.
3. Disability and Life Insurance: Protect Your Income, Equity Compensation, and Family
Insurance isn’t always the most interesting part of a benefits package. But it can be one of the most important.
Your ability to earn an income is often one of your family’s largest financial assets, especially during your working years.
Disability Insurance: Could Your Family Manage Without Your Paycheck?
Many employers offer short-term and long-term disability insurance.
Before assuming you’re adequately covered, review how much income the policy would actually replace.
Pay attention to the replacement percentage, monthly benefit cap, waiting period, benefit duration, and definition of disability.
For higher-income tech professionals, the monthly maximum can be particularly important.
A policy might replace 60% of eligible salary but cap benefits at a level well below your family’s ongoing spending needs. Bonuses or equity compensation may not be included in covered earnings.
An Overlooked Opportunity: After-Tax Disability Insurance Premiums
Some technology companies allow employees to elect to pay their disability insurance premiums with after-tax dollars rather than having the employer pay them on a pretax basis.
Why does this matter?
Generally, when your employer pays disability premiums without including their value in your taxable income, the disability benefits you eventually receive are taxable.
But when premiums are paid with after-tax dollars, the corresponding disability benefits may be received income-tax-free.
That can make a meaningful difference if you ever need to rely on the coverage.
For example, a policy providing $10,000 per month in disability benefits could leave you with considerably more spendable income if those payments are tax-free rather than taxable. However, this potential benefit should be weighed against the additional taxes paid on the premiums, and actual tax treatment will depend on how the coverage is structured.
The tradeoff is that you may pay a little more in taxes today in exchange for potentially better protection if you become disabled.
Not every employer offers this election, and the tax treatment depends on how premiums are funded and administered. It’s worth asking your benefits team whether an after-tax disability premium option is available.
If employer coverage still leaves a meaningful gap, an individual supplemental disability policy may also be worth exploring.
Life Insurance: Think Beyond the Employer-Provided Amount
Employer-provided life insurance is a helpful starting point, but it may not be enough if you have children, a mortgage, or other people depending on your income.
Consider what you would want the coverage to accomplish.
Would it pay off a mortgage? Fund education? Allow your partner to reduce work hours? Provide several years of financial flexibility?
For many families, the right amount is based on those needs – not simply a multiple of salary.
Individual term life insurance may also offer something employer coverage doesn’t: portability.
A personally owned policy can remain in place when you change jobs, and level-term policies can offer predictable premiums for a specified period.
Accelerated RSU Vesting: What Happens to Your Company Stock if You Die?
For tech professionals, life insurance isn’t necessarily the only financial protection available to surviving family members.
Some companies offer accelerated vesting of restricted stock units (RSUs) in the event of an employee’s death.
Depending on the employer and the terms of the equity award, this could mean that some (or even 100%) of your outstanding unvested RSUs vest upon death.
For someone with a substantial equity compensation package, accelerated vesting could represent a significant financial benefit for surviving family members. However, the actual value depends on the employer’s policies, the terms of the equity awards, applicable taxes, and the value of the underlying shares.
Some policies vary considerably.
Some companies accelerate only a portion of outstanding awards, while others offer full acceleration. Certain awards may have different treatment, and the timing of settlement and applicable taxes also matter.
Review your equity award agreements and company stock plan documents to understand what would happen to your unvested shares.
This is especially important when calculating how much additional life insurance your family may need.
Executive Survivor Benefits: An Additional Layer of Protection
Some companies also provide special survivor benefits for executives.
These arrangements may offer a surviving spouse ongoing payments for the remainder of their life, functioning similarly to a lifetime annuity.
For families eligible for these benefits, the potential value can be substantial.
However, these arrangements are often governed by separate executive compensation or survivor benefit agreements.
Eligibility, payment amounts, duration, tax treatment, and whether benefits are guaranteed can vary significantly.
If you’re an executive, review your total compensation package, not just the standard employee benefits guide, to understand what additional protections may be available.
When evaluating your family’s financial security, consider all the resources that may become available if something happens to you: life insurance, disability coverage, accelerated equity vesting, survivor benefits, and your existing assets.
Understanding how these pieces work together can help you avoid both gaps in protection and paying for coverage you may not actually need.
