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Tips for Becoming a Data-Driven Financial Advisor With Jud Mackrill of Milemarker

Updated: May 17, 2023

Jud Mackrill

Jud Mackrill is the Co-founder of Milemarker, a specialized team of experts focused on solving the data and integration problems of leading financial services companies. He is also the General Partner of Mammoth and an Advisory Board Member at LifeYield.

Jud is passionate about connecting the future of financial advice through design, software integration, and investing in financial services companies. As a multi-award-winning marketer and designer, his work has contributed to the success of many leading financial services and advisory firms.

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

  • Jud Mackrill talks about Milemarker and the services they offer

  • Milemarker’s ideal client profile

  • What inspired Jud to join the financial services industry

  • The early customers of Milemarker

  • Tips for creating excellent customer experiences

  • How does Milemarker help financial advisors become more present with their clients?

In this episode…

Are you struggling to thrive in the financial service industry as an advisor? What can you do to unlock your potential and make your business more efficient and scalable?

Financial advisors nowadays are facing data and integration problems hindering their progress. Jud Mackrill recommends leveraging modern infrastructure and tools to become data-driven advisors. They simplify integration, automate processes, and create remarkable experiences for advisors and clients. Learn how to take control of your data and start delivering proper solutions to your internal and external customers as an advisor.

Listen to this episode of The Customer Wins as host Rich Walker welcomes Jud Mackrill, Co-founder of Milemarker, to discuss how financial advisory firms can thrive. Jud talks about Milemarker and its services, why he got into the financial services industry, his first role at Orion, and how Milemarker helps financial advisors become more present with their clients.

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 0:16

Hi, I'm Rich Walker, the host of The Customer Wins where I talk to business leaders about how they help their customers win and how their focus on customer experience leads to growth. Some of our past guests have included Rick Williamson of Redtail Technology, and Chris Wallner at Chiefoutsiders. Today I'm speaking with Jud Mackrill, co-founder of Milemarker, and today's episode is brought to you by Quik! the leader in enterprise forms automation. When the last step to earning your clients business requires filling out paperwork, don't ruin a good relationship with a bad experience. Instead, get Quik Forms make filling out forms a great experience and the easiest part of your transaction. Visit to get started. Now to introduce my guest, Jud Mackrill is the cofounder of Milemarker and a general partner at Mammoth and alternatives and fun technology platform. He is passionate about connecting the future of financial advice through design, software integration, and investing in tomorrow's leading companies. As a multi-award-winning marketer and designer, Jud work has contributed to the success of today's leading financial services and advisory firms. Jud was previously the CMO of Orion co-founder of Mineral which is sold to Carson in 2018. And the CMO of Carson, Jud and his wife Kim reside in Charleston and have four school-aged children. He enjoys spending time with his family biking, spicy food, and Nebraska football man, I love spicy food to Jud. Jud, welcome to The Customer Wins.

Jud Mackrill 1:42

Glad to be here. Thanks for having me.

Richard Walker 1:43

Yeah, it's really a pleasure, I'm looking forward to hearing your perspective. And if you 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 a great customer experience. And the challenge is to grow in their own company. And I've known Jud for a few years. And I know you excel at creating great customer experiences. So I want to talk about that. But before we do that, I want to understand your business a little better. How does your company help people?

Jud Mackrill 2:09

Yeah, we help people really, if you think about being a financial advisor, today, you are juggling a lot of different things. And ultimately, we want to help financial advisors truly improve their business to actually leverage all this data that they collect on their clients, all the solutions that they subscribe to, or pay for in various ways, and really make that an asset when it comes to part of their business, not just an expense. And so we do that through leveraging a lot of effectively productized services, and then ultimately software that we build and deploy for our customers helping them connect the sources of data they use, whether it's like Orion, or Black Diamond, or their Salesforce or CRM, that may, in fact, actually integrate with the Quik Forms or some sort of thing like that, capture all that data and store it in the cloud using modern data warehousing, and then be able to get an ALEC analytics on top of that, and then be able to put that in front of their advisors or their staff to help improve the lives of their advisors and their clients in all kinds of ways, by their definition, because I've experienced that might, myself and being inside of an IRA is really hard to do. But once you have it, it's very valuable for your business to be able actually make better decisions, completely curate your experience and design and deliver workflows that truly get work done.

