top of page

The CRM Experience for Financial Advisors With Rick Williamson of Redtail Technology

Rick Williamson

Rick Williamson is the Director of Training at Redtail Technology, the leader in web-based client relationship management solutions for financial advisors. He develops training and education initiatives, working hands on to improve team management and even public speaking. Rick is an expert on all things CRM-related and has a background and experience in film production and public speaking.

Here’s a glimpse of what you’ll learn:

  • Rick Williamson talks about Redtail and how it helps people

  • Redtail’s ideal customer profile

  • Rick’s role at Redtail as the Director of Training

  • Tips for creating and delivering great customer experience

  • How the Redtail and Orion merger improving their clients lives

  • Redtail’s customer success stories;

  • How AI is impacting customer experience

In this episode…

As a financial advisor, do you desire to transform how you scale your business through technology and outsourced solutions? Where can you get a CRM that offers you the necessary tools to assist you in your efforts?

For over a decade, Rick Williamson has been in all things CRM related. He has discovered that financial advisors struggle with managing their client base and scaling their business because they lack the necessary tools for their work. Rick recommends CRM that integrates widely and deeply with other popular tools in the financial services industry.

In this episode of The Customer Wins, host Rich Walker welcomes Rick Williamson, Director Of Training at Redtail Technology, to discuss CRM that best serves financial advisors. Rick talks about Redtail and how it helps people, tips for creating and delivering great customer experience, how Redtail and Orion’s merger improves their clients' lives, and its customer success stories.

Resources mentioned in this episode:

Sponsor for this episode...

This is brought to you by Quik!

At Quik!, we provide forms automation and management solutions for companies seeking to maximize their potential productivity.

Our vision is to become the leading forms automation company by making paperwork the easiest part of every transaction.

Meanwhile, our mission is to help the top firms in the financial industry raise their bottom line by streamlining the customer experience with automated, convenient solutions.

Go to to learn more, or contact us with questions at

Episode Transcript:

Intro 0:02

Welcome to The Customer Wins podcast where business leaders discuss their secrets and techniques for helping their customers succeed and in turn grow their business.

Richard Walker 0:12

Hi, I'm Rich Walker, the host of The Customer Wins where I talk to business leaders about how they help their customers win how their focus on customer experience leads to growth. Some of our past guests have included Alan G at Finlocity, and Pem Guery with SIGNiX. Today I'm speaking with Rick Williamson the Director of Training at Redtail. Now today's episode is brought to you by Quik! the leader in enterprise forms automation, when the last step to earn your clients business requires filling out paperwork. Don't ruin your relationship with a bad experience. Instead, get Quik Forms to make filling out forms a great experience and the easiest part of your transaction, visit to get started. So before I introduce today's guest, I want to give a big thank you to Jack Anderson, who sponsored and co-hosted a recent webinar with Redtail and Quik. Go check out Redtail's website at and get a huge discount on using Quik! with red tail. All right, I'm really excited. Let's introduce today's guest, Rick Williamson, better known as Ricky Redtail has been with Redtail for over 11 years where his role of director of training allows him to lead as well as oversee all training and education resources, presentations and content with a background and experience in film production public speaking, and time as a cast member at Walt Disney World, Rick has been able to make a significant impact at both Redtail and in the FinTech industry. His experience in numerous marketing, media training and presentation projects make him an exciting and entertaining voice and fintech client experience and practice management. So I'm really excited to talk to you, Rick, welcome to The Customer Wins.

Rick Williamson 1:53

Rich, thank you so much for having me. Thank you, for anybody listening. I was so excited to be invited on this. I love podcasting in general, I love talking about the client experience getting people thinking a little bit differently than just the services that they offer. So I'm really, really excited to talk to you today.

Richard Walker 2:14

Man, I'm so glad to have you, I've been looking forward to this too, you're gonna have a great story to tell. Now, for those who haven't heard this podcast before I talk with business leaders about what they're doing to help their customers win, how they built and deliver great customer experience and the challenge to growing their own company. Rick, I want to understand your business a little better. How does Redtail help people?

