Choosing the Right Legal Tech in the Age of AI, with Scott Clasen

Episode Notes

Transcript

Chad Fox:

Hi, I’m Chad.

Zack Glaser:

And I’m Zack, and this is episode 611 of the Lawyerist Podcast, part of the Legal Talk Network. Today, I talk with Scott Clasen about choosing legal technology, SaaS platforms in the changing, I guess, tech atmosphere that we’ve got right now with artificial intelligence and basically how to know what to think about, how to know what to think about. Yeah. How to know what to think about when you’re implementing, changing, building, developing, all those things that you’re doing with your technology in your law firm.

Chad Fox:

Yes, sir.

Zack Glaser:

Chad, what’s up with Lawyers Lab right now? I know I haven’t seen you in a while. I haven’t been at LabCon in a while.

Chad Fox:

Yeah, it’s good. It’s exciting times right now. We just brought on a new business strategist, Richard Carr. So that’s going great. And he’s new to lawyers, but not new to coaching and strategizing with business owners. He was an entrepreneur for many years and then got into doing some work with the Small Business Association in an advisory role. Gained a ton of knowledge and experience through that. Awesome. So yeah, we’re excited.

Zack Glaser:

Someone told me that he actually holds the record for the amount of pennies balanced on somebody’s elbow. Is that true or am I just making stuff up?

Chad Fox:

I have no idea. That might be AI. That might be a

Zack Glaser:

Hallucination.That’s a human hallucination. Ladies and gentlemen, that’s the type of stuff that you get when you just let AI create things. That is 100% untrue. Well, I mean, I guess it could be true, but as far as I know, that is untrue and just totally made up. So what’s exciting about Richard coming into the stable, the group?

Chad Fox:

Well, I’ll say first, I know he’s an outdoors guy, so I don’t know if he’s into pennies though, but he’s an outdoors

Zack Glaser:

Guy, likes to hike. Not all of us can be. Good. So that opens up the amount of people that get help with our business strategists. And so has he gotten started yet? Has he jumped in?

Chad Fox:

Yeah, he’s actually … We gave him his first labster yesterday. I think he’s meeting with his labster tomorrow, his first labster tomorrow.

Zack Glaser:

Nice.

Chad Fox:

So it’s pretty exciting stuff.

Zack Glaser:

So who do we have over there with you now? We got Richard, we got you. Bernadette.

Chad Fox:

And Leticia.

Zack Glaser:

Leticia.

Chad Fox:

Yeah.

Zack Glaser:

Okay.

Chad Fox:

Got Jeff.

Zack Glaser:

Jeff. Nice.

Chad Fox:

We got you.

Zack Glaser:

Yeah. I spend some time over there on that side

Chad Fox:

Of the

Zack Glaser:

Building.

Chad Fox:

Yeah.

Zack Glaser:

It’s floor two of the affinity consulting building.

Chad Fox:

Floor two. Yes.

Zack Glaser:

Floor two. Yeah. And

Chad Fox:

Then we have the lovely Katie.

Zack Glaser:

Oh yeah. Yeah.

Chad Fox:

Who some people have met. She’s our lab experience manager.

Zack Glaser:

Fun story. Katie and I have worked together, I guess, five years now. And I didn’t meet Katie in person for two years at least, and I’ve probably actually met her in person maybe twice now. So that’s the life of a distributed workforce, right?

Chad Fox:

Yeah.

Zack Glaser:

Well, fun fact, Katie lives in Minnesota, I guess Minneapolis, maybe St. Paul, one of the Twin Cities, which is where Scott Clayson is. And so let’s get into my conversation with Scott.

Scott Clasen:

Hi, I’m Scott Clasen. I’m a go- to-market strategist who is working with various legal consulting firms, including Affinity and Lawyerist spent the last 10 years working for legal tech software companies, including TimeSolve, ProfitSolve, which ended up including both TimeSolve, Rock and Matter, CosmoLex, Tab three, Orion Law Ruler, a whole variety of legal tech solutions. And that’s where I’ll stop.

