How Clearbrief designs and uses NLP to help litigators
Clearbrief (https://clearbrief.com/) is a technology startup in the US that has built an incredible piece of software to solve problems that litigators encounter in their work. Similar to Syntheia, they use natural language processing technology in an incredibly interesting way to improve access to and efficiency of working with legal information.
We had a chat with their CEO, Jackie Schafer, a week ago about their award winning company (which won the New Law Company of the Year at Legalweek in 2022 and Legal Tech Startup of the Year at the American Legal Technology Awards), how they are helping their customers, and how she and her team designed their products.
“I am very practical when it comes to how you can change the world... my biggest insight is that it is the most boring, unsexy things that actually change the world, and actually make a difference... ”
You can watch the full conversation between Jackie and Horace in the video below.
Transcript of Conversation
(Note: transcript is automatically generated, and may contain misspellings and typographical errors)
0:00
jackie schaefer thank you so much for
0:02
joining me um you are the ceo of this
0:04
amazing company called clear brief um
0:07
tell us more about clear brief and tell
0:09
us about yourself
0:11
yeah thank you for having me this is fun
0:13
um so yeah i'm i'm the founder and ceo
0:15
of clear brief and i am a litigator
0:18
that's you know how i spent most of my
0:20
career um in law and i started you know
0:23
in in big law at paul weiss um you know
0:26
as a litigation associate but most of my
0:29
practice was for government um as an
0:31
assistant attorney general doing um
0:34
appeals complex litigation
0:36
and so i've just you know lived the pain
0:39
point that clear brief is solving uh
0:42
many many many times which is
0:44
you know
0:45
you enjoy the creative
0:48
um
0:49
you know uh analytical aspects of
0:52
writing a brief but then there's this
0:54
terrible crunch period right when you
0:56
need to file um that involves you know a
1:00
mix of sort of
1:01
actual attorney review and a bunch of
1:04
you know administrative type work
1:06
and so what clear brief does is it's in
1:08
microsoft word
1:10
and it's sort of like bringing ai into
1:12
word so that while you're writing
1:15
you can do things like
1:16
select a sentence and clear brief will
1:20
pop up suggestions for like here's a
1:22
page from the discovery that you've
1:24
uploaded into clear brief
1:26
that would support this sentence in word
1:29
and here's a list of of pages
1:31
that feature really is thrilling to
1:34
litigators because um who among us has
1:36
not like
1:37
realized you know the day before
1:39
something's due you're like oh my god
1:40
there's just 20 places where i
1:43
i you know pushed the burden onto my my
1:45
future self and i was like add facts
1:47
site find a facts i was later
1:49
and
1:50
you know keyword searches don't cut it
1:52
you know a lot of times you're like i
1:53
know somebody said this idea
1:56
in the transcript but i'm just not
1:57
finding it and clearbrief is able
1:59
because it's using ai it doesn't need to
2:01
be an exact keyword it knows
2:04
how to pull up the most relevant ideas
2:06
from the the factual documents so that's
2:09
huge um it also can help you spot
2:12
mistakes it it color you know color
2:14
codes
2:15
the scoring on you know the different
2:17
things you've already cited and just
2:19
pulls it up for you so you can look and
2:20
say oh wait a minute
2:22
clear brief is flagging this and yeah
2:24
this was the wrong statute or this was
2:26
the you know
2:28
um and then
2:29
at the end of the process you can do a
2:31
table of authorities like using ai in
2:33
just a few clicks and share a
2:37
cloud-based version of not only your
2:39
word doc but all of the sources
2:41
um with clients and with the court
2:44
um and so that's probably my the thing
2:46
that i'm i'm most um bullish on for um
2:50
2022 is we're seeing um
2:54
a pretty quick you know expansion of
2:55
adoption of clear beef by courts and by
2:57
government agencies
2:59
um
3:00
not only by the lawyers who are
3:01
