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Tax-Efficient Executive Benefits: Strategies for Financial Optimization

March 18, 2024, by New City Insurance

business people working in office, top viewStrong executive leadership can help propel companies forward and drive organizational growth. It’s important to optimize executive benefits and compensation packages to ensure that great executives don’t stray.

Navigating the complex landscape of tax-efficient executive benefits can be overwhelming, but help is available to achieve financial optimization.

Let’s delve into the key components of executive benefits and how to build a sought-after benefits package.

Stock Options and Equity Grants

Equity compensation differs from traditional cash-based compensation as full equity ownership is not awarded until after the vesting period. Shares can be purchased or sold once certain requirements are met and the vesting period has passed. Depending on the type of equity, the owner may be liable for taxes.

There are three main types of executive equity grants, including:

  • Restricted Stock: The two types of restricted stock include restricted stock awards (RSAs) and restricted stock units (RSUs). With RSAs, a person is awarded stock when they join an organization and become an immediate shareholder. For RSUs, an employer promises to provide shares of the company’s stock on a future date if certain conditions are met.
  • Performance Shares/Units: This equity grant is usually only available to executives. They typically align with performance and are designed to incentivize executives to achieve strategic goals and boost shareholder value.
  • Stock Options: With stock options, executives can buy a certain number of shares at an agreed-upon cost at a future date once vesting has passed. Common types of employee stock options include NSOs and ISOs. NSOs tend to be restrictive in terms of eligibility, while ISOs are generally more tax-favorable.

Stock Options and Equity Grants – Tax Implications

Tax implications relating to equity grants and stock options depend on the executive equity grant type. For RSAs, a person is taxed at the time of the grant and sale, and with RSUs, income tax is charged at vesting and capital gains tax (CGT) at purchase.

Performance stock awards (PSAs) and RSAs have similar tax events, whereas RSUs and performance stock units (PSUs) have similar tax events.

For NSOs, tax implications include ordinary income tax at exercise and CGT at sale. For ISOs, there is no income tax for the regular tax exercise. However, there may be an Alternative Minimum Tax (AMT) due.

Executive Benefits Strategies for Favorable Tax Treatment

senior manager working with executive assistantQualifying contributions occur when individuals hold shares for a minimum of two years following the grant date and a minimum of one year following the exercise date.

After this period ends and the stock is sold, long-term capital gains on the gain can be acquired. The gain refers to the sale price minus the grant price multiplied by the number of sold shares.

Deferred Compensation Plans

Executive deferred compensation plans enable employers to defer a portion of their executives’ income to allow them to pay taxes on it at a future date when they begin withdrawing from it.

By contributing to an executive contribution plan, an executive can protect their income from taxes until they fall into a lower tax bracket, usually at retirement.

Tax Advantages of Deferred Compensation

Many highly compensated employees’ expected income is considerably higher in their last several years of service than in early retirement. This means their tax bracket is likely lower when their compensation is paid out in retirement.

With deferred compensation, employees are only required to pay taxes when they take a distribution or make a withdrawal. Although taxes are ultimately paid on withdrawn funds, this type of plan gives the benefit of tax deferral.

The Correlation Between Employee Wellness and Productivity

Offering attractive executive benefits can help improve employee wellness, which in turn can boost employee productivity. Employees with improved physical and mental health are less likely to experience burnout and more likely to be motivated to perform at their best.

Retirement Benefit Optimization

Top-level employees may be offered a supplemental executive retirement plan (SERP), a deferred compensation plan. As a SERP is not a qualified plan, employees and companies are not eligible for special tax treatments.

Tax-Efficient Retirement Benefit Structures for Executives

Companies often use SERP plans to reward and retain top executives. Under this arrangement, the business and executive both sign an agreement that promises that the executive will receive a certain amount of supplemental retirement income based on certain eligibility conditions.

group of diverse executive managers doing executive benefits paperwork at meetingBalancing Deferred and Current Income to Optimize Overall Tax Liability

Deferred income is a liability as it involves money owed rather than received. However, a strategic investing approach can help maximize retirement income while minimizing investment taxes.