4. Wellness, Legal, and Family Benefits: Look Beyond the Obvious
Some of the most useful employee benefits are the ones people forget they have.
Take a few minutes to review the full benefits guide, not just the health insurance comparison.
Mental Health and Wellness Support
Your employer may provide access to counseling, therapy, employee assistance programs, wellness reimbursements, fitness memberships, or mindfulness resources.
These benefits may help with costs you’re already paying out of pocket.
Legal Services and Estate Planning
Employer-sponsored legal plans can sometimes provide access to attorneys for estate planning, landlord disputes, or other personal legal matters.
If you’ve been putting off creating a will, powers of attorney, or other estate documents, this may be an opportunity to get started.
Just confirm what the plan actually covers. More complex estate planning may require additional services outside the benefit.
Pet Insurance and Other Everyday Benefits
Pet insurance, commuter benefits, adoption assistance, fertility benefits, and family-building support can also be worth exploring.
Not every benefit is right for every household. But knowing what’s available helps you avoid paying separately for something your employer may already subsidize.
5. Educational Benefits: Invest in Your Future Self
One of the most overlooked benefits at many employers is educational assistance.
Some companies reimburse tuition for degree programs. Others support professional certifications, continuing education, language learning, or personal development courses.
If you’re thinking about changing career paths, developing a new skill, or simply exploring something you’ve always wanted to learn, take a look at your employer’s policy.
You may be surprised by what qualifies.
Some programs require coursework to be directly related to your role. Others are considerably more flexible.
Before enrolling, review approval requirements, reimbursement limits, and any repayment obligations if you leave the company.
And remember that career development doesn’t always mean climbing the next rung of the ladder.
Sometimes the most valuable education is the kind that gives you more choices about what comes next.
6. Charitable Giving Tax Changes: What to Know for 2027
New federal tax rules that took effect beginning with the 2026 tax year continue to shape charitable giving decisions in 2027.
If charitable giving is already part of your financial life, check whether your employer offers a matching gifts program.
Many technology companies match eligible employee donations, sometimes up to several thousand dollars annually.
That can meaningfully increase the impact of gifts you were already planning to make.
One important detail: Employer matching programs often require cash donations made directly to eligible charities. Contributions of appreciated stock or grants from a Donor Advised Fund (DAF) may not qualify for the match.
Before making your gifts, review your employer’s matching policy, eligible organizations, annual limits, and submission deadlines.
Cash Donations vs. Appreciated Stock: Two Different Opportunities
If you regularly give to charity, there may be an opportunity to be more intentional about how you give.
Cash donations can be particularly valuable when your employer matches them.
A $2,000 contribution to an eligible charity, for example, could become $4,000 of support with a dollar-for-dollar employer match.
But for larger charitable gifts, especially if you own highly appreciated company stock, contributing eligible shares directly to a charity or Donor Advised Fund may be more tax-efficient than selling those shares and donating the proceeds.
A DAF allows you to make an irrevocable charitable contribution, potentially receive a tax deduction subject to applicable rules, and recommend grants to eligible charities over time.
For eligible long-term appreciated securities, contributing shares directly may also avoid realizing the capital gain you would otherwise recognize by selling them personally.
This can be especially useful for tech professionals who have accumulated substantial gains in company stock following an IPO or other liquidity event.
The goal isn’t necessarily to choose between cash giving and appreciated-stock giving.
It’s to understand which assets make the most sense to give, and how each gift fits into your broader financial plan.
2027 Charitable Giving Tax Changes: What to Know
Beginning with the 2026 tax year, new federal tax rules change how charitable deductions work.
If you take the standard deduction:
You may now deduct up to $1,000 in qualifying cash charitable contributions, or $2,000 if you’re married filing jointly, in addition to your standard deduction.
This creates a new tax benefit for households that don’t itemize.
However, the deduction applies only to qualifying cash contributions made directly to eligible charitable organizations. Contributions to Donor Advised Funds do not qualify for this particular deduction.
For families who already make regular cash gifts, this is an opportunity worth understanding.
If you itemize deductions:
A new limitation applies to charitable giving.
Only the portion of your total qualifying charitable contributions that exceeds 0.5% of your adjusted gross income (AGI) is generally deductible, subject to other applicable limitations.