preparing the documents but the court
3:03
deals with the same type of
3:05
challenge when they're reviewing these
3:07
documents so that was a long explanation
3:09
but that's that's what clear brief does
3:11
you presented at a um startup uh pitch
3:14
event last september and i saw a demo of
3:17
clear brief and i think i wrote to you
3:20
immediately afterwards and i said this
3:21
is the most impressive use of nlp i've
3:23
seen in any legal tech um in a very very
3:26
long time
3:27
um
3:29
no
3:30
it's i genuinely mean it like it's it's
3:33
pretty rare that i would look at a piece
3:35
of tech and go
3:36
oh
3:37
i don't know exactly how that's working
3:40
but that is so impressive
3:42
um and there was that moment for me when
3:45
i saw yours and your description of it
3:47
is um um i think
3:49
really quite fascinating because um
3:53
there are several points there which
3:55
come out from there and i was jotting
3:57
notes down as you were talking um the
3:59
first is your reference to pain point um
4:03
and how important that is when you have
4:06
a startup or a scale-up especially for
4:08
for startup founders the the idea of
4:10
pain points and
4:11
i i think i've had a lot of learning
4:14
about that since starting the company
4:16
where
4:17
um one of the first things if you talk
4:19
with someone who does like user research
4:21
for a living
4:22
um
4:23
it's just a very different type of
4:25
interview that you have with
4:27
with users than a lawyer would have
4:29
during a deposition or something for
4:30
example where
4:32
um
4:33
although you know maybe
4:34
um the truly skilled uh
4:38
you know little litigators can are you
4:40
know are good at sort of leaving things
4:42
open-ended and letting people kind of
4:43
hang themselves that's
4:45
the the deposition kind of perspective
4:47
but um but yeah i mean with with user
4:49
research you're not going to really
4:51
understand the pain point
4:53
if you go in with too many leading
4:54
questions and and you're too
4:56
um
4:58
you know opinionated about you know
5:01
how the problem should be solved
5:02
basically and so that i think it's it's
5:04
a strength that i deeply understand the
5:06
work that our users do
5:08
but i had to sort of learn how to hold
5:10
myself back a little bit more when i was
5:12
talking to people
5:14
and that's what really
5:16
i think made the difference in helping
5:18
us you know refine our focus and also
5:21
make the product improvements that we've
5:22
done over the past year
5:24
and
5:25
you know read between the lines um of
5:27
what's annoying them or you know what
5:29
they love and that kind of thing
5:32
yeah and so i found that to be
5:34
i know it's it's um maybe a cliche but
5:36
it's just
5:37
i was reminded by a number of my
5:39
advisors like early on it's like
5:41
you need to always be talking to
5:42
customers and just because you hire
5:44
other people on the team to you know
5:46
help with sales or you know help with
5:48
customer success like i need to also be
5:50
in those conversations as the product
5:52
leader i need to really
5:54
um
5:55
you know give myself a lot of
5:56
opportunities
5:58
you know ask questions sort of because
5:59
sometimes you know if someone just sends
6:00
an email they're like oh how do i do
6:02
this and you could answer it and give
6:04
them that immediate answer but um
6:07
you'll learn a lot more if you can get
6:09
them on a call and then
6:11
help figure out like
6:12
why wasn't it intuitive to them what to
6:14
do next
6:16
and and that's super fascinating uh the
6:18
the words why was it not intuitive to
6:20
them um
6:22
you obviously do a lot of research do a
6:24
lot of conversations with customers to
6:25
find out what exactly they're looking
6:27
for um
6:29
and there's this i don't know if you've
6:30
seen this there's a uh i forget the
6:32
lady's name at google she gave this talk
6:35
about microwaves um have you have you
6:38
seen that no
6:39
oh she's wonderful i'll send you a link
6:41
afterwards um
6:46
no it's it's genuinely a really good
6:48
talk she is um
6:50
an ai researcher an ai lead at google
6:54
and
6:55
what she was talking about is
6:57
as developers as product owners we care