Rick Williamson 2:35

Man? Well, Redtail is a CRM company. And for those who don't know what CRM is, it means Contact Relationship Management. So I mean, it's literally built into the product name, we help all of our clients manage their relationships with their contacts, not just their clients, their prospects, their business, contacts, things like that, not just all of the many compliance-related things that need to be done in the financial technology industry, there's just no taking and calendar management and making sure all of that stuff is on the up and up. But giving people a central repository, basically a digital memory for the things that you might remember about your spouse, hopefully, your children, your relatives, your best friends, but you can't remember for your 300 clients or your 500th client things like you know the type of car that they drive, or their favorite sports team, or how they take their coffee, all of those types of things go into, and we're going to talk a ton about it, obviously. But those are the things that go into building a really valuable relationship. And when you build those valuable relationships, there's actually a article that is one of my favorite articles to reference from Harvard Business Review, it goes back in like 2015. So it's been a while. But they found that the value of a client increases, I believe it was 52%, if they go from just highly satisfied, which I think a lot of people if I could guarantee you an entire book of business of highly satisfied customers, I think a lot of people would take that. But 52% increase from highly satisfied to fully connected. And that increase in value means that they are more loyal to you and your business, they are more likely to advocate for you, to their friends to their family, they are more interested in doing repeat business with you. So those type of deep connections that a CRM can provide that we try to teach about. Those types of things are just so like literally proven to be valuable to a business. So I love that we can help provide tools, technology and strategies to help people execute those types of things.

Richard Walker 4:42

Yeah, and it's been amazing watching Redtail over the years, I think I met Brian the founder way back in 2005 or so we were both working with Transamerica to win that deal, which took four years by the way. I think Redtail may have won that earlier. But it seemed it's such an evolution from the idea of I just have to have a place to keep somebody's phone number to, I need this to run my business, and it becomes the hub and the centerpiece of most advisory businesses. And I think Redtail has done a good job of building out features that add way more value than just what CRM represents. So, who is your direct customer of your products, who are the users of your product?

Rick Williamson 5:21

So the direct customer of our product is financial professionals, all over the industry, whether they be advisors, whether they be planners, and a great majority of them are office staff, members of those advisors and planners, they are the ones who are living in there, who are managing the schedules, who are updating the contact information, who are answering the phones, and then are able to use the information in our product to actually engage in a personal conversation. You brought up how we have gone from just collecting phone numbers to collecting all of this type of information, stuff like that. And I think it's necessary, we've become more and more and more efficient with our time, I think there was some, I read some crazy statistic that like, the amount of work that we put into a single day now, is equivalent to like two weeks of work back in, like 100 years ago, or something like that, I can't remember what the name was or what the amount was. But that type of efficiency means our brains are operating at a higher capacity means that we are collecting and processing more information in our brains at a higher rate. And a CRM, just like anything, just like, my glasses helped me see, just like, you know, a hip replacement, helps you walk a little bit better, a CRM helps you remember better, it helps you track those things better. So it really is a valuable, valuable tool when you are in the relationship business, which I think everybody is in. And then the services they provide are just that conduit for that relationship.

Richard Walker 6:53

Yeah, right. So in a way, you are helping advisors be more effective, more efficient, their staff be better, but also that means you're having a better impact on the service they're delivering. And you and I were talking previously, that what you really care about, or the maybe even the company does focus on quality of life. Can you talked about that?

Rick Williamson 6:53

Yeah, it's all about making things easier, right. And that trickle-down effect of if we can make our users lives easier if we can make that support staff members life easier. If we can make that advisors life easier than that is going to give them time to make their clients life's easier and to give an increased whatever that experience is even just by a little bit. We'll talk about this a little bit later. But I always like quoting Walt Disney. And this is a quote that I actually am stealing from Jack. Jack is the one who reminded me of this quote, but Walt Disney famously said, like, there is no magic and magic, magic is in the details. And that is all of what a CRM is, it is the details. And of course, it meets the needs of like compliance, because that is a big thing that needs to be taken care of in the financial technology industry, in the financial professional industry, you have to keep concrete recorded notes, you have to notate every client touch every client task, everything that's going on, you have to notate their records, you have to get their best interests, agreements signed, and all of these types of things. So obviously, it helps track with that type of stuff. But as we are talking about on this podcast, and as I, I love to kind of tout myself, I'm a big relationships guy. So I always focus on the relationship aspect of it.

