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Citrix Systems Employees: Strategic Ways to Reduce Capital Gains on Appreciated Stock

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'Citrix Systems employees can benefit from understanding that strategies like a Section 351 exchange, charitable donations, and tax loss harvesting may work together to help manage appreciated stock efficiently while aligning with broader long-term financial goals.' – Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

'Citrix Systems employees should recognize that thoughtful planning with tools such as Section 351 exchanges, gifting strategies, and tax loss harvesting can help them manage highly appreciated stock while supporting both personal and philanthropic objectives.' – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

How a Section 351 exchange can defer capital gains on highly appreciated stock.
Alternative tax-efficient strategies such as charitable donations, tax loss harvesting, and gifting.
The role of inheritance rules, step-up in basis, and combined approaches in long-term tax planning.

A Tax-Aware Q&A on How to Manage Highly Appreciated Stock

From the Section 351 exchange to other practical approaches, this Q&A addresses key considerations Citrix Systems employees may encounter when dealing with highly appreciated shares.

Section 351 Exchange: The Fundamental Approach

Q: What is an exchange under Section 351?
A: Under certain circumstances, an investor may transfer property, such as highly appreciated shares, to a company in exchange for its stock under a provision of the Internal Revenue Code that allows the deferral of capital gains or losses.

Q: What is the primary advantage of exchanging my appreciated stock through a Section 351 exchange?
A: The main advantage is tax deferral. Gains transferred to corporations may be postponed under Section 351, though this applies only if specific diversification requirements are met, especially when transferring to investment companies like exchange-traded funds (ETFs). ¹

Q: What is meant by the “Control Test”?
A: The investor or group of investors who use their portfolio assets to fund the new entity must own at least 80% of the voting power and 80% of the total number of shares of all other classes of stock in the new company immediately after the exchange. ¹

Q: When seeding an ETF, how is the Control Test usually satisfied?
A: It is typically satisfied by either a single substantial investor making a significant asset contribution or multiple investors pooling assets to create a seeding pool for the ETF’s launch.

Q: What is the ultimate tax payment date for the deferred gain?
A: The deferred gain is recognized when the ETF shares acquired through the exchange are sold; distributions from taxable funds must also be reported in the meantime.

Other Tax-Efficient Techniques

Q: What is a straightforward method, aside from a Section 351 exchange, to sell highly appreciated shares without incurring large taxes?
A: Donating shares directly to a qualified charity is one option that some Citrix Systems employees may benefit from.

Q: What tax advantages come with donating valuable stock to a charity?
A: Subject to holding period and adjusted gross income (AGI) limits, you can bypass capital gains taxes on the appreciation and may receive an income tax deduction for the stock’s full fair market value.

Q: What is a Donor-Advised Fund (DAF)?
A: A DAF allows you to donate appreciated stock, receive an immediate tax deduction, and then recommend grants to charities over time, while the assets in the DAF grow without tax impact. ²

Q: Can I give a family member my appreciated stock as a gift?
A: Yes. In most cases, the cost basis from the donor carries over to the recipient.

Q: Why would I give a family member in a lower tax bracket appreciated stock?
A: If they sell the stock, the lower income could result in a reduced capital gains rate, potentially as low as 0% for long-term gains. ³

Tax Loss Harvesting and Other Approaches

Q: What is harvesting tax losses?
A: Selling investments at a loss to offset gains from other sales is known as tax loss harvesting, a strategy sometimes considered by Citrix Systems employees seeking opportunities to leverage bouts of market volatility.

Q: Can I deduct a certain amount of loss from my regular income?
A: Yes. If your capital losses exceed your gains, you can use up to $3,000 per year ($1,500 if married filing separately) to offset ordinary income, with remaining losses carried forward indefinitely. ⁴

Q: What is a Qualified Opportunity Fund (QOF)?
A: A QOF provides investors with tax incentives for investing in tracts of land designated as 'opportunity zones'. Capital gains reinvested in a QOF within 180 days of being realized can be temporarily tax deferred, while QOF investments helpd for at least 10 years may confer a permanent capital gains exclusion. ⁵ That said, 2025 legislation changes may prompt IRS updates to this rule.

Inheritance and Step-Up in Basis

Q: What is meant by a “step-up in basis”?
A: This adjusts an inherited asset’s cost basis to its fair market value at the time of the owner’s death, eliminating capital gains accumulated during their lifetime. ⁶

Q: If I gift shares while living, will I receive a step-up in basis?
A: No. The original cost basis transfers to the recipient without adjustment.

Determining the Right Strategy

Q: What is the best course of action for me?
A: The most suitable approach will depend on factors such as your gain size, income level, charitable intentions, and liquidity needs.

