October 6, 2025 • 8 mins
I spoke with Timothy Keith, the Founder and CEO of Propense.ai, which develops technology to empower cross-selling in professional services, including at law firms. We discussed how AI can help law firms improve cross-selling, the most common business development challenges they face, and where lawyers should leverage technology to enhance their business development.
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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 speaking todaywith Timothy Keith, the founder and CEO
(00:22):
of Propent ai, which develops technologyto empower cross-selling in professional
services firms, including at law firms.
Hi Tim, how are you?
Hi, Ari.
Thanks for including me.
I'm really looking forwardto our conversation.
It's great to see you.
I'm looking forward to it as well.
So tell us about your backgroundand the genesis of Propent ai.
(00:43):
Steve Jobs had this famous quote youcan't connect the dots going forward.
And that's really how Iended up in this role.
It wasn't something chosen.
It was a necessary need.
I grew up in the Northeast wentto school in PA and started my
first business outta college.
It was a note taking business.
Essentially.
I would hire high achievingstudents and sell the notes back
to the students in colleges.
I fell in love with entrepreneurship,but it wasn't a business built to scale.
(01:06):
I fell in love with solvinga problem that doesn't exist.
So I got into CRM consultingworked it with a large enterprise
businesses implementing Salesforceunderstand business processes
and in New York for some time.
And then I just got tired of the coldand decided to take a job at Miami
because I basically wanted to get theclosest to family, but also warm as well.
I started to work at an accountingfirm implementing CRM, and I realized
(01:30):
very quickly that professionalservices businesses work completely
opposite the normal standard businessesgoing through a sales process.
First of all, the sellerdoor model is very unique.
And everyone's siloed intheir own domain expertise.
And the most interesting thing, althoughthese professionals are very highly
trained, they're not the best at selling.
There's just a natural fear of rejection.
(01:51):
It's more of a reactive businessthan a proactive business.
So randomly, when I was on a walkgetting frustrated with rolling out the
serum project, outta Whole Foods I waslooking at eyelet, ketchups, and I saw
all these options and I basically waslike, this is how a professional feels.
There's so many options to give theirclients, and I'm only an expert of one,
so I don't wanna approach my client withanything new to cross sell because I'm
(02:14):
not an expert and I fear that rejection.
We have all this data.
We have all this datawithin the billing system.
Everything's billed by timeand everything's accounted for.
Why isn't a system like Amazon or Netflix?
A prediction model, have been built forprofessional services and accounting
firms to predict what is servednext to help these accounting firms.
Firms better serve theirclients on their needs.
And that's where theoriginal idea came about.
(02:35):
Fast forward two and a halfyears , I took the leap to do it.
We started with working with seven ofthe top 70 accounting firms, and now
we're working with three top globallaw firms, and we're rolling out in
2026 to the broader market of legal.
Working at an accounting firm,understanding that the pain of it,
working with law firms as well,and then connecting those dots got
us to the point where we're today.
How can AI help law firms improvetheir cross-selling activities?
(02:59):
It really comes down topsychology more than it is ai.
AI can be able to, with massand scale take large data sets
and give you data back decisionsfor you to take that first leap.
For law firms, this is very importantbecause we're dealing with very.
Strong experts, opinions, and people thatare afraid to be wrong towards a client.
(03:20):
But what AI is able to do is give youdata back insights against your clients
for you to take that leap forward,to take down that barrier at scale.
The second part of what AI is ableto do is able to take all that
busy work that you would have todo to crunch all this information.
Create the action that's needed.
We'll be able to do that right upand serve that information up to you.
(03:41):
There's three different elements.
What's the most likelything to happen here?
Can we take the friction out ofthe sales process by creating
assets so people can action it?
And then also that will lead to thechange behavior across the board.
Obviously technology right now, that'sonly a piece of the journey about
changing behavior and helping firms grow.
But this, it is a essential piecebecause it helps change that culture.
(04:04):
What are the most common challengesthat law firms have with improving
their business development?
Change behavior.
it's a very reactive business and likethe law firms, what makes it very unique?
