September 19, 2025 • 11 mins
I spoke with John Lee, the General Counsel and Head of Strategy for Ruli, a legal AI platform for corporate law departments. We discussed how legal teams should calculate the ROI or value of a legal technology investment, the qualities buyers should consider when selecting a legal AI vendor, and ways that client expectations have changed due to advanced AI transparency, speed, and cost-efficiency.
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:01):
Welcome to Reinventing Professionals,a podcast hosted by industry analyst
Ari Kaplan, which shares ideas,guidance, and perspectives from market
leaders shaping the next generationof legal and professional services.
This is Ari Kaplan and I'm speaking todaywith John Lee, the general counsel and
(00:24):
head of strategy for Ruly, a legal AIplatform for corporate legal departments.
Hi John.
How are you?
I'm great.
Nice.
Great to be here, Ari.
I'm looking forward to the conversation.
So tell us about your backgroundand your role at Ruly.
I started my career as a corporatem and a lawyer in New York, and a
number of jurisdictions overseas.
(00:45):
Before settling in the BayArea at a number of law firms.
And then actually I went in-houseat one of Google's investment funds
was there for a number of years andthen took the dive into startups.
First as being the general counsel at Ivo,which is another legal AI company before
joining Rurally a number of months ago.
And really in my role as generalcounsel head of strategy at an
(01:07):
early stage company, it's like.
You're doing everything andthat applies to me as well.
My, my title is General Counsel,but I probably only do 20% of my
work as actual real legal work.
A lot of it isn't I'm involved inthe product since it's a legal AI
company working with our customers,working with our GoTo market team.
And so it's a pretty varied trajectory.
Very varied role as well.
What specific legal tasks andworkflows do you use AI to support
(01:34):
In my day-to-day, we do a lot.
Even though there's not actually a ton oflegal work at an earlier stage company.
We actually use our own AI tohelp develop the product further
, which is pretty interesting.
So some of it is to test, some ofit is to create, examples or, test
cases or, try trying to iteratemore on improving the product.
(01:58):
And we also, speak to our customersa lot about this and help with their
workflows as well to try to integratethe AI into their workflows, which
helps us integrate, the AI intoour workflows even more as well.
What distinguishes Ruly from otherlegal AI platforms on the market?
There is a lot of noise out there,there are a lot of competitors and
(02:22):
so we take a different approach.
Our team is probably moreexperienced, more mature more
knowledgeable in a lot of ways.
We like to take the approachof a more holistic . Top
down, understand the industry,understand the technology approach.
Our founders, their, previous Google Meta,a whole lot of experience behind them.
(02:42):
And so they know how to execute.
And even though really hasn't beenaround that long we've basically
built the whole platform ofcorporate legal in-house, like tech.
And we have modules that can help,parts of the legal in-house teams
if you think about it law firms,actually have a very simple workflow.
You have a partner, you have an associate,you have a client who's probably a lawyer.
(03:05):
You're dispensing legaladvice in a very thorough way.
But in-house, it's avery different workflow.
You have many different stakeholdersusually on the business side sales,
procurement, hr, your C-suiteand each one of those have very,
particular needs and requirements.
And the in-house lawyer there is.
(03:26):
Often not even a lawyer dispensing,like strategic le business advice, so
we need to understand that customerand so we really want to take that top
down holistic approach to be able tounderstand all those workflows, to be
able to understand their day to day andbe able to provide them real return on
investment when they purchase our product.
How should legal teams calculate the ROIor value of a legal technology investment?
(03:51):
The quick and easy way is how muchtime you save, but at the end of the
day, how much time you save might notactually translate into the biggest
return on investment, because everylawyer's day-to-day is very different.
You might be saving timeon the low end work.
But then that high end work you're notsaving as much time on and maybe that's
(04:15):
what you actually would provide the mostreturn on investment, so the tools that
can be developed to address those morecomplex issues might actually be the
ones that are more important to helpyou, provide more return on investment.
At the end of the day it's probablya combination of things like how
much time you save, how much outsidecounsel spend, you're saving by
(04:37):
not outsourcing some of the work.
Maybe you're saving the time of certainpeople that you know are overburdened
in your team and so maybe you can takesome more off their shoulders and put
it more on the junior folks on yourteam . The more you can take an overall
approach to calculate and turn ourinvestment is the best way to do it.
(04:58):
What qualities should buyerslook for in a legal AI vendor?
The best way to do it is the onesyou can trust . First obviously,
security wise, privacy wise.
SOC two certification or somethingalong those lines is table stakes.
Making sure that they're not trainingon your data or, saving your data.
Beyond what's permitted in youragreement, which you're aware of,
(05:20):
that is also the absolute minimum.
Beyond that, the key quality of legalAI in particular it developed so quickly.
