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Real Estate Sales and Capital Gains Taxes For DocuSign Employees

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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

In recent years, the real estate market has seen a significant rise in property values, leading to an increase in homeowners facing capital gains taxes from the sale of their homes.  CoreLogic reports that in 2023 , approximately 8% of U.S. home sales resulted in profits exceeding $500,000—a stark rise from nearly 3% in 2019.


This $500,000 profit margin is crucial as it ties into a significant tax exemption. Profits from the sale of a primary residence are exempt from capital gains taxes for married couples filing jointly up to a $500,000 ceiling, and $250,000 for single filers. It’s important to note that these exemption limits, set in 1997, have not been adjusted for inflation. The combination of this static threshold and climbing home prices means more homeowners are crossing these limits, triggering capital gains taxes.

Capital gains tax rates on profits that surpass these exemptions can vary from 0% to 20%, depending on the seller's income. In high-cost regions like Colorado, Massachusetts, New Jersey, New York, and Washington, the proportion of properties selling with profits over $500,000 has notably increased in 2023.

To qualify for the capital gains tax exemption, the Internal Revenue Service (IRS) mandates adherence to specific criteria. The 'ownership test' requires that the individual has owned the home for at least two out of the five years preceding the sale. Additionally, the 'residence test' stipulates that the property must have been the seller's principal residence for at least 24 months during that five-year period, which need not be consecutive.


DocuSign employees can reduce their capital gains tax liability by accounting for significant home improvements, which increase the home's 'basis' or original purchase price. It’s crucial to differentiate between mere maintenance and actual enhancements; costs for upgrades like a new roof or an extension can be added to the property's basis, whereas minor repairs cannot.

When a home is sold, details such as the closing date and gross profits are reported to the IRS using Form 1099-S. Homeowners must maintain detailed records of all improvements, as these records are essential in the event of an IRS audit.

Given the current trends in the real estate market, understanding these tax implications and planning accordingly is crucial. This knowledge can significantly influence the financial outcome of a home sale, particularly in a steadily appreciating market.

As retirement approaches, it's vital for DocuSign employees to strategize the timing of their home sales to optimize tax benefits.  A 2022 study by the National Association of Realtors  suggests that selling homes during years of reduced income can help retirees qualify for lower capital gains tax rates. This timing can lessen tax liabilities and fully leverage the exemptions, aiding in a smoother financial transition from an active working life into retirement.

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Discover effective strategies to minimize capital gains taxes when selling your high-value property. Learn how home improvements can increase your tax base and about the exemptions available for earnings up to $500,000 for couples and $250,000 for singles. Familiarize yourself with the IRS's ownership and residency requirements to efficiently manage your tax obligations and secure exemptions. Essential reading for homeowners contemplating a sale or residing in expensive areas.

Like pruning a mature tree, managing a home sale and its associated capital gains taxes requires careful planning. Proper timing and home improvement management can enhance financial outcomes just as strategic pruning fosters tree health and growth, ensuring the financial benefits of the sale are maximized for homeowners, especially those in the DocuSign sector contemplating a post-career relocation.

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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