Q: Do any of these strategies call for professional guidance?
A: Yes. Given the complexity of the tax code, working with a qualified financial advisor and tax professional is strongly recommended before implementing these strategies.

Q: Is it possible to combine these strategies?
A: Yes. For example, you might execute a Section 351 exchange on part of your portfolio for tax-deferred rebalancing while donating another portion to a DAF for an immediate deduction.

Q: Is there a loophole in the Section 351 exchange?
A: No. This is a legitimate tax code provision designed for corporate restructuring and adapted for use in the ETF market. It is intended for tax deferral, not permanent tax elimination.

Featured Video

Articles you may find interesting:

Sources:

1. Kitces. ' Using Section 351 Exchanges to Tax-Efficiently Reallocate Portfolios With Embedded Gains ,' by Ben Henry-Moreland and Brent Sullivan. 12 Mar. 2025.

2. Kiplinger. “ A Donor-Advised Fund Can Give Your Charitable Giving a Boost ,” by Samuel Gaeta. 9 May 2024.

3. Internal Revenue Service. “ Topic No. 409, Capital Gains and Losses .” IRS.gov , 8 July 2025.

4. Wealth Enhancement. ' 6 Essential Tax-Loss Harvesting Tips ,' by Jim Wiley. 6 April 2022.

5. Congressional Research Service. ' Tax Incentives for Opportunity Zones ,' by Donald Marples. 26 Apr. 2022.

6. Investopedia. “ Carryover Basis: What It Is, How It Works, Gift Taxes ,” by Julia Kagan. 16 Jan. 2023.

What is the 401(k) plan offered by Citrix Systems?

The 401(k) plan at Citrix Systems is a retirement savings plan that allows employees to save a portion of their salary on a tax-deferred basis.

Does Citrix Systems match employee contributions to the 401(k) plan?

Yes, Citrix Systems offers a matching contribution to the 401(k) plan, which helps employees grow their retirement savings.

What is the maximum contribution limit for the Citrix Systems 401(k) plan?

The maximum contribution limit for the Citrix Systems 401(k) plan is determined by the IRS guidelines, which can change annually.

When can employees of Citrix Systems enroll in the 401(k) plan?

Employees of Citrix Systems can enroll in the 401(k) plan during their initial onboarding period or during the annual open enrollment period.

What investment options are available in the Citrix Systems 401(k) plan?

The Citrix Systems 401(k) plan offers a variety of investment options, including mutual funds, target-date funds, and other investment vehicles.

How can employees of Citrix Systems change their 401(k) contribution amounts?

Employees can change their 401(k) contribution amounts by accessing the benefits portal or contacting the HR department at Citrix Systems.

Is there a vesting schedule for the employer match in the Citrix Systems 401(k) plan?

Yes, Citrix Systems has a vesting schedule for the employer match, which means employees must work for a certain period before they fully own the matched contributions.

Can employees take loans against their 401(k) plan at Citrix Systems?

Yes, employees of Citrix Systems may have the option to take loans against their 401(k) plan, subject to specific terms and conditions.

What happens to the 401(k) plan if an employee leaves Citrix Systems?

If an employee leaves Citrix Systems, they can choose to roll over their 401(k) balance to another retirement account, cash it out, or leave it in the Citrix Systems plan if allowed.

Are there any fees associated with the Citrix Systems 401(k) plan?

Yes, there may be administrative fees and investment fees associated with the Citrix Systems 401(k) plan, which are disclosed in the plan documents.

With the current political climate we are in it is important to keep up with current news and remain knowledgeable about your benefits.

For Citrix Systems, the company offers a 401(k) plan that is known for its matching contributions, which are managed by Fidelity. Employees can contribute a percentage of their salary to the plan, and Citrix matches up to 3% of eligible compensation. This matching contribution makes the 401(k) plan a valuable benefit for Citrix employees, helping them to save for retirement with the company's assistance. Citrix Systems' 401(k) plan does not have a unique name, but it is part of the broader benefits package that includes other retirement and health benefits. To qualify for the 401(k) plan, employees must meet eligibility criteria based on their job classification and tenure with the company. The company ensures that employees are well-informed about these benefits, especially during times of corporate transition, such as the merger with TIBCO, where benefits were a point of assurance for employees. The information regarding the Citrix Systems pension plan is less detailed, as the company primarily emphasizes its 401(k) plan. However, it is clear that Citrix Systems prioritizes maintaining a competitive benefits package, which includes retirement savings options designed to support long-term financial security for its employees

Restructuring and Layoffs: Citrix Systems has undergone significant restructuring in 2023-2024 following its merger with Tibco Software to form Cloud Software Group (CSG). This restructuring included a substantial reduction in workforce, with layoffs affecting up to 15% of its employees globally. These cuts were implemented as part of a broader strategy to streamline operations, eliminate redundant roles, and reduce costs, particularly after the merger. This situation is crucial to address given the current economic pressures and the need for companies to remain competitive amid a shifting political landscape that impacts taxation and investment decisions. The restructuring efforts also included the closure of certain offices and facilities, contributing to the overall reduction in operational expenses (Enterprise Technology News and Analysis) (Enterprise Technology News and Analysis).