It's the partnership model.
Normal enterprise businesses, theCEO says, this is what we're gonna
do and this is how we're gonna grow.
And everyone has to stand in line.
Everyone has to do it.
'cause that's just howthe how the form works.
(04:25):
But the people of professionalservices run the business.
The people of the lawfirms run the business.
A partner is not gonna really changebecause they have the biggest book in
the business, and that culture doesn'tallow change holistically at berms.
That's why they reallystruggle with tech adoption.
That's why they really strugglewith any type of change from a
business development perspective.
Lawyers get into the bus becausethey're experts and basically
people come to them for answers.
(04:47):
They don't go out there to the market andsay, here's my services, and I'm hunting
down these doors for you to work with me.
people have problems and they cometo them and it's very reactive.
So the natural of the businesshas been built by that.
So change behavior is always gonnabe a struggle with professional
services because the partners,the professionals, that's just
not their natural capabilities.
So there's several things thatyou have to do to fit into those
(05:11):
workflows to make that happen.
But no matter what, it is a struggle.
Where should lawyers get started ontheir journey of using technology to
enhance their business development?
They need to start thinking of technologyas an additive, not the magic wand.
A lot of what lawyers and thenatural intuition for them is.
(05:32):
What's great about this?
What's what?
What's the magic wand?
Is this right or wrong?
That's the natural ofwhat makes them great.
But what makes technology verypowerful for business development
is the consistency in taking theburden off of your consistent
actions in business development.
Because business developmentreally is the numbers game.
Can I understand a client?
Can I do this consistently overtime for a long amount of time?
(05:54):
And can keep that consistency up?
Where a lot of lawyers struggle,especially professionals, they were like.
What does this tool do that I can't do?
What does this tool do?
Give me this hidden thing thatI am can't do as my own thing.
And that's the wrongway to view technology.
Technology always should be supportiveof the process that you already have
and try to help it make it scale.
So if I can do once a week,this naturally technology can
(06:17):
help do it 10 times as fast.
We're not trying to replace humans.
There's a lot of AI going out there,replace workers, all that things.
I think that's a bunch of garbage.
Technology should be able to acceleratethings a lot faster, take all the
busy work out of our things so we canactually think and do what human beings
do well, that human condition, thatnuance to make the right decisions.
(06:38):
That 90% work that you're doing all thetime, let's let AI do that so you can have
that 10% be the real, trusted advisor.
What do you see as the most common waysthat lawyers can use AI for raising their
profile and enhancing their practices?
There's several platforms out therethat would basically take that busy
(06:59):
work and help with that consistency.
There's some social media platformsthat would take all that things
that they're doing and post for themevery week to grow their network.
There's several prospecting tools that youcan give the profile who the right client
for you to do all those outreach for you.
There's several data companies likePropent that would look at your client
base and serve up the highest propensityneeds for your clients so you can actually
(07:19):
action it versus scrub it yourself.
Look at that and just beconsistent with that effort.
The way that an individuallawyer can do is like starting
with some of these platforms andmake it part of their routine.
It's a toothbrush, not a magic wand.
Sometimes you'll get some magic, but themost important thing is that consistency.
How do you see the useof AI and legal evolving?
(07:40):
We're in a very interestingtime because people don't know
what the limits of AI are.
But I still go back tothe human condition.
There's an art to the practice.
I see AI taking away anything that couldbe automated and going past that 90%.
I also can see leadershipteams having a very clear view.
Of what is effective work andwhat's really profitability and
everything else can be automated.
(08:01):
And then some of these legal works willhave lower margins and more at scale
and be commoditized across the space.
And then there will be some new legalways to do it just because so many
businesses are changing so quickly.
There's such an opportunity here.
If you can find a niche within thismarket because of the picks and shovels
that are happening with ai, that's atremendous opportunity for any type
(08:22):
of lawyer or any type of law firm.
This is Ari Kaplan speaking withTimothy Keith, the founder, and CEO of
Propent ai, which develops technology toempower cross-selling and professional
services, including at law firms.
Tim, thanks so very much.