For example, if your household has $400,000 in AGI, the first $2,000 of charitable contributions would fall below the deduction threshold.
If you contributed $10,000 to eligible charities during the year, generally $8,000 would remain potentially deductible before considering other applicable limitations.
This rule also applies to contributions to Donor Advised Funds.
For households making substantial charitable gifts, the new floor makes it even more important to consider the timing and structure of contributions.
In some situations, combining several years of planned charitable giving into one larger contribution to a DAF may be worth evaluating.
This strategy, often called bunching, can help coordinate deductions while allowing grants to charities to be distributed over time.
For taxpayers in the highest federal income tax bracket, an additional limitation generally caps the federal tax benefit of itemized deductions at 35% rather than 37%.
These changes don’t necessarily mean you should give more or less.
They simply mean that how and when you give may have a greater impact on the tax benefits you receive.
Bringing It All Together
For many tech professionals, a thoughtful charitable giving strategy might include:
- Making qualifying cash donations directly to charities to capture employer matching contributions.
- Taking advantage of the new charitable deduction if you use the standard deduction.
- Contributing eligible appreciated company stock to a DAF when charitable giving is already part of your long-term plan.
- Coordinating larger charitable contributions with unusually high-income years, IPOs, or other liquidity events.
Charitable giving should start with the causes and people you care about.
The tax strategy comes afterward, helping you make the most of the generosity you already intended.
Learn more: Using a Donor Advised Fund for Charitable Giving
7. Your Equity Compensation: One More Benefit Worth Reviewing
If you work in technology, equity compensation may represent a significant portion of your overall compensation.
Although RSUs, stock options, and employee stock purchase plans (ESPPs) are not always part of open enrollment, this is a useful time to review how they fit into your financial plan.
Employee Stock Purchase Plans
If your employer offers an ESPP, understand the purchase discount, offering periods, contribution limits, and rules for selling shares.
Some plans offer meaningful discounts that can create an attractive employee benefit.
But participating also increases your exposure to your employer’s stock, particularly if you’re already receiving RSUs.
Review how much company stock you’re accumulating and whether you have a plan for diversification.
RSUs and Concentrated Stock
RSUs can create significant wealth, but they can also leave your financial future dependent on the performance of one company.
Consider whether your current stock holdings, future vesting schedule, and other investments are appropriately balanced.
A useful question is:
If these shares were cash today, would you choose to invest that much in your employer’s stock?
You don’t necessarily need to sell everything.
But your decision to keep company stock should be intentional, rather than simply the default outcome of receiving equity compensation.
Final Thoughts: Your Employee Benefits Should Work Together
Open enrollment can feel like a series of disconnected decisions.
Which health plan should I choose? How much should I contribute to my HSA? Should I elect additional life insurance? Am I maximizing my 401(k)?
But these choices aren’t really separate.
Your healthcare elections affect your cash flow. Your retirement contributions affect your taxes. Your insurance protects the income supporting your family. And your equity compensation can influence everything from your investment allocation to your estate plan.
The goal isn’t to check every box or take advantage of every program.
It’s to make sure the benefits you’re choosing are supporting the life you’re living now – and the one you want to create.
A little thoughtful attention during 2027 open enrollment can make the rest of the year feel much simpler.
This material is provided for informational and educational purposes only and does not constitute legal, tax, or investment advice. The strategies discussed may not be appropriate for all individuals or situations. Eligibility and suitability depend on your specific circumstances, financial objectives, and current laws, which are subject to change.
Any examples are hypothetical and provided for illustrative purposes only. They do not represent actual client outcomes, and results will vary. You should consult with qualified tax, legal, and financial professionals before making decisions related to the topics discussed.
References to third-party resources or websites are provided for informational purposes only. SeedSafe Financial, LLC does not endorse or assume responsibility for the accuracy or completeness of external content.
SeedSafe Financial, LLC provides tax preparation and planning services for advisory clients; however, this material is for educational purposes only. Transmission of this information does not create a client-preparer relationship. Please consult with your SeedSafe advisor or a qualified tax professional before implementing these strategies.
Advisory services are offered through SeedSafe Financial, LLC, an SEC-registered investment adviser. Registration with the SEC does not imply a certain level of skill or training.
