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Creating Better Retirement Solutions Through Technology with Cheryl Nash and Steve Gresham

As the population of retirees continues to grow, this puts a lot of stress on the traditional retirement system. Finding better retirement solutions is becoming increasingly important. What can financial advisors and industry leaders do to provide better retirement planning and solutions?

In today’s episode, Jack talks with Cheryl Nash, CEO of Financial Supermarket at InvestCloud, an established and trusted leader in wealth technology, and Steve Gresham, CEO of The Execution Project, a wealth management consulting firm that helps companies create better wealth management and retirement solutions.

Cheryl and Steve are true industry leaders. Cheryl grew up in the wealth management industry and has held roles in nearly every functional area. Steve is a leader in understanding trends facing the wealth management industry. His focus is on improving retirement solutions for a wave of retiring clients.

Cheryl and Steve talk with Jack about the project they have been working on together, The Next Chapter Leadership and Action Initiative. They also discuss the role of technology in retirement planning, what industry leaders and top financial advisors do differently to provide retirement solutions, and how investors are becoming more concerned about their retirement income.

What Cheryl has to say

“We’ve talked about goals-based planning for years. Everybody wants a goal. Everybody has a retirement goal. So, now that we’re at a point where 10, 000 people are retiring every day, we’ve got to figure this out. And technology has to be the enabler and you’ve got to get working with the right people.”

– Cheryl Nash, CEO, Financial Supermarket at InvestCloud

Read the full transcript

Jack Sharry: Thanks for joining us and welcome to wealth tech on deck. Each week I have the pleasure of speaking with industry leaders around the issues of wealth management, retirement, financial advice and technology. I talked with those who are leading the way as we seek to help financial advisors and their clients enjoy better financial outcomes all around the confluence of digital and human advice. Today, we will have a conversation with two true industry leaders and longtime friends Cheryl Nash, CEO of InvestCloud Supermarket and Steve Gresham, CEO of The Execution Project. Both Cheryl and Steve had been on our podcast in the past talking about their respective businesses. Our conversation today will be a departure, we’re going to talk about a project that three of us have been working on together called the next chapter leadership and action initiative. Cheryl, Steve, welcome to WealthTech on Deck, I think our audience is in for a treat.

Steve Gresham: Hey, great to see you, Jack. Hey, Cheryl, great to have you here.

Cheryl Nash: Hey, Steve, good to see you.

Jack Sharry: Thanks. I should know we’re doing this night Friday after recording this on a Friday afternoon at four o’clock after past four o’clock, and we are looking forward to having some of what Steve is having. So nice to be here with you all. And let’s get started. So Steve, wanting to kick us off with the high level view of the next chapter. And then I’ll ask Cheryl to describe the current program that we’re rolling out. So Steve, kick it off.

Steve Gresham: Sure. Thanks, Jack. Again, it’s terrific to have a chance to talk about leadership and action. So next chapter was something that was created by a number of us in the industry, as we sat there thinking about the beginning of the pandemic, wondering about retirement and why retirement was so difficult, lots of moving parts, people would like it to be simpler, but it’s very hard to support advisors with unless you have the right kind of tools and all that together. So what we found is that like an awful lot of processes in any kind of business, most of the problem really is us. So the friction associated with the different kind of supportive systems, tools, products, they’re really not coming together around the solution of retirement. And that’s bad timing, because there’s an enormous historic age wave of retiring baby boomers that we’ve been talking about for years. So next chapter is a coming together of the money management institute with it’s almost 190 members across the industry, and supported by financial advisor magazine, which is distributed to well over 100,000 financial advisors and industry professionals. Basically what we did is to divide up retirement in as an industry into six different categories of interest to somebody to be put together with somebody else’s. So you got six different parts includes financial wellness, digital adoption of tools, innovation in retirement programs, and products, try to put all that stuff together to synthesize it so that there is much more of a frictionless solution for the clients simpler, easier to understand, help them actually achieve that retirement that they’re on the cusp of, but then also in supportive advisors. So we’re working at the same time with advisors, and the needs of the consumer trying to pull those things together. And again, we’re two years deep, we do thought leadership, we hold events. And now we’re kicking off this next gen leadership program that we’re talking about today.

Jack Sharry: Terrific. We’ll talk a little bit more about the conference that’s coming up in May. But for now, only we turn it back to Cheryl, Cheryl, tell us about the next chapter leadership and action initiative.