Richard Walker 8:37

So let's talk a little about your role. Yeah, I mean, you're involved in training and education and helping people I'm guessing and be more effective with the toolset overall, is it externally facing training, internal training?

Rick Williamson 8:49

A little bit of both, honestly. So I'm the Director of Training here and I oversee both internal and external training team for the Redtail, I don't even know what the right word is branch or arm of Orion. But my internal team is all focused on helping our staff become better making sure that they are knowledgeable about product releases and updates and release notes. But we also help run our continuing education programs which we call core competencies we call agility training, to help them level up to help them grow in their career paths we help with call recordings and work with our customer service managers to help coach their team members, we do our welcome tailor new hire training, which is an introduction to the culture to the company to the products themselves and things like that. So the internal side of things does that exact same type of building raving fans on the internal side as our external team does. An external team focuses primarily on scheduling one on one trainings with individuals who want more knowledge on how to use the product but we do so much more than that. There are so many training offerings out there that are just like, we're gonna teach you how to use a product point here, click here, this is how you do that. But we give strategies we give best practices, we give samples we give a lot of stuff that we talked about on here, we motivate people and try and encourage people to use those smaller details, so that they can build better relationships with their clients as well. So it's not just product training, although we do a load of product training, but it is also strategic training, it's client experience training. And then of course, we do Redtail university events, which I could go on and on about, we do webinars, which you were a part of, and all of them are about offering knowledge and education on not only what the product can do, but what also is out there in the tech universe that can help them meet these challenges. And more than anything, like we try to have fun, like our goal with Redtail training, it's not a money-making game, we don't charge anything for our training with the exception of Redtail University. And the only reason we charge for Redtail University is so that we can put it on, like my goal, my main directive, from high on down is to break even like financially speaking, right. But building raving fans is all about being a good hang. Like to put it simply, be fun, be funny, have a good time. And that's what we try to do in every interaction that we have, we try to be fun and funny. We try to be supportive. We try to teach people how to fish, so to speak. And that helps with brand loyalty that helps with client retention, that helps with all those types of things by just being somebody wants to hang out with, when the times are tough when the economy is down, and people are looking to, you know, shed extra costs. Yes, they'll look at the numbers, and yes, to look at the value. But they'll also remember, I really liked those people. And that's incredibly valuable. It can't always be measured, but it's so valuable.

Richard Walker 12:13

Yeah, you speak to a lot of things that are related to your company culture. And I mean, even just the theme of dogs at work, because I know the company name, you can tell us how the company name was formed. How would you describe, is there a succinct way to describe the culture at Redtail?

Rick Williamson 12:31

Yeah, man. So Redtail, as you mentioned, Redtail, we just celebrated our 20th birthday or 20th anniversary. So that was really cool. We're one year away from being able to buy alcohol. And I'm really excited about that for the company. Redtail was born out of a financial services office. And that's one of my favorite parts about our origin story, if you will, is that we weren't just built in some tech area, we started in an office who needed a solution to this. And that office was gracious enough to let our founders or creators, our CEO, Brian McLaughlin, our former COOs now retired the lucky guy, Andy Hernandez, to branch out of their office and actually build this for the industry. And the name Redtail came from Brian's first red tail Golden Retriever named Tucker me out, McLaughlin. And the whole dog thing is really just like an ace in the hole, especially when you're at conferences, because somebody can be walking up to me. And they might be angry, they might have some feedback, they might, hey, this isn't working the way I want or whatever. But there's a giant dog on the banner behind me. And that's just like an immediate diffuser. So I've always been a fan of that.

Richard Walker 13:41

You guys had puppy memes and the dog theme before the internet had it.