Richard Walker 3:37

Wow. Okay, so there's a whole bunch there. So you're putting all this data together? Are you building dashboards for them to run their business like KPIs?

Jud Mackrill 3:44

Correct? Yeah, we'll build dashboards, we have a, it's really a chief data officer as a service sort of offer where we engage and we provide either if somebody needs to know how far they want to travel, and how fast they want to get there, we can engage in the early in, just help them get a clearer sense of that. But then we provide a service where it's not just like one person you hire off the street you find on LinkedIn, or wherever it really is like a dedicated team, helping you actually get results, whether it's building connections to the data you already subscribe to, or even data you have in some sort of closet in your office, because that's not necessarily uncommon, still, and 2023. And then putting that into the cloud, using a data warehouse, and then putting that into effectively your BI solution of choice, we have opinions, but ultimately, you probably pay for one already. Let's help you use it. And then we take that forward, and we can turn that into all kinds of things. Once you have all that data under your definition.

Richard Walker 4:49

And that's so cool. Before I started as a financial planner, I was actually getting trained in business intelligence tools, and billing data warehouse systems myself. I mean, that's part of my technology. background. And it's amazing. You're doing that for advisory firms, because that's bringing it down to a scale that is much smaller than I was dealing with. I mean, what is your typical client look like?

Jud Mackrill 5:11

Yeah, our typical clients are probably around 500 million and then up. Usually they are b2b, b2c, they have their effectively corporate RAA tamp a broker-dealer, or even like an A field marketing organization, and IMO FMO. We also work with insurance carriers that are looking to modernize how they distribute information on their different products. And we're really just working to modernize the piping of all that. So if you think about, I got started in this industry in 2004. And when I got started, I was like, I was a little surprised, even then, because we were like, still in like the pre-Facebook era, or like, right at the very cusp of it being relevant, like, how antiquated some of this stuff was, then? Well, the truth is, most of that stuff hasn't really changed. DST fan mail, it is literally not changed in my entire career is the same landing page, and same solutions. And the customer deserves evolution in terms of how things work. And we sat here and looked at this, and we're like, why somebody's not making this better? We can, and we should do this, nobody's advocating, people are building products. And that's a way of advocacy. But like, no one's building like a true like, elastic sort of center that brings together the integration that needs to happen for firms. What if we just did that? And I think you and I got to know each other a little bit through, we did an event last when I was CMO at Orion called Fuse. And we called you up and said, hey, you guys are doing some awesome stuff for our advisors. Why don't you come to this event at some ski lodge in Park City, and let's do a Hackathon for a few days. And it was so fun, because we got to see your business. And I love entrepreneurship. And I love how different people come at different solutions in different ways. And it's fun to see all the things that you're doing for all the customers, you serve all the different forms you guys manifest for people, it's awesome. How many things? Yeah. And through that, I think it was like a real taste for me of like, what if we just help keep going on this because we had to go back and build our own portfolio accounting company, and like, really focus on that mission there, which is very good. And it's been very successful for the team there. But I couldn't get past that. I like I like, why don't we just keep working on this and keep making it better every day?

Richard Walker 7:45

Yeah, I think that's the best start for any entrepreneur is you have this pain, this need, you see an opportunity that nobody's filling. I remember in the 90s. In college, I actually interned at a lot of financial companies, and some of the people remark, especially from the tech world that I knew that financial services is one of the slowest to catch up to tech. And then we've seen this over and over and over again, exactly, you're saying fan mail is still the same? Because it works. And everybody's using it so fine, don't change it. But what you're really addressing is the need to put information and data together to create decisions and help people have insights into what they're doing for their clients. Right.

