July 23, 2025 • 14 mins
I spoke with Milan Bobde, the co-founder and CEO of Oddr, an AI-powered invoice-to-cash platform for law firms. We discussed how law firms are addressing the invoice-to-cash process, the benefits of integrating legal technology platforms in law firms, and ways that improving billing and collections can enhance client service.
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Episode Transcript
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(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 speakingtoday with Milan, Bob De, the co-founder
(00:24):
and CEO of Otter, an AI poweredinvoice to cash platform for law firms.
Hi Milan.
How are you?
Hi Ari.
Good to see you again.
Thank you for having me.
I'm looking forward to the conversation.
Mil, we've spoken before.
How are law firms addressing the invoiceto cash process in the current climate?
(00:47):
Invoice to cash is a relatively newproduct category in the legal space.
If you look at non-legal ornon-professional, the invoice
to cash or revenue cycle hasbeen around for a long time.
But most of these horizontal solutions arenot built to the way law firms function.
Simple things on how partnershipsfunctions, how attorneys are
(01:10):
involved in this process.
The horizontal solutions do not caterto that, but with order and more
awareness within law firms to want.
A single platform that letsthem manage their entire revenue
cycle is picking up steam.
And we are seeing more and more firmsinterested in having that single glass
(01:32):
pane view to know exactly A, where theirinvoices are, B, where their bottlenecks
or where their issues, and C, have theteam be able to go tackle those which.
With point solutions, you canreally never do that because it
does not give you a full picture.
It gives you a silo of a view.
(01:55):
What are the benefits of integratinglegal technology platforms in law firms?
Most law firms have.
A great ERP system, like a leador admin to do their finances.
But once an invoice is finalized,they're left on their own to figure
out how to efficiently dispatch this,how to follow up with clients, where
(02:15):
are clients in their payment cycle?
How do you make it easy for clients?
So with.
A platform like Order, which is asingle platform, the whole revenue
cycle becomes a lot more intelligent.
And a few things to mention, likea, it starts with deep automation.
You are not working with silo productsthat do not integrate with each other.
(02:35):
But we have a single platform that becomesthe collaborative bench for the billers,
the collectors, the cash receipts team,the finance leaders, the attorneys.
And that gives.
All of them, the right view of whatthey are interested in and then
how they participate in this cycle.
It also improves the productivity ofthe team drastically because you're not
(02:58):
trying to go to three different systemsto find, Hey, why this invoice has not
been paid, or you're not trying to go to.
Multiple systems to see, hey,which clients should I reach
out to that are not paid?
The invoices.
So the intelligence is a big different.
When you have a single platform,you end up with zero ar leakage,
nothing falls through the cracks.
(03:19):
A very typical symptomof multiple solutions.
But the best part in my mind, isbecause you have the end to end.
Platform, the insights that it brings.
So simple things like, hey, isa client behaving differently
from their typical patterns?
Or, if I'm in collections, whichare the 10 clients I should focus
on when I come to the system?
Have my clients even looked at my invoice?
(03:41):
What payments have come throughand that I've been reconciled
with my accounting system?
All of these are answered witha single platform that today.
Are a big challenge, and if you thinkabout the client's experience in all
of this which is the utmost thing.
Law firms spend so much timeand money and effort to provide
the best legal experience.
(04:03):
They don't have the tools toprovide a similar consumer grade
experience to their clients.
If a client reaches out and says, Iwant to make a payment, the generic
payment links are not easy for clients.
They have to put the client number,matter number, invoice number amount.
No one wants to make, and.
An effort to pay their invoices.
(04:23):
You have to make it easy, right?
The age old saying, wealways say make it darn easy.
If you want someone to pay you andthe business results of because
of this, Ari, you know what weare seeing in our customers?
The invoice outstanding days drop,the write offs drop because fewer
invoices end up in the 90 or one 20plus buckets and clients are happier.
(04:44):
Clients love their experience,so I think it's a win-win for.
The clients and the law firms tohave that single unified platform
that looks through the entirety ofthat revenue cycle or invoice cycle.
Are billing and collectionsseparate or connected functions?
They are a hundred percentconnected, but till now phones
(05:06):
didn't have a good solution.
That lets the building and collectionteams collaborate, so they would have some
other way or manually sending invoices.
And then it comes to the collectionsoftware with our integrated
platform, it's one platform.
Sending invoices is just a few clicks,but it's not just about sending invoices.
Yes, you gain a lot ofefficiency, but when it moves to
(05:28):
collections, the real question is.