Consult with New City Insurance to Improve Your Executive Benefits

Understanding executive benefits and compensation complexities is essential to achieving financial optimization. At New City, we help organizations improve their executive benefits to retain top employees. Contact New City Insurance to learn more.

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New City Insurance
New City Insurance
5.0
Briar Schwartz
Briar Schwartz
05:38 10 Apr 25
Working with the team at New City Insurance was a great experience, couldn’t recommend it enough. Being completely new to the insurance world, both Clayton and Eric were thoughtful and kind, and most importantly patient with my many questions. All in all 5/5 stars. Thank you New City!
Iris deBruin
Iris deBruin
03:24 10 Apr 25
The team at New City was incredible. Clayton walked me through every step, made everything easy to understand, and was always there when I had questions. I felt supported the whole way through—can’t recommend them enough!
Lea R
Lea R
22:46 09 Apr 25
New City was outstanding from start to finish. Incredibly professional, responsive, and genuinely caring. They made everything easy to understand and completely stress-free. Couldn’t recommend them more!
Brooks Chiongbian
Brooks Chiongbian
21:21 07 Apr 25
I ran into an issue with our carrier and Nick got right to the bottom of things. He and his team were incredibly responsive and helpful, making what could have been a frustrating situation so much easier to handle. They really went above and beyond to make sure everything was resolved quickly and smoothly. I’m super grateful for their support and highly recommend New City Insurance to anyone looking for a team that truly cares about their clients!
Elizabeth Teposte
Elizabeth Teposte
23:35 02 Apr 25
My Experience with New City has been amazing. Team Eric has been great, especially Nicholas Rebis their follow up time is a 10/10. I'm currently helping an employee out with her questions and have been running to Nicholas, before I say bye to our team member, letting her know I will follow up as soon as I hear something, I see his response. Thank you to the team for making it easier for me to assist our employees during difficult times.
Chelsea Antczak
Chelsea Antczak
17:54 02 Apr 25
New City Insurance is an outstanding company that genuinely prioritizes its clients. They are professional, highly knowledgeable, and always delivers the best solutions. I highly recommend them to anyone seeking a trusted insurance advisor who truly has your back.
Stephanie Gillon
Stephanie Gillon
19:16 22 Mar 25
I'm here to tell the world to look no further in your insurance search! Seriously, this company is it. I am beyond impressed with the skill set of this team. They are extremely motivated and dedicated to helping their clients and offer top-tier service. I was treated with such care and professionalism throughout our entire interaction together. Thank you, Eric and team, for being so thorough, kind, and efficient while helping me find the lowest prices possible!
Roshaun LaForce
Roshaun LaForce
23:06 20 Mar 25
New City Insurance has such a great team. They genuinely care about their clients and make the whole process easy!
Alec Remington
Alec Remington
00:54 20 Mar 25
A great team of hard workers. My experience with them has been nothing but positive. Highly recommended.
Morgan Ostrander
Morgan Ostrander
16:00 19 Mar 25
Great team to work with! They lowered our costs and have provided excellent service.
Zach Baker
Zach Baker
15:19 19 Mar 25
Eric and the team at New City Insurance are truly top-notch. It’s clear they genuinely care about their clients and work hard to provide the best service possible. Their integrity and dedication really set them apart. Highly recommend!
Momo Furusho
Momo Furusho
13:24 19 Mar 25
New City is run by not just a competent team, but people who genuinely care about providing the best service possible. Eric Calciano is a gem!
Allie B
Allie B
19:34 04 Feb 25
Excellent service and support from start to finish! The NCI team is professional, responsive and truly cares about their customers.
Deana Hartland
Deana Hartland
16:04 14 Jan 25
