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How DocuSign Employees Can Navigate the Great Wealth Transfer and Build a Lasting Legacy

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Healthcare Provider Update: DocuSign offers 100% employer-paid health plans from day one, including medical, dental, and vision coverage. Employees benefit from HSAs, FSAs, and mental health support. The company provides up to six months of paid parental leave, fertility and adoption assistance, and caregiver support. Additional perks include wellness reimbursements, financial planning services, and a 401(k) with matching 7. DocuSign With ACA premiums expected to surge in 2026, DocuSigns fully covered health plans and family-focused benefits help employees maintain coverage without facing steep marketplace costs. Click here to learn more

We are at the cusp of a historic change at a period marked by a major financial revolution called the Great Wealth Transfer.  A stunning $16 trillion is predicted to change hands in the upcoming decade alone, out of an estimated $84 trillion that will be left to Gen Z, Millennials, and Gen X over the following 25 years.  This estimate captures a critical juncture in inheritance and wealth distribution.


But there are difficulties during this time of financial adjustment that DocuSign employees should be aware of. The 'third-generation curse' is a real problem that threatens the continuity of wealth transfer between generations.  According to AMG National Trust figures, this curse indicates that a combination of poor spending and poor management may cause 90% of wealthy families' money to be lost by the third generation.

Families' reluctance to have an honest discussion about estate planning adds to the complex dynamics of wealth transfer.  Even while 98% of U.S. business owners acknowledge having an estate plan in place, a sizable amount (94%) have not shared these plans with their family members, according to research by Brown Brothers Harriman.  Fears about the possible consequences of these conversations are frequently the cause of this lack of communication.

Estate planning, however important, is only the beginning of a process that necessitates constant communication and intentional clarity. Tax planning is certainly vital, but it is not the only component of a successful asset transfer strategy. It is also crucial to articulate the values and objectives that guide these financial decisions. DocuSign employees can reduce the likelihood of misunderstandings and disputes by explaining the 'why' behind estate planning, protecting wealth from being lost to future generations.


It is essential for DocuSign employees to first reflect on and comprehend their own values and how these affect their plans before starting down this path of open communication. This knowledge acts as a lighthouse, directing the development of a values-based estate plan that goes beyond a simple financial transaction to become a legacy infused with the goals and values of the individual.

The discretionary trust, along with a non-binding side letter of desires, is a useful instrument in this process. This strategy permits flexibility while guaranteeing that the beneficiaries and trustee are aware of the underlying intents and values that inform distribution decisions. These letters can specify goals for beneficiaries and provide expectations for the use of trust funds, such as giving priority to paying for education, which helps ensure that beneficiaries have a clear grasp of the trust's mission for future generations.

But sharing the estate plan with family members is the final step in all of this. This stage, which is frequently done piecemeal, entails sharing not only the data and statistics but also the core principles that guided the creation of the strategy. Basic estate and financial planning education can start a conversation and set the stage for more in-depth talks regarding the family's legacy and purposeful asset transfer structuring.

In addition to preparing heirs for their future responsibilities, this dialogic approach gives them the knowledge they need to uphold the family's tradition and ideals. With careful, well-informed planning, it addresses the wider implications of stewardship, responsibility, and the perpetuation of a family's legacy, going beyond the immediate goal of wealth transfer.

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In summary, the Great Wealth Transfer poses a challenge to ensuring that wealth persists and grows, as well as a chance for generational wealth transfer. DocuSign employees may negotiate the difficulties of wealth transfer, stay clear of the third-generation curse, and ensure a legacy that goes beyond material possessions by establishing estate plans based on core values and maintaining open lines of communication. Not only is wealth creation a duty, but money care throughout generations is as well, requiring insight, comprehension, and a dedication to values-driven planning.

One noteworthy feature of estate planning that is especially pertinent to those in their sixties is the deliberate use of charitable contributions as a means of fostering financial responsibility in the next generation. In addition to offering tax advantages, incorporating donor-advised funds or charitable trusts into an estate plan gives families a forum to talk about the importance of money, charity, and the effects of wealth on those outside of the immediate family. This strategy can help break the 'third-generation curse' by encouraging a purposeful and accountable approach to managing inherited money. According to Fidelity Charitable's research from 2021, having charitable conversations with heirs helps them comprehend and respect wealth management concepts, the family's heritage and values for future generations.

With our in-depth research of estate planning tactics, you can uncover the secrets to protecting your family's fortune across many generations. Learn how to steer clear of the third-generation curse, make sure your legacy survives, and negotiate the Great Wealth Transfer. Our in-depth approach addresses the critical functions of values-based planning, communication, and comprehending the intentions behind your estate plan. Find out how to efficiently protect your wealth for future generations, regardless of whether you're a DocuSign retiree or just making retirement plans. Build the groundwork for a long-lasting legacy now so that you can confidently face the future.

When it comes to avoiding the 'Third-Generation Curse,' estate planning is comparable to a seasoned gardener tending to a perennial garden. Just as a gardener chooses plants with care to ensure that they will flourish over time and leave a beautiful and sustainable legacy, so too must those who are nearing retirement or have already retired from DocuSign firms prepare their estate with care. Like watering, pruning, and soil enrichment, this planning entails not only the initial planting—or money accumulation—but also nurturing through ongoing communication, education, and alignment of values with heirs. If such care is neglected, the garden may thrive in the first or second season but may collapse by the third, reflecting the curse of prosperity evaporating through carelessness and lack of direction. But by making careful estate plans, one can make sure that their financial legacy, like a well-kept garden, endures for many generations, bucking the 'Third-Generation Curse.'

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.

*Please see disclaimer for more information

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