Cheryl Nash: Great. And thanks, Steve, for that. So as Steve said, we’ve been working together Jack, Steve and I and others on this initiative. And what’s really exciting about this retirement leadership and Action Program, is we’ve actually tapped some of the best and the brightest in our industry, some of the next gen, we even have a high school student coming into this to help us think differently, and help us put together a real solution for retirement. And there’s just so many statistics out there about why this is so important. But it really is truly important. And as Steve said, There’s six different focus areas and study groups, we call them and we’ve assigned different people to each study group. And I’ll go through what those study groups are. Because it’s really when we thought about this in the next chapter, and thought about where the key focus areas need to be. We decided to break it out, make it into chunks that are really easy to understand and things that we could actually get done, and then bring it all together. So we’ve got the six groups client communication is one. Think about, you know, journey maps. Every organization has different journey maps, why clients across any organization really need to follow the right journey to retirement. So let’s help with that. The second is an easy client experience. I think that’s something that every technology firm is focused on right now. But also personalization, and how do we define solutions that meet the concerns and objectives of every investor. The next is family financial management. at the household level, this is Jack’s favorite subject really focused on the household and really making sure that we’ve got solutions that support that financial wellness, which is a big topic in our industry, right now. Let’s go attack that. How do we define financial wellness? What is longevity planning look like? So let’s really go focus on that. digital capabilities coordination. So digital, everything needs to be digital today, mapping solutions. And, you know, how do you map those against goals and an easy way? How do you score criteria, and also make it digital clients and investors are used to digital capabilities today, like Netflix and others, let’s make this easy. And then lastly, retirement income, which is really one of the big focus areas of every technology organization today, supporting advisors to let’s focus in that area as well. So we have six study groups, we have over 60 participants that are assigned to each of these groups. And we have a program that we’re kicking off on Monday, that actually enables each of these groups to come together and help think through in a new way with fresh thinking, product sets that we can do across this industry to support retirement, which is so important.

Jack Sharry: So I want to underscore some things that Cheryl covered amplify a bit. Some of the 60 folks, most of whom are coming from firms such as the large wirehouses, independent broker dealers, asset managers, insurance companies, Fin tech, so we have the best in the brightest of this next gen that we’re referring to that was part of our criteria on that folks that are newer in the business, not necessarily rookies, but certainly people that have been in the business for a while that have fresh thinking. It’s really what we’re after, I’m gonna ask Steve to amplify that a bit in a moment. But what really what we want to do is bring together folks with a fresh perspective. And that’s really what we’re going to charge them with this is being recorded in late February, probably won’t appear to for another few weeks, but will be underway. And over the next many months, the six different groups will be getting together, they each have a mentor that is Steve could probably expand upon. And they’ll be looking at different ways, ultimately presenting a deck to the leadership team here that includes Cheryl, Steve, myself and many others, we’re gonna be looking at what they have to say we want to have a fresh perspective, one of the issues that we’re really looking at and want to deal with. And I had this question from one of the leading asset management firms like so what is this? We already work on this every day? Why is this different? Of course, each firm works on in their own way, frankly, contemplating their navel about their process. What is the industry process look like? What does the client need look like? And Are we fulfilling on that? I would argue and Steve is expert on this as anyone but if you look at the demographic wave, the ALI that he’s done so much good work within for it was a 10 or 12,000. Retiring each day, we’re going to 14,000 over the next few years. Our industry, frankly, was not prepared is not prepared just as any large wealth management firm, they’re struggling to meet the demand. That’s that’s in place. So what we’re looking to do is kick into high gear, what can we as an industry do to accelerate the ability to serve clients as they increasingly retire, and are looking for our industry to help them in figuring this all out. I’ve covered a bunch of stuff they’re all which I know is near and dear to your heart. So if you’d only take it further, I’d appreciate it.

Steve Gresham: You kind of lit the fuse Jack by saying you know what’s different. And so what’s different is unifying. One of the guidelines that we have here, maybe the path to follow, seems to us to be something very similar to something that we’ve experienced in our careers, which was the launch of the managed account business. And so the MMI is now 25 years old. Well, you know, here was a product, a concept, a service that was dropped in place, because an awful lot of people heading toward that retirement said, Well, I’m not really sure how I’m doing. You know, this was a land before there was performance reporting, most people didn’t even know how they were doing in their accounts. The typical financial advisor was really a stockbroker. And at best, they were peddling products and ideas that weren’t really joined together and certainly weren’t part of anything that you would call planning. So the transition of that industry really became a transformation. And it became now a very easy thing to be able to delegate the management of the assets of the clients assets to a third party that was professional that was working with the same kind of approach for institutions, pension funds, you know, large endowments, and that kind of professional management became a standard in our industry. And basically it is funded what we now call wealth management. Unfortunately, Wealth Management when you head toward retirement becomes how do I survive my retirement? And when you have to manage somebody’s assets and work with them with a terminal point out there is an awful lot different standard than what we’re all saying, well, that retirements out there 20 30 40 years in the future, I don’t have to worry about that this retirement has now jumped up and then punched everybody right in the face.