Jud Mackrill 8:23

Correct. I mean, think about how much experience has changed in the 19 years I've been in this industry, it's extraordinary different, like, everything's run off of your smartphone. And that is the guide, essentially, for client experience in my client accomplish this quickly, or can they get the insight they need? Well, that's influencing advisors just as much as clients because they're ultimately clients the other day. And so when their expectations have changed, the underlying infrastructure expectations, unfortunately, haven't changed that much. And so everybody needs to catch up and be able to, actually, in some way be much more simplistic and how we are able to deliver what it is we do for people. But to get there, man, it's going through, it's chopping through a jungle with a machete to do. That's what we do.

Richard Walker 9:11

Just a quick perspective on again, in 2004, you enter the financial services market, what were you doing? What was your first role?

Jud Mackrill 9:18

Yeah, I took a role as an analyst with Orion, I think we had about 20 people time. And went started there, went part-time, went to grad school for a couple years got done with grad school and my oldest son who's just turning 16 this week, was born. And I said, hey, I called up Kyle Hyatt was my boss at the time, like, hey, I think about come back full time to Orion. You guys have it for me. And they said, Yeah, sure. So I came back around a key account and then ultimately took over all their onboarding. So I got to know some of the fastest growing most amazing wealth management firms in the country. Through that time, but a five and a half years of time. It felt like it was due Anytime because it was like it was hard work, we were evolving from more of a locally installed software into a truly cloud software into like an integrated software, we were the largest distributor of Salesforce to financial services for a time. Because we were reselling Salesforce to all these firms that wanted to CRM portfolio accounting, hybrid, it was highly successful is the time of like, I think the, you know, TD Ameritrade was like at its all-time peak in terms of relevance and ease to work with. All right, for this industry, and we are close to them. And we just had a really good thing going. And we started then building we open sourced the client portal we built and that really kind of started an evolution to how can we become the easiest friendliest to work with technology vendor in our space was kind of our mission, our aspirational goal. And that for me, I started building products and different solutions for the company. And eventually, like, I was just it made sense for me to take over the marketing and really help us like, open the whole brand up to be that identity. And it was so fun to see.

Richard Walker 11:09

You had a great impact over there. Orion's got such an amazing story and evolution and continues to unfold. It's amazing. Going back to Milemarker, who is your first customer? I mean, how did you overcome that first customer jitter? And get them to say yes, et cetera.

Jud Mackrill 11:25

Yeah, the thing about my first customers are, they're my people, like along the way you pick up people that you just care about, and you're going to work together, regardless of if I'm selling snow shovels, or I'm selling data infrastructure as a service and advisor experiences. So one of our early customers is a firm called Tyco. And they are a third-party asset manager built on top of and OCIO, based in Chicago. And so like we got started with them, and one step at a time, really a built an ability for them to uniquely articulate all their investments, and have a very turnkey, super-fast experience for advisors to get really advanced Asset Management Solutions at like, I would rival their speed and experience to anybody in the industry, I think it's second to none, I'm highly biased. But that team has been really, really awesome to work with, they're doing really good work for advisors, it's so fun for us to see them grow, add new firms, add new advisors, add more assets, and do that really through experience that's informed by data and integration. It really is like, that's the dream. And it's so fun for us to have other people come on, and see that their own vision uniquely, there's some common denominators, but like to be able to realize that vision that they have for their business in a way that is theirs is really kind of what we're all about, how do we make that truly happen for people?

Richard Walker 12:57

I share that with you, because one of my favorite thing is to see as a customer take our technology and turn it into their technology, their experience. And I've seen customers and I wish I could showcase some of them because they're so proprietary. I've seen them do some amazing things that blown me away. I didn't know if they could do that with our technology as a footprint. Is every install customize then? Or is it just a flexible architecture?

