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Twilio Retirement Roadmap: Creating Income Confidence Beyond the Paycheck

Healthcare Provider Update: Twilio provides health insurance coverage to its U.S.-based employees through partnerships with major providers. Employees can choose from medical, dental, and vision plans, with access to mental health services, fertility benefits, and generous parental leave. Twilio also offers Health Savings Accounts (HSAs) with employer contributions, flexible work arrangements, and wellness reimbursements. Twilio Healthcare costs in the United States are projected to continue rising through 2026, with insurers proposing significant premium increases for Affordable Care Act (ACA) plans. A recent analysis found that ACA insurers are seeking a median premium increase of 15% for 2026, marking the largest hike since 2018. This surge is attributed to factors such as the anticipated expiration of enhanced premium tax credits, rising medical costsincluding expensive medications and increased hospital staysand a shift in the risk pool towards higher-cost enrollees. Without the renewal of enhanced subsidies, out-of-pocket premiums for ACA marketplace enrollees could increase by more than 75% on average. Click here to learn more

'For Twilio employees navigating retirement without the cushion of traditional pensions, income annuities may offer a practical way to structure consistent monthly income, helping to reduce stress around spending and reinforce confidence in long-term planning.' – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

'For Twilio employees transitioning from a savings mindset to spending in retirement, establishing predictable income through annuities can help create a sense of control and clarity, empowering retirees to use their resources with greater confidence.' – Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

How income annuities can help Twilio retirees create a consistent retirement income stream.
Why behavioral finance research shows retirees may spend more confidently with steady income.
The role annuities play in supplementing Social Security and addressing the decline of traditional pensions.

Creating a reliable income stream to support decades of life without a paycheck is a central focus of retirement planning for Twilio employees—not simply accumulating assets. Many retirees face the challenge of balancing lifestyle spending with the risk of running out of resources due to longer lifespans, market fluctuations, and inflation. One popular option is using annuities to help generate regular income. Income annuities, in particular, have been shown to reduce anxiety tied to portfolio withdrawals and support more confident retirement spending.

Studies on Retirement Spending Patterns

For Twilio retirees, shifting from saving to spending can be emotionally difficult. Research from the Retirement Income Institute (RII), ¹ a nonprofit in Washington, D.C., finds that uncertainty about portfolio longevity often leads to overly cautious spending. About one-third of retirees surveyed said they prefer to live off investment earnings alone, without touching principal—even when they have room in their budget for additional expenses like travel or dining.

This cautious mindset is frequently tied to concerns about longevity risk. Even Twilio retirees with large portfolios may feel uneasy without consistent income. According to RII, 60% of respondents said they would feel more comfortable spending if they received an extra $10,000 in annual income, compared to only 40% who favored a $140,000 increase in net worth. This illustrates the emotional and practical impact of consistent cash flow over portfolio size.

Traditional Retirement Income Sources Present Difficulties

In past generations, pensions and Social Security played a larger role in retirement income planning. However, fewer Twilio employees now retire with traditional defined benefit pensions. According to U.S. Bureau of Labor Statistics data, only 15% of private sector workers have access to such plans. ²

Meanwhile, the average Social Security benefit—$2,005 per month as of June 2025 ³ —often does not cover core expenses such as housing and health care.

Delaying Social Security benefits can help raise monthly income. Benefits increase by about 8% for each year postponed after full retirement age (67 for most), with those who wait until age 70 receiving monthly payments more than 24% higher than at 67.

Annuities as an Alternative to Private Pensions

With traditional pensions less common, annuities are gaining attention as a way for Twilio employees to establish consistent retirement income. Michael Finke, co-author of the RII study and professor at The American College of Financial Services, notes that annuities shift longevity and market risks to insurance providers. Fixed income annuities convert a lump sum into scheduled payments for life or a fixed term.

This consistent payment structure can help build confidence. Finke’s findings show retirees with annuities are about twice as likely to use their savings for enjoyment compared to those relying solely on investment accounts.

How Income Annuities Work

An income annuity involves an agreement with an insurance provider to deliver fixed payments in exchange for an upfront premium. Depending on the terms, payments may last for life or a specific period. Twilio retirees often appreciate that this income is unaffected by market performance.

Some common features that add value to income annuities include:

Cost-of-Living Adjustments (COLAs): Designed to align payments with inflation
Cash-Refund Options: Allow a payout to beneficiaries if the annuitant passes before the full value is paid

These features can offer greater peace of mind for retirees who are planning for inflation or family legacies.

Using Income Annuities Wisely in Retirement Planning

For those seeking stable cash flow, income annuities can help fund basic living expenses. Start by identifying which needs—housing, utilities, groceries—are covered by Social Security or other sources. Any gap may be addressed by annuity income.

With core costs accounted for, retirees may use remaining funds more freely for lifestyle choices such as travel, home improvements, or philanthropy—potentially enabling them to enjoy retirement more fully.

Limitations and Considerations

Although annuities offer predictable income, they come with trade-offs. After the “free-look” period, the lump sum invested is generally no longer accessible. This could be a concern for retirees who expect significant one-time expenses.

Additionally, annuity payments depend on the claims-paying ability of the issuing insurer. It’s important to review the strength of the insurer through independent agencies such as AM Best, Moody’s, or S&P Global.

Because annuities can be complex and may involve tax consequences, Twilio employees are encouraged to consult financial professionals who can help structure a retirement plan that integrates annuities, Social Security, and other sources of income.

More General: Spending Confidence and Behavioral Finance

Annuities may offer more than just income. They can act as psychological anchors. Behavioral finance research suggests that predictable income can reduce hesitation around spending. ⁴ For retirees, even those with strong portfolios, the presence of steady payments may reduce worry about depleting their assets.

This predictability may help retirees focus more on enjoying their time—whether it’s with family, traveling, or pursuing goals—rather than closely monitoring their investments.

In Conclusion

Annuities are attracting renewed attention among retirees looking for consistent income and emotional reassurance. In an environment where traditional pensions are rare and markets are volatile, income annuities may help fill essential budget needs.

For Twilio employees, converting a portion of their savings into annuity income may help support consistent lifestyle spending and reduce financial stress in retirement.

Takeaway:

Learn how annuities may reduce the risk of running out of retirement savings, offer predictable payments, and support more confident spending. This article draws from research by the Retirement Income Institute and The American College, comparing annuities to pensions and exploring ways to handle market and longevity risks effectively.

Analogy:

Planning for retirement is like embarking on a cross-country road trip without a precise weather forecast or final destination. Your retirement savings are the fuel, but without a reliable guide, each turn may feel uncertain. For Twilio employees, annuities can serve as the GPS—offering structure, regular updates, and peace of mind. With consistent income to cover the basics, retirees are free to explore life’s scenic routes—whether that means traveling, pursuing passions, or simply relaxing—without constantly checking the fuel gauge.