Jack Sharry: So Cheryl, you know a little bit about technology I hear that seems to be at the center of what we’re talking about, because the products continue to evolve. Now, it’s direct indexing as the hot product that is going to solve it all. Steve, I know you’ve done a lot of work around protected income. And that continues to have a challenge that people somehow think that’s not part of what clients want come back to you on that one. Because I know, frankly, that’s in fact, what they want, but not getting it. So show what brings us all together makes it easier. You were talking about that earlier, is out of use technology to foster all this and what role that play with our six different study groups, I would assume and I don’t know the answer. I assume that’s all about technology, bringing it all together.

Cheryl Nash: Absolutely. I think, you know, Steve was talking about the beginning of manage accounts. And I think all three of us has probably been there from the beginning. And from a technology perspective, I remember sitting in a room with an asset manager saying, Hey, there’s this company, Merrill Lynch, who wants a connection, we don’t know what to do, like, what does that look like? So we built an interface. And then we built another interface and another interface. And technology enabled that industry to grow. Right, US and other technology vendors really supported, how the scale the ability to have asset managers talk to broker dealers and sponsors. I mean, that is all technology that enabled that it’s the same thing that’s going to happen here, right. We’ve talked about goals-based planning for years. I remember being on a panel five years ago talking about you need goals-based planning, everybody wants a goal, right? Everybody has a retirement goal, they have a, I want to buy a car goal even. So now that we’re at a point where I think you said 10,000, people are retiring a day, we’ve got to figure this out. And technology has to be the enabler. And you’ve got to get working together with the right people in our industry, we’ve got the best and the brightest in this industry, that we all know, and the best firms out there, they all want to fix this. And they all want to make it better so that the end investor can retire comfortably. But it can’t be done without technology. So I’m really excited about this. And when Steve called and asked me to participate in this two years ago, so exciting because it is such an opportunity to do things differently, think differently, bring in fresh minds, like you said, Jack, we’re bringing in people who are new, they know this industry, but maybe new to thinking about ways in which technology can help define a problem. So we can add a lot of value with the right tools and technologies. So my whole career has been technology. So this is going to be the next one right the next year.

Jack Sharry: Absolutely, you really focused on this. So I’m excited for and something that the three of us all share in common, we recognize that the future is not only is born of technology will be enabled by technology already is but even more so as we go forward. And that is that as an industry, if you’re going to solve the retirement challenge, problem, opportunity, you really need to coordinate a lot of technology, you need to coordinate a lot of product types. And Steve, I’m gonna ask you about that in a moment. So it’s not just manage money. It’s not just direct indexing. It’s not just ETFs it’s not just annuities. It’s not just, I could go on all the products that we know, it’s how do they coordinate together. And as you guys have heard me say, tirelessly, if you’re going to improve outcome, if you’re going to maximize your retirement income, you have to look at issues of cost and risk and tax and optimizing Social Security. That’s just how it works. If you want to improve outcome, because none of us have met anyone that consistently beat the market. So if you leave market performance aside, the way to get a better outcome, which is ultimately we’re all these retirees who are not only retiring in droves, but they’re retiring earlier than ever. Lot of them born of the pandemic, either by choice or by whatever, more people are retiring earlier. So they’re living longer, they have more of a span in which to generate retirement income, they’ve got more fears. And we’ve got all sorts of events happening around us today that have a lot of people scare between inflation and wars in the Russia and Ukraine, whatever all is going on lots of things to be concerned about. So now more than ever, it’s really a requirement for us as an industry to help investors help advisors help investors do a better job. So Steve, I’m gonna ask you something more specific. So among those six different categories and groups that we’re going to be helping to create new ideas. You and I were just having a conversation around some of the key issues, and that is that one of the fundamental issues is the client has a different set of needs, expectations wants versus what the advisor tends to talk about. I’m thinking of things issues around longevity and health care. Why don’t you expand on that a little bit in terms of why that’s so important and how that fits into a retirement income context?