Jud Mackrill 13:21

Yeah, we have a flexible core architecture. And then the install themselves is uniquely localized to them to allow them to be able to uniquely riff on it. We will have common denominator things that we make available. And we'll have more and more of that as we go. We're building all kinds of things all the time. But really, we believe that you should have your own unique area to enhance and grow your business. For folks that are using like our data as a service, our whole outsourced, Chief Data Officer, for lack of a better word, a fractional chief data officer, probably better way, say it. For the folks that are using that we're going to start with where you're at, do you have a data warehouse? Do you have a cloud provider? Are you on Azure? or AWS? Or even Google Cloud? Like how do we start there, not change it? But how do you actually start putting it to work? Because a lot of people pay for things they don't use? Think about all the different subscriptions we have for just TV and entertainment. Right? How much time do you actually spend watching that subscription that you have? I seriously don't, but I still pay for it every month. So let's help you take advantage that actually put it to work and make it an asset for you and help you become data driven. And we tried to do that over like a year, like how do we go that way through a year? Like let's just walk in and chip away all the time. And we have guides that get assigned to firms and say hey, how do we make real progress and not be consultants because consultants come in and just take your money and share the ideas that they share with everybody else? And it's generally leaves a bitter taste in a lot of people's mouths like how do we do tangible, valuable things that are clearly measurable? At the end of the day?

Richard Walker 15:06

Yeah, that's actually one of the reasons I wanted to get out of consulting is because I felt like I had no ownership, no accountability to what I was suggesting, or helping them figure out the solution to and then I walked away from it. And I liked being accountable to this, this one, I like having a product. I'm just kind of curious, what are some of the techniques and processes you use to create excellent customer experiences, whether that's for your customers, their customers, etc? What do you think some of the keys are to creating excellent customer experience?

Jud Mackrill 15:35

Yeah, I mean, I think that nobody knows the customer better than the advisor that's dedicated to serving them. And the thing about this, there's a kind of like a sacred thing in this whole thing, right? If somebody trusts you with their well-being financially, that's a really amazing thing. And I think that we get very transactional about that all the time. But it's really, really important that we acknowledge that. And then we think about that collectively and say, how do we do that with absolute excellence? How do we actually improve this over time, and make that experience evolve. And so we work with these firms and sit down. I usually personally go to the founders and spend the spend a day with them at least, and the deep dive on everything they want, everything that their business is today, and everything their business wants to become in the future, and who's influencing it? And if they could change anything, what would it be? And then we go back, and we say, all right, based on what we know, based on the constraints, they already have, the contracts they already have, how do we help them get results as quickly as we can, and put that plan into action and follow a strong framework? I mean, we're not going to like, say, hey, everybody has a special snowflake, process-wise, that's not how you deliver excellence. But how do you put them into our process, so they truly do achieve excellence at scale. And, and that's where then we constantly, make sure we have the right guides in place. People that know them, know them really well know where they're gonna go really well. And so that's always a big part of our journeys that we built.

Richard Walker 17:12

So I think that two things there that catching my attention, number one is transactional. And you're right, I remember when I became a financial adviser, it was about my first transaction, the next transaction, because ultimately, it's how I get paid. It's how do I know I'm delivering something to my client. But then you also mentioned process, which I'm a big fan of really good structured process, because I think efficiency stems from great design, design of your process, your software, your people, how they interact, etc. So I'm gonna get to a question around this, because not every advisor is thinking in terms of process, they are probably thinking transactional, how do you help them become more present with their clients? Because clients don't just want to do a transaction, they want to get advice, they want ongoing help and support? How do you guys help them do that with data and the systems you're putting in place?

Jud Mackrill 17:58

Well, I think ultimately, you need to have, like, how do you want to construct the client experience today, and if I think mostly advisors, I know have like five different places, they have all their data. And I think that there's a lot of different like, kind of the monolithic systems out there that have most of that data. But even still, the adviser wants to uniquely package that for their clients. So we help them how do we get that to you as quickly as possible? So you are completely dialed in everything about that client, whether it's the kids birthdays, important anniversaries, it's milestones and goals that we have set forth, and how are we truly doing toward that? You know, I found that my experience has been as much as we talk about financial planning in this industry, it's honestly, mostly marketing for most firms. It's usually done at a point in time, it's not generally applied consistently. I know there are people that will totally differ with that fact. And they're really doing something different. But I'm saying for most people, most retail clients, financial planning is a point in time. And so how do we change that and make that really practical? How do we think about tax? How do we think about estate? How do we think about family? How do we think about broader goals? How do we think about all that in not just a one-time hey, this is a plan, but like continually chip away at that and I think that starts with data. And then it starts with synthesizing all the different things they need to add more change more like enhance that. And then how do we take that and say this is the most ideal client experience for XYZ advisors and XYZ, this is what we do. And you can deviate but only in a way that enhances this you cannot get out of this meeting and not accomplish these things, because this is how we work and this is done by a science because we know that when we do this, our clients have better returns, save more money, have increased happiness over time, because we'll actually ask them and survey them. And we capture that data. And that creates better referral opportunities over time. Like all this stuff is a science and it takes data to accomplish it. But that's, that's the world that I see. And I've seen it firsthand. It's been fun. My time at Carson was extraordinary to be able to see a firm that was really dialed into doing this working with firms like a creative planning and Mariner and all the many of the focus firms, I had a privilege of working alongside of seeing that done well and continually iterated on his inspirational but it shouldn't be just them. It should be the whole.

