Do you work at Rakuten?
Get expert insights from financial advisors who specialize in helping Rakuten employees and executives make the most of their compensation package and benefits.
Looking for a financial advisor who specializes in working with Rakuten employees? You’re in the right place. Below, you’ll find advisors who understand Rakuten benefits and compensation — along with their answers to common financial questions from Rakuten employees and executives.
Whether you recently joined Rakuten or you’ve advanced into a management or executive leadership role over a multi-year career, making smart decisions about your income and Rakuten benefits can have a lasting impact on your financial future. For example:
✅ Do you know the right moves to get the greatest value from the Rakuten benefits available to you?
✅ If you’re thinking about leaving Rakuten for another job or planning to retire in a few years, are you taking the right steps today to receive all the compensation and benefits you’ve earned?
Key Takeaways
Set Up Your Daiwa Account and Exercise Vested Rakuten Options
Rakuten “stock options” work more like RSUs, and they must be exercised before they can be sold. Many employees never set up the trading account, leaving thousands of dollars — up to about 10% of total compensation in some cases — unclaimed.
Rakuten’s Mega Backdoor Roth and HSA Match Are Often Overlooked
The mega backdoor Roth can dramatically increase tax-free savings, and Rakuten matches up to $2,000 in HSA contributions for family plans — a benefit many employees don’t know about.
Handle Your Rakuten Equity Before You Resign
Once you leave, you lose access to the equity platforms, so exercise and ideally sell vested options before your last day.
Why Rakuten Employees Work with a Specialist Financial Advisor
Throughout the year, Rakuten provides its employees and executives with updates about their benefits, ranging from health insurance and health savings accounts to retirement plans like a 401(k) with a mega backdoor Roth option — along with equity compensation in the form of Rakuten stock options and an HSA match. While the company offers many useful resources and access to knowledgeable staff who can assist with questions, you’ll also find financial professionals not affiliated with Rakuten who specialize in helping Rakuten employees make the most of their income and benefits.
Rakuten Group is headquartered in Tokyo, Japan, and its U.S. businesses, including Rakuten Rewards, are based in the San Francisco Bay Area in San Mateo, California. Whether you work at one of those sites, another office, or remotely from home, you may have questions about your compensation package and benefits better suited for a financial professional who can offer unbiased advice and guidance.
Sensitive topics — like the steps you should take before quitting your job at Rakuten to work elsewhere, protecting yourself in advance of a corporate layoff, or deciding when you should plan to retire — are all conversations that may be more comfortable with a trusted financial advisor.
Should You Hire a Rakuten Specialist or a Local Financial Advisor?
You’ll likely find dozens of nearby financial advisors well-suited to help you reach your money goals with a personalized plan. But it can be harder to find a financial advisor who specializes in serving Rakuten employees. Fortunately, many financial advisors offer virtual services, so you can meet online no matter where you (or they) live — which means you can hire a specialist financial advisor who lives hundreds of miles away if their knowledge and experience working with Rakuten employees is the better fit for your unique needs.
💡 In the Q&A below, you’ll gain insights from financial advisors who work with Rakuten employees to help them make smart decisions, get the most value from their compensation and benefits, reduce their money stress, and prepare for a comfortable retirement.
🙋♀️ Have a question not yet answered? Use the form below to submit your question. You can also contact financial advisors directly to set up an introductory call or contact them with your questions.
Q&A: Financial Planning Tips for Rakuten Employees & Executives
In this section, you’ll learn how you can make the most of your Rakuten employee benefits and gain valuable tips from financial advisors who specialize in working with Rakuten employees and executives.
Financial Advisor Q&A · Rakuten Employees
John Boyd, CFP®
MDRN Wealth · Los Angeles, CA · Serves clients nationwide
Helping people retire early, years before 65John Boyd is a financial advisor based in Los Angeles, California, who specializes in offering financial planning services to Rakuten employees. John helps his clients get the most value from their Rakuten benefits and compensation package so they can enjoy life and feel confident about their financial future.
QAs a financial advisor with experience helping Rakuten employees save for their retirement, how do you help them make the most of their employee benefits?
Rakuten stands out for having an equity compensation plan, but it’s not structured like those of traditional large tech companies. Their equity can be complex to understand and access, yet it has the potential to add thousands of dollars to your total compensation.
When we first start working together, reviewing this aspect is one of our top priorities. In addition to equity, Rakuten is one of the few big companies that offers a mega backdoor Roth option, allowing you to contribute over $70,000 annually to a Roth account. Incorporating this strategy into your financial plan can accelerate your path to retirement and help you accumulate significantly more tax-free wealth.
QWhen you first speak with a Rakuten employee, what questions do you like to ask to better understand their unique circumstances and determine how you can best help them achieve their goals?
One of the first things we want to assess is whether they have set up their DAIWA trading account. This account is essential for trading Rakuten “stock options,” which are not like traditional stock options but are more comparable to RSUs. We also want to review which options have vested and ensure they are exercised, as this is a prerequisite for selling them.