Steve Gresham: Sure. So what’s ironic about all this, as you could say, I’ve heard this from many advisors along the way here, that the clients have moved the cheese. Well, that’s what clients do so when they were Growing up, because again, it’s the same group of people, right. So when they were growing up and these first started to put money away, there wasn’t really a whole lot of defined contribution options, IRAs, all that still pretty new stuff. Now, that’s kind of standard fare. When you think about where we are today, most of those people have come off of a really, really long earning curve. So they’ve been spending a lot of time earning, saving and putting the money away. And the industry has been responding, responding, responding, and to all the competitive challenges out there, people who are responding those firms, those advisors have been trying to make it simpler, easier and less expensive. And that’s where the game is bad. The game has been there for 30 years, trying to provide better solutions, better solutions, cheaper, simpler to operate. But that’s all been on the accumulation side. Now you get to that end of that runway, now you’re starting to talk about something else. Now all of a sudden health and health care is my most important issue. You know, it probably always was for retirees, but they didn’t verbalize it in quite the way that they do today. Second part that they’re most concerned about is having some level of guaranteed or protected income. So again, it’s not that you can’t create that in a portfolio. But it’s a very different thing to have a client look at the abstraction of a portfolio and how it’s going to generate total return over time that’s turned into cash as compared to something that writes you a paycheck and your retirement. So that’s important. The third one is about security protection, and something they call liquidity, which is the ability to not only meet current expenses, but then also the unexpected events that will come along in that retirement, when you don’t have a regular paycheck, it is a big concern to people, now I’ve got something that broke, I need a new roof, I have to buy a refrigerator, I have to get a car, or I may have to support a parent that didn’t save enough, well, where’s all that money going to come from? And managing all of that through is now become much more of a view of the balance sheet. Because there are very, very few people in America that are going to be completely galvanized financially for retirement. So they’re going to need to be able to look at balancing those expenses. And those liabilities along with the assets they’ve accumulated.

Jack Sharry: So Cheryl, you were one of the early on technology companies way back when we’re on the managed care business, and all sorts of evolution has taken place over there over time, and you were really been involved in every step of the way, as far as I know. And now what we’re talking about is connecting dots and I know in your day job, that’s what you do is you connect a lot of dots with your clients around all these different issues that we’re talking about, that’s really having that much more of a household orientation, much more of a how do we pull it all together? If it’s not just portfolios with SMA or UMAs, or models or what have you, but it’s also annuities and planning and all sorts of stuff. So I know this will be part of what our study groups will be looking at. But why don’t you just give a little hint as to where you see the world going around pulling it all together, what you hope will come from our study groups as they start to examine this.

Cheryl Nash: That’s a great point, Jack. So I read a stat that 81% of the industry profits are going to come from clients 55 and older 320 30. So talk about that in the aspect of what we’re trying to do and the complexity of everything that we’re trying to manage. And you know what Steve said people are living longer, there’s just a lot of complexity, I think from you know, connecting the dots, it has to start from and everybody has the wheel right? Where it starts from, you know, communications, goes to planning goes to, you know, buying the securities through a model, whatever that might be, then through continuing to monitor. And there’s that whole continuous, you know, we call it a wheel. But I think there’s a lot happening in that wheel. I think, you know, you mentioned there’s annuities. There could be ETFs, there could be some direct indexing, there could be alternative investments. People want to know about Bitcoin and you know, those types of cryptocurrencies. So, when you think about all that complexity that’s out there today, and how do you bring it together in a simple, simple view, but, you know, keeping the complexity in each area that needs to be? I think that’s going to be the key here because people want, they don’t want to run out of money in retirement. And I think Steve, you and I sometimes talk about our mom’s my mom’s 85, your mom’s 87. I’m helping my mom with a lot of her financial, she knew nothing when my dad passed away in 2020. And she’s come a long way. But if she didn’t have me to kind of help her, I just don’t know where she would be. And I’m not a financial adviser, but helping her get through that. I just think there’s ways in which technology through advisors and even some of this digital the digital platforms that are out there can help bring this together in a simpler view, and help really the investor understand what they own. where it sits, what is it an income, you know, stock? Is that what it looks like for them? And I think that you know, the average American, this is our world, we live in this world every day. So we understand it doesn’t. So really making sure that I think the six study groups that we put together, we’re really going to focus on that and make sure from a perspective of the investor and the average American who’s going to retire, how do we make sure that they have a simple view of what they need and what they have, because it’s very complex out there today. And it’s just getting more complex, with everything that you know, more and more types of securities are coming out. And I was talking to an advisor on Tuesday. And he’s like, I have to go, I’m getting so many calls from my clients, because of the war, right, because of what’s happening in Russia and Ukraine. And he’s like, if they didn’t have their advisor to call and the advisor didn’t have technology to share, this is what’s happening, don’t worry about it, you’re in good stocks, you’re in good bonds, it would be really hard, I think, for that individual to understand. So I think that’s probably a long winded way of saying there’s we can simplify this we can put it in one place is technology for this industry, and really drive the simplicity of what needs to happen in a very complex industry.