Zack Glaser:

Scott, thanks for being with me. It’s always odd. I actually love that we do it on the Lawyers Podcast this way where guests introduce themselves, but it always feels odd as the guest when I have to do it myself. But for people that don’t know you, I’ve been around you for a while in the legal tech space. Like you said, you’ve been with Tabs three, CosmoLex, Rocket Matter, the whole ProfitSolv family of products. And so you’ve seen, oh man, and that brings in … Yeah, that is a pretty big and broad spread of SaaS products. And so I kind of thought who better to talk about delivery of SaaS products and how we might assess them in today’s world than you. So thanks for being with me.

Scott Clasen:

Happy to be here. Zack, good to see you again.

Zack Glaser:

Yes, yes. Same to you. So let’s kind of go ahead and jump into that. I’ve been toying with this idea recently, and I know a lot of people have, of quote unquote, SaaS is dead. And that whenever we say blank is dead, billable hour is dead, SaaS is dead.

Scott Clasen:

I was going to say, it doesn’t make you think the billable hour is dead. I started in this industry almost exactly 10 years ago. In fact, it was 10 years ago yesterday. Oh wow. And I think literally my first week I was hearing about the billable hour is dead and I feel like it’s not dead 10 years

Zack Glaser:

Old. Man, yeah, it keeps kicking. And so I think that’s a great entry point into here because we hear the term SaaS is dead. And the idea is that with vibe coding, with this really, really low barrier to entry to building some of these, let’s at least say some of the more simple platforms, that it’s a little more difficult to think about investing your time, your data, your infrastructure into an existing SaaS platform. And I’m kind of wondering how this affects how we look at our SaaS platforms now.

Scott Clasen:

I think we could step back one step behind that a little bit, Zack, and think about how many lawyers and small law firms today really understand the realm of the possible with building your own products via vibe coding, right? And the idea of using, let’s say Cloudcode, that’s sort of the de facto place where people will feel like they can go to build tools without having to know the coding behind it. And the idea that if you invest maybe half a day, a day into kind of how Claude code operates, that you could create your own very custom software that’s really just unique for your firm and build it at the scale that you need now with the concept that you could always grow it and modify it later. And so the appeal to that, of course, is we heard a lot on the software side of, “Hey, I’m paying for your tool, but I’m only using 30% of it.

” And so it’s that I’m paying for things that I’m not using kind of mentality, that this idea of vibe coding helps. That’s a real attractive, I think, part of this is like, wait a minute, I only have to pay, let’s say I’m going to do the team version of Claude, 100 bucks a month or

Chad Fox:

Whatever

Scott Clasen:

It might be. And it’s like, wait a minute. So instead of paying 100 bucks a month for a tool that I may be only using 30% of, I could spend $100 a month on a tool that I can build exactly what I need and not have to pay for five tools that accomplishes 100% of my thing, but I’m only using 50% of all their features and so on. So

That’s an attractive idea for really, I think, forward thinking law firms. On the flip side, of course, we still know, and I would say the vast majority of law firms are like, “Look, I’m not into coding. I’m a lawyer. I don’t want to learn how to do this. ” That’s not my jam. My jam is to sit and read a 50-page brief every night. God bless the people who can do that because I’m not one of them. So it gets back to your original question of if we’re trying to analyze how do I look at me and evaluate my SaaS tools anymore, especially through an AI lens, because a lot of these tools that you are either using or evaluating, you’re going to be hearing pitches all the left and right now about AI enabled. We have built-in AI and it’s like, “Okay, well, what the hell does that really even

Zack Glaser:

Mean?”

Scott Clasen:

And trying to decipher that and weave your way through that, you really need to start asking yourself some simple questions when you are evaluating these tools and asking those vendors like, “Okay, first of all, what exactly does your AI baked into the tool do? ” And here’s the key question, I think, how is it different from something that I could just go out to ChatGPT or Gemini or Claude and ask the same question and get the same damn answer in many ways, interacting with my data that’s in that software tool and having a meaningful difference.