Richard Walker 20:47

It should, I agree. So I mean, you're mentioning all this do you have like a favorite customer success story of how they were transformed, they had a great outcome?

Jud Mackrill 20:56

Man, I guess being able to see just continual iteration, on any firm that's able to go in and take a plan that we give them a journey that we map out, and to be able to accomplish it by their own definition and actually see it come into place and see that actually provide a true ROI. I don't even need names, but like being able to come up and see people that you know, worked with over my entire career and not just even the time of Milemarker. That is the most fulfilling thing. And being able to hear things that we've guided people into and say I was at a dinner with some of the folks from Allianz and DPL. And the other. It was actually done at T three, and Sampah. And one of the people shared with me, she's like, you told me this, like, five years ago, and it was the most helpful thing for me, that changed my entire career. I'm like, what's really, I never thought about it. But like being able to see that thing when you're just investing all the time, in making this world better. And being able to see little fruit. Sometimes that's the best thing, whether it ever made you $1 It's worth it to just to keep investing and keep doing that. And if we stop because we feel like things are hard. We're selling ourselves short, in terms of the impact we can make.

Richard Walker 22:21

Yeah, I've often said the difference between success and failure is persistence. And that persistence pays off with these types of stories. I 100% agree. When I'm at a show, or I'm at a conference and somebody walks up there a user of our product, and they've had a direct benefit there. I feel like I was a rockstar. They're like, oh my gosh, you changed my life. Yeah, I hate filling out forms. I don't want to do it anymore.

Jud Mackrill 22:44


Richard Walker 22:45

Let's switch gears a little bit. Because one of my favorite topics is artificial intelligence. I'm sure you're all immersed in it as well. Being in tech, and I should do an entire podcast on this, because I love it so much. But I want to understand, from your perspective, how do you see AI changing or impacting customer experience?

Jud Mackrill 23:04

Yeah, I think that so much about AI right now is understanding how to query and understanding how to prompt. And like people are making all these different things like prompt engineering, and like, that's the future. I think, to some degree, it is, I think it's going to change the way we think about things. We've always had ways we Google, there's Google, and then there's like an academic Google. And then there's like, all these different advanced ways to do that. And when you really understand how to do that it is an unlock for you. And so as much as we can become students of what this can do, and also be able to be increasingly discerning to say, just because of the, I always called the robot, just because the robot told me this doesn't mean it's necessarily factual, let's continue to validate this, and run with it. But understand that it's extraordinarily powerful, and what it can do for us, or do for us. And so I fundamentally believe it's gonna be a big part of what we do, I think it's going to help unlock interesting insights that you never knew, and helping you as a business care about things that you didn't care about before. But now the data tells you how meaningful they are, if you could think about this, if you had a number that you could actually lean on as an advisory firm and say, This is how much we've saved our clients and taxes this year. Think about that, like if you could put a number on that. Oftentimes, a great adviser will pay their fee alone and just tax savings for the client. And like, being able to do that and measure it is an extraordinary thing. Even if it's just like your scorecard. You never show anybody but your team and you continually are inspired by that. That's what this stuff is going to give us and it's going to help us by putting an AI model on top of our data securely. isolated to our data. And starting to see that and then even looking at benchmarking, think about the Schwab benchmarking studies and things like that. I know a lot of firms spend a lot of time participating in that stuff. Think about what AI model is going to do for that. You put like a language model on top of all that stuff. And you'll have instant insight. And you can have real-time insight across firms and really thinking about how are we continually improving this understanding that it's a law of abundance here, where if we continue getting better, we rise every boat lifts, as we continue to get better. It's not like we're taking from each other, we're simply just all improving. And we're serving people better, because there's always deeper ways that our craft can improve and change people's lives. So I'm very excited about how it's gonna help and all the different things that unlocks for the way that we see the world.