Rick Williamson 13:46

Yeah, ain't nobody out there doesn't like dogs. I mean, sure, there are some people who do and I get that. But it's just a really fun thing to build a company around. And we've always been very dog friendly, people are allowed to bring their dogs into the office, we would offer training courses and things like that in the before times when everybody was coming into the office, but that's a whole other podcast. And our culture is really based around having fun, being innovative, and work hard, play hard, doing our absolute best for our customers. And again, being a good hang being able to have these types of really fun, interesting conversations with people and get them thinking differently, get them working differently. And I love that I've always loved that. I've always loved the fact that ever since I was handed the reins to the training team, I've been allowed to build like themes around our Redtail universities that have been adopted by the company you can kind of see behind me. I got 10 years’ worth of Redtail University workbook covers behind me, and we've done themes around back to the future and superheroes and this year's theme, it's all about the kids. kitchen and cooking and cooking up relationships. And not only are they fun, but they serve as really great analogies for what our advisors provide and put into the work that they do with their clients, cooking and putting together a great meal, takes a recipe takes ingredients, takes kitchen tools. And if you are able to serve somebody up a delicious meal, like that can change their entire worldview. And when you combine that with what the CRM can help you do with people, it's really, really fun. And more than anything, the fact that I have been able to be myself and be fun and bring that theatricality to this, I think is a big part of why Redtail's been successful. It's a big part of why I've been successful. And I'm, like, I tell everybody, like, you're gonna have to be like, kill me and bury me to get rid of me around here. Because I'm in I drink the Kool-Aid.

Richard Walker 15:56

I can speak to that, because the webinar we did with Jack was so much fun. It was probably the best webinar I've ever done in terms of vibe, energy, and just interaction. And then the other thing is, I admitted to her that I had taken improv comedy classes. And she's like, oh, my gosh, I've done improv. And so we're like, okay, let's do it. What happens on this call, and I think next time we do it, we're going to try even harder to go off script.

Rick Williamson 16:22

Oh, man we used to, and again, we've grown up where we're 20. Now, so we got to act like adults, but we used to do all sorts of pranks, like at RTU, we would look up on Urban Dictionary, if nobody's familiar with Urban Dictionary, it's not safe for work. There are some very, very naughty things on there. But it's terminology, so what does this mean? What does that mean, and we would hit random on urban dictionary, and as long as it wasn't overtly inappropriate, we would challenge ourselves to try and find a way to fit that into the day. And it was hilarious. But again, we got to grow up a little bit. So we try and find really fun ways to do that, like, I myself come from a public speaking background, from a performance background. A lot of the people I look for in my team, I look for those big personalities, because personality is a hard thing to teach, right? That type of on the fly thinking and, and wits, you can learn it, as you said, you can go to improv classes, you can go stuff like that, you can learn that. But it's way easier to teach somebody how to learn the technology, and then use their personality to convey that. So I always look for big personality, when it comes to my team, and when it comes to really encouraging them to use those personalities in their work.

Richard Walker 17:46

So that's interesting. I don't think I've had anybody kind of say it this way, I'm gonna repeat back to you something that I think you're saying, which is one of the ways to create and deliver a great customer experience is to actually bring your personality out in the delivery of that experience, is that fair?

Rick Williamson 18:01

Very much. So bring out the things find those connection points, between the stuff, and we're going to talk about this a little bit more. But I love to encourage people to focus on the things that quote unquote, they choose to waste their time on, as my father might tell me back in the day, or whatever, but like, this type of industry is so focused on connecting with people in ways that they can't control anything about it, we usually couldn't connect with people based on their age, obviously, retirement being a big deal in this industry, college planning, just financial planning, in general, is tied to age, we focus on gender, we focus on income, we focus on education. And that's all. Exactly, tie that into age, right? But who we are as people, is what we choose to waste our time on. We all have to go to work. We all have to go to school to get better opportunities, stuff like that. But when we have our free time, what do we choose to do with it? Do we choose to play fantasy football? Do we choose to go fishing? Do we choose to build small wooden boats in glass bottles, and once you can connect with people on the things that you love and the things that they love, it's just natural, it becomes a really deeper client experience, because you are now engaging with not only who the people are that you're talking to, but you're engaging with yourself as well. And you're showing them yourself as well. And that just, that's just the psychology of building relationships.

Richard Walker 19:35

Yeah. Awesome, man. So let me just switch gears and ask you because you mentioned Orion. Yep. And we know that Orion purchased or merged with, I don't know how you say it with Redtail. And those types of things have an impact. Right. We saw Brian go off to go work more on the Orion side. And I'm curious, how has this merger impacted on how you're improving people's lives with your products?