Where should I focus and today the mostcollection tools have become glorified
notetaking tool, whereas we believethat there needs to be a paradigm shift.
The collection software needs to.
Tell the law firm and the team wherethere are potential issues before
they become serious, or where shouldtheir time be spent and less time on?
(05:52):
The mundane things of just gettingthings done, like statements and others.
It's amazing how firms spend hours anddays today to send statements out, but
with order, it literally takes them threeminutes to send all the statements out,
and then that time is better utilized.
On knowing which clients to reach out tofollow up and get those invoices paid.
(06:13):
So these are the automation things.
They are absolutely related toeach other and a single platform.
Makes it easier for them.
I would also add the cashreceipt scheme on that.
So the reconciliation part is alsoa manual activity, but with order
pay, you know what payments we get.
Those are reconciled back toyour accounting system, so you
(06:34):
don't have to worry about, oh,the, we got a payment of 14,352.
How does this apply to theinvoices that are outstanding?
All of that is automated.
How does improving the billingand collections process
enhance client service?
The clients, have certainexpectations when they are
(06:55):
interacting with different systems.
Like when we go and buy things orwhen we are paying our invoices, we
expect a certain level of automationand self-service capabilities.
Unfortunately, law firms really don'thave those tools, but in our mind.
If you make it really superior experiencefor your client, like real consumer grade
(07:16):
experience, have a self-service portal.
Make it easy.
One click payments and if it is secureand something that they don't have
to reach out to the law firm for all.
Hey, copy of invoicesor copy of statements.
That's the experience that law firmsare looking to provide to their clients.
I recently was at one of theconferences for our investors.
(07:37):
And I met a person over there, he'sthe founder of a different company,
and he said to me, oh, order.
I get my invoices from order from thislaw firm, and he said it was so easy.
And we signed up forthe self-service portal.
We could access our historical invoicesand this was our first experience for
the full circle where we have clientssending invoices to their clients and we.
(08:02):
Ran into someone who's using orderthrough one of our customers, then
the feedback was pretty amazing.
We definitely have data points thatclients really appreciate having a modern,
secure way to deal with their invoices.
And we all know happyclients mean most business.
So definitely it's a key part ofthe platform and most firms are
(08:24):
really working hard to providethat best client experience.
What billing and collections insightsshould law firms be capturing?
You think about billing and collections,it is such a critical function because
for professional services like law firms,the money coming in is directly related
to what invoices are going out at leastfor most parts, most practice areas.
(08:48):
And that is the critical part of thisrevenue cycle and revenue intelligence.
So if I talk about.
As a law firm, what are the things that Iwant to know so we can reduce our invoice
outstanding days, reduce our write offs?
I think it's just knowingwhere their invoices are.
It's also knowing whereproblems can appear before
(09:09):
they become serious problems.
It's also making that.
What's the pattern of a client?
So a good example is, in our platformwhen you're sending the invoices
out, based on the client's pattern,when that invoice will be paid
and that feeds into your cashflow.
It is such a critical thingbecause now law firms know
what payments are coming in.
(09:30):
And, or at least expected overthe next, 2, 3, 6, 9 months.
And that is really powerful.
And then it's about eliminatingall the manual work, right?
So as I give you examples, statements,sharing invoices just working in
excels it's time consuming andeliminating all of that is where.
(09:51):
Law firm really wants to know whereto focus, which clients to reach out.
Where are my invoices,where are the bottlenecks?
And this in a fragmented solutionsis not feasible because you
don't have a clear single glasspane view across the lifecycle.
What are some overlooked timewasters and traditional billing
(10:11):
and collections workflows?
Sending invoices out manually, we alwayscalculate this as a part of our ROI.
Even if you take five minutes tosend an email if you are sending
thousands and thousands of these,that's a lot of productivity loss.
All of that needs to be automated.
But one thing I'll mention is law firmstake a lot of pride in having that
(10:32):
personal touch, our platform does not doesnot take away that capability they want.
They can still have the personaltouch, but do it in a efficient way.
Single click, send hundreds andthousands of invoices out with that
pre-configured personal touch note you.
Another example whereforms faced a lot of.
Time in terms of not where theycan gain efficiency is statements
(10:56):
or where client requests come in.
Simple things as when a collectionteam comes in the morning, they
look for which are the 2030collections that I need to follow up.
How do you get that prioritized list?