Richard Walker 25:54

When I joined my mentor in his business and financial planning, one of the things I found about him is he was highly meticulous, he tracked almost every minute of his time, like the lawyer would with the clients he was serving. And I remember he had a call with somebody, and he said, hey, I'm looking at my spreadsheet, you're a waste of money to me, like you call me every week and waste time, and I'm not making that much money. And honestly, you would think like, that's a great way to fire a client, the client says, oh, my gosh, I had no idea. Yeah, I'll send you more money. I like this working relationship we have, I will pay you more what do I need to do? So you have an interesting take on this, that you can use the data to give yourself insights to how you're working to benchmark? I think that's an amazing view of it.

Jud Mackrill 26:38

Yeah, I think Man, the crazy thing is, like, I was talking to a student at Carnegie yesterday, and he's working in AI, and doing all this interesting stuff. And like, it's so inspirational in so many different ways. At the same time, you have to kind of like, just, if we just wait a second, it'll get 10x. Better. Yeah, that's the crazy thing, but I really do encourage all of us to just start walking toward it and start figuring out how it works and getting very familiar with it be a student of this change, because it's going to change everything. Whether you like it or not, it's going to change.

Richard Walker 27:13

I think everybody should find a tool that makes their job easier. That's AI-driven and figure it out. Hey, Jud, as we wrap this up, I do have another question for you. But before I ask that, what is the best way for people to connect with you and find you?

Jud Mackrill 27:26

Yeah, my email is just, feel free to reach out to them there. Or go to, and we'll happily reach out. Love to learn more about your unique firm and how you provide advice and your vision for the future. I mean, our whole thing is like, how do we help you get there? How do we help you make that progress? Milemarker is all about progress. It's never a destination? There's always part of the journey, and how do we help you prolong your path?

Richard Walker 27:58

Awesome. Okay, here's my last question. Who has had the biggest impact on your leadership? Or how you approach your role?

Jud Mackrill 28:04

Yeah, I think for me, it's probably Eric Clark. I got to work alongside Eric for a long time. And it's not necessarily like, it's really the dedication to building Orion the way it is, and like a relentless focus on that and just continually doing the work and being patient with people. I mean, understanding like how to really lead people well. And he's absolutely by all measures, one of the most successful people in our space. But in the moment, you don't realize how lucky you are to get to like, see somebody that cares that much. Because a lot of times, people don't, not to that measure. I remember working on really complicated things we were working till super late in the night, and he's just there helping support our team and like being part of it and leading and also helping develop us as leaders. It was really, really good for me. And I've had a lot of good people in my life, but professionally to understand, like perspective shifting, thinking bigger thinking about like, how do I do something right now and not worry about how we're making money on it. But realizing like we're making an impact, and it will take care of itself. If you keep doing enough good things for people and keep investing in the experience you provide it. It will compound in an extraordinary way. And it really can change people's lives and build something greater.

Richard Walker 29:33

Yeah, I actually really admire Eric. I got to spend a little bit of time with him at that park city fuse event and get to know him a little bit better. I wish I had that experience. You had to work next to him because he's a great guy. Hey, I want to say thanks to Jud Mackrill, cofounder of Milemarker for being on this episode of The Customer Wins go check out Milemarker's website at And don't forget to check out where we take the work out of paperwork. I hope you've enjoyed this discussion, and we'll click the like button, share this with someone and even subscribe to our channels for future episodes of The Customer Wins. Jud, thank you so much for joining me today.

Jud Mackrill 30:13

Thanks Rich. Glad to be here.

Outro 30:16

Thanks for listening to The Customer Wins podcast. We'll see you again next time and be sure to click subscribe to get future episodes.


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