Rick Williamson 19:58

That's a really good question and I always make the joke that from the side of the purchaser, we purchased Redtail from the side of the purchase, it's a merger. Like, that's always like the joke, how it goes and things like that. But honestly, like, the biggest struggle has just been like the internal technology like, oh, I got to use Outlook. Now bummer. That kind of stuff is obviously weirdly disruptive. But from the Redtail training side of things, like we really have been allowed to do, our particular brand of nonsense, as I like to say it like, we've been able to do Redtail university this year, they were incredibly gracious with us, we just got done with the wonderful ascent conference in Orlando, and they were super open to strategizing with me on what would be the best version of RTU. To present there, and I was very, I wasn't rude or anything, but I was like, anything less than a full RTU is not going to be an art to you. That's just the fact. And I thought I was going to have to show my work and have a huge battle over it. And they were just like, okay, like, we'll do a full RTU. And that's was incredible, that made me feel great. It was so validating. And I love more than anything that Orion has been incredibly open to learning more about us. I literally have been doing a bunch of calls with a bunch of different business entities and a bunch of different departments, to spread the word of red tail, and what we do and how we do it, and what has made us so successful. And I think the most interesting thing is that, for the longest time, Orion and all of their tech offerings and stuff like that, they have been really geared towards the advisors themselves, the financial planners, and Redtail really, as I mentioned before, it is geared a ton towards the office staff. And so I think really the biggest thing that we are working on is just informing each other and teaching each other how to build those relationships. And this is how we build our relationships with our client service team. And this is how we build our relationships to our training to our sales. This is how we build our relationships at our conferences. And then Orion teaching us like this is how we build our relationships, from the organizational side of things from the enterprise side of things and stuff like that. So it's been really, really interesting. But, again, the big changes into how, like we serve our customers, I think one of the most exciting aspects is that our customers now have access to not that they didn't have access before, but the fact that it's all underneath one umbrella, which we're not the first people to do the whole one umbrella thing, we're not the first people to put everything in one stack, or offer a best in one solution or an all in one solution. But I do like that Orion for the most part, saw these needs and then didn't try and build their own half-baked thing. They have purchased a financial planning tool, a risk assessment tool, a CRM tool, and then they've kept on the people who are part of those tools. As you said before, Brian, rather than being, thank you for your work, thank you for product, have a nice day. He's committed, he's in on this. He's committed to this working and he's now the president of all of Orion Technologies. So he gets to have an aspect and build in kind of interject and inject this attitude that we have had for the longest time into the Orion entire advisor technology suite, which is amazing. And the same is true of us collaborating with their trainers, we realize that our trainers, here at Redtail, we're like a ton of hats. And over at Orion, they have people who just do like specified things and like, oh, that's super interesting, that opens up the floodgates for what we can do here. But going back to the technology, obviously, we've talked about CRM, that's our core product. That's our flagship product. But there are things like Redtail speak, for example, that allow compliant texting and internal office messaging, which is massive, because for texting has been around since the late 90s, early 2000s. And only just in the last few years have has it finally found a compliance solution for financial professionals to communicate in the literal most common way to communicate in the world. That's a huge advantage now that's been presented to our users and the industry. And then things that Orion offers not just the risk assessment in the planning that I mentioned before, but things like a client portal that clients can now access a mobile app that clients can now access that is very similar to mobile apps offered by like banks like I don't call Chase Bank ever. I don't even order my pizza over the phone anymore, like I can do anything online, and the fact that through that client portal, their clients now have access to real time information like that. So that's going to cut down on the amount of calls that maybe are incoming, just because sometimes they're looking for that close bit of information. And if it's going to cut down on calls for that close bit of information, then it's going to increase in offices time to dedicate to building that relationship, if I don't have to worry about looking up somebody's account balance or whatever, if I don't have to spend my time doing that I can spend my time talking with them about the about UConn winning the Final Four, if that's what they're into, or the new John Wick movie, if that's what they're into. And even though it seems a little impersonal, or unpersonal to text, or to give somebody a client portal, even though that feels like it's taking the personal aspect out of it, what it is doing is just making the trading of normal regular information faster and more efficient. So that the personal stuff, you can dedicate more time to. So that's really exciting to me.

Richard Walker 26:09

So Rick, let's put that in a more concrete perspective. Tell me about one of your favorite customer success stories. How did you help them win? What was their outcome? How did you transform them?