Why More DocuSign Employees Are Considering Social Security Early — And How Medicare Changes Play a Role
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'DocuSign employees weighing when to file for Social Security should consider both current health care costs and long-term income needs, so they can stay adaptable as retirement unfolds.' — Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement.
'DocuSign employees can benefit from thoughtfully coordinating Social Security timing with health care expenses so their retirement income stays aligned with their evolving needs over time.' — Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.
In this article, we will discuss:
How Social Security filing age affects retirement income.
How Medicare expenses factor into when retirees claim benefits.
Why emotional concerns are shifting filing behavior for many Americans.
Written by Wealth Enhancement advisors Kevin Landis, CPA and Wesley Boudreaux
Advisors in the retirement-income space have long suggested that retirees consider delaying filing for Social Security benefits. For those with a full retirement age (FRA) of 67, waiting until age 70 can result in monthly payments that are around 24% higher.
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And for those with an FRA of 66, the increase if one waits until age 70 is closer to 32%.
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DocuSign employees nearing retirement often hear this same message.
However, new national data indicates a growing number of Americans plan to claim Social Security before age 70. Cost pressures and health care related issues are major influences in this trend.
The Retirees’ Reality
Today’s retirees face a very different environment than those in past decades, including less access to traditional pensions, rising health care costs, and mounting everyday living expenses. In the private sector, only about 15% of workers still have access to defined benefit pensions,
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affecting many households and DocuSign employees.
According to retirement consultant Wesley Boudreaux, 'most retirees are not choosing to claim early for the sake of it.” Instead, rising medical and living costs are driving earlier benefit decisions because of cash flow pressures.
One major factor? Health care. Nearly 39% of out-of-pocket health care spending by Medicare beneficiaries was equivalent to Social Security payments received, on average, in 2022.
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Medicare Advantage: A Key Planning Factor
Additionally, shifts in Medicare Advantage plans have left many retirees unsure about upcoming costs. Benefit structures can vary significantly by year or by region, causing cost surprises that DocuSign workers and their families may need to plan for.
“We are already seeing clients paying more for health care than expected,” said Kevin Landis, CPA. “When medical expenses rise, Social Security often becomes the first lever people pull to handle that burden.”
This is why coordinating Social Security filing decisions with Medicare coverage choices remains important, particularly when plans change annually.
“This is the intersection of Social Security and health care planning,” Landis adds. “Changes in one can influence the other.”
Emotional Considerations Also Matter
Money matters aren’t the only reason retirees claim earlier. Concerns about the future of Social Security have caused many to look for the emotional comfort of taking benefits sooner, including some DocuSign workers preparing for retirement.
While benefits are expected to continue—even if trust fund reserves decline in the 2030s—worries about future payouts can play a role.
“It’s not just about math,” Boudreaux explains. “People want control and stability in retirement, even if that means receiving less over time.”
Finding the Right Approach for You
Whether filing early is a good fit depends a lot on health, cash flow needs, and longer-term retirement goals. Thoughtful planning helps maintain flexibility, rather than driving you to respond under pressure.
“The best approach balances today’s needs with what lies ahead,” Landis says. “And that begins with understanding how Medicare and Social Security interact.”
Need Help Reviewing Your Options?
The Retirement Group, a division of Wealth Enhancement, helps individuals evaluate Medicare electives, analyze Social Security filing alternatives, and design retirement income strategies based on personal goals—including guidance tailored to those employed by DocuSign.
📞 Call (800) 900-5867 before your next enrollment period to schedule a Social Security & Health Care Review.
Work toward confidence in your long-term retirement income decisions.
About the Authors
Wesley Boudreaux and Kevin Landis, CPA, provide retirement income and tax planning guidance through Wealth Enhancement, helping people make informed choices about Social Security, Medicare, and financial well-being.
1. Social Security Administration.
When to Start Receiving Retirement Benefits: Publication No. 05-10147
. May 2024. U.S. Government Publishing Office, Washington D.C.
2. Topoleski, John J., Elizabeth A. Myers, and Sylvia L. Bryan.
Worker Participation in Employer-Sponsored Pensions: Data in Brief and Recent Trends (R43439)
. Congressional Research Service, 18 Sept. 2024.
3. Medicare Payment Advisory Commission.
Report to the Congress: Medicare Payment Policy – Chapter 11: The Medicare Advantage Program: Status Report
. Mar. 2025, medpac.gov/wp-content/uploads/2025/03/Mar25_Ch11_MedPAC_Report_To_Congress_SEC.pdf.