7:00
how the microwave works we care that you
7:03
know there's this wave this is power
7:05
inlet outlet etcetera but as customers
7:08
they just want their food food heated up
7:12
i don't know if things are sort of
7:13
changing but um
7:14
early when i when i started clear brief
7:16
in 2020 like actually right before the
7:18
pandemic hit um
7:21
when i would kind of talk to lawyers
7:23
about ai that seemed like it kind of
7:25
turned them off like people are very
7:27
wary of ai and ai of replacing lawyers
7:30
so i actually just found it easier to
7:33
just talk about it more as like a tech
7:34
product and i did not emphasize the ai
7:37
now i do think there's more education
7:39
and understanding of like okay yeah ai
7:42
is not going to replace lawyers anytime
7:44
soon um
7:45
but if ever right
7:47
cool stuff and um
7:49
so i think just i kind of
7:51
think of it as you know we're we're a
7:53
sas product with a sprinkle of ai in the
7:55
right places
7:57
and that seems like it um
8:00
is less intimidating to people
8:02
yeah i think so it's it's um
8:05
um there's been a shift in the
8:07
marketplace right i think people were
8:08
disillusioned by the early wave of ai
8:11
that was in the legal space and there
8:12
was a lot of inflated marketing um and
8:15
now people have toned it back
8:17
it's a lot more grounded which i am very
8:20
thankful for
8:21
um
8:23
and
8:24
more and more i'm seeing the really
8:27
advanced technologies become sort of
8:29
invisible as a sort of part of the
8:30
workflow but it doesn't you know scream
8:33
and shout and say hey i'm here i'm super
8:35
powerful and amazing it just does the
8:37
job and help lawyers and you mentioned
8:40
at the start you've got yours inside of
8:43
microsoft word which has been a sort of
8:45
trend in the last three or four years
8:48
tell us more about how you designed it
8:50
tell us more about you know
8:52
what is it that you want the user
8:53
experience to be like
8:56
yeah
8:56
so i really um because i come from like
8:59
i said most of my careers in government
9:01
i am very practical when it comes to how
9:04
you can change the world like i have
9:06
worked on projects i also was in-house
9:08
for a national um like three billion
9:10
dollar non-profit that was working to
9:12
try to change the child welfare system
9:14
so i've just like been a part of a lot
9:16
of different um kind of like policy
9:17
initiatives to try to change things
9:19
improve things
9:20
and my like biggest insight is that
9:23
it's the most boring unsexy things that
9:26
actually
9:27
change the world and that actually make
9:29
a difference
9:30
and so
9:31
i
9:32
initially did think oh wouldn't it be so
9:33
cool if we could like have a totally new
9:36
platform and like build our own word
9:38
processor that's modern it's like
9:40
well everyone it's like 99 of
9:43
lawyers and something ridiculous like
9:45
that um
9:46
and and courts and judges all use word
9:49
and even you know companies that
9:52
where their in-house legal teams maybe
9:54
they they don't even use or they still
9:56
have word they all have it
9:58
so
9:59
um that's really
10:01
not not something to be sneezed at that
10:03
you have kind of a captive audience of
10:05
people who
10:06
when they when they sit down to write
10:08
they're working in word and anything
10:11
anytime they have to use a different
10:12
platform it's costing them in terms of
10:14
their
10:15
um their focus
10:17
and because
10:19
the act of writing is you know
10:21
like this masterpiece you're pulling
10:23
together things from all these different
10:24
like diverse places and sources and
10:26
ideas and
10:27
um
10:28
you know i wanted to sort of
10:30
create something that could make that um
10:32
the cost of finding what you need
10:34
less so that your most of your effort
10:37
and energy is your concentration is not
10:39
broken you can really focus on the
10:41
writing in the craft of writing
10:43
and
10:44
yeah again like it's like microsoft word
10:46
the the fact of finding sources and
10:48
citations
10:50
is so important when it comes to the
10:52
outcomes of these cases and when it
10:55