Every day they do an analysis,what's outstanding, what's there,
but having an intelligent perspectiveon that makes a lot of difference.
(11:16):
Hey, this client is behavingdifferently from their pattern.
I need to follow that up with,or, this client typically
views my invoice in seven days.
Now it's been 20 days.
Why hasn't the client viewed, maybethe person I'm reaching out to has left
the client's organization And ratherthan waiting for another 40 days for.
An outstanding report, they can reach out.
(11:37):
So the anomalies, intelligenceeliminates a lot of these bottlenecks
where team is spending time todaythrough manual and Excel efforts that
completely needs to be automated.
How do you see the invoiceto Cash lifecycle evolving?
I think the Pace Act picture is evolving.
(11:58):
I think the two key things overthere in my mind are deep automation
and, AI assisted support, andI'll talk about both of them.
Deep port deep automation is thatthings don't need to be manual.
Everything should bedone in an automated way.
Sending invoices, trackingfollowing up statements.
(12:18):
All of that needs to be automated.
But then, when we look at the theAI stuff, I feel the billers and
collectors, they're working so hard,but we believe, and I believe that.
Not to in distant future, thereshould be things that support that.
We talk about the whole agent AI andhow we can make the lives of billers
(12:41):
and collectors a lot simpler, whetherit is, genetic ai, like genetic
summaries or emails that capture thesentiment of the client status and all
of those things, or whether it is just.
Managing things through, whether itis workflows or triaging escalations
or suggesting things like, Hey,this client should reach out to this
(13:02):
client because every time you reachout within a week you get paid.
Like having all of these AI-basedassisted assistive capabilities for
the team is where we think it will be.
The billers and collectors.
Think of it as like having, and for lackof a better word, having a co-pilot that
keeps guiding them and helping them oh,I'm trying to reach out to a client.
(13:25):
Here's a suggestive email with theright tone and right information
that pops up on their screen.
Or which client should I follow up on?
These are the clients that you reachedout with these many outstanding invoices.
We see a payment orwhere to give discount.
So I think the system and AI based.
Support for the willers and collectorsis going to be the trend for sure.
(13:50):
This is Ari Kaplan speaking withMilan, Bob De, the co-founder and
CEO of Otter, an AI powered invoiceto cash platform for law firms.
Milan, thank you so much.
Thank you, Ari, for having me as always.
Great conversation andI appreciate your time.
(14:10):
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 speakingtoday with Milan, Bob De, the co-founder
(00:24):
and CEO of Otter, an AI poweredinvoice to cash platform for law firms.
Hi Milan.
How are you?
Hi Ari.
Good to see you again.
Thank you for having me.
I'm looking forward to the conversation.
Mil, we've spoken before.
How are law firms addressing the invoiceto cash process in the current climate?
(00:47):
Invoice to cash is a relatively newproduct category in the legal space.
If you look at non-legal ornon-professional, the invoice
to cash or revenue cycle hasbeen around for a long time.
But most of these horizontal solutions arenot built to the way law firms function.
Simple things on how partnershipsfunctions, how attorneys are
(01:10):
involved in this process.
The horizontal solutions do not caterto that, but with order and more
awareness within law firms to want.
A single platform that letsthem manage their entire revenue
cycle is picking up steam.
And we are seeing more and more firmsinterested in having that single glass
(01:32):
pane view to know exactly A, where theirinvoices are, B, where their bottlenecks
or where their issues, and C, have theteam be able to go tackle those which.
With point solutions, you canreally never do that because it
does not give you a full picture.
It gives you a silo of a view.
(01:55):
What are the benefits of integratinglegal technology platforms in law firms?
Most law firms have.
A great ERP system, like a leador admin to do their finances.
But once an invoice is finalized,they're left on their own to figure
out how to efficiently dispatch this,how to follow up with clients, where
(02:15):
are clients in their payment cycle?
How do you make it easy for clients?
So with.
A platform like Order, which is asingle platform, the whole revenue
cycle becomes a lot more intelligent.
And a few things to mention, likea, it starts with deep automation.
You are not working with silo productsthat do not integrate with each other.
(02:35):
But we have a single platform that becomesthe collaborative bench for the billers,
the collectors, the cash receipts team,the finance leaders, the attorneys.
And that gives.
All of them, the right view of whatthey are interested in and then
how they participate in this cycle.
It also improves the productivity ofthe team drastically because you're not
(02:58):
trying to go to three different systemsto find, Hey, why this invoice has not
been paid, or you're not trying to go to.
