Clio Con Clips 2025 - A.J. Axelrod - E09

13 Nov 2025 · 14 min · 12 chapters

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In short

ClioCon Clips 2025 interview with AJ Axelrod (VP, Payments & Financial Services) about Clio’s payments, Pay Later with a firm, and Clio Capital—aimed at improving legal affordability, speeding cash flow, and reducing friction while maintaining compliance.

Guest background

AJ Axelrod is VP of Payments and Financial Services at Clio; first ClioCon; grew up in New York; allergic to pineapples.

Key claims

Law firms shouldn’t act as creditors/lenders; Pay Later shifts payment-plan burden away from lawyers and gives clients optionality, especially where credit access is limited. Clio Payments gets firms paid 2.5x faster; lockup is ~90 days. Fintech/legal tech intersection should “disappear” transactions like Amazon-style ease, delivered in lawyer-specific language.

Notable examples

Pineapple allergy anecdote; clients turning on Textify after it shipped Monday; over 50 customers enabled it in settings; audience applause for Pay Later and Capital.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Interview Introduction

0:58 to 1:21

Host introduces AJ Axelrod, VP at Clio.

“Welcome to the Legally Speaking podcast recording live here from Boston for our ClioCon Clips 2025 sponsored by Clio and I'm joined by...”

Fun Fact about AJ

1:21 to 1:42

AJ shares a unique fact about his pineapple allergy.

“I don't know how fun it is, but it is unique.”

ClioCon Highlights

1:42 to 2:26

Discussion on ClioCon and updates in legal payments.

“Well, let's get into it because it's been an incredible CleoCon.”

Transforming Legal Payments

2:26 to 3:48

AJ explains how 'Paylater' and Clio Capital can reshape legal payments.

“So if we start with pay later with the firm, the reality is law firms too often are actually getting into the business of being a creditor or a lender, right?”

Improving Access to Justice

3:48 to 5:14

Discussion on how affordable legal services can close justice gaps.

“And so, you know, someone wants to engage with a lawyer and they don't have that money, say right now for, for, for a trust retainer, or, you know, they don't have right now to pay that bill, but they want to.”

Ensuring Compliance and Trust

5:14 to 6:11

AJ discusses compliance and trust in Clio's fintech solutions.

“And I know Clio, you know, that mission is true, transform the legal experience for all.”

Feedback on Clio Products

6:11 to 7:22

AJ shares feedback and success stories of Clio payments.

“And I always talk a lot about we is greater than me and people will be sick and tired of me talking about this on the show, but collaboration is domination.”

Fintech and Legal Tech Intersection

7:22 to 8:51

Exploring how fintech innovations are impacting legal tech.

“And that shows how willing your existing clients are and wanting of tech and these features.”

Future of Clio Payments

8:51 to 10:54

AJ discusses the vision for Clio payments and financial innovation.

“You know, and that's one thing, you know, we all want to protect where possible.”

Cultural Shifts for Adoption

10:54 to 12:11

AJ elaborates on necessary cultural shifts for fintech adoption in law.

“is just super exciting for me yeah and i can feel that energy and it's just so exciting all round and we touched on this bit earlier, but I want to go a little bit deeper again before we look to close.”
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Highlights from ClioCon

12:11 to 13:06

AJ shares highlights and experiences from this year's ClioCon.

“Can you just explain to me what they just said?”

Where to Learn More About Clio

13:06 to 13:55

AJ provides resources for learning more about Clio and its offerings.

“where people were celebrating the products that you've been working day in, day out on and strategizing on.”
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Transcript

Automatic transcript. May contain errors.

0:00Welcome to ClioCon Clips 2025, recorded live from Boston and proudly sponsored by Clio, the world's leading legal technology company transforming the legal experience for all. I'm your host, Rob Hanna, and over this special Legally Speaking podcast series, we'll be bringing you exclusive conversations with the brilliant minds behind Clio, the innovators, strategists, visionaries driving one of the most transformative companies in legal tech. Across these interviews, we'll explore how Clio is uniting brilliance across teams, technology, and communities worldwide. From AI and data to leadership, culture, and the future of client experience, you'll hear from people shaping what's next for law and redefining what's possible for legal professionals everywhere.

0:45So whether you're a lawyer, technologist, or leader passionate about innovation, you're in the right place. This ClioCon Clips 2025 is where brilliance meets purpose and the future of law takes shape. Let's get into it.