Jack Sharry: Yeah, one of the things that as your brother, you’re sharing your perspective, which I wholeheartedly agree and endorse. Three words that popped to mind is connect coordinate, collaborate, that a lot of what we really look for our study group participants, and we’re very excited about the work that they will produce over the coming months. And that is that it’s one thing to buy a product or to buy a technology or to save a financial planning tool as an example, or have a, I don’t know, a rebalancing tool, or whatever, they’re the various tools are a model management capability. But frankly, the investor isn’t so interested in the discrete elements. They’re interested in how they get coordinated, connected, integrated. And they’re also interested in the collaboration that they would have with their advisor, and that people like us, Gerald, myself, Steve, and many others, how do we work together to make it easier for them to get a better outcome to understand what that means, frankly, to sleep better at night? So a lot of what we hope to achieve with the next chapter, Next Chapter Leadership in Action, is to ask the younger folks in our industry, not so young, but young, relative to some of us around this podcast mic, to ask them, what’s a fresh approach? How can we collaborate better as an industry? How can we coordinate what we do not just integrate, but coordinate capabilities, whether you’re coming from a find contribution plan, or you’re coming from a wealth management context, or use inheritance, or who knows what wherever you’re coming from, inevitably, you’re gonna have multiple accounts, multiple holdings, multiple products, including annuities, and alternatives, and many others, how does that come together to produce a better outcome, that’s ultimately what we’re after. And it’s going to take technology, this doesn’t happen by waving a magic wand, as Cheryl will notice. And she and I are both actively involved in this day to day, this is hard work, it’s not easy, you know, the systems weren’t, frankly designed right in the first place. So we get a lot of work to sort of make them talk together. But what we hope to achieve with our friends that are going to be participating in the Next Chapter Leadership in Action Program, really want to see some fresh new answers, ways that we can collaborate share that with the industry promoted widely. Before we check out for our podcasts for today, Steve, if you would maybe give a Vance look at a report conference that you started a year or so ago that you’re looking to have come off, I think it’s May 23 and 24th. Want to just talk a little bit about that give people a teaser as to what might up see?

Steve Gresham: Yes, absolutely. So if you’ve heard so far, that retirement is the big challenge. And we need to come together, one of the ways we get people to come together is with an event. And so a virtual event that combines I think, the most important constituent groups for this whole story. So we will always have financial advisors in the mix, because they are the folks that they you know, candidly, they can tell us exactly what they need. And they can never be too insistent, because we got to get there. And then also we have at the same time, we’ve got the product companies who are trying diligently to create solutions. And they’re the ones that want to connect with those consumers and make the world easier for those advisors. And then we have representatives of the advisory firms. So we’ve got basically the entire group of folks that we need in order to solve most of the problems. As I said at the top, this is really all about reducing friction, as Jack said, connecting the dots, as Cheryl has lived for her entire career is trying to facilitate those connections. So once they see it in front of them, and they see each other and they have that opportunity, we get to surpass one of the problems that we’ve had not only as an industry, but as a country and as a world over the past couple of years, which is being able to talk to each other freely, openly collaborate and see each other try to get some of this stuff done. So I think it’s one of those opportunities where we can raise the quality of the dialogue, all of the contributing firms the 50 or 60 years So they participate in next chapter, have an element in here as well. And so we’re gonna get the best of the best from the best.

Jack Sharry: Terrific. Cheryl, before we sign off anything to add to our conversation before we say farewell for now.

Cheryl Nash: Yeah, no, I thought this was great. I’m so excited about this, I think you’ll all everybody listening, you’ll learn more about where we’re, you know what we’re going to deliver what we’re coming up with, I think the next chapter is really the next new thing. And we’re really excited about it and excited to share where you know what these great minds are going to come up with as they go through this.

Jack Sharry: And Steve, for those that would like to learn more about next chapter, whether it’s the leadership and action or the upcoming conference or the program at large, what’s the best way to reach you?

Steve Gresham: The best ways to get us is to hit the landing page for next chapter that’s on the financial advisor magazine website. We also have a new LinkedIn page. So I’d ask you to join that and then you can always get me at

Jack Sharry: Terrific. Well, Cheryl and Steve, this has been great as always fun to talk to you guys. I learned more stuff that I didn’t know and much appreciated to spend this time together. For our listeners. If you’ve enjoyed our podcast, please rate review, subscribe or share and share I should say what we are doing here at WealthTech on Deck. We are available wherever you get your podcasts. Again. Thanks Cheryl and Steve, it’s been a real pleasure. Have a good one.