Our Story

Cheryl Robertson Helps Advisors Plot a Course to a More Secure Retirement for their Clients

January, 2015: Returning to the workforce after taking ten years off to focus on raising the first four of her five children, former labor and employment attorney Cheryl Robertson secured her insurance and securities licenses in order to become a financial services professional and partner at Commonwealth Financial, a Mass Mutual general agency located in Boston, Massachusetts.

Immersing herself in that realm and working almost exclusively with current and prospective retirees, she quickly realized that the vast majority of those with whom she met lacked the proper information, advice and resources regarding one of the most critical issues regarding their financial future: when and how to claim their Social Security retirement benefits.

Six months into this new chapter in her life, she gave birth to her fifth child. But some powerful statistics she encountered motivated her to figure out a way to balance motherhood while living out her passion to help people understand the complexities and nuances of the Social Security system.

Once Cheryl learned nearly 10,000 baby boomers were retiring each and every day – all of whom could benefit greatly by working with advisors that possessed the expertise necessary to help them make the best possible decision about when and how to file for Social Security retirement benefits, she embarked on the course to create that which was to become CSSCS. With American corporations eliminating more than 84,000 pension plans since 1985, and with the stock market experiencing over a decade of unprecedented volatility, Cheryl was acutely aware of how important this decision had become for what is the first generation in history required to self-fund their retirement. While the average working American might know enough to file and receive their Social Security benefits, the system, thanks to the nearly 3,000 filing rules, is wrought with traps and run by a government agency that is prohibited from dispensing advice.

Cheryl’s company, the Corporation for Social Security Claiming Strategies (CSSCS) is an outgrowth of the cottage marketing industry that has sprung up in recent years thanks to the new filing strategies made available as part of the Senior Citizens Freedom to Work Act, passed into law in 2001. Launched in October 2014, with a home base in Plainville, MA, CSSCS is engineered to provide financial professionals with the level of expertise needed to help the Boomer generation plot the course to a better retirement. By utilizing various Social Security claiming strategies, sophisticated retirement income advisors, like those that have completed her course, are able to use this knowledge to mitigate the long-term risk their clients face of running out of money in retirement. While the original program was piloted in the independent advisor community, CSSCS has now opened up its educational doors to a wider universe of advisors, legal, CPAs, estate planners, tax advisors and Human Resources professionals.

The only comprehensive retirement training organization in the financial services industry focused exclusively on educating professionals on the nuances of Social Security retirement planning, the organization creates and provides a training course on Social Security retirement benefits and claiming strategies and provides advisors with the opportunity, for those inclined to do so, to sit for a comprehensive exam that if completed successfully will provide them with the Certified in Social Security Claiming Strategies designation.

While she has her immediate sights set on webinars and live training in various parts of the country, Cheryl and her staff offer students online access to a dynamic curriculum that can be studied at their own pace. As mentioned earlier, students have the option of enrolling in the educational course by itself, or they can couple the course materials with a comprehensive exam – successful completion of which will result in the CSSCS designation.

While there are multiple membership levels, Gold membership includes receipt of a copy of their Comprehensive Guide to Social Security Retirement Benefits course book, immediate access to the Social Security Claiming Strategies online course, unlimited access to a team of Social Security experts and a tool kit that includes a variety of condensed Social Security facts and graphics. Platinum membership includes all of those components in addition to the certification exam and a listing in the organization’s “Find An Expert” search query designed for use by the general public to locate Certified Social Security Claiming Strategists in their local area.

After learning of some surprising realities about the level of misinformation being disseminated about Social Security, Cheryl has made it her goal to provide students with a deep understanding of the multitude of factors that play a role in determining how retirees can achieve the maximum value available to them from Social Security. As Cheryl sees it, Social Security expertise goes beyond understanding which filing strategy may provide the most aggregate income during a stated period of time. It focuses on the more intrinsic value a proper strategy will provide in preserving capital by minimizing the risks posed by longevity, inflation and taxes.

“As the very first generation of retirement “do-it-yourselfers” boomers have important, valid questions and many mistakenly assume that everything they need to know is easily and accurately spelled out in some free online internet resource or available through their advisors,” says Cheryl, a J.D. from Roger Williams University School of Law, in Bristol, RI. Long before she embarked upon the journey that is now the Corporation for Social Security Claiming Strategies, Cheryl was an avid researcher and writer as Managing Editor of the Law Review and clerk in the appellate screening division of the Rhode Island Supreme Court where she had several successes…..As a native Rhode Islander, Cheryl is proud to have been in the very first graduating class at Rhode Island’s first-ever law school.

“As an advisor, I worked with some colleagues to develop a beautiful report that covered the basics of when and why one should file for Social Security retirement benefits and what you should consider doing with the balance of your retirement assets. While we learned a lot about Social Security retirement benefits when developing the report, we also found there were many questions we couldn’t initially answer. As a lawyer, you’re trained to think analytically so I took it upon myself to investigate ALL the legislation and history that played a role in the development of those rules so that we could truly understand why various aspects of the system operate as they do. After a while, it became apparent that if I could share what I’ve learned, we could empower thousands of professionals in many advisory arenas and, potentially, millions of American retirees could benefit. The need for deeper advisor awareness and understanding of the broader role Social Security claiming strategies can play in creating a secure retirement was becoming abundantly clear and it was at that point I realized a firm dedicated solely to the education of financial professionals made sense.”