4. Board of Trustees, Social Security.
2025 Annual Report of the Board of Trustees of the Federal Old-Age and Survivors Insurance and Federal Disability Insurance Trust Funds
. 30 June 2025. U.S. Government Publishing Office, Washington D.C.
What is the 401(k) plan offered by DocuSign?
The 401(k) plan at DocuSign is a retirement savings plan that allows employees to save a portion of their paycheck before taxes are taken out.
Does DocuSign match employee contributions to the 401(k) plan?
Yes, DocuSign offers a matching contribution to the 401(k) plan, helping employees maximize their retirement savings.
What are the eligibility requirements to participate in DocuSign's 401(k) plan?
Employees of DocuSign who are at least 21 years old and have completed a specified period of service are eligible to participate in the 401(k) plan.
How can I enroll in DocuSign's 401(k) plan?
Employees can enroll in DocuSign's 401(k) plan through the company's benefits portal during the enrollment period or after meeting eligibility requirements.
What investment options are available in DocuSign's 401(k) plan?
DocuSign's 401(k) plan offers a variety of investment options, including mutual funds, index funds, and target-date funds.
Can I change my contribution percentage to DocuSign's 401(k) plan?
Yes, employees can change their contribution percentage to DocuSign's 401(k) plan at any time, subject to the plan's guidelines.
What is the vesting schedule for DocuSign's 401(k) matching contributions?
DocuSign follows a specific vesting schedule for matching contributions, which typically requires employees to remain with the company for a certain number of years.
Are there any fees associated with DocuSign's 401(k) plan?
Yes, there may be administrative and investment fees associated with DocuSign's 401(k) plan, which are disclosed in the plan documents.
What happens to my DocuSign 401(k) if I leave the company?
If you leave DocuSign, you have several options for your 401(k) savings, including rolling it over to another retirement account or leaving it in the DocuSign plan if eligible.
Can I take a loan against my 401(k) with DocuSign?
Yes, DocuSign allows employees to take loans against their 401(k) balance, subject to the plan's terms and conditions.
With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.
DocuSign provides its employees with a Defined Contribution Plan, specifically the DOCUSIGN, INC. 401(K) PLAN. This plan allows employees to contribute a portion of their earnings to individual accounts, with possible employer matching contributions (Capitalize) (SimpleQDRO). The plan is administered by Vanguard, covering around 2,463 employees as of recent filings (Capitalize).
The DOCUSIGN, INC. 401(K) PLAN is a cash or deferred arrangement under section 401(k) of the Internal Revenue Code, allowing employees to defer part of their compensation in exchange for contributions to the plan. Participants can direct their investments, with default options available for those who do not specify an investment direction (SimpleQDRO).
As for the company's retirement plan, DocuSign does not offer a traditional pension plan. Instead, the focus remains on the 401(k) and profit-sharing elements, where contributions are tied to company profitability (SimpleQDRO). The DOCUSIGN, INC. 401(K) PLAN includes participant-directed accounts and provides options for lump sum withdrawals or rollovers into IRAs (SimpleQDRO). The plan is designed to allow immediate distribution of benefits upon qualification, such as retirement or employment termination.
Restructuring and Layoffs: In early 2024, DocuSign announced a significant restructuring plan due to slowing growth and increased operational costs. The company is reducing its workforce by approximately 10%, affecting various departments including sales and support. This move aims to streamline operations and focus on core business areas. The decision comes as a response to the challenging economic conditions and a shift in the market dynamics which have pressured tech firms to optimize their cost structures. This is important to address given the current economic environment where many companies are reassessing their strategies due to inflation and market fluctuations.
DocuSign offered stock options and RSUs to its employees as part of their compensation package. These were typically available to senior executives and employees at various levels depending on their role and tenure.
DocuSign used acronyms like ISO (Incentive Stock Options) and RSU (Restricted Stock Units) to denote their stock options and equity awards.
Benefits Overview Page: DocuSign's benefits information for employees is detailed on their official website, covering medical, dental, vision insurance, and other health-related benefits. Look for specific terms like “Comprehensive Health Coverage,” “Preventive Care,” and “Mental Health Support.”
Employee Reviews: Glassdoor often provides insights into employee satisfaction with benefits, including specific terms like “401(k) matching,” “HSA (Health Savings Account),” and “FSA (Flexible Spending Account).”
For more information you can reach the plan administrator for DocuSign at 221 Main St, Suite 1550 San Francisco, CA 94105; or by calling them at (877) 720-2040.
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