Zack Glaser:

I think that’s a really good point there that I want to tease something out in our jump is the idea of quote unquote, again, SaaS is dead is really talking about pure SaaS, not AI, quote unquote AI enabled SaaS. So the big benefit that we have now with products being built by the big names is that they’re building the AI in. That’s the real draw now because if I build my own product into my own data and with Copilot inside of Microsoft 365 coming out with cowork now where you can start to use these agents against your own documents safely, what then is the benefit if I can do that? And so the benefit is putting thoughtful and secure artificial intelligence on top of this SaaS. And so I think what you’re saying there is like, well, if you’re just slapping it on, what do I care at this

Scott Clasen:

Point? There’s a newer term I’ve come across of contextual AI. And if you go and ask a question to ChatGPT right now or Cloud or whoever, without any context, you’re going to get a crap answer. And so some of the selling features I’ve seen with some of these SaaS platforms is the fact that, hey, this isn’t just AI, it’s AI with the context of your firm and your data. So it can see all in theory, if it’s built properly, I’ve seen all the emails you sent to all your clients around this particular practice area and I see how you handle things. I see your workflows. I have context now in how I’m going to be answering that question for your firm specifically because I have context on how your firm operates. And that’s a little bit, I think, where Clio Work is going with their whole white space of, everything is connected together between the various things that they own now.

In one place, it provides you the ultimate context of not even just within your world of Clio, but the outside part with the, whether it’s, well, it’s not Harvey for them, but the things that, was it Vincent? Vincent.

Zack Glaser:

Yeah.

Scott Clasen:

Yeah. Vincent’s

Zack Glaser:

One they

Scott Clasen:

Acquired. And legal research and such. And then you have the best of both worlds. The cross reference of the outside world that AI is always touching with your specific way in which you run things at your firm. I think that’s the thing to really help evaluate is asking the question of what kind of contextual AI do you have built into your tool?

Zack Glaser:

Yeah, because that’s the value add now is it’s taking our data that we already have in this product and hopefully being able to act upon that inside this product instead of just essentially being a glorified little help bot to the side.

Scott Clasen:

I mean, the transition just in the last four to five months of real good agentic AI that we’ll be doing tasks for you, but not just doing tasks for you, but doing it because it’s been trained specifically how to do it in your way

Through whether it’s Claude skills that you do over on the Claude side or whether it’s within the built-in tool of that is going to be a … It’s like you have a junior associate or a paralegal that you have trained in your way. And it’s not just asking an off-the-shelf paralegal that question, which is maybe the analogy of Claude or somebody else. It’s like the 1-800-Paralegal hotline and asking a question in those LLMs. But now the idea that you’re asking to do a task, but that they’re doing that task in the way that you specifically have told it you want it to be done, and it just repeats over and over again.

Zack Glaser:

I’m going to reference back to a podcast that I did with Matt Spiegel recently, who was with Lawmatics and was with MyCase, and I say was with … He built. Yeah, he built. And so Matt’s very sharp on these things, and he’s actually one of the people that I got this idea of if you don’t have SaaS with AI on it, it’s really not that valuable to the end user as much now. And his is going exactly where, or his argument was going exactly where you’re going of it needs to be SaaS with a gentic AI that has this knowledge inside of your firm, or this firm knowledge in it.

But the big question that I kind of get to that you and I have been kicking around a little bit is like, okay, well, that’s where we’re at right now. We weren’t there three weeks ago or three months ago or whatever. How do I, to use what I think somebody from Minnesota like yourself would do, how do I skate to where the puck is going with these SaaS products? How do I confidently invest my time, my infrastructure, my company’s knowledge into one of these products when I look around and I say, either I could spend that up on my own or Microsoft Copilot or the Google built-in AI, for the life of me, I can’t think of what theirs is right now, Jim and I. Yeah. That these products are going to supplant that. How do I invest my time in these legal specific SaaS products?

Scott Clasen:

I think, and by the way, you do my heart well using a hockey analogy of, and I know you can take the North Dakota boy Zack out of North Dakota, but you’ll always be there. You can take him out of ND, but Indy will always be in him.

I think that question of skidding towards the puck and how we even think about trying to invest in these things, it involves thinking through not just what tools should I be using, but getting back to what problems am I solving? And the whole idea of viewing it through like, okay, I have a workflow of some sort. Let’s say it’s intake from my marketing. And this is something Matt could have talked a lot about with Lawmatics around the intake CRM end of a law firm, but it’s like, okay, what am I bottlenecks now? What are my inefficiencies now that are beyond just like Lawmatics or other CRM tools that have automations built in? When X is filled out on a form, then Y happens in the CRM that triggers Z, which is an email to that client that is specific to that answer and then sets up a task for so on.