1:03Welcome to the Legally Speaking podcast recording live here from Boston for our ClioCon Clips 2025

1:10A.J. Axelrod:sponsored by Clio and I'm joined by... My name's AJ, VP of Payments and Financial Services at Clio. You absolutely are and it's a real pleasure to have you on the show live here at Boston. But before we get into it, what's one fun fact people may not know about you here at CleoCon? I don't know how fun it is, but it is unique. I am allergic to pineapples. Oh, wow. Okay, so pineapple and ham pizza, that's out of the question. I also grew up in New York, so pineapple and pizza is out of the question. But for me personally, unfortunately, that or a fruit salad with pineapple in it gets a little dangerous.

1:42Absolutely. Well, let's get into it because it's been an incredible CleoCon. We heard from Jack's keynote a lot of updates, particularly in your area. You've introduced Paylater with a firm, Anclio Capital. So how will these reshape how firms and clients experience legal payments?

1:57A.J. Axelrod:Yeah, let's start with the mission, right? Transforming legal services for all. Lack of access is a major issue, right? And it's hard enough to find a lawyer. It's hard enough to find a good one. It's hard enough to get through an engagement, to navigate the system, to add constraints of the financial system as another barrier is, it's unfortunate, I guess, to say the least. And there's no panacea. There's no perfect solution for this. But I think it's a worthwhile endeavor. So if we start with pay later with the firm, the reality is law firms too often are actually getting into the business of being a creditor or a lender, right?

2:37A.J. Axelrod:Putting people on payment plans and following up and doing this correspondence. and that's taking time away from serving clients. Yeah. And so hopefully that shifts some of that burden, gives clients optionality in how they pay. And I think important for us also to remember that, particularly in the US, not everyone has access to credit. Not many people have actually enough money should there be an emergency. And so this helps give them some of that. I think the other side is we think about Clio Capital is, if we think about Clio, as it was historically, an incredibly powerful set of tools, right?

3:10A.J. Axelrod:For running sort of the business of law, as Jack talked about today. And how we think about VLACs and coming soon, right? And about sort of the practice of law. But again, tools, right? The other side of that is resources. And many law firms are small businesses. Small businesses have challenges with cash flow and capital. They want to invest in growth. They want to have that flexibility as resources. And so to the extent we can make that easy, use the data we have in our system to make sure you get a great offer, make repayment easy. that means no more navigating this complex system of like how do i get a loan how do i fund this business right just make it easy happen in the product meet you where you are and get you back to what you should be doing which is serving clients i love that and i love i talk a lot about you know the more you can remove friction and actually you know ease that process the adoption levels go up the higher you get more client-centered you don't love going to the bank and filling out forms yeah exactly i want to go a bit deeper because legal affordability is one of the biggest sort of access to justice barriers that we were touching on there so how do these tools actually help close that gap specifically yeah let's just focus on on pay later for a second yeah the average bill on clio is is a big number for the average person yeah right you know i forget the exact number but if we look at how much does the average sort of american have in their savings right now for an emergency it's like four hundred dollars yeah and you know the average paid bill on clio is a lot more than$400.

4:34A.J. Axelrod:And so, you know, someone wants to engage with a lawyer and they don't have that money, say right now for, for, for a trust retainer, or, you know, they don't have right now to pay that bill, but they want to. Yeah. Um, this eliminates that part with the sort of what could be an embarrassing back and forth with the lawyer if I can't afford this. Yeah. Um, but also they'll learn longer has to do like, you know, as a payment plan or should I wait a little to get work started? It's get paid up front, move the process of dealing with that onto someone whose job is that in a firm and you can just get on with it.

5:09Yeah, love that. And it's so important, isn't it? The more we can do that, the amount of impact you can have. And I know Clio, you know, that mission is true, transform the legal experience for all. Yeah. And that's huge. Okay. So how do you ensure then financial compliance and trust, big words, when embedding new fintech solutions into Clio payments?

5:27A.J. Axelrod:We take compliance very seriously. And we take trust enormously seriously as well. I think the first thing is we adhere to the highest standards of security. We make sure that that information is safe and secure to the absolute highest standard. And in terms of compliance, we take that burden incredibly seriously. And I think the way we deal with it is in two parts. One, we work with only the most reputable partners. The reality is in any financial system, you don't do it alone. You're integrated into a much larger ecosystem. and we're only working with great partners and we will prioritize that partnership, the quality of it and how they deal with these issues much higher than we will, you know, that extra basis point of revenue.