These guys are great and definitely go above and beyond. We were overcharged for a surgery that my husband had in Aug 2024 due to the contract that they had with our health insurance. It was very difficult trying to work and deal with trying to get this refund back from the surgical hospital we went to. A lot of playing phone tag with them. My husbands HR team got "Nicholas" involved and OMG.....he just handled everything. He stayed in constant contact with me via email on every step of the way. Eventually he was able to get this money refunded that was $997. He has been on top of it from day one. I must say he took all of the stress off of me dealing with this situation during my working hours and went ABOVE AND BEYOND the call of duty. I am so happy they got involved and relived me from dealing with this and the stress it would've caused me. You will be very blessed working with a company such as this. Keep doing what your doing!
Justin Hoffman
Justin Hoffman
02:52 17 Oct 24
Always quick to respond. This team is up early and late.
Roger
Roger
16:30 30 Aug 24
Eric Calciano, is as sharp and knowledgeable about health benefits and insurance, as anyone I've ever come across. If you need any kind of benefits analysis I highly recommend him and his firm. He is easy to work with and highly professional.
Timothy Burke
Timothy Burke
04:02 30 Aug 24
I don't leave reviews often, but this one is well deserved and overdue. Clayton provided services to my company prior to his move into the insurance world a few years ago. Always being incredibly impressed with his talent and strong communication skills, I decided to switch our insurance broker and give New City a shot. That turned out to be a great move.The first year, Clayton actually jumped on a plane and flew from Oregon to California just to be onsite and administer open enrollment for my 45 employees. Clayton, Eric, Jeff, Brendan, and the entire team have been a pleasure to work with over the years. The communication, response time, and insurance knowledge is second to none in my opinion. A legitimate 10/10. They are great listeners and strive to really understand the needs of their customers.I'm very selective about giving referrals and making recommendations, but New City has never disappointed. If you are reading these reviews to help make your decision on selecting an insurance broker, this team is 100% a solid option. And if you don't believe me, just look at the other reviews.
Megan Ketter
Megan Ketter
19:48 28 Aug 24
Excellent customer service. Brendan and team are professional, timely, and so appreciated when navigating this complicated insurance world. Very thankfully for them! Highly recommended.
Ailene Chow
Ailene Chow
23:15 26 Sep 23
We have been working with New City Insurance since 2019 at the start of our company and has not look back since. They are responsive and proactive when it comes to advise and also market analysis on what's there in the marketplace. Unfortunately insurance benefits costs has been increasing yearly with differences in the percentage of increase . The New City folks reaches out months before the impending increase takes places and help relook into options or recommendations that they see fit. We were a company of 2 to now 7 permanent staff . While we are small , this company still takes care of us well.
Carol Zhang
Carol Zhang
04:29 06 Mar 22
As a rapidly expanding national media organization, the employee benefits strategy and administration that New City has provided us during our growth has been invaluable. They have been proactive about informing us of the different benefit strategies available to us as we grow as well as managing the additional compliance laws and reporting requirements at each stage of our growth.
Claudia Villalobos
Claudia Villalobos
20:14 03 Mar 22
New City Insurance made navigating through all the health insurances super EASY. Their documents are highly informative, professional, and easy to work with. Thank you for making the process of choosing a health plan so simple. You guys are THE BEST!
Philippe Salas
Philippe Salas
17:02 22 Feb 22
I never expected to have a good time talking to an insurance salesman, but let me tell you Brendan was quite the treat. He was very helpful explaining the options and has a wonderful sense of humor. I hope to speak with him every time I call.
Jennifer Polito
Jennifer Polito
17:15 09 Feb 22
Super easy enrollment process. Fast and friendly customer service. If you are looking for an insurance company that is there for you every step of the way I highly recommend New City Insurance.
Rocky Salas
Rocky Salas
23:46 07 Jan 22
So friendly, I hope to speak to him again in all my future insurance needs.
Rocky Salas
Rocky Salas
23:38 07 Jan 22
So friendly and soft spoken. I hope to speak to him again in all my future insurance needs.
Jose Brena
Jose Brena
13:20 06 Jan 22