It’s not even just setting up those automations, which was kind of like low end agentic workflow before we had that,

Chad Fox:

You

Scott Clasen:

Set up automation, but it’s like, okay, there’s that, but then it’s the, what’s the step beyond that that is still takes time and effort and maybe some sort of manual touching perhaps? And how could I reimagine that first? In the perfect world, what would it look like instead? Then you think about what are the tools then that can make that happen? And is that part of my SaaS tool and the AI that’s been incorporated contextually perhaps? Or what I just am thinking through of how to make this workflow better, can it only be solved with maybe a direct LLM and some vibe coding and so on, I think is one way to think about the skating towards the puck. It’s like, oh yeah, you want to skate towards the puck, but at the end of the day, your end goal is to put it in the net

Chad Fox:

And not

Scott Clasen:

Just skate toward the puck. So it’s like you go get the puck and then where does it go from there? It’s that thinking through the, I have the best ice skates and the best hockey stick and all of that, but I got to figure out where I want to go next and see around the corner kind of thing

Zack Glaser:

And

Scott Clasen:

Think about that first before you think about the right tool, the right skate, the right hockey stick and so on.

Zack Glaser:

I think that I love that because that goes to what I do in a lot of legal tech assessment calls that I do with labsters and attorneys that I know is I like to build things platform agnostic to where people can shift platforms if they need to. If they don’t like blank color, they can go to this other tool that does moderately the same thing. And I think that idea of, okay, well, what do you ultimately want to do? You can skate to where the puck is going, but it could be going the wrong direction. You don’t want to go that direction at all. So what do you ultimately want to do with your stuff? With that, at least inherent in that is knowing, documenting this stuff, are you seeing more of a … In the SaaS products that you’re using, we use HubSpot a lot.

We use obviously Claude Code, Claude Cowork, Claude, Claudcoe, a significant amount. What is giving you the benefit of using those tools across each other?

Scott Clasen:

Yeah, right now, today, frankly, it’s not using the baked in HubSpot AI tools. It’s using CloudCowork to access the data in HubSpot and produce some things that even HubSpot can’t produce. From a reporting point of view, and I think anybody who’s worked with any SaaS tools as a law firm when it comes to reports, that’s a huge deal, dashboards and the type of reports. And we always run into those limitations around, but I want to see things exactly like this-

Zack Glaser:

How I want it.

Scott Clasen:

… but I can’t do that with this tool. And HubSpot as great of a tool as it is, and I love HubSpot. There’s still things within there. I want to see things in a certain way, in a certain visual perhaps, and so on,

That is not achievable. But if in cloud cowork, I can describe exactly how I want it, and it’ll produce a dashboard that looks just as pretty, just as good, and it’s exactly how I want it. And it goes back to, we talked at the top about vibe coding, and you just mentioned talking to a lot of the labsters about, “Hey, if you don’t like flavor…” Well, color orange of this tool, there’s always color red. And it’s kind of funny when you think about the whole development of software historically, the 40s, 50s, 60s, 70s, 80s, 90s, a lot of software was custom-built software. My dad used to sell mainframe computers for the old control data corporation back in the 60s and 70s, if those are old enough to remember controlled data. It was like an IBM type company.

But the point is, every single client, they were essentially building custom software for that company. And small businesses weren’t using any software because it was way too expensive at the time. But then we got to personal computers into the 80s and 90s, and people were building their own homegrown or having somebody build their own homegrown solutions. I’m sure a lot of Law Firms were around in the 80s and 90s, and some partners that are around today might remember those days. I remember working for organizations where we ran sports events, speaking of hockey and it was soccer, but we ran those tournaments on custom-made software because there wasn’t anything available that was SaaS-based back in those days because the internet was still a very young thing. So now we had all these SaaS-based software as a service, comes out of the box with some level of customization that should meet 80% of your needs.

And now we’re almost back full circle with AI and vibe coding that you can get back to having, without having to spend as nearly as much time or money or effort to build the custom software that you want. So Zack, you could say to that firm, “Well, if you don’t like Color Orange, you can get color red.” It’s like, “Well, no, what’s your favorite color?” Because you can now build it in your favorite color that you want. It doesn’t have to be you get orange, red, or yellow, and those are your three options. You know what I’m saying?