comes to the workload of litigators
10:58
and courts um
11:00
so that's where you know this the unsexy
11:04
area of citations is is how i think you
11:06
know ai can really be helpful it's also
11:09
um where natural language processing is
11:11
really perfect for this type of
11:13
knowledge work so
11:14
um
11:15
i i you know i'm really excited about
11:18
again like it's it's wonderful to just
11:20
hear from the users now and we started
11:22
um we have like a slack channel that's
11:24
like the wall of love where we
11:26
just the things that our customers say
11:29
and when we're on a call with them and
11:30
stuff like
11:31
you know
11:32
my mind is blown like you know and just
11:34
to hear that excitement it literally
11:37
happens every call now and so
11:39
um
11:40
you know and when i've talked with other
11:43
um
11:44
you know sales people and some of the
11:46
sales folks on our team come from other
11:48
legal tech you know
11:51
areas and they're like yeah i've never
11:52
experienced that before like lawyers are
11:54
pretty
11:55
um
11:56
not easily impressed you know what i
11:58
mean so um so that that's really
12:00
gratifying that we've taken something
12:02
that's very
12:03
dry and stressful for people and we've
12:06
brought kind of this ai magic to it so
12:08
yeah they can work more efficiently they
12:11
can actually
12:12
you know win their case because if you
12:14
can find that killer piece of evidence
12:17
like that is what's going to persuade
12:19
yep yep it's okay so so first of all it
12:22
is not an unsexy area it's just very
12:25
dressed down
12:26
[Laughter]
12:32
i think i think it's like a really cool
12:35
area and the more i work with nlp the
12:37
more i work with this sort of like um
12:40
machine learning and ai space um the
12:42
more i realize there's a
12:44
big difference between
12:46
what
12:47
is successful and what is not successful
12:49
um in terms of the adoption
12:52
and it's stuff that actually
12:55
fits in a person's workflow
12:58
like if
12:59
if you can insert something into the way
13:02
they work today
13:05
and they just go right pick it up off
13:06
they run
13:08
that
13:09
is so much easier
13:11
than trying to say okay it's a brand new
13:14
thing go train a model go do x go do y
13:17
go do z and then you're gonna get the
13:19
benefit three months later
13:21
so i love you the way you go about and
13:24
and create this inside the ecosystem
13:27
where lawyers are working today
13:29
um exactly
13:31
and something that um you said at the
13:33
very beginning of this which made me i
13:35
think was a very interesting point was
13:37
um
13:38
there's a big difference between
13:39
litigators and transactional lawyers
13:42
um
13:43
and
13:44
um you know what we do
13:46
on our side of defense we look after
13:48
transactional lawyers um and on what you
13:50
do you're looking after litigators
13:52
but there's a lot of parallels as well
13:55
what would you say are
13:57
the key things that litigators looking
14:00
for
14:00
and also what do you think are the key
14:02
things
14:03
that are different between litigators
14:05
and transactional lawyers
14:08
in terms of what they're looking for in
14:09
a product or like in
14:11
yeah in terms of what they're looking
14:13
for
14:14
for for something that helps them um not
14:16
necessarily a product but something that
14:18
actually helps them solve their
14:20
day-to-day needs
14:21
yeah and so like when i was in-house at
14:24
the non-profit i did like a high volume
14:26
of um contracts
14:28
and you know contract negotiation so i
14:30
do have some sense of like what that
14:32
pain is like too
14:34
um
14:35
i always found that on the transactional
14:37
side yeah there's al it was more about
14:40
um the relationships in in the deals and
14:44
trying to figure out okay like i'm not
14:46
the person who's
14:48
you know actually owning the
14:50
project or whatever that i'm negotiating
14:52
or the deal so
14:54
um but i yet have to like foresee all of
14:57
the pitfalls and
14:58
risks and challenges and
15:00
um
15:02
so
15:03
yeah i think like to me there yeah
15:04
there's just there is so much complexity
15:06
that the transactional lawyers face and