6:06A.J. Axelrod:And, you know, we go out of our way to make sure we're not even flirting with that line of compliance. Yeah, I love that. And I always talk a lot about we is greater than me and people will be sick and tired of me talking about this on the show, but collaboration is domination. But Cleo do it so well. And I see that from all the various partners you have. It's incredible. And one thing you also do super well, and Jack touched on his keynote, is listening. So what feedback are you hearing from firms already using these products and what have you been most excited about? Yeah. So, I mean, let's just focus on core payments here for a second.

6:35A.J. Axelrod:Clio payments gets you paid two and a half times faster. And so, you know, with lock up being around 90 days, we can ask Joshua exactly the particular number in the legal trends report. But suffice to say, that's a long time compared to most businesses. And so to get you paid faster, you know, means running that business a little bit easier. It also means getting onto client work a little bit better. We get great feedback around that, excited about where Textify has gone on. So if you aren't using Textify, please go turn it on. And you saw today, right, with the reaction to Pay Later and to Capital, people applauding, and we're just really excited about it.

7:11A.J. Axelrod:That code actually shipped on Monday morning, and without us saying anything, over 50 customers found it in settings and turned it on. So yeah, just very excited. That kind of feedback's the best, right? Using it. Yeah, usability, adoption. And that shows how willing your existing clients are and wanting of tech and these features. And one thing Jack said, actually, this was during this series, F-rays, when it was the 900 million, that legal tech is now at the table because historically, fintech has been years and light years ahead of legal tech. Legal tech in recent years has really kind of come up.

7:41So in terms of fintech and legal tech now sort of intersecting, where do you see the biggest opportunity for growth? I mean, there's so many choices.

7:50A.J. Axelrod:I think it's important to maybe like zoom out a second. Like FinTech is this horizontal application of how do we take financial services, which have been in sort of a walled garden, hard to access and make them easily accessible. Yeah. And that the pillars of financial services have always been about distribution, underwriting and cost of capital. And software companies like Clio have great distribution and underwrite. We know all these things about you that show that you're a good business. Yeah. And we're meeting you where you are. And so I think that intersection is like these things belong together.

8:23A.J. Axelrod:And financial services are must-consume products. They're not optional. So we should make them as pain-free as possible, as high quality as possible, and meet you contextually in a way that matters to you. I joke, but going to the bank is not a fun experience. And it takes away from what you are doing. And so if we can make that work better, it's hugely impactful to just like running a better firm. And, you know, it gives us our greatest commodity back, which is time. Yeah. You know, and that's one thing, you know, we all want to protect where possible. And that kind of leans into what you're saying around quality and everything else.

8:57And the whole theme this year of CleoCon is uniting brilliance. So, you know, how does uniting brilliance sort of apply to bridging finance, technology and law all under one ecosystem?

9:06A.J. Axelrod:I think the best sort of financial services, transactions, if you will, are the ones that disappear. You don't even notice them. You know, sort of like if you notice what paying for something was like, it's usually because it didn't go away. And so, you know, I think what we look for in this like this brilliant moment, if you will, is like it's the, you know, when Amazon brings us like brings us just a click to pay or just make things easy. Yeah. And and that's where this stuff comes together in the ecosystem. but to do that well it has to be interconnected it can't just be like hey these two things are next to each other it has to meet you like in that moment right whether it's your billing workflow or you're starting a firm for the first time you know do you are you bringing those things like i said before in contextually specific way yeah because if you don't if you confuse people you'll lose people and i say that so much and the more you can kind of just simplify and make it sometimes and also it's better to be clear than it is to be clever sometimes you can kind of just keep it simplicity you'll see adoption levels go up and happiness levels go up and all of that good stuff the feedback will come racing in and you can continue moving forwards which has been a big theme of this conference in terms of moving forward in terms of obviously a system of action so looking ahead for you in terms of what excites you most about the future of Clio payments and financial innovation and law what do you say?

10:22A.J. Axelrod:I mean we have an incredibly I think compelling vision around where billing and payments and now taking that next step into capital you know are to try to just like make you the most successful firm you can be and and to make sure you know that it's success defined on your terms yeah so for some people that's growth for some people that may just be time back whatever it may be but to just to have this opportunity for this stuff to just be easy be clear and to let you succeed on whatever those terms are for you is just super exciting for me yeah and i can feel that energy and it's just so exciting all round and we touched on this bit earlier, but I want to go a little bit deeper again before we look to close.