While there was a clear educational void Cheryl hoped to fill, there were several other important economic factors that played a role in driving her desire to increase advisor awareness around the opportunities with Social Security retirement claiming strategies as well. In particular, she had experienced firsthand the deficiencies in many boomer’s retirement savings thanks in no small part to the protracted and unprecedented market volatility that began in 1997 and remains to this day. This coupled with the abundance of underfunded boomer retirement plans, increasing life expectancies, and growing tax burdens led Cheryl to believe that Social Security would no longer remain an afterthought in the retirement income planning process. Not only was she convinced it would no longer be an afterthought, she realized it could be a catalyst in the growing challenge to develop and design retirement income plans that deliver the security boomers need and deserve.

While realizing it’s literally impossible for an advisor or client to learn and retain all the rules and nuances of a system as complex as the Social Security retirement system, Cheryl was passionate about developing a training course and providing the ongoing support and expertise advisors need in order to solve even the most complex of Social Security claiming riddles. “If every husband and wife were the same age or close to it and had the same earnings throughout their lives,” Cheryl says, “there wouldn’t be a need for my program, but in six out of ten filing cases, there is a hitch – from an age or earnings difference to the possibility that someone worked for the government or worked outside the U.S. – the list at times seems endless!”

Cheryl began her formal research in the Fall of 2012 and began writing her foundational materials in January 2013. By March of that year, she began beta testing her first draft. Unwilling to officially launch with materials that were anything less than revolutionary, she took on some consultants, including former Social Security employees, and had them examine her work and give her their approval or suggestions for improvement.

“My background in the law really drove my desire to do this, and once I saw all the confusing and inaccurate advice people were getting about Social Security, and realized the extent of the growing retirement crisis, I knew it was important to ensure that my system be as comprehensive as possible. I wanted to do more than provide information for advisors to answer basic client questions. I wanted the advisors I worked with to understand why things happen the way they do, why the rules worked the way they did, and how that information would impact their clients and what that would mean for them down the road. I needed my system to be comprehensive. Those investing in the program and committing to Social Security planning as a key practice differentiator deserved no less.”

As Cheryl closed in on her final draft of the course material, a potentially troubling piece of news hit that intensified her motivation to succeed with CSSCS. In March 2014, President Obama presented his 2015 budget proposal – which in its small print targeted what an article in Investment News called “one of the best retirement income planning tools on advisors’ shelves: Social Security claiming strategies.” Found buried on the 150th page of the 214 page, $3.9 trillion budget, was this key sentence: “In addition, the budget proposes to eliminate aggressive Social Security-claiming strategies, which allow upper-income beneficiaries to manipulate the timing of collection of Social Security benefits in order to maximize delayed retirement credits.”

The reaction among advisors was mixed, with some saying it’s aimed to prevent high income people from gaming the system and others saying there are other, better ways to strengthen Social Security. Cheryl says, “I realized that if this happened, it could completely change how advisors viewed Social Security claiming strategies and diminish their appetite for more in depth knowledge. This became a watershed moment in the evolution of our program and the development of our story. It forced me to think long and hard about the value of my program and the importance of helping advisors and their prospective clients understand the integral role claiming strategies play in combating some of the most insidious retirement risks, even if they changed the rules.

The budget announcement that first filled Cheryl with trepidation ultimately helped her develop a more thorough and detailed educational system. “Analyzing how these rule changes could impact the system inspired me to tweak and expand my materials from being all about the rules, regulation and methodology into more practical applications of how advisors can take these rules and convert them into systems that can help sustain retirement income for their clients,” she says. “That one line in the budget made me think a lot more about how this could help not only me in building the program but more importantly, the people I am helping to educate.

Cheryl believed she had devised an outstanding product, and is pleased to say that in just a few short months since her launch, the program is already helping countless advisors across the U.S. build more fortified retirement income plans for their clients. “The educational portion of the course has a component which speaks directly to how an advisor can apply this knowledge in their every day practices to further benefit clients,” she says. “It starts with a true working knowledge of the rules and it can include taking advantage of something as simple as how one benefit is superior to another, or a concept like ‘some now and more later’. The idea that after completing my course advisors can take plans that wouldn’t work before and, by leveraging all the value and power that Social Security can bare, now have the skill set needed to turn them into something that works is very satisfying!

“The most important and fulfilling thing in my day to day life is taking care of my five children, who are ages 3-13 but on the business side, it’s knowing CSSCS has so quickly made a difference in people’s lives that makes the sacrifices I have made all worthwhile. The facts that retiring boomers who work with our graduates are getting better advice, and our graduates are bringing in more clients, only fuels my commitment to growing my firm as a resource. I’m proud of the impact our graduates are having and will continue to have on the retirement security of many more people.”

Written By: Jonathan Widran