Eric Calciano has been extremely helpful in finding and selecting the right insurance coverage for our company. With many options out there Eric assisted us on getting a low cost provider saving more than 20% than from our competitors and providing excellent coverage for our employees.
Anastasia Beaverhousen
Anastasia Beaverhousen
17:05 28 Dec 21
Signing up for insurance was quick and easy. Felicity Sundsboe
SFCC
SFCC
22:08 29 Nov 21
Jeff Stoltey and his team provide excellent customer service. Jeff has always provided my company SFCC with straightforward options. I went to a larger insurance company only to RUN BACK to Jeff at New City Insurance. I recommend them to anyone needing insurance without hesitation.
Kevin Luby
Kevin Luby
19:13 22 Oct 21
Quick, easy & informative. We were able to secure quality insurance for our small business on a tight deadline. Thanks for the help New City.
Theresa Ruybol
Theresa Ruybol
19:30 01 Jul 21
Eric was so great with us. He was very patient and kind as we are a newer smaller organization who is growing rapidly. With that said, we had made our inquiry, he had great rapid response and mostly had to wait on me. Any request that we made and/or questions we had, he was great answering and helping us understand. Then when we were ready for all documents and to move forward, Brendan helped with getting that together and the two of them worked their magic on New City's end to notify me of what was needed, assist me in that process and confirming that all was complete and approved for the coverage. I just want to say thank you all again so much, as insurance has always been confusing to me, and you all made that process go a lot smoother.Thank you
Andrea Ordendorff
Andrea Ordendorff
21:06 07 May 21
I've been working with both Clayton and Brendan for well over a year. As the purchase of our dental practice was delayed well over 14 months they both patiently supported me and continued to make themselves available. When we were officially ready to sign up they made the whole process seamless and super easy. This team is highly knowledgeable, professional, supportive, and efficient! I can't thank them enough for everything they've done.
T W
T W
22:32 30 Aug 20
I love New City Insurance. I never had a good experience dealing with insurance brokers until I started working with Brendan. He’s awesome! He is patient with me and takes the time to answer all my questions. I’m very grateful for all his help and hard work!
Mary Jane Deyette
Mary Jane Deyette
00:57 11 May 20
Jeff Stoltey is so awesome...even thru my company had only two employees, he took the time each year to research and find the best plan for us. The only reason I am leaving New City Insurance is because we no longer have any employees. Thank you Jeff
Alma Ortiz
Alma Ortiz
22:25 23 Feb 20
Brendan was awesome! I couldn't figure out how to pick my plan and he returned my call on a weekend to help me. Outstansing service!
jessica kavanagh
jessica kavanagh
19:53 13 Feb 20
Brendan was so helpful I definitely recommend him if you’re in need of good help and getting it done promptly. Thankyou so much again.
Tricia DeYoung
Tricia DeYoung
19:49 13 Feb 20
I was very thankful I inquired about this info. with Brendan. He was very helpful so I understand the benefits available much better now. Thank you Brendan.
B Bayer
B Bayer
17:43 24 Sep 19
NCI handled almost everything from start to finish. Clayton and Brendan made the plans easy to understand and walked me through the application process. They got me my ID numbers before my cards arrived so that I could keep an appointment I had already scheduled. My last broker wouldn't have done that. 5 stars!
Jessica Lehr
Jessica Lehr
03:36 07 Jun 19
Our staff was interested in a health plan, but we didn't know how beneficial a solid employee benefits package would be for our business to expand. We'd lose prospective employees because they had more options for their medical insurance which was sometimes more valuable than more pay. The New City team was amazing and gave us as many affordable options as possible so that everyone had their needs met.
Mike McClay
Mike McClay
19:36 03 May 19
My employer uses New City as their insurance broker, and I'm always amazed when I call in for assistance by how knowledgeable and attentive their staff is with my requests. Their online benefits platform makes selecting insurance plans pretty darn easy. I would highly recommend their services.
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