Your Rakuten Benefits & Career: Financial Planning for Employees and Executives

Do you work at Rakuten? Get the resources you need and expert insights from financial professionals who specialize in helping Rakuten employees make the most of their compensation package and benefits.

Whether you’re a new Rakuten employee or you’ve moved up the ranks into a management or executive leadership role over a multi-year career, it’s important to make smart money moves with your income and employee benefits. For example:

✅ Do you know the right moves to make 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 from the company in a few years, are you taking the right steps today to ensure you will receive all of the compensation and benefits that you’ve earned?

Get the Most Value from Your Rakuten Benefits and Compensation Package

Throughout the year, Rakuten provides its employees and executives with updates about their benefits ranging from health insurance and health savings plans to retirement plans like a 401(k) and deferred compensation plans. 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.

Whether you work in the Rakuten US office in San Mateo, California, another office location around the world, 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.

For example, sensitive topics like discussing 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.

💡 In the Q&A below, you’ll gain insights from financial advisors who work with Rakuten employees to help them make smart decisions to get the most value from their compensation and benefits, reduce their money stress, and prepare for a comfortable retirement.

🙋‍♀️ Do you have questions not yet answered? Use the form below to submit questions anonymously and watch this article for updates with answers to your questions. You can also reach out to the financial advisors below to set up an introductory call or contact them with your questions by email.

💸 Smart Money Insights for Rakuten Employees & Executives

This page is organized into sections to help you quickly find the information you need and get answers to your questions:

1. Q&A: Financial Planning Tips for Rakuten Employees & Executives
2. Get Answers to Your Questions About Your Rakuten Benefits and Career
3. Browse Related Articles

Q&A: Financial Planning Tips for Rakuten Employees & Executives

Answers to Employee Questions with John Boyd, CFP®

John 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.

Q: As a financial advisor with experience helping Rakuten employees save for their retirement, how do you help them make the most of their employee benefits?

John: 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.

Q: When 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?

John: 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.

Q: Is there a particular benefit available to Rakuten employees you feel isn’t as well utilized or understood by employees as it should be?

John: 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.

Q: Beyond 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?

John: 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.

Q: For Rakuten employees thinking about leaving the company to accept a job elsewhere, what actions do you recommend they take before resigning and shortly thereafter?

John: 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.

Q: For 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?

John: 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.

Q: For 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?

John: 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.

Q: What 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?

John: 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.

Q: What questions do you recommend Rakuten employees ask financial advisors they’re considering hiring to help them decide if they’re a good fit?

John: 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.

Q: Is there anything that comes up frequently in your initial meeting with Rakuten employees that surprises you?

John: 100% it is the HSA money. Most people have no idea it’s even a benefit.

Q: For 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?

John: 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.

Q: Is 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?

John: 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!

Get to Know John Boyd, Financial Advisor for Rakuten Employees:

View John’s profile page on Wealthtender or visit his website to learn more.

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