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.

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