Previous to my role here at Rural,I was general counsel at Ivo.
When I first joined, Ivo, the attitudetowards AI amongst legal teams was very
different than it is, when I left Ivoand now it is even more different the
ability of folks to adopt AI and trustAI ha has increased exponentially.
(05:46):
Also the capability of aihas increased exponentially.
Granted there's a bit of a plateauamongst AI capabilities but that makes
it even more important for folks to,rely on a trusted vendor that's able to
make the most of the AI tools out there.
Because at the end of the day,there's probably not a huge
secret behind these tools.
(06:07):
A lot of them are using chat GBT orClaude or something along those lines.
And it's about developing thebest tools for your team and the
teams that you trust the most too.
Take advantage of the incrementalimprovements in the AI to
develop the better tools for you.
How have client expectations of legalservices changed as a result of the
(06:29):
transparency, speed, and cost efficiencythat has been generated through ai?
Right now, the expectationsare still shifting.
There probably isn't a clear expectationyet that, let's say outside counsel
using AI tools, then your fee shouldbe so much cheaper because they're
not telling their clients thatthey're actually using the AI tools.
(06:52):
There probably does need to bemore transparency in terms of,
whether you're using AI tools ornot, and how you're using those
and how it's, improving your work.
The other thing is, as it develops,we will find more ways to use it.
I think the way things are goingAI makes a amazing training tool.
Like it's I know like when I was ajunior associate, like the partner.
(07:16):
Call all of us in on the weekend forfor, like a huge diligence exercise.
And they would spend five minutesexplaining the deal to us.
And, as the first year, I barely knewwhat a change of control provision
was and I didn't even know what thestructure of the transaction was.
And all of those things are important.
But when you use an AI tool forsomething like that, for diligence.
(07:37):
It'll show you what it's doing,it'll explain what it's doing.
And you can ask what it's doing andwhy , it made certain decisions.
I know partners may say, there's nosuch thing as a stupid question but
let's face it, there are dumb questions.
And those don't always get asked.
So then people don't know the answer,, in a regular law firm environment.
But AI doesn't make judgments.
(07:57):
It'll tell you whatever the answer is.
What skills do you see as most valuablefor lawyers in a future where AI is
integrated throughout legal workflows?
Most important is somebody who'sfamiliar with using the tools.
It's not just having used them andknowing the interface, but actually
(08:19):
AI has been good at certain thingsand it's not good at certain things,
and understanding that through moreusage, through more ability to, apply
to different tasks, will really helpthe actual lawyer or legal practitioner
to understand where it'll excel . Thisis where I need to be checking more.
This is where, I need to be careful.
(08:41):
Maybe I shouldn't useit in this situation.
The other point is, understanding,trust, and then trust flows both ways in
terms of, who on the business side willrely on this work product and on the
business side, understanding that, you'rea lawyer using ai, but you're still a
lawyer and you still need to be thoroughand provide meaningful advice to your
(09:05):
client and not just, putting somethingthrough AI and just giving to them.
And so and this is probably the same asit always has been for lawyers in-house.
Law firm, whatever but understanding yourclient, understanding their priorities,
understanding the relationship withthem and building that trust with
them I think is important as well.
So not abusing ai , toabuse that relationship.
(09:27):
How do you anticipate the role of a lawyerchanging as these AI capabilities mature?
That's the ultimate question how do wepredict a future here basically, where
the future of law, where the futureof legal practitioners is headed.
AI is getting smarter, AI isgetting more advanced and, the
ability to take on more tasks.
(09:47):
For the foreseeable future,the next year or two at least.
It probably is still likejunior, mid-level, associate, in
terms of what can actually do.
I have to imagine the next few yearsit'll develop in a way that it could
take the repetitive lower levelwork and make that a lot easier.
I would imagine the role of yourin-house legal counsel, it's going
(10:08):
to be easier in a lot of waysbecause you're not gonna have to do
that type of very repetitive work.
You can integrate AI into yourworkflows and help that be taken over.
What's left is, a lot more strategicadvice, a lot more thinking about
the business and, applying theoutputs from AI to your business
and being very, contextual andthoughtful about that stuff.
(10:29):
That will only make the role of thein-house legal counsel as well as the
outside counsel, and especially legalops folks, all the more important.
This is Ari Kaplan speaking with JohnLee, the general counsel and head of
strategy for Ruly, a legal AI platformfor corporate legal departments.
(10:51):
John, thanks so very much.
Thanks.
It's great.
Great to be here.
I.
Thank you for listening to theReinventing Professionals Podcast.
Visit reinventing professionals.com orari kaplan advisors.com to learn more.