Thank you, Ari.
This.
Is very fun and I'mhappy to be on anytime I.
(08:43):
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 Timothy Keith, the founder and CEO
(00:22):
of Propent ai, which develops technologyto empower cross-selling in professional
services firms, including at law firms.
Hi Tim, how are you?
Hi, Ari.
Thanks for including me.
I'm really looking forwardto our conversation.
It's great to see you.
I'm looking forward to it as well.
So tell us about your backgroundand the genesis of Propent ai.
(00:43):
Steve Jobs had this famous quote youcan't connect the dots going forward.
And that's really how Iended up in this role.
It wasn't something chosen.
It was a necessary need.
I grew up in the Northeast wentto school in PA and started my
first business outta college.
It was a note taking business.
Essentially.
I would hire high achievingstudents and sell the notes back
to the students in colleges.
I fell in love with entrepreneurship,but it wasn't a business built to scale.
(01:06):
I fell in love with solvinga problem that doesn't exist.
So I got into CRM consultingworked it with a large enterprise
businesses implementing Salesforceunderstand business processes
and in New York for some time.
And then I just got tired of the coldand decided to take a job at Miami
because I basically wanted to get theclosest to family, but also warm as well.
I started to work at an accountingfirm implementing CRM, and I realized
(01:30):
very quickly that professionalservices businesses work completely
opposite the normal standard businessesgoing through a sales process.
First of all, the sellerdoor model is very unique.
And everyone's siloed intheir own domain expertise.
And the most interesting thing, althoughthese professionals are very highly
trained, they're not the best at selling.
There's just a natural fear of rejection.
(01:51):
It's more of a reactive businessthan a proactive business.
So randomly, when I was on a walkgetting frustrated with rolling out the
serum project, outta Whole Foods I waslooking at eyelet, ketchups, and I saw
all these options and I basically waslike, this is how a professional feels.
There's so many options to give theirclients, and I'm only an expert of one,
so I don't wanna approach my client withanything new to cross sell because I'm
(02:14):
not an expert and I fear that rejection.
We have all this data.
We have all this datawithin the billing system.
Everything's billed by timeand everything's accounted for.
Why isn't a system like Amazon or Netflix?
A prediction model, have been built forprofessional services and accounting
firms to predict what is servednext to help these accounting firms.
Firms better serve theirclients on their needs.
And that's where theoriginal idea came about.
(02:35):
Fast forward two and a halfyears , I took the leap to do it.
We started with working with seven ofthe top 70 accounting firms, and now
we're working with three top globallaw firms, and we're rolling out in
2026 to the broader market of legal.
Working at an accounting firm,understanding that the pain of it,
working with law firms as well,and then connecting those dots got
us to the point where we're today.
How can AI help law firms improvetheir cross-selling activities?
(02:59):
It really comes down topsychology more than it is ai.
AI can be able to, with massand scale take large data sets
and give you data back decisionsfor you to take that first leap.
For law firms, this is very importantbecause we're dealing with very.
Strong experts, opinions, and people thatare afraid to be wrong towards a client.
(03:20):
But what AI is able to do is give youdata back insights against your clients
for you to take that leap forward,to take down that barrier at scale.
The second part of what AI is ableto do is able to take all that
busy work that you would have todo to crunch all this information.
Create the action that's needed.
We'll be able to do that right upand serve that information up to you.
(03:41):
There's three different elements.
What's the most likelything to happen here?
Can we take the friction out ofthe sales process by creating
assets so people can action it?
And then also that will lead to thechange behavior across the board.
Obviously technology right now, that'sonly a piece of the journey about
changing behavior and helping firms grow.
But this, it is a essential piecebecause it helps change that culture.
(04:04):
What are the most common challengesthat law firms have with improving
their business development?
Change behavior.
it's a very reactive business and likethe law firms, what makes it very unique?
It's the partnership model.
Normal enterprise businesses, theCEO says, this is what we're gonna
do and this is how we're gonna grow.
And everyone has to stand in line.
Everyone has to do it.
'cause that's just howthe how the form works.