15:08
trying to sort of see the future and
15:10
anticipate
15:11
um and when i
15:13
think about the work that you know
15:15
litigates are doing when they sit down
15:16
to microsoft word it's more about
15:19
um
15:20
telling a story
15:22
and
15:23
um there's a lot of
15:25
you know
15:27
there's a strong need to tell a story
15:29
that is actually grounded in substance
15:32
and
15:33
everything that you say literally every
15:34
single sentence
15:36
is supposed to have a source backing it
15:38
up in litigation and so
15:40
if you can really help people um make it
15:43
quicker to tell a good story
15:45
and also help them figure out well what
15:47
is the right story to tell because
15:48
sometimes you sit down
15:50
in litigation and you know you can be
15:53
i mean this is maybe a similarity too
15:54
because i've had this experience with
15:55
contracts where you're sort of like
15:57
i understand this deal okay this is what
15:59
they're going for and you start crafting
16:01
up the statement of work or whatever and
16:02
then
16:04
you hear back they're like no that was
16:05
not
16:06
what the actual
16:08
trying to achieve you you totally like
16:11
added all this burden some stuff we
16:12
don't need um and the same thing that
16:14
sort of happened to you
16:16
when you're writing
16:17
a brief where you could be like this is
16:19
my theory of the case and you you read
16:21
all the you know
16:23
the transcripts and
16:25
you've done the depositions and you sort
16:26
of know
16:27
what you're going to argue and you know
16:29
your motion for summary judgment or
16:30
whatever and then you
16:32
go back to find your sources and you're
16:34
like oh i misremembered it like no they
16:36
didn't actually say that what i wanted
16:38
them to say or um okay i've got to
16:40
change my argument and i want to find a
16:42
case that
16:43
can work with these these weird facts
16:45
that i now have and um so yeah i mean i
16:48
think it's that same
16:49
the importance of like
16:51
making sure the writing is capturing
16:54
you know what's what's happening on the
16:55
ground yeah yeah i think you've
16:59
you've said something super interesting
17:00
and and that is the difference between
17:02
forward looking and backwards looking i
17:04
think
17:05
litigators are very much about taking
17:07
historical information and presenting a
17:09
story from that
17:10
whereas transactional lawyers is about
17:12
taking intent and then building and
17:14
crafting the future of what it could be
17:18
um
17:19
i think that's a good point and i mean
17:21
i would say that
17:23
you know the best litigators even at
17:25
trial are also sort of thinking about
17:26
the future because they're like okay
17:28
i'm gonna lose at trial but this is
17:30
gonna go on appeal and so i need to to
17:33
lay the foundation so that the appellate
17:35
lawyer can
17:36
knock it out of the park and so yeah
17:38
it's kind of like you have to balance it
17:39
all
17:40
but
17:42
when it comes like
17:44
um
17:45
yeah and and
17:46
there is also the ability similar to
17:47
contracts where you're like okay if i
17:49
don't have what i need i can reach out
17:51
to the parties involved and get what i
17:53
need so that
17:54
i can understand the story um
17:56
[Music]
17:57
at trial you can do that
18:01
but i feel you're stuck with with the
18:02
past for sure yeah
18:05
it's it's so interesting because um um
18:09
if the best litigators are the ones who
18:11
also have to build the path for the
18:12
future i think the best transactional
18:14
lawyers are also the ones who have to
18:16
look deep into the past because they're
18:19
using the past deals and the marketness
18:21
if you like to shape the negotiation to
18:24
shape
18:25
how the contracts can finally look so
18:27
it's it's interesting
18:30
and also
18:31
i'm sure there's like you know
18:33
there's a big litigation about something
18:34
you're like see i told you that was a
18:36
risk you know
18:39
although although you you never want to
18:41
be on either side of that conversation
18:43
as a transactional lawyer
18:46
yeah
18:47
it's one of my greatest fears back when
18:49