Multiple systems to see, hey,which clients should I reach
out to that are not paid?
The invoices.
So the intelligence is a big different.
When you have a single platform,you end up with zero ar leakage,
nothing falls through the cracks.
(03:19):
A very typical symptomof multiple solutions.
But the best part in my mind, isbecause you have the end to end.
Platform, the insights that it brings.
So simple things like, hey, isa client behaving differently
from their typical patterns?
Or, if I'm in collections, whichare the 10 clients I should focus
on when I come to the system?
Have my clients even looked at my invoice?
(03:41):
What payments have come throughand that I've been reconciled
with my accounting system?
All of these are answered witha single platform that today.
Are a big challenge, and if you thinkabout the client's experience in all
of this which is the utmost thing.
Law firms spend so much timeand money and effort to provide
the best legal experience.
(04:03):
They don't have the tools toprovide a similar consumer grade
experience to their clients.
If a client reaches out and says, Iwant to make a payment, the generic
payment links are not easy for clients.
They have to put the client number,matter number, invoice number amount.
No one wants to make, and.
An effort to pay their invoices.
(04:23):
You have to make it easy, right?
The age old saying, wealways say make it darn easy.
If you want someone to pay you andthe business results of because
of this, Ari, you know what weare seeing in our customers?
The invoice outstanding days drop,the write offs drop because fewer
invoices end up in the 90 or one 20plus buckets and clients are happier.
(04:44):
Clients love their experience,so I think it's a win-win for.
The clients and the law firms tohave that single unified platform
that looks through the entirety ofthat revenue cycle or invoice cycle.
Are billing and collectionsseparate or connected functions?
They are a hundred percentconnected, but till now phones
(05:06):
didn't have a good solution.
That lets the building and collectionteams collaborate, so they would have some
other way or manually sending invoices.
And then it comes to the collectionsoftware with our integrated
platform, it's one platform.
Sending invoices is just a few clicks,but it's not just about sending invoices.
Yes, you gain a lot ofefficiency, but when it moves to
(05:28):
collections, the real question is.
Where should I focus and today the mostcollection tools have become glorified
notetaking tool, whereas we believethat there needs to be a paradigm shift.
The collection software needs to.
Tell the law firm and the team wherethere are potential issues before
they become serious, or where shouldtheir time be spent and less time on?
(05:52):
The mundane things of just gettingthings done, like statements and others.
It's amazing how firms spend hours anddays today to send statements out, but
with order, it literally takes them threeminutes to send all the statements out,
and then that time is better utilized.
On knowing which clients to reach out tofollow up and get those invoices paid.
(06:13):
So these are the automation things.
They are absolutely related toeach other and a single platform.
Makes it easier for them.
I would also add the cashreceipt scheme on that.
So the reconciliation part is alsoa manual activity, but with order
pay, you know what payments we get.
Those are reconciled back toyour accounting system, so you
(06:34):
don't have to worry about, oh,the, we got a payment of 14,352.
How does this apply to theinvoices that are outstanding?
All of that is automated.
How does improving the billingand collections process
enhance client service?
The clients, have certainexpectations when they are
(06:55):
interacting with different systems.
Like when we go and buy things orwhen we are paying our invoices, we
expect a certain level of automationand self-service capabilities.
Unfortunately, law firms really don'thave those tools, but in our mind.
If you make it really superior experiencefor your client, like real consumer grade
(07:16):
experience, have a self-service portal.
Make it easy.
One click payments and if it is secureand something that they don't have
to reach out to the law firm for all.
Hey, copy of invoicesor copy of statements.
That's the experience that law firmsare looking to provide to their clients.
I recently was at one of theconferences for our investors.
(07:37):
And I met a person over there, he'sthe founder of a different company,
and he said to me, oh, order.
I get my invoices from order from thislaw firm, and he said it was so easy.
And we signed up forthe self-service portal.
We could access our historical invoicesand this was our first experience for
the full circle where we have clientssending invoices to their clients and we.
(08:02):
Ran into someone who's using orderthrough one of our customers, then
the feedback was pretty amazing.
We definitely have data points thatclients really appreciate having a modern,
secure way to deal with their invoices.
And we all know happyclients mean most business.
So definitely it's a key part ofthe platform and most firms are
(08:24):
really working hard to providethat best client experience.
What billing and collections insightsshould law firms be capturing?
You think about billing and collections,it is such a critical function because
for professional services like law firms,the money coming in is directly related
to what invoices are going out at leastfor most parts, most practice areas.
