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When Wealth Moves Sideways: What Horizontal Transfers Mean for DocuSign Households

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'DocuSign employees should treat the first spouse’s death as a bracket stress test—model RMDs early, pace Roth conversions, engage both partners, and coordinate with tax and legal professionals before surprises hit.' — Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement.

'For DocuSign employees, charting how assets shift to a surviving spouse can reduce unexpected surprises. Talking to qualified tax and estate advisors can help.' — Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

  1. The horizontal transfer of wealth between spouses and its growing impact on estate planning for DocuSign families.

  2. The tax implications of Required Minimum Distributions (RMDs) and strategic Roth conversions to manage income brackets and help preserve assets.

  3. The evolving role of charitable giving and spousal financial engagement in shaping effective multi-generational legacy plans.

Major wealth transfers are anticipated over the coming decades. By 2045, more than $84 trillion is expected to change hands—$11.9 trillion to charities and $72.6 trillion to heirs and family members 1 —and many of those dollars will first move “across” to surviving spouses rather than straight “down” to children.

Because women often live longer than men, a sizable share of assets may shift laterally to widows before any vertical bequests occur, a point stressed by Wealth Enhancement senior wealth advisor Mike Corgiat. This is important for DocuSign retirees with sizable IRAs to note. 

Pre-boomer generations are projected to pass $15.8 trillion in the next decade, while baby boomers may transfer nearly $53 trillion 1 —frequently after the first spouse dies—illustrating how wealth rarely travels in a clean vertical line. 

This horizontal detour has real implications for required minimum distributions (RMDs), retirement savings, and estate tax exposure that can affect DocuSign employees late in retirement.

Current rules require RMDs to begin at age 73 for those born 1951–1959 and at 75 for those born in 1960 or later, and a surviving spouse can often roll an inherited IRA into their own to delay distributions—sometimes compressing taxable income into fewer years.

Brent Wolf, a retirement income planner with Wealth Enhancement, notes that once RMDs start and the survivor files as single, identical withdrawals can land in higher brackets—an issue that can surprise a survivor when income sources are already shifting.

Strategic Roth conversions while both spouses are alive—often in the 60s or early 70s—may help trim future RMDs and give the survivor more control, a tactic many DocuSign retirees may want to evaluate while they still benefit from joint tax brackets.

Corgiat emphasizes that conversions executed at comparatively lower rates can lessen the tax hit on both the survivor and heirs, while Wolf adds that thoughtful timing lowers the odds of large, forced taxable withdrawals later—key considerations for DocuSign employees eyeing estate efficiency.

Philanthropy is shifting too, as more affluent families embrace “living legacy” giving so they can witness impact, but a sudden asset windfall can delay or confuse charitable intent if the less-involved spouse isn’t already engaged in the broader plan. 

Wolf recommends that spouses who haven’t driven the finances start participating early, since many women may ultimately steer multimillion-dollar portfolios and will benefit from hands-on experience before the transfer moment arrives. 

Coordinated planning across tax, investment, and estate disciplines can answer pivotal questions for DocuSign retirees: How large might RMDs become with only one personal exemption? Would spreading Roth conversions over several years keep income in more favorable brackets? Are beneficiary designations current on retirement plans and insurance? Do charitable goals call for donor-advised funds, qualified charitable distributions (QCDs) from IRAs, or a family foundation? Has the estate been reviewed for credit shelter or portability strategies and potential federal or state estate taxes?

The death of the first spouse often triggers the most dramatic ownership and tax changes, so acting earlier—stress-testing single-life cash flows, harvesting gains or losses, accelerating withdrawals in low-income years, and reviewing insurance and titling—can materially influence outcomes for DocuSign retirees.

Those headline numbers—$84.4 trillion overall, $72.6 trillion to heirs, $11.9 trillion to charities—signal the size of what’s coming, but the net amount that actually arrives depends on how transfers occur and which tax rules apply, especially for families with layered benefits and investments.

As this horizontal phase of wealth transfer approaches, DocuSign employees may benefit by preparing actively to pass the baton to a suriving spouse.

SEO Snapshot / Keywords (keep for internal use or meta purposes):  estate tax preparation; IRA rollover regulations; widow inheritance; RMD age 73–75; Roth conversion strategy; wealth transfer 2045; horizontal wealth transfer; charitable giving in retirement; DocuSign retirement planning; DocuSign retirement benefits.

Analogy:  Picture a family’s wealth as a relay baton on an L-shaped track headed toward a $84.4 trillion finish line—$72.6 trillion earmarked for heirs and $11.9 trillion for charity—and the baton must first take a sideways turn between spouses, a reality many DocuSign couples will face before assets sprint down the straightaway to children and philanthropy.

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Sources:

1. Cerulli Associates. “ Cerulli Anticipates $84 Trillion in Wealth Transfers Through 2045 .' 20 Jan. 2022.

2. MassMutual. “ The horizontal wealth transfer: Redefining women’s wealth ,” by Shelley Gigante, 10 Mar. 2025.

3. MarketWatch. “ When a spouse dies, there can be a ‘tax explosion’ for the one left behind ,” by Beth Pinsker, 18 Jan. 2025.

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).”
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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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