Zack Glaser:

Oh, man. Okay. So you’re going to a further place than I anticipated us going with this because my vision of the internet in the next little bit is that it is going to be less about people, humans opening up a webpage, viewing it, reading it and saying, “Oh, so let’s take our website as an example. So lawyers.com.” I don’t think that people are going to go to lawyers.com to view articles or the information that’s on there. We have tons of resources on there, but they’re going to be creating dashboards for themselves that are going to go out and gather that information and bring it back to them. And it’s going to be going to lawyerist, it’s going to be going to Law Next, it’s going to be going to their Clio platform, it’s going to be going to all of these things. And so that’s what’s in my brain that I’m not quite ready to throw … Well, I guess I am ready to throw out into the world because I’m doing it on the podcast here, but because I’ve been building, like you’re saying here, is dashboards on top of these things.

And so it kind of becomes, what’s my ROI on doing that myself versus just using what is already there? So if we think about it as like a case management platform and it’s like, well, what data does it have? What data does it do a good job of keeping track of? And can I use it for that? And is it priced well for that?

Scott Clasen:

Yeah. I think at the end game, it probably might end up being like the big decision is just like, where do I keep the data?

Zack Glaser:

Yeah.

Scott Clasen:

And you let the tools decide, access to that data, obviously, and do everything to do in a very customized way. So it’s like, okay, if I’ll just keep it in Microsoft 365, just keep it there. It’s simple enough. All the LMs are going to connect there and I can build my own homegrown practice management solution how I want it to be. And the thing is, the thing that’s mind-boggling is today you could make it look just as pretty and user experience as Rocky Matter, CosmoLex, Clio, Mike, A’s, PracticePanther, all of them right now today, if you wanted to, with just a few prompts.

Zack Glaser:

Okay. So I do a lot of the website and some tool building on our site inside of Lawyers, and I connect with a lot of our devs on the Affinity side. And one of the things that has been coming to my mind though in this whole argument is there’s a maintenance cost. Anytime you build one of these platforms, a dashboard, a backend, anything that you have and you build it yourself, there’s a maintenance cost to that. And

I think in some ways it’s like, well, do I want to do the maintenance on my client database or do I trust this other product to protect it, to keep it up to date, to keep it up and running, to know where it is? And I think that is potentially another thing to think about is just like, because yeah, again, I can spin up Postgres or MySQL or just SQL. I can spin up databases right now, but do I want to? And I think it becomes, again, an ROI issue, kind of like changing your own oil.

Scott Clasen:

Yeah. Yeah.

Zack Glaser:

I can.

Scott Clasen:

It’s a convenience time versus money kind of component to it. And then there’s a personality part of it too. Some people are like, “I don’t care if it’s super cheap to do it. I enjoy changing my oil and I like spending my time in the garage doing that. It’s just it puts me in my happy place, whatever.” And some people are like, “You mean I can only get … I don’t have to do this ever again. I want you to pay 20 bucks every three months. Sign me up forever tomorrow. By the way, I’m in that cam.” Zack, we started at the top with talking about SaaS debt and you and I had a conversation off camera around this, the whole concept of what is available with AI and these LLMs and what they can do and produce that threatens SaaS companies, is this a evolutionary or revolutionary thing for SaaS company?

And I think that’s completely revolutionary was how Uber disrupted the tax industry. And that was within five years or less, it completely changed how we go about paying for public transportation, taxis and so on. Whereas the internet versus print media was more evolutionary. I mean, today, very few people read as print magazines, let’s use that as the one part of that industry, print magazines-

Architecture

Zack Glaser:

Digest. People would get that and have stacks of them and-

Scott Clasen:

Hey, I used to show geographics and that sort of thing, but that took time. That took

Zack Glaser:

20,

Scott Clasen:

30 years, 30 years just about of that evolution to where we are today. And some of those print manufacturers figured out how to become the best digital version of themselves and have survived a lot, haven’t some, so you have to be really smart with this. So what we’re trying to postulate here is, is this where SaaS companies, is this more evolutionary or revolutionary? And what are we going to be 20 years from now? And let’s just keep it in the legal lane. Are we going to have a 15 to 20, let’s say, practice management solutions out there that cater to solo firms up to enterprise level, let’s say 30 of whatever the number is today, let’s say, is that going to be down to two or three that really got it figured out how to incorporate AI into that

Chad Fox:

Or where

Scott Clasen:

Are we going to be in that? I mean, I’m not going to pretend like I have the answer and I don’t think anybody has the answer. Anybody who says they doesn’t know what they’re talking about.