(04:25):
But the people of professionalservices run the business.
The people of the lawfirms run the business.
A partner is not gonna really changebecause they have the biggest book in
the business, and that culture doesn'tallow change holistically at berms.
That's why they reallystruggle with tech adoption.
That's why they really strugglewith any type of change from a
business development perspective.
Lawyers get into the bus becausethey're experts and basically
people come to them for answers.
(04:47):
They don't go out there to the market andsay, here's my services, and I'm hunting
down these doors for you to work with me.
people have problems and they cometo them and it's very reactive.
So the natural of the businesshas been built by that.
So change behavior is always gonnabe a struggle with professional
services because the partners,the professionals, that's just
not their natural capabilities.
So there's several things thatyou have to do to fit into those
(05:11):
workflows to make that happen.
But no matter what, it is a struggle.
Where should lawyers get started ontheir journey of using technology to
enhance their business development?
They need to start thinking of technologyas an additive, not the magic wand.
A lot of what lawyers and thenatural intuition for them is.
(05:32):
What's great about this?
What's what?
What's the magic wand?
Is this right or wrong?
That's the natural ofwhat makes them great.
But what makes technology verypowerful for business development
is the consistency in taking theburden off of your consistent
actions in business development.
Because business developmentreally is the numbers game.
Can I understand a client?
Can I do this consistently overtime for a long amount of time?
(05:54):
And can keep that consistency up?
Where a lot of lawyers struggle,especially professionals, they were like.
What does this tool do that I can't do?
What does this tool do?
Give me this hidden thing thatI am can't do as my own thing.
And that's the wrongway to view technology.
Technology always should be supportiveof the process that you already have
and try to help it make it scale.
So if I can do once a week,this naturally technology can
(06:17):
help do it 10 times as fast.
We're not trying to replace humans.
There's a lot of AI going out there,replace workers, all that things.
I think that's a bunch of garbage.
Technology should be able to acceleratethings a lot faster, take all the
busy work out of our things so we canactually think and do what human beings
do well, that human condition, thatnuance to make the right decisions.
(06:38):
That 90% work that you're doing all thetime, let's let AI do that so you can have
that 10% be the real, trusted advisor.
What do you see as the most common waysthat lawyers can use AI for raising their
profile and enhancing their practices?
There's several platforms out therethat would basically take that busy
(06:59):
work and help with that consistency.
There's some social media platformsthat would take all that things
that they're doing and post for themevery week to grow their network.
There's several prospecting tools that youcan give the profile who the right client
for you to do all those outreach for you.
There's several data companies likePropent that would look at your client
base and serve up the highest propensityneeds for your clients so you can actually
(07:19):
action it versus scrub it yourself.
Look at that and just beconsistent with that effort.
The way that an individuallawyer can do is like starting
with some of these platforms andmake it part of their routine.
It's a toothbrush, not a magic wand.
Sometimes you'll get some magic, but themost important thing is that consistency.
How do you see the useof AI and legal evolving?
(07:40):
We're in a very interestingtime because people don't know
what the limits of AI are.
But I still go back tothe human condition.
There's an art to the practice.
I see AI taking away anything that couldbe automated and going past that 90%.
I also can see leadershipteams having a very clear view.
Of what is effective work andwhat's really profitability and
everything else can be automated.
(08:01):
And then some of these legal works willhave lower margins and more at scale
and be commoditized across the space.
And then there will be some new legalways to do it just because so many
businesses are changing so quickly.
There's such an opportunity here.
If you can find a niche within thismarket because of the picks and shovels
that are happening with ai, that's atremendous opportunity for any type
(08:22):
of lawyer or any type of law firm.
This is Ari Kaplan speaking withTimothy Keith, the founder, and CEO of
Propent ai, which develops technology toempower cross-selling and professional
services, including at law firms.
Tim, thanks so very much.
Thank you, Ari.
This.
Is very fun and I'mhappy to be on anytime I.
(08:43):
Thank you for listening to theReinventing Professionals Podcast.
Visit reinventing professionals.com orari kaplan advisors.com to learn more.
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