Welcome to Reinventing Professionals,a podcast hosted by industry analyst
Ari Kaplan, which shares ideas,guidance, and perspectives from market
leaders shaping the next generationof legal and professional services.
This is Ari Kaplan and I'm speaking todaywith John Lee, the general counsel and
(00:24):
head of strategy for Ruly, a legal AIplatform for corporate legal departments.
Hi John.
How are you?
I'm great.
Nice.
Great to be here, Ari.
I'm looking forward to the conversation.
So tell us about your backgroundand your role at Ruly.
I started my career as a corporatem and a lawyer in New York, and a
number of jurisdictions overseas.
(00:45):
Before settling in the BayArea at a number of law firms.
And then actually I went in-houseat one of Google's investment funds
was there for a number of years andthen took the dive into startups.
First as being the general counsel at Ivo,which is another legal AI company before
joining Rurally a number of months ago.
And really in my role as generalcounsel head of strategy at an
(01:07):
early stage company, it's like.
You're doing everything andthat applies to me as well.
My, my title is General Counsel,but I probably only do 20% of my
work as actual real legal work.
A lot of it isn't I'm involved inthe product since it's a legal AI
company working with our customers,working with our GoTo market team.
And so it's a pretty varied trajectory.
Very varied role as well.
What specific legal tasks andworkflows do you use AI to support
(01:34):
In my day-to-day, we do a lot.
Even though there's not actually a ton oflegal work at an earlier stage company.
We actually use our own AI tohelp develop the product further
, which is pretty interesting.
So some of it is to test, some ofit is to create, examples or, test
cases or, try trying to iteratemore on improving the product.
(01:58):
And we also, speak to our customersa lot about this and help with their
workflows as well to try to integratethe AI into their workflows, which
helps us integrate, the AI intoour workflows even more as well.
What distinguishes Ruly from otherlegal AI platforms on the market?
There is a lot of noise out there,there are a lot of competitors and
(02:22):
so we take a different approach.
Our team is probably moreexperienced, more mature more
knowledgeable in a lot of ways.
We like to take the approachof a more holistic . Top
down, understand the industry,understand the technology approach.
Our founders, their, previous Google Meta,a whole lot of experience behind them.
(02:42):
And so they know how to execute.
And even though really hasn't beenaround that long we've basically
built the whole platform ofcorporate legal in-house, like tech.
And we have modules that can help,parts of the legal in-house teams
if you think about it law firms,actually have a very simple workflow.
You have a partner, you have an associate,you have a client who's probably a lawyer.
(03:05):
You're dispensing legaladvice in a very thorough way.
But in-house, it's avery different workflow.
You have many different stakeholdersusually on the business side sales,
procurement, hr, your C-suiteand each one of those have very,
particular needs and requirements.
And the in-house lawyer there is.
(03:26):
Often not even a lawyer dispensing,like strategic le business advice, so
we need to understand that customerand so we really want to take that top
down holistic approach to be able tounderstand all those workflows, to be
able to understand their day to day andbe able to provide them real return on
investment when they purchase our product.
How should legal teams calculate the ROIor value of a legal technology investment?
(03:51):
The quick and easy way is how muchtime you save, but at the end of the
day, how much time you save might notactually translate into the biggest
return on investment, because everylawyer's day-to-day is very different.
You might be saving timeon the low end work.
But then that high end work you're notsaving as much time on and maybe that's
(04:15):
what you actually would provide the mostreturn on investment, so the tools that
can be developed to address those morecomplex issues might actually be the
ones that are more important to helpyou, provide more return on investment.
At the end of the day it's probablya combination of things like how
much time you save, how much outsidecounsel spend, you're saving by
(04:37):
not outsourcing some of the work.
Maybe you're saving the time of certainpeople that you know are overburdened
in your team and so maybe you can takesome more off their shoulders and put
it more on the junior folks on yourteam . The more you can take an overall
approach to calculate and turn ourinvestment is the best way to do it.
(04:58):
What qualities should buyerslook for in a legal AI vendor?
The best way to do it is the onesyou can trust . First obviously,
security wise, privacy wise.
SOC two certification or somethingalong those lines is table stakes.
Making sure that they're not trainingon your data or, saving your data.
Beyond what's permitted in youragreement, which you're aware of,
(05:20):
that is also the absolute minimum.
Beyond that, the key quality of legalAI in particular it developed so quickly.
Previous to my role here at Rural,I was general counsel at Ivo.
When I first joined, Ivo, the attitudetowards AI amongst legal teams was very
different than it is, when I left Ivoand now it is even more different the
ability of folks to adopt AI and trustAI ha has increased exponentially.
(05:46):
Also the capability of aihas increased exponentially.
Granted there's a bit of a plateauamongst AI capabilities but that makes
it even more important for folks to,rely on a trusted vendor that's able to
make the most of the AI tools out there.