Surprisingly, many employees have not set up this account or exercised any of their options, even after working at Rakuten for years. Addressing this is a priority for Rakuten employees, as it often represents thousands of dollars in missed compensation. Once this is resolved, we can focus on developing a more comprehensive cash flow and tax plan.
QIs there a particular benefit available to Rakuten employees you feel isn’t as well utilized or understood by employees as it should be?
Going back to your other question, it’s 100% the “stock options.” I don’t blame employees for being confused—HR provides little education on the topic, and the platforms used to exercise and trade options (Rsocks and Daiwa) are often clunky and slow. As a result, most people don’t bother dealing with it, even though it can account for as much as 10% of their total compensation in some cases.
QBeyond Rakuten employee benefits for retirement savings, are there other types of benefits offered by the company that you find valuable to discuss with your clients?
Rakuten offers an extremely generous HSA match—up to $2,000 for family plans. Most Rakuten employees are in higher tax brackets and could greatly benefit from contributing to an HSA and taking advantage of the free money Rakuten provides. However, I’ve found that most employees we work with are unaware of this option.
QFor Rakuten employees thinking about leaving the company to accept a job elsewhere, what actions do you recommend they take before resigning and shortly thereafter?
Make sure your DAIWA trading account is set up and that you exercise any stock options that have vested. Once you resign, you will no longer have access to Rsocks or your trading portal. This means you’ll be stuck emailing the trading team for your equity options, and they are notoriously unresponsive. Ideally, you should sell all equity associated with any vested options before you leave and plan for this well in advance.
QFor Rakuten employees approaching retirement age, how do you recommend they prepare to make the transition from living off their salary to relying upon other sources of income?
Make sure to review the allocation of your retirement account. Most employees are invested in a target-date fund, which may not align with your cash flow goals. I recommend maximizing your HSA contributions in the years leading up to retirement as much as possible, since your HSA can be used to cover COBRA premiums. Additionally, check how much you’ve saved in pre-tax retirement dollars, Roth dollars, and non-retirement dollars. Ideally, you’ll have a well-balanced mix of all three, which can create excellent tax efficiency in retirement.
QFor Rakuten employees who have managed their finances on their own to this point, what would you suggest they consider to help them decide if they should begin working with a financial advisor at this stage in their lives?
I want you to stop for a moment and think: Do you know how much you paid in taxes last year? What are you doing with your non-retirement dollars—those in brokerage accounts, potentially including Rakuten stock? Do you have a tax plan? Do you know how you would live off your accounts in early retirement? If you want to leave corporate America, how would you tax-plan around it? If the answer to any of these questions is “no,” you’re a great candidate to start working with a financial planner.
QWhat are some of the unique financial planning challenges you commonly see among your clients who are Rakuten employees and how do you help them overcome these obstacles?
Aside from figuring out how to sell their Rakuten equity, taxes are a major concern. Rakuten employees are often in higher tax brackets and frequently owe money on their tax returns. Unfortunately, many of them have been paying underwithholding penalties without even realizing it. One of the key things we address when we start working together is creating a tax plan—not only to reduce their taxes but also to avoid underwithholding issues.
QWhat questions do you recommend Rakuten employees ask financial advisors they’re considering hiring to help them decide if they’re a good fit?
Ask them if they have experience with tax planning around stock options. Ask them if they review your paystubs and tax returns during the planning process.
QIs there anything that comes up frequently in your initial meeting with Rakuten employees that surprises you?
100% it is the HSA money. Most people have no idea it’s even a benefit.
QFor highly compensated Rakuten employees and executives, are there any special benefits you believe it’s important to take into consideration when preparing their financial plan?
Rakuten options, utilizing the mega backdoor Roth, and reviewing health insurance choices to determine if the HDHP with the HSA benefit is the right fit.
QIs there a particularly memorable experience or a moment you recall with a client who worked at Rakuten when you realized they have unique opportunities and circumstances when it comes to their financial planning needs?
I’ll never forget connecting with a client who had about $20,000 in stock they could sell but had no idea they even had it. It felt like getting a Christmas bonus when we discovered it!
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About the Author
Brian Thorp
Founder & CEO, Wealthtender · Editor-in-Chief
Brian Thorp is the founder and CEO of Wealthtender and serves as Editor-in-Chief. With over 25 years in the financial services industry — including nearly 22 years at Invesco, where he led strategic partnerships with wealth management firms representing more than $100 billion in assets — Brian founded Wealthtender to help people find financial advisors they can trust and make more informed money decisions.
A member of the National Society of Compliance Professionals and its SEC Marketing Rule Working Group, Brian was recognized by WealthManagement.com as one of its “Ten to Watch in 2024” for his work reshaping how financial advisors market their services. He holds a B.B.A. in Finance from The University of Texas at Austin.
Brian and his wife live in Austin, Texas.