i was when i was doing transactional
18:50
work where a litigator would ring me and
18:52
go can we have a conversation and i'm
18:54
like oh maybe maybe not i'm very busy
18:57
right now
18:58
yeah no it's fascinating when you're in
19:01
house as well because then you can kind
19:02
of see if you're there long enough you
19:04
can live to see the
19:06
um
19:07
the unfolding yeah exactly like what
19:10
happens after you gave your legal advice
19:11
and how it turned out and um
19:14
sort of down the road how it impacted
19:16
other engagements and
19:18
that that is something that i really did
19:20
enjoy about being in-house you get to
19:22
really
19:23
understand
19:24
um yeah the impact of the legal advice
19:28
that's awesome so to wrap up um tell us
19:31
what is the most exciting thing on your
19:32
roadmap for 2022
19:35
oh i would say it's um you know we have
19:38
some new features that we're going to be
19:39
launching
19:40
um that were you know honestly based on
19:42
that feedback that we
19:44
painstakingly got from our early users
19:47
um
19:48
and
19:49
just we're on boarding some of our
19:51
larger kind of enterprise and government
19:53
um
19:54
customers
19:55
and so we're going to be really learning
19:56
a lot about the most efficient way to
19:59
teach um
20:01
you know a tech product and onboard
20:03
people um so
20:05
that's yeah because right now i mean
20:07
we've had our a lot of our early growth
20:09
was with um you know small firms solar
20:11
practitioners
20:13
um and so we had a lot of opportunity
20:15
for that one-on-one dialogue and
20:17
um it's going to be interesting to see
20:19
as we scale
20:20
you know i really i am super interested
20:22
to learn about the best way to on like
20:24
for example to train and onboard a group
20:26
and
20:27
um when you're working with a solar
20:30
practitioner
20:31
you know i might be just writing the
20:33
whole brief myself and i'm doing my
20:35
table of authorities and i'm site
20:36
checking it and i'm getting it filed
20:38
so many of the solar practitioners don't
20:40
even they don't have a legal assistant
20:41
they don't have anybody to help them
20:43
um or some might have one you know one
20:46
person a paralegal or something like
20:48
that um
20:49
but when you start going to larger firms
20:51
there it's really about writing a brief
20:53
as a team sport like they're doing it as
20:56
a team and so
20:57
you know the
20:58
associate is going to start with the
21:00
draft they're going to send it to the
21:01
partner you know that's going to go
21:04
to the paralegal it's going to go to the
21:05
client for comments it's going to go to
21:06
three other partners for comments back
21:08
to the paralegal back to the you know
21:09
it's going to
21:10
go through a lot of different people who
21:12
need to touch that document and review
21:14
it um and each of them might use clear
21:16
brief a little bit differently so
21:18
we're trying to be really thoughtful
21:20
about
21:21
the training process
21:23
that's super exciting uh and i think i
21:25
think you're gonna do so well and also
21:28
congratulations on being one of the top
21:30
three at the aba tech show um
21:34
i i heard about your your musical
21:36
talents from that show as well so i look
21:38
forward to hearing that in person one
21:40
day
21:40
yeah i mean i am all about karaoke so
21:44
that's one of the reasons i was really
21:46
sad to miss um legal week this year i
21:49
just couldn't you know i couldn't swing
21:51
two weeks of travel in a row um because
21:53
the texture was last week but
21:54
um i know some there was a special
21:57
karaoke benefit concert arranged that i
21:59
was like i wish i could go
22:02
so fun
22:03
next year next year we might even be at
22:05
the same show at the same time so
22:07
i hope so
22:08
yeah you gotta tell me which ones you're
22:10
going to and uh all of them um
22:15
so until then um thank you so much for
22:17
joining us and having this conversation
22:19
um i really enjoyed learning more about
22:21
clea brief and where you're taking it
22:23
and all the exciting things you have
22:24
planned for this year thank you so much
22:26
thanks for having me