Zack Glaser:

That’s a good point because I would probably say that I have the answer and I don’t know what I’m talking about. No, in all seriousness though, I think that’s the question is getting to, if I’m going to invest my time and my company’s infrastructure into one of these, and again, Then let’s use the practice management software area. I don’t want to pick on them, but into one of these 15. I think if we expand out into very specific areas, some niche areas, we can get much bigger

Chad Fox:

Than

Zack Glaser:

That. How do I choose the one that is going to be here in the near future? What do I look like? I don’t want to make you tell the future, but if you had to have one or two things that would potentially be an indicator in your mind of what is making them potentially stick around? Not who, but what type of thing is the move that we’re looking for now?

Scott Clasen:

Well, let’s use an example like Harvey, which is essentially, correct me if I’m wrong, it’s a legal LLM in many ways. So is the future that instead of people going to these generic large language models, Claude, Gemini, Copilot, ChatGPT, there will be the really, really good industry specific LLMs that they access. And maybe it’s not just Harvey blanket for the legal industry, but it’s small solo Harvey, it’s mid-market Harvey, it’s enterprise level. I don’t know. If I were to ask where it could go, I could see it being having very industries and I could see that being across all sorts of industries where they’re not just pulling from these generic LLMs, but they’re creating their own industry specific LLMs. I don’t know. I’m just-

Zack Glaser:

I like that. It’s the add value.

Scott Clasen:

Right.

Zack Glaser:

Is it adding value to what we’re doing or is it just grabbing something that already exists and saying, okay, well, we’ve got Claude Five Point, whatever we’re at at the time of print here and we’re just using it on the SaaS software that we’ve already built. Yeah. Or is it adding

Scott Clasen:

That? That’s why I think it was so intriguing. I mean, Claude’s kind of going in the right direction with that real disruptive event in, I think it was late February now or early March, maybe it was late February with they’re coming out with that legal productivity plugin in that, hey, now they’re creating these agents and these skills that are very, very specific to how the legal industry works, the workflows, the processes, and where it’s pulling from and so on. I mean, it’s amazing that an event like that could for a few days tank some of the major legal tech stocks. I mean, I know Bob talked a lot about it on his website. I

Chad Fox:

Don’t know

Scott Clasen:

If lawyers you guys have with your podcast, but that’s like a seeing the future kind of thing. And so will these big LLMs branch out into spend off a subsidiary that is specifically the agents and the LLM together. I don’t know. It’s just a fascinating time right now that we’re living in trying to see around the corner, skate where the puck is, whatever analogy we want to use towards your investment in your tools and how even your existing tools match up to that, adapt to that. It’s just unbelievable.

Zack Glaser:

Yeah. I think in the spirit of this conversation of we can’t tell the future, what I’d actually like to do here is ask our listeners, what are they looking for? What are their indicators? What are the things that are making them comfortable with the products that they’re using? Are they looking for something that’s sticking its neck out really far? Or I don’t know, I’m not all of them. So I would love to hear in the comments on our website, on our LinkedIn page, what are you the listener thinking about when you’re really looking into the investment that you have in your SaaS platforms now? Well, Scott, I appreciate your thoughts on this. This was very nice. This was eye-opening in a lot of ways as well. So thank you.

Scott Clasen:

Yeah, like I said, it’s fun to be on here and discuss these things because it is such interesting times and it’s come upon us, I think, relatively quickly, the realm of the possible now. And knowing where we are six months from now, we could be having a completely different conversation. That’s what’s so interesting about this all. Because I think back, okay, six months ago was what, end of September roughly?

Chad Fox:

Yeah.

Scott Clasen:

Think about where we were there then with AI versus even now six months later with Claude and Cowork and these legal plugins and productivity. Yeah, we’ll schedule another check-in in six months and do this again.

Zack Glaser:

Right? Right. I mean, that’s kind of what we have to do now. So yeah, let’s do that. Well, Scott, once again, thank you for being with me. And I know people can find you, Scott Glayson, on LinkedIn if they want to connect with you.

Scott Clasen:

That would be great. Appreciate the time, Zack, as always.

Zack Glaser:

Thanks, Scott.

Continue Reading