Because at the end of the day,there's probably not a huge
secret behind these tools.
(06:07):
A lot of them are using chat GBT orClaude or something along those lines.
And it's about developing thebest tools for your team and the
teams that you trust the most too.
Take advantage of the incrementalimprovements in the AI to
develop the better tools for you.
How have client expectations of legalservices changed as a result of the
(06:29):
transparency, speed, and cost efficiencythat has been generated through ai?
Right now, the expectationsare still shifting.
There probably isn't a clear expectationyet that, let's say outside counsel
using AI tools, then your fee shouldbe so much cheaper because they're
not telling their clients thatthey're actually using the AI tools.
(06:52):
There probably does need to bemore transparency in terms of,
whether you're using AI tools ornot, and how you're using those
and how it's, improving your work.
The other thing is, as it develops,we will find more ways to use it.
I think the way things are goingAI makes a amazing training tool.
Like it's I know like when I was ajunior associate, like the partner.
(07:16):
Call all of us in on the weekend forfor, like a huge diligence exercise.
And they would spend five minutesexplaining the deal to us.
And, as the first year, I barely knewwhat a change of control provision
was and I didn't even know what thestructure of the transaction was.
And all of those things are important.
But when you use an AI tool forsomething like that, for diligence.
(07:37):
It'll show you what it's doing,it'll explain what it's doing.
And you can ask what it's doing andwhy , it made certain decisions.
I know partners may say, there's nosuch thing as a stupid question but
let's face it, there are dumb questions.
And those don't always get asked.
So then people don't know the answer,, in a regular law firm environment.
But AI doesn't make judgments.
(07:57):
It'll tell you whatever the answer is.
What skills do you see as most valuablefor lawyers in a future where AI is
integrated throughout legal workflows?
Most important is somebody who'sfamiliar with using the tools.
It's not just having used them andknowing the interface, but actually
(08:19):
AI has been good at certain thingsand it's not good at certain things,
and understanding that through moreusage, through more ability to, apply
to different tasks, will really helpthe actual lawyer or legal practitioner
to understand where it'll excel . Thisis where I need to be checking more.
This is where, I need to be careful.
(08:41):
Maybe I shouldn't useit in this situation.
The other point is, understanding,trust, and then trust flows both ways in
terms of, who on the business side willrely on this work product and on the
business side, understanding that, you'rea lawyer using ai, but you're still a
lawyer and you still need to be thoroughand provide meaningful advice to your
(09:05):
client and not just, putting somethingthrough AI and just giving to them.
And so and this is probably the same asit always has been for lawyers in-house.
Law firm, whatever but understanding yourclient, understanding their priorities,
understanding the relationship withthem and building that trust with
them I think is important as well.
So not abusing ai , toabuse that relationship.
(09:27):
How do you anticipate the role of a lawyerchanging as these AI capabilities mature?
That's the ultimate question how do wepredict a future here basically, where
the future of law, where the futureof legal practitioners is headed.
AI is getting smarter, AI isgetting more advanced and, the
ability to take on more tasks.
(09:47):
For the foreseeable future,the next year or two at least.
It probably is still likejunior, mid-level, associate, in
terms of what can actually do.
I have to imagine the next few yearsit'll develop in a way that it could
take the repetitive lower levelwork and make that a lot easier.
I would imagine the role of yourin-house legal counsel, it's going
(10:08):
to be easier in a lot of waysbecause you're not gonna have to do
that type of very repetitive work.
You can integrate AI into yourworkflows and help that be taken over.
What's left is, a lot more strategicadvice, a lot more thinking about
the business and, applying theoutputs from AI to your business
and being very, contextual andthoughtful about that stuff.
(10:29):
That will only make the role of thein-house legal counsel as well as the
outside counsel, and especially legalops folks, all the more important.
This is Ari Kaplan speaking with JohnLee, the general counsel and head of
strategy for Ruly, a legal AI platformfor corporate legal departments.
(10:51):
John, thanks so very much.
Thanks.
It's great.
Great to be here.
I.
Thank you for listening to theReinventing Professionals Podcast.
Visit reinventing professionals.com orari kaplan advisors.com to learn more.
Popular Podcasts
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
CrimeLess: Hillbilly Heist
It’s 1996 in rural North Carolina, and an oddball crew makes history when they pull off America’s third largest cash heist. But it’s all downhill from there. Join host Johnny Knoxville as he unspools a wild and woolly tale about a group of regular ‘ol folks who risked it all for a chance at a better life. CrimeLess: Hillbilly Heist answers the question: what would you do with 17.3 million dollars? The answer includes diamond rings, mansions, velvet Elvis paintings, plus a run for the border, murder-for-hire-plots, and FBI busts.