11:03Legal finance has traditionally lagged behind other sectors in innovation specifically. So what cultural or mindset shift do you think still needs to happen inside firms for fintech adoption to really take off?

11:15A.J. Axelrod:You know, I think we're in like a really great transition moment in the legal industry. You would have said this about like any technology and law and AI, I think it's like dramatically changed how people are thinking. So we're in this moment of adoption that I think is great. I think what has to happen is we need to do even more at delivering these things in a way that is specific to how you practice law. And so it's not, you know, here's a revolving line of credit and you're like, what does that mean? You know, or like, you know, the difference between that and a term loan or installment based.

11:51A.J. Axelrod:We need to take away that financial language and make it meet people where they are, which is as lawyers. And so I think that's the major innovation is just delivering things to people in their day-to-day at the right moment in an easy way to understand. It doesn't require you to sort of like go find – when you were in law school to go find the friend who was getting his MBA or her MBA. Can you just explain to me what they just said? Yeah. I think that's crucial, isn't it? And again, I say this so much to people, and you're talking about being specific, but specific is terrific. The more you can be specific, the more adoption you're going to have, the far more great success you're going to have.

12:25And AJ, you've had huge success and you made a real impact with your role and what you're doing at Clio. And let's go to ClioCon then because this has been another incredible year. I know we're still quite early on into day one, but what's been a highlight moment for you thus far of ClioCon?

12:39A.J. Axelrod:This is my first ClioCon. So it's all highlight at this point. But the keynote this morning is just incredible. Jack's phenomenal on stage, of course, but to see the reaction from the audience and to know that the things you're doing really fill their need. You don't want to just build a thing for the sake of building it. You want to make a difference in your customers' lives. And to see those reactions, I think, just reminds you that you are making a difference and inspires you to go do more. Yeah, and you could hear that in the audience, you know, where people were celebrating the products that you've been working day in, day out on and strategizing on.

13:11And there was a real roar when going through a lot of the Clio payments, Clio Capital and everything else. And so testament to you, testament to the team and everything you're doing. And if people want to know more about Clio or indeed things you're working on or building, where's the best place for them to go? So is it LinkedIn, social media? Is there an email address?

13:25A.J. Axelrod:I think starting on clio.com is the best place to go, particularly around payments. It would be slash payments. But if you're a Clio customer, reach out. If there's something specifically I can be helpful on, you can find me on LinkedIn. I think there's only one AJ Axelrod, so it shouldn't be that hard to find me. But there's a ton of resources at your disposal around Clio. And I'd encourage you to just engage with all of them. and where there's an opportunity to talk to one of us, we'd be more than happy to try to help you. Couldn't agree more. Well, AJ, it's been an absolute pleasure doing this live here in Boston, sharing how Clio is revolutionizing all things legal finance and client accessibility.

14:03But for now, from all of us on the Legally Speaking podcast, sponsored by Clio, over and out.

14:07A.J. Axelrod:Thank you for listening to this week's episode. If you like the content here, why not check out our world-leading content and collaboration of the Legally Speaking Club over on Discord. Go to our website, www.legallyspeakingpodcast.com. There's a link to join our community there. Over and out.

From the publisher

Welcome to Clio Con Clips 2025, recorded live from Boston and proudly sponsored by Clio, the world’s leading legal technology company transforming the legal experience for all.

On today’s minisode, we talk to A.J. Axelrod. He is the VP of Payments and Financial Services at Clio, responsible for leading the company’s payment and financial product innovations. A.J. is focused on making legal services more accessible through new solutions like Pay Later and Clio Capital, aiming to remove financial barriers for both clients and law firms. A.J. is dedicated to compliance and security, works closely with reputable partners, and values customer feedback to drive adoption and usability. His approach emphasizes clear, context-specific solutions for legal professionals, and he is enthusiastic about Clio’s mission and advancements showcased at his first Clio Con.


So why should you be listening in? 

You can hear Rob and A.J. discussing:

- Innovation and Updates in Clio’s Legal Payments

- Addressing Legal Affordability through Flexible Payment Solutions

- Ensuring Compliance and Building Trust in Financial Technology

- User Feedback and Rapid Adoption of Clio Payment Features

- The Evolving Intersection of Legal Tech and FinTech


Connect with A.J. Axelrod here - https://www.linkedin.com/in/ajaxelrod

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