(08:48):
And that is the critical part of thisrevenue cycle and revenue intelligence.
So if I talk about.
As a law firm, what are the things that Iwant to know so we can reduce our invoice
outstanding days, reduce our write offs?
I think it's just knowingwhere their invoices are.
It's also knowing whereproblems can appear before
(09:09):
they become serious problems.
It's also making that.
What's the pattern of a client?
So a good example is, in our platformwhen you're sending the invoices
out, based on the client's pattern,when that invoice will be paid
and that feeds into your cashflow.
It is such a critical thingbecause now law firms know
what payments are coming in.
(09:30):
And, or at least expected overthe next, 2, 3, 6, 9 months.
And that is really powerful.
And then it's about eliminatingall the manual work, right?
So as I give you examples, statements,sharing invoices just working in
excels it's time consuming andeliminating all of that is where.
(09:51):
Law firm really wants to know whereto focus, which clients to reach out.
Where are my invoices,where are the bottlenecks?
And this in a fragmented solutionsis not feasible because you
don't have a clear single glasspane view across the lifecycle.
What are some overlooked timewasters and traditional billing
(10:11):
and collections workflows?
Sending invoices out manually, we alwayscalculate this as a part of our ROI.
Even if you take five minutes tosend an email if you are sending
thousands and thousands of these,that's a lot of productivity loss.
All of that needs to be automated.
But one thing I'll mention is law firmstake a lot of pride in having that
(10:32):
personal touch, our platform does not doesnot take away that capability they want.
They can still have the personaltouch, but do it in a efficient way.
Single click, send hundreds andthousands of invoices out with that
pre-configured personal touch note you.
Another example whereforms faced a lot of.
Time in terms of not where theycan gain efficiency is statements
(10:56):
or where client requests come in.
Simple things as when a collectionteam comes in the morning, they
look for which are the 2030collections that I need to follow up.
How do you get that prioritized list?
Every day they do an analysis,what's outstanding, what's there,
but having an intelligent perspectiveon that makes a lot of difference.
(11:16):
Hey, this client is behavingdifferently from their pattern.
I need to follow that up with,or, this client typically
views my invoice in seven days.
Now it's been 20 days.
Why hasn't the client viewed, maybethe person I'm reaching out to has left
the client's organization And ratherthan waiting for another 40 days for.
An outstanding report, they can reach out.
(11:37):
So the anomalies, intelligenceeliminates a lot of these bottlenecks
where team is spending time todaythrough manual and Excel efforts that
completely needs to be automated.
How do you see the invoiceto Cash lifecycle evolving?
I think the Pace Act picture is evolving.
(11:58):
I think the two key things overthere in my mind are deep automation
and, AI assisted support, andI'll talk about both of them.
Deep port deep automation is thatthings don't need to be manual.
Everything should bedone in an automated way.
Sending invoices, trackingfollowing up statements.
(12:18):
All of that needs to be automated.
But then, when we look at the theAI stuff, I feel the billers and
collectors, they're working so hard,but we believe, and I believe that.
Not to in distant future, thereshould be things that support that.
We talk about the whole agent AI andhow we can make the lives of billers
(12:41):
and collectors a lot simpler, whetherit is, genetic ai, like genetic
summaries or emails that capture thesentiment of the client status and all
of those things, or whether it is just.
Managing things through, whether itis workflows or triaging escalations
or suggesting things like, Hey,this client should reach out to this
(13:02):
client because every time you reachout within a week you get paid.
Like having all of these AI-basedassisted assistive capabilities for
the team is where we think it will be.
The billers and collectors.
Think of it as like having, and for lackof a better word, having a co-pilot that
keeps guiding them and helping them oh,I'm trying to reach out to a client.
(13:25):
Here's a suggestive email with theright tone and right information
that pops up on their screen.
Or which client should I follow up on?
These are the clients that you reachedout with these many outstanding invoices.
We see a payment orwhere to give discount.
So I think the system and AI based.
Support for the willers and collectorsis going to be the trend for sure.
(13:50):
This is Ari Kaplan speaking withMilan, Bob De, the co-founder and
CEO of Otter, an AI powered invoiceto cash platform for law firms.
Milan, thank you so much.
Thank you, Ari, for having me as always.
Great conversation andI appreciate your time.
(14:10):
Thank you for listening to theReinventing Professionals Podcast.
Visit reinventing professionals.com orari kaplan advisors.com to learn more.
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