Stock Options at Citrix Systems: Citrix Systems offers two types of stock options to its employees: Non-Qualified Stock Options (NQSOs) and Incentive Stock Options (ISOs). NQSOs are the most commonly offered and are available to a broader group, including employees, contractors, and directors. These options provide the right, but not the obligation, to purchase company stock at a fixed strike price, which is determined at the time of the grant. The value realized from exercising these options depends on the difference between the strike price and the market price at the time of exercise. For example, if the strike price is $30 and the stock's market price at the time of exercise is $50, the employee can buy the stock at $30 and either hold or sell it at $50, realizing a profit. However, if the market price is below the strike price, the options might not be exercised. RSUs at Citrix Systems: RSUs at Citrix Systems are granted to employees as part of their compensation package, vesting over a set period, typically linked to tenure or performance milestones. Upon vesting, the RSUs are converted into actual shares of Citrix Systems stock, which the employee owns outright. These shares are typically taxed as ordinary income upon vesting, which can affect the overall financial planning for the employees.

Citrix Systems has been actively involved in enhancing healthcare IT through their technology solutions, which have significant implications for employee health benefits as well. In 2022 and 2023, Citrix focused on improving the healthcare employee experience, particularly in response to industry challenges such as staffing shortages and cybersecurity threats. Citrix's solutions, including Desktop as a Service (DaaS) and secure cloud environments, are designed to support healthcare organizations by enabling flexible work environments while maintaining high levels of data security and compliance with patient privacy regulations. Some of the specific healthcare-related terms and acronyms used by Citrix in their healthcare IT solutions include HIPAA (Health Insurance Portability and Accountability Act) compliance, DaaS (Desktop as a Service), and BYOD (Bring Your Own Device) policies. These terms highlight Citrix’s commitment to providing secure and efficient digital workspaces that cater to the healthcare sector’s unique needs. Recent employee healthcare news related to Citrix includes partnerships with healthcare providers to enhance patient care and reduce IT costs, as well as initiatives to address cybersecurity threats in healthcare environments. Citrix's technology is increasingly being adopted by healthcare organizations to improve both patient outcomes and the work experience for healthcare professionals.

Additional Articles

Check Out Articles for Citrix Systems employees

For more information you can reach the plan administrator for Citrix Systems at 851 W Cypress Creek Rd Fort Lauderdale, FL 33309; or by calling them at (954) 267-3000.

https://www.thelayoff.com/t/1lCxKY4w https://www.thelayoff.com/citrix-systems https://www.theregister.com/2021/11/18/citrix_restructuring_program/ https://www.theregister.com/2023/01/11/citrix_tibco_csg_redundancies/ https://www.thelayoff.com/t/1pJQMnVG https://www.investopedia.com/ https://www.milliman.com/en/ https://www.wealthspire.com/ https://www.harrishealth.org/Pages/retirees-plan-documents-notices.aspx https://www.theregister.com/2022/02/10/citrix_staff_faq_update/ https://thevcfactory.com/employee-stock-ownership-plans-esop-rsu/ https://zajacgrp.com/insights/a-comparison-of-employee-stock-options-vs-restricted-stock-units/ https://www.sofi.com/learn/content/stock-options-vs-rsu/ https://en.wikipedia.org/wiki/Citrix_Systems https://v2cloud.com/blog/true-cost-of-citrix https://www.citrix.com/blogs/2022/01/11/employees-resolve-to-shape-new-future-of-work-in-2022/ https://www.kiplinger.com/taxes/tax-planning/604591/net-unrealized-appreciation-a-hidden-tax-strategy https://www.investopedia.com/terms/n/netunrealizedappreciation.asp https://www.taxfavoredbenefits.com/resource-center/retirement/net-unrealized-appreciation-nua-explained https://bogartwealth.com/nua-strategy/ https://www.bdo.co.uk/en-gb/insights/tax/private-client/pensions-changes-for-2023-24-onwards-how-they-work https://www.pwc.co.uk/pensions/insights/uk-defined-benefit-pensions-survey.html https://mypensionexpert.com/2023/05/19/rising-interest-rates-how-will-they-affect-your-pension-planning/ https://www.business-standard.com/article/technology/desktop-virtualization-firm-citrix-begins-layoffs-thousands-impacted-123011100371_1.html https://www.sunsethq.com/layoff-tracker/citrix https://www.